Westport, Connecticut is a town that blends traditional looks and culture with a modern zest. Located along the Gold Coast, it’s not only home to plenty of sandy beaches but also green hills and lakes. Historic neighbourhoods such as Saugatuck or Old Hill are teeming with a history that’s just waiting to be explored, while Downtown Westport is lively, with shophouses and restaurants all around. There are so many exciting things to do for every traveller here, be it a peaceful getaway in a farmhouse, an exciting vacation in a studio near the beach or a family trip to spend some time together. Read on to find the top Airbnb vacation rentals in Westport, Connecticut.
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 April 08, 2024.
1. The Benjamin on Franklin (from USD 168)
Experience modern comfort at this cosy rental, featuring two spacious bedrooms, each with a queen bed. Delight in amenities such as a contemporary kitchen, speedy Wifi, Roku TV and essential laundry facilities. You can also take advantage of the on-premises parking facilities for a convenient stay. While here, begin your mornings by stepping outside to a tranquil private garden patio for wonderful views.
Furthermore, the rental’s strategic location ensures easy access to shops, dining and entertainment venues. However, despite its closeness to major routes, the indoor ambiance remains peaceful. For larger gatherings, combined unit rentals are also an option, with prices between 350 USD and 375 USD nightly.
Top guest reviews
Amenities & Room:
comfortable beds with premium linens are the icing on the cakecharmingly restored property very comfortable cheery and well-organizedCleanliness:
very clean and well set-up unither place is lovely clean and well-appointedkarena's place was lovely very clean and comfortablethe place was bright and cleaneverything we needed was in place and it was very cleanHost:
karina was a wonderful hostshe was very responsive and a great hostthe host was incredibly responsive very nice and knowledgeablehost was very responsive and helpful throughout the staykarena was a wonderful host and responded quickly to any questions we hadRead more reviewsLocation:
cute little place with a great locationwe loved the locationthe location was very convenient and safegreat restaurants in walking distanceit was comfortable & close to everything
2. Cosy residence in a peaceful neighbourhood (from USD 385)
Nestled in a serene neighbourhood, this residence offers three well-appointed bedrooms, including a master suite. Modern conveniences such as Wifi, a comprehensive entertainment system and an equipped kitchen ensure a comfortable stay. The property also features a beautifully lit patio for peaceful evenings. Furthermore, a child-friendly garden frequented by deer will be the ideal place to enjoy a barbecue with your family.
For fitness enthusiasts, a private gym with diverse equipment awaits. This home ensures easy access with smart lock check-ins and convenient parking. However, visitors should note the presence of a hypoallergenic Maltipoo on the premises and some areas of the house that are not included with the rental.
Top guest reviews
Amenities & Room:
we found it to be quite comfortable and loved the back patio and yardCleanliness:
clean comfortable cozyHost:
janelle a great host and very responsivewonderful house with special touches by hostjannelle was very responsive and helpfulwe loved the yard janelle was a great host and very communicativeas a first time airbnb renter i totally lucked out with a super host janelle and a fabulous houseRead more reviewsLocation:
great location for exploring westportgreat house in a quiet neighborhood but close to everythingwell appointed and a a good locationthis place was perfect for our family
3. Modern studio atop historic mill (from USD 77)
If you ever wanted to live in a studio apartment that’s sleek and modern yet has historical roots, this is your chance. Located atop a renovated mill, this long-term Airbnb rental in Westport, Connecticut, is bright and beautifully decorated with hardwood floors and plenty of skylights. From the house, you’ll be able to catch views of the Sasco River down below and also hear the streams of water from the nearby waterfall.
For those who need to get some work done during their trip, there’s high-speed Wifi available. There’s even a co-working space downstairs near the mill that all guests have free access to. And after getting that work done, head out to Lighthouse Point, which is 2 miles (3.2 kilometres) away, to catch the sunset.
