Break away from the city once in a while and recharge in a peaceful environment. There’s a town close to the beaches in the name of Madison in Connecticut, USA which is the perfect sanctuary for those seeking solitude. Aside from its charming beaches, Madison is also home to several parks and other recreational activities such as The Shoreline Greenway Trail and The Sculpture Mile. For all the above reasons and more, Madison proves to be the ideal long weekend or summer getaway destination. Save a whole lot by renting in some of the locals’ friendly and hospitable apartments and guesthouses via Airbnb. Here are our top picks for Airbnb vacation rentals to help you get started on that Madison trip you’ve been planning for the next holidays.
We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on October 23, 2024.
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1. Spacious beachfront holiday home with free car parking (from USD 650)
Overlooking its own private beach, this seafront holiday home comes complete with lavish bedrooms and can comfortably accommodate as many as 10 guests. The comfy queen beds ensure a good night’s rest. Guests can make use of a washer, dryer, and iron parked in the unit if clothes need to be laundered.
You can lounge the evening away on the plush sofa while knocking back a drink or two. Picturesque views of the pristine waterscape can be enjoyed while drinking tea and chatting with a loved one over free Wi-Fi. If work brings you here, you can make use of the laptop-friendly nook for work meetings and Zoom calls. A fireplace keeps you warm indoors on chilly evenings. Cars can be parked on the property premises at no surcharge.
Top guest reviews
Host:
great home and even better hoststhe host was the bestrosemarie was a superb hostrosemarie the host was so easy to communicate withrosemarie and lee were super responsive and great hostsLocation:
just a wonderful relaxing locationbeautiful house in a great locationgreat house and what a wonderful locationbeautiful home in a beautiful locationit’s location just steps from the beach was perfect we are already looking forward to booking it againCleanliness:
very clean and roomyhouse was clean and we enjoyed our stay very muchthe home is exceptionally clean and has everything you would need with many special touchesthe house was very clean and it was very easy to check in and checkoutclean spacious great views easy check-in and communicationRead more reviewsAmenities & Room:
the deck and sun room were so lovelybeautiful place easy check in cozy beds everything you could need lots of space loved it
2. Charming vacation rental with free Wi-Fi (from USD 150)
Nestled along the harboring banks of Long Island Sound, this charming house by the beach is a perfect choice for couples on a romantic getaway.
The comfortable double bed in the bedroom helps you to drift off to sound sleep after a tiring day of sightseeing. You can decompress in the bathtub with a relaxing bath. A coffee maker is parked for guests to satiate their caffeine cravings. Free Wi-Fi keeps you connected with loved ones back home. If you are visiting in a car, you can park it in the residential garage without a parking fee.
Top guest reviews
Host:
super friendly hosts and private spacethe hosts were friendly and communicated quicklyleslie is a delightful hostgreat stay nice beach wonderful host fun weekendleslie and tom were great hostsLocation:
great location close to the beach and downtown area with restaurantscute little place to staybeautiful house and location surrounded by different things to doit was wonderful to be so close to a quiet beachnice area with good close downtownCleanliness:
this place was clean and spacious for a studioit was very clean and was perfect for what we were looking forthe room was very clean and the area was quietit's a beautiful home and the space was clean and welcomingRead more reviewsAmenities & Room:
inside the room are two plastic chairs like you will find at a banquetthe full size bed pretty much took up the entire space in the bedroomsuite with a beach is an adorable room just steps from the private beachthe room was pretty much as described on the website
3. Greenfield Cottage (from USD 250)
Nestled in a quiet neighborhood, Greenfield Cottage offers delightful accommodations. Hammonasset Beach State Park and Chatfield Hollow State Park are a short stroll away from the cottage.
Queen beds let you sleep peacefully after a tiring day of exploration. Favorite Netflix web shows can be enjoyed on the high-definition TV and Alexa sound system. If you are traveling with a baby, it would be a good idea to book this property since it has a travel crib and high chair. You can bake cookies on the baking sheets of the full kitchen if you are craving some. The sunkissed patio is a great place to soak up the sun and raise a toast to loved ones.
If you are visiting with your fur babies, you can book this pet-friendly property. It welcomes small to medium-sized dogs with a non-refundable fee of 25 USD every night of your stay here.