Top guest reviews
Amenities & Room:
the beds and furniture are really comfortableexceptional studio apartment with great amenities and nice touches like extra towels linens and bottles of waterthe beds and linens are very comfortable - even the sofa bed was comfortablenice set-up with alexa for music etc and everything you need for comfortable staythe furnishings are fun and funky the bed very comfortable and the kitchen had everything i neededCleanliness:
really clean and neatthe apartment was incredibly clean and stylishspotlessly clean well appointed perfectly situatedthe studio is bright clean and spaciousvery clean and host super helpfulHost:
great hoststhe host was very helpful and provided excellent service and attention to detailhost are amazing and very helpfulgerard is the greatest host ever very professional all requests handled and service was amazing the rental was also amazinggerard is a great host and always availableRead more reviewsLocation:
and close to charming downtown fairfieldthe location is convenient and safethe location is great and convenient for whatever you needthe location of perfect and close to anything you might need or wantthis studio apartment is so adorable the location is great because there is trader joe’s and terrain close by
4. Bright and airy studio home (from USD 118)
This pet-friendly Airbnb in Westport, Connecticut, has enough natural lighting to make it bright and airy. With a plethora of windows and skylights, you also get a ton of views of the mill and pond outside. The furniture feels contemporary and was designed to celebrate artists like Van Gogh.
You’ll be surrounded by an endless amount of trees, flowers and animals during your stay. Take a trip down to the pond and the woods nearby and view some of the mallards, egrets or swans in their natural homes.
Top guest reviews
Amenities & Room:
amazing kitchen (bonus- the view from the kitchen was so tranquil) comfortable bedsthe kitchen is a beautiful full working kitchenwe had access to smart tvs during our staythe added beehive work space and conference rooms are great if you have a business meetinggreat property but bathroom smallCleanliness:
it was impeccably clean and also stylishan incredibly clean and delightful placesuper clean and tons of great little detailsi very clean and beautifully decorated place to stayit was so clean we wondered if nobody had ever been there beforeHost:
site staff responsive and professionalsplendid stay excellent hostthe host went above and beyond to make sure our stay was perfectoutstanding host and an amazing spacethis place was wonderful the host was truly amazingRead more reviewsLocation:
the location was great toothe location is superb with direct access to 95 train stations shopping and beacheslocation was wonderful and was within a short drive of all our activitiesthe location was great with easy access to main roads but also some walkable restaurants etcgreat location everything was easy and made our stay so pleasant
5. Cottage with a panoramic view of a relaxing pond (from USD 586)
If you are wondering where to stay in Westport, Connecticut, then look no further! Situated on a private street, this two-storey cottage has three bedrooms and a view to die for. Overlooking Mill Pond, you’ll wake up to and be greeted by the delightful sounds of the aquatic animals and birds roaming the pond. Not to mention the warm, angelic natural light that enters the accommodation through the open kitchen, dining room and living room. Guests can head to the upper deck, which makes a perfect viewing area and relaxing spot.
Aside from the short walk to Mill Pond, you can also walk an extra 0.5 miles (800 metres) and reach Mill Pond Beach, a quiet, tranquil and peaceful spot. If you want more action, head to Compo Beach - a three-minute drive away - for more restaurants and shops to explore.
Top guest reviews
Amenities & Room:
great wifi and televisions with cable channels were much appreciatedthe view is absolutely amazing every amenity you could ask for and enough room for our familyCleanliness:
the place was clean quiet and peacefulsecond lj’s home was sparkling clean extremely well appointed and cozythe house was very clean and had such amazing viewsthe home was spotless exactly as represented and perfectly located for what we wantedHost:
host is very kind and helpfuli highly recommend this home and hostlaurajean was the most wonderful host and responded to messages immediately she made us feel so welcomelaurajean was super helpful and went out of her way to make sure we had the best experiencelaurajean is a fantastic host and her home is truly a special placeRead more reviewsLocation:
excellant location close to everywhere great valuegreat spot close to everything very tranquilthe location is perfect for enjoying all of the best of westportit is a great place to spend a weekendamazing location with fantastic views
6. Redecorated barn near the beach
This guest barn was decorated by the host to ensure the comfiest and most luxurious stays to all travellers. With a bunk bed and a queen-size bed in the loft, it’s perfect for families who want to bring their kids out for a vacation. The accommodation is cosy and warm, and there’s also a garden that’s managed by the owner right outside.
Old Mill Pond Beach is a 10-minute walk away if you want to catch some rays or swim on the beach. Other nearby attractions include Compo Beach, Longshore Golf, shopping spots and restaurants in Downtown Westport.
Westport, Connecticut, United States
1.32 km (0.9 mi) from Sherwood Island State ParkTop guest reviews
Amenities & Room:
a bit cozy to entertain it is the perfect size for sleeping and one's morning coffeethe beds including the bunk beds were some of the most comfortable we've encountered in an airbnbCleanliness:
very private very cozy and very cleanvery clean and the hosts were welcoming and attentiveHost:
ed is a very nice hosthe and buddy were great hostsed was super welcoming and attentiveed and buddy are great hostsed is a great host and very friendlyRead more reviewsLocation:
this is a very well located place a short drive or walk to the beachbeautiful little house in westport walking distance from the closest placethe barn is wonderful and it's location is top notchjust a 10 min walk to the beach it's the perfect getawayed’s place is great and we loved being so close to the beach
7. Charming farmhouse for large groups
This farmhouse accommodation looks like something straight out of a movie. With an antique look and charming feel to it, the white-painted exterior makes it very welcoming for guests. Moreover, the space can be modified to have up to four bedrooms for seven guests, making it the perfect house for big families or large groups of friends.
Better yet, the beach is only a mile (1.6 kilometres) away, meaning that you can get some fun in the sun at your convenience. If you want to head out on a longer trip, it only takes an hour to get to New York City.
Westport, Connecticut, United States
3.82 km (2.4 mi) from Sherwood Island State ParkTop guest reviews
Amenities & Room:
wifi speed was good in all parts of the placethe place was clean and comfortable with wonderful amenities including coffeecomfortable a little tight for two couples but it worked out wellthe beds and sofa are very comfortable the feeling in the home is warm and invitingCleanliness:
ronald's house is clean and charmingfantastic rental in every way cozy stylish and super clean and all for an excellent priceHost:
ron is a wonderful hostshe’s friendly and a good neighborronald was very responsive and accommodating when i asked for the possibility of an early check-inron was a great host: super accommodating excellent communicator and flexibleRead more reviewsLocation:
the location is greatgreat location convenient to everythingproximity to the highway and train station was good and inside you could not hear eitherthis place is a gem great location super comfortable and roomyeasily accessed via i-95 and very close to the train station
8. Beautiful fairytale-like cottage
If you want to experience a fairytale-like stay, choose this old cottage surrounded by trees, grasslands and a flowing river. Walking across a small bridge will bring you to your new home that screams rustic yet charming. On the porch, you can watch all the animals that roam across the spacious land, and in front of the stone fireplace, you and your family can gather together for a peaceful night.
It’ll be hard to leave the tranquillity of this space, but there are still restaurants and a beach nearby if you’d like to. It’s also an hour’s drive to New York City in case you want to visit this bustling metropolis.
Westport, Connecticut, United States
6.02 km (3.8 mi) from Sherwood Island State ParkTop guest reviews
Amenities & Room:
the house had all the little things for a great stay: complete kitchen washer dryer roku extra linens/towelscomfortable beds and furniture helped to make this a very relaxing retreatquiet serene and comfortablebeautiful cute cottage on huge grounds our stay with 2 young kids was magical and super comfortablethe great room and dining area allowed me to host a family lunch comfortablyCleanliness:
beautiful home and very cleannice clean and quietthe house was spotless & super cozyeverything was great super clean spacethe house was sparkling clean and beautifully appointedHost:
steven was very communicative and a trustworthy hoststeven was also super responsive regarding any questions we hadthe hosts were immediately responsive to any issuesthe hosts were all so accommodating and thoughtful even bringing over bagels and treats for ussteven and laurajean were amazing hosts first and foremostRead more reviewsLocation:
located perfectly near downtown westport with shops and restaurantsthis place was an amazing location in a beautiful town near the beach and plenty of great restaurantsclose to a bunch of delicious places to eatbest for getaway from the city and close to supermarketthe location is perfect as it is close to both the merritt and 95
9. Victorian-style farmhouse near villages and beach
This farmhouse is modelled after those in Victorian times, carrying a traditional and classic feel. The furniture is carefully chosen in bright, beige and pastel colours. Combined with the natural lighting from the windows, it makes the entire space feel so much lighter. Not to mention the comfy queen-size bed with fluffy sheets.