Top guest reviews
Host:
susi was a wonderful hostsusi is a great hostsusi was an amazing host from start to finishsusi was an excellent host and a quick communicatorgracious host provided thoughtful welcome treatsLocation:
quiet safe neighborhood with easy access to all major roadswe also enjoyed delicious meals at nearby restaurants and shopping at nearby shopsgreat location - close to beaches and towns of madison and guilfordgreat location beautiful surroundings comfortable home with fantastic kitchen space and outdoor areastruly a great place to stay for a couple of days of r&rCleanliness:
very clean and beautifully decoratedthe cottage is spotless and just so warm and comfortablethe house was clean and there were delicious treats waiting for ussusi and skip’s place is comfortable spotless and spaciousthe space was charming and decorated for christmas clean and cozyRead more reviewsAmenities & Room:
a most comfortable cottage in very desirable madison connecticutthe entire ambience was laid back comfortable and chicwonderful kitchen and outdoor patiosuch a nice comfortable stay with a great outdoor spacethere were also groceries for us to enjoy for breakfast
4. Exquisite vacation Airbnb near Hammonasset Beach State Park (from USD 500)
Found in the heart of the city and minutes away from Hammonasset Beach State Park, this exquisite Airbnb features lavish bedrooms. A perfect choice for big families, this can comfortably host 10 guests at any given time.
Guests can wind down in the bathtub and tend to their sore muscles after a tiring day of traveling. You can do your laundry in the washer available in the unit. A spacious wardrobe helps with storage. The living room is equipped with a high-definition TV. You can put your feet up on the cushy sofa and enjoy a Netflix movie night. Guests who love homemade fare can prepare hearty meals in the functional kitchen.
Enjoy bonfire evenings in front of the outdoor fire pit while relishing a nice barbeque made on the charcoal grill. Security cameras are installed on the property for added safety. A first-aid kit is in place for emergencies.
Top guest reviews
Host:
kevin as a host is wonderful accomodating communicativeeasy to contact hostkevin was very communicative helpful and pleasant to work withLocation:
location is perfect for beach access highway and the cute downtown areathe location is perfect within walking distance of great beaches and just a short drive to townlove the walk to the beachgreat location beautiful house big enough for our whole extended familywell appointed and comfortable in a great locationCleanliness:
everything was very clean and as pictured and great access to the beachit’s clean spacious comfortable with well thought out detailsold classic home in beautiful condition and sparkling cleana large historical house made fresh clean and comfortable with everything you could need for a fun relaxing getawaythe house was clean antique but newly and nicely modernized with all the conveniences one would needRead more reviewsAmenities & Room:
the furnishings were nice and comfortablecomfortable plenty of parking and a lovely interior
5. The Barn (from USD 300)
This beautiful Airbnb stands on the old Boston Post Road and is surrounded by historic houses. Only a few meters away from Long Island Sound, The Barn offers modernly furnished rooms inside a free-standing building that resembles a barn.
Guests will have the comfort of a king-sized bed in the bedroom for relaxation and sound sleep. The Airbnb features a lush garden that offers a comfortable spot to read and savor the joys of solitude under the ripe sun. You can also roast a barbeque on the patio grill. If you want to stay indoors and enjoy lazing about, the HDTV and board games provide good entertainment. Guests can bring their pets along with them to this pet-friendly Airbnb home.
Top guest reviews
Host:
the owners are very communicative and helpfulthe hosts are quite nice as wellthey were fantastic hosts and we had everything we neededpeter and vicky are gracious hosts very attentive and responsive; they also provided excellent local recommendationspeter and vicky were amazing hosts would love to visit againLocation:
the neighborhood in excellent for walking running or biking and so close to the soundwhat a cozy and comfortable space great location close to townbeautiful place great location felt comfortable and privatestylish loft close to the beach in a beautiful neighborhoodthis is a unique place in a beautiful neighborhoodCleanliness:
very clean and updatedit’s a very clean and comfortable staystylish comfortable clean and inspiring - it was the perfect perch in madisonit is clean well appointed and is in a great locationyou will not be disappointed the barn was charming private clean and very comfortableRead more reviewsAmenities & Room:
the bedding pillows and bed were so cozy like sleeping on a clouda sweet little kitchen a sitting area lovely windows and views out to neighboring treesi found the bed - fitted with quality cotton sheets - quite comfortable
6. Comfy guesthouse with a grape vineyard (from USD 285)
This two-bedroom guesthouse welcomes you to Madison, Connecticut. One of the closest properties to Hammonasset Beach State Park, this home offers a restful vacation for all travelers who stay. The kitchen is equipped with silverware, a Keurig coffee machine, a stove, a fridge, and an assortment of coffee and teas for your cooking and dining needs.
Each bedroom has a queen-sized bed, and with a wonderful view. There is also a grape vineyard on the property and you are free to pick the grapes if they are ripe as well as a firepit nearby to enjoy the grapes while under the night sky. This property is close to many notable places as it is only 1.5 mi (2.4 km) from downtown Madison and 1 mile (1.6 km) from the beach.
Top guest reviews
Host:
he was a great host with a great homekevin was very responsive and accommodatingkevin was very informative and made it very easy and enjoyablekevin is incredibly communicative and makes sure you're all setfantastic apartment and host our stay was unexpected but we are already looking forward to coming backLocation:
the park was within walking distance on a nice trailvery close to the beach and we hope to come backwalking and riding my bike was a lot of fun and safe hereclose to so many things yet you feel like you're in a quiet home spaceit’s just a skip and a jump from wonderful hammonasett park and close to the town of madisonCleanliness:
it was clean and comfortableit is spotlessly cleanthe house was extremely clean and cozywonderful place very clean bright and invitingthe house is beautifully decorated and cleanRead more reviewsAmenities & Room:
this place was great plenty of natural light in every roomthe apartment is nicely decorated with lots of thoughtful touches
7. Architectural modern guesthouse in Madison (from USD 616)
Designed by an architectural firm STUDIOATE, this modern guesthouse sits on stilts and is located at the back of a 3 acre (1.2 hectares) property with its own driveway and parking. As a well-planned structure, guests can enjoy a user-centred design, besides being undoubtedly pretty to the eyes. The guesthouse has a private bedroom with a king size bed, a modern bath adorned with high-quality fixtures and fittings, and large windows plus a high ceiling. The kitchenette is well equipped and guests can enjoy indoor dining or opt for one outdoors in the property’s gorgeous front deck. This modern masterpiece is not only well designed but is also located in a convenient location, close to the historic towns of picturesque Stony Creek and Guilford, only a short distance to the Westwood hiking trails, and several other beaches, restaurants, and shopping establishments.
Top guest reviews
Host:
they were great hoststhey were incredibly responsive and welcoming: really great hostsgreat place and amazing hostsour host gave us some good recommendations ethe host goes out of their way to make you feel comfortableLocation:
perfect location on connecticut coastthe place is very near guilford with good restaurants and cute shopsit’s close to many great restaurants and hiking trailswhat a lovely lovely bnb the location is simply idealgreat place to relax and get away from the cityCleanliness:
clean and stylish in a beautiful settingvery clean comfortable and easy communication with the hoststhis place is very clean and modern as well as comfortablethis place is beautifully kept impeccably clean and serenely quietthe house looks modern very clean very cozyRead more reviewsAmenities & Room:
the wifi worked very wellthe property is gorgeous and the view from the living room is so relaxingheated bathroom floor was a nice touchwe loved the heated floor (and towel rack ) in the bathroom - such a great touch
8. Quiet, serene escape by the shore (from USD 89)
Are you comfortable, better yet, happy to be living with pets? Then this property is for you! The host has two sweet rescues, which make the experience in this home all the more unforgettable. It is located just a few miles from the beach and although the house rests in a quiet, tranquil, and romantic area in the woods, there are also dreamy restaurants and various activities to enjoy such as kayaking and biking. Guests can expect to have a memorable stay close to the shore and be surrounded by lush greens. Inside is a clean bedroom, complete with a queen bed and two aerobeds. Guests have full access to the house’s first floor including the kitchen, living and dining, and laundry room. For guests bringing in their own cars, there is off street parking. From the property, guests can also explore nearby museums, vineyards, and state parks either by walking or by cycling.
Top guest reviews
Host:
10/17/2018 alisha & family were wonderful hostsalisha was a wonderful hostshe is a perfect host and made us feel at home quicklyalisha was the perfect hostalisha ia a wonderful hostLocation:
great location when you want to be close to the beachit was only an 8-10 minute drive to the resort so the location was perfectvery close to the beach and the accommodations were perfecti would highly recommend alisha's place for a trip to connecticutbeautiful home great location welcoming and hospitable hostsCleanliness:
very clean and nicely decoratedeverything is clean and in ordervery clean comfortable homeit was clean comfortable and cozyit was gorgeous and very clean and comfortableRead more reviewsAmenities & Room:
the amenities were nice (coffee toiletries) and you have a bathroom of your ownthe keurig and toiletries in the room are a nice touchthe snacks and coffee maker in the room were a wonderful bonusthe bedroom was picture-perfect and comfortable bedhaving use of kitchen and living room was especially nice
9. Madison cozy studio (from USD 100)
A cozy Madison studio resting in a private home in the quiet residential neighbourhood of Madison Ct, this property is just 5 minutes’ away from the beach and the Shoreline East train station. The property comfortably sleeps four guests, with one full-size bed and a trundle with two twin beds. There is also an available kitchenette with refrigerator, microwave and coffeemaker. The kitchen trestle table seats four. For a unique outdoor dining, head over to the fire pit where you can enjoy grilling s'mores. The place is nothing fancy but this humble house is just perfect for a small family or an intimate group of friends or business travellers wishing to have a well-deserved retreat or getaway.
Top guest reviews
Host:
our hosts were kind and thoughtfulkevin and mia were wonderful attentive hostsmia and kevin were wonderful hostskevin and mia are super responsive hostskevin and mia were the perfect host and hostessLocation:
the location was greatvery cute place in madisongreat location to madison town beachesclose to the beaches and the most perfect little downtown of madisonvery sweet suite in a perfect location for meCleanliness:
very clean and welcominggreat place clean and thoughtfula lovely setting clean and comfortablethe studio is clean comfortable & private - just as advertisedcozy comfortable clean and convenientRead more reviewsAmenities & Room:
the room was stunningwe are telling all our friends to stay in your cozy cottage in madison ctgreat bathroom and outdoor spacewe really enjoyed staying in your delightfully cozy cottage in madison cteverything was as described for a smooth and comfortable stay
10. Entire home for two guests (from USD 126)
This entire home is only a few minutes’ walk away from a slice of heaven which is none other than the windy Madison beaches! This private accommodation is the perfect temporary nest especially for couples or honeymooners looking for quality time together. A great alternative to hotel room accommodations, this lovely fully furnished house is close to boutique shops, movie theatres, and even a farmer’s market. The bedroom has a queen-sized bed and guests will be able to enjoy a spacious living and dining area, with the addition of a small but ample outdoor seating. One thing to note is that heavy indoor cooking is not possible as the kitchen is only equipped with a light stove and a microwave. However, with many nearby restaurants, you can treat your date to a romantic dine out instead!
Top guest reviews
Host:
hosts were very responsive and helpfuljoanne was the perfect hostjoanne and pat were great hoststhe hosts were great and very responsiveshe was very responsive and accommodated all of our needs before and during our stayLocation:
great location very short walk to a beautiful beachlocation was neat and area was quietbeautiful home great location very relaxingloved the privacy the location & joanne’s attenditiveness to our needslovely house quiet neighborhood short walk to the beachCleanliness:
very clean and nice looking placethis house has all the beachy charm but is updated and impeccably cleanplace very clean and comfortablevery clean and comfortable home in a nice quiet neighborhoodthe house is very clean and modern and spaciousRead more reviewsAmenities & Room:
very clean with updated furnishings and a nice quiet patio area to sit outside and enjoy breakfast and coffeeoutdoor patio tv room open kitchen) and took a nice walk down to the water
11. A charming cottage, steps away from the beach (from USD 130)
Enjoy a perfect escape with your loved ones as you stay at this charming cottage that is only steps away from beautiful Pent Road Beach. Equipped with two bedrooms, the cottage can perfectly accommodate four people. It is beach day every day at this cottage and you can enjoy all the included beach equipment for free, such as the beach chairs and a beach umbrella.
You are also welcome to cook up a tasty meal in the fully equipped kitchen. The deck area comes with a small grill for a barbecue party in the evening. You can also use the outdoor shower to wash away the sand after playing on the beach.
Top guest reviews
Host:
connie was an incredibly gracious host with great local recommendations and we would highly recommend staying heresteph is a terrific hoststephanie was very responsive and always available if need begreat tips from host stephanie and her grandmother for places to eat and things to dostephanie and her grandmother constance were great hosts- super sweet and communicativeLocation:
the location was fantastic we were close to everythingthe location is amazingthe location is perfect close to shops and restaurants but only steps away from the beachloved staying in this cute homey little cottage close to the wateran nice sweet place a 2 minute walk to the beachCleanliness:
very clean and well equippedclean kitchen and bathroom well equippedstephanie and connie's beach cottage was exactly as described clean & cozyhelpful local tips provided and a cute clean beach cottagewe loved staying in this cozy cottage sparkling clean with so many thoughtful touchesRead more reviewsAmenities & Room:
true beach cottage/ cabin feel with modern amenities like wifi cable and well appointed kitchenthe perfect cozy cottage for a quiet fall getawaythe grill was perfect the fireplace cozy and the hot cocoa was the cherry on topit stays very cool in the main bedroom and the living room with the ac onthis cozy cottage was just as advertised or better it included everything needed to make it relaxing and enjoyable
12. Charming farmhouse with a barnyard (from USD 115)
Two bedrooms are available for rent in this unique remodelled 1840’s farmhouse with private quarters. For those looking for a unique but equally rewarding experience, stay in this property and meet the animals! Guests can also enjoy the pond nearby with a paddle boat or simply explore the rural vibes that is the property’s main charm. From the interior, the decors are country and rustic, leaving an authentic impression of being in the countryside. Some nearby attractions include the Historic Town Center, Madison beaches, and the Hammonasset State Park.
Top guest reviews
Host:
she was a hospitable host and very responsive to questionsexcellent host nice little townwonderful stay the host was very accommodatingnathalie was a great hostthe home is gorgeous and nathalie is such a gracious hostLocation:
location was greatclose in location to downtown madison with cute shops and restaurantsa homey farm place with interesting animals and quite close to the beach accessthe old homestead has been renovated very well and located in a quiet areabeautiful farm that's very close to downtown madison and the beachCleanliness:
very clean and spacious facilitiesthe house is very clean and quitethe space was clean and bright - and very quietthe room is very clean and the bed is really comfortableit was a charming house very clean and comfortableRead more reviewsAmenities & Room:
the breakfast made by nathalie on our last day was delicioussuper comfortable quiet and definitely charmingbreakfast the next morning was a treat comfortable bed and immaculatewe had a great breakfast and enjoyed our conversation with nathaliewe had a sweet little room with very large comfortable bed
13. Private woods home near beach park (from USD 69)
This private house is tucked away in a peaceful green forest — like your perfect hideout from all the stresses of the busy city work life! What you’ll get to have as guests in this property is a private room with ensuite bath in a beautiful home at the end of a quiet New England town, close to many private beaches and nearby Whest Wharf. Please take note that the host is living with their friendly dogs, so it’s still safer to stay away from this accommodation if you have pet allergies.
For those who’d be more than happy to live with their pets, you will enjoy a cosy bedroom and the surrounding woods being literally your playground! Breakfast is even included in the room rate so you can save more time from cooking and instead visit other popular Madison Ct attractions.
Top guest reviews
Host:
mary jo and ken were great hostsmary and ken were incredibly gracious hosts so welcoming and warmmary jo and ken are very kind and amazing hosts who made is feel at homemary jo & ken were great hosts - as were their three lovable dogslovely hosts offered us a warm welcomeLocation:
the location is easy to get to and from the downtown area and various beachesif you like pups this is a great place to bebeautiful place in the woods close to the beach and with wonderful hostsa satisfactory room in madison close to the shorewe appreciated the ride from the train station the clean and spacious room and the refreshing breakfastCleanliness:
clean as a whistlelovely clean place to stayhouse was clean and comfortablevery comfortable and very clean room and bathroomthe room/bathroom was clean lovelyRead more reviewsAmenities & Room:
the bed is comfortable and the room has a ceiling fan and air conditioningsoft white linens ceiling fan and fresh air lent to a beautiful nite's sleepbreakfast on the patio was a great way to start the daylovely breakfast part of the staythe house was charming the room was well-provisioned and comfortable
14. Cottage life: stroll to the beach! (from USD 170)
This beach cottage-style accommodation is simply the definition of a perfect beach getaway destination, ideal for graduation parties or family vacations! The cottage has three bedrooms, 1.5 baths with an outdoor shower, and can generously accommodate up to ten guests! The style is quaint and cozy, washed out in grey, cream and turquoise paints and embellishments, all coherently adding up to the overall beachside feel of the property. This beach house is carefully decorated with a gorgeous kitchen complete with bar stools, and where the four bunk beds are located, kids will surely love the fun but functional play of the interior. Furthermore, this property is a safe and secure environment, whilst being only minutes away from the beach!
15. Shoreline apartment (from USD 84)
This one’s a tidy apartment with a large outdoor space perfect for a grill, quick dip in the property’s small pool, and where organic gardens bloom. The location is close to Clinton Crossings, nearby train stations, shoreline attractions, and of course, Madison beaches. The property is furnished with everything that you will find in your own house, including toiletries. There is a second level where a beautiful large deck awaits. Tere is also a hot tub in a private sunroom off the main house, so you can enjoy a well-deserved pampering session. The property can sleep two guests and is also perfect for solo adventurers and business travellers.
Top guest reviews
Host:
emily was a great hostshe was kind and helpfulemily is a very gracious hostemily is very helpful and a great hostemily is a fantastic hostLocation:
great place close to everythinggreat location for the wedding we attendedgreat spot close to townemily's place is very cute and comfortablesuch a great location and peaceful place to stayCleanliness:
super clean comfortable and quietvery clean for the most parta very clean place to stay with everything you needa clean airbnb within easy access of a highwaybeautiful clean worth every pennyRead more reviewsAmenities & Room:
great second level apartment - private entrance large back deck with patio furniture and a beautiful spacequaint apt in lovely settinglighting hot water tv options wifi are all awesomebeautiful little apartment with a great outdoor deckwe were able to utilize the kitchen deck and hot tub and loved every minute of it
16. Shoreline guesthouse
Looking for a place close to the beaches, New Haven, train station, shopping, dining, and entertainment? This shoreline guesthouse is in close proximity to every exciting activity in Madison but also offers ample privacy. The interior is quite standard with a living room, bedroom, kitchen, bath, and dining but what stands out from this property is the lively outdoor ambience. There is even a hot tub available and a semi-private patio for guests to enjoy fresh air and cool ocean breeze. The property accommodates a maximum of four guests and has off street parking for four cars. If you enjoy being outdoors, this property is the best option!
2.79 km (1.8 mi) from Hammonasset Beach State ParkAccommodates: 4
Top guest reviews
Host:
emily was a great hostemily was a gracious hostemily and rob were kind thoughtful hostsemily is a super hostemily is a lovely host who really was helpful with suggestionsLocation:
super close and easy tripexcellent value for the locationgreat central location quiet and comfortablegreat location near tons of beaches shopping and restaurantsthe location was perfect it was close to town but still had that secluded feelingCleanliness:
very clean with comfortable bedsher space is clean and organizedthe house was clean and comfortablethe guest house was very clean and comfortableher place is clean and comfortable decorated wellRead more reviewsAmenities & Room:
we did have a fan in each roomthe cottage is deceivingly large and comfortablespace is larger than the photos show and very comfortable and quietwe loved relaxing on her patio and even took a dip in her dipping poolthe window air conditioner kept the space comfortable during high humidity 90 degree weather
Connect with nature at Madison in Connecticut
For a relaxing and restorative vacation, head to Connecticut in the town of Madison. It’s the perfect town to discover or simply laze away together with family, friends, and loved ones. There’s a whole lot to do including hiking, fine dining, and even sightseeing. Alternatively, you can simply enjoy the solitude of being indoors by staying in a private accommodation that makes you feel totally at home. It’s no denying that once in a while, we need retreats like this in order to regain a work-life balance and thus achieving a healthier lifestyle. The friendly and charming neighbourhood of Madison is easy to fall in love with. You may find yourself coming back to this humble coastal town over and over again.
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