Guests can also head to nearby attractions, including Levitt Pavilion, Compo Beach or Saugatuck Village - all within walking distance. You can also explore the massive grounds around the property to enjoy nature and relax.
Westport, Connecticut, United States
2.63 km (1.7 mi) from Sherwood Island State ParkTop guest reviews
Amenities & Room:
the bed and room were comfortable with air conditioning availablethe room itself is lovely and full of natural light impeccably cleanthe room was private and comfortablewe had a great comfortable set up and had a lot of privacywe both immediately felt comfortable and warmly welcomedCleanliness:
clean and perfect hospitalitythe space was clean comfortable and a solid place to staythe bathroom was bright and clean with higher-end products and soft towelsthe room itself is spacious and clean and the bed is comfortable— i slept so wellthe room and the bathroom are very clean and comfortable i had a very nice and restful time thereHost:
she was easy to communicate with thoughtful and kindchristine is a great host she's quick at responding very accommodating and made us feel right at homechristine was an excellent host and made my stay at her rambling victorian westport home very enjoyablethe room is great and christine is a courteous hostchristine is a delightful host and the space was more than i expectedRead more reviewsLocation:
it's a good location toothey loved the location and quietness after traveling many milesthe location is great as it is near town and the beachwe really enjoyed our stay at christine's placewe absolutely enjoyed our stay at christine’s place
10. Peaceful studio with meditative grounds
This accommodation was built all the way back in 1806, over two centuries ago. But don’t let the age fool you because it has been renovated and furnished with the latest furniture and gadgets. The bathroom is fully equipped with a bathtub and a shower. The kitchen has a microwave, a fridge and a coffeemaker for you to whip up some meals. Surrounding the house itself are unique art pieces that will definitely intrigue you.
For a more peaceful and tranquil getaway, the meditative grounds are right next to you. Find some zen at the copper beech tree that’s 300 years old, or at the ponds, gardens and sculptures nearby.
Westport, Connecticut, United States
6.44 km (4.1 mi) from Sherwood Island State ParkSuperhost
Accommodates: 2
Top guest reviews
Amenities & Room:
good size room with bed and couch areacheck in/out was easy the studio was very stylish and the mattress was especially comfortablethe bed--that memory foam mattress---was the best i will stop again when i am in the areathe adaptation to an innovative/limited “kitchen” was a challenge but never any difficultywe had a wonderful stay at the studio the room was charming and cozyCleanliness:
everything was very cleanthe room was clean and comfortableit is also very clean and well-decoratedit is clean quiet private and so comfortablethoughtful details were left throughout studio and place was very cleanHost:
jeanine & frederic were wonderful hostsgracious host and lovely settingfrederic and jeanine are wonderful hosts attentive to every detail and very responsivejeanine and frederic are wonderful hostsa lovely stay the perfect hostsRead more reviewsLocation:
cute place perfect location for usgreat location with easy access to surrounding town and train stationgood location if you are traveling around fairfield countyalthough close to attractions restaurants and shopping the property is a quiet retreatit was close to downtown westport and far enough away that it felt like a retreat
11. Newly renovated cottage
This house is aptly called Cottage 1790 and was renovated to reflect how traditional houses of the 18th century looked. You’ll get a mixture of traditional and modern, with a rustic fireplace as well as a comfortable queen-size bed. The kitchen is fully equipped with pots, pans, a fridge and even a dishwasher, while the garden outside contains a large barbeque grill and a terrace.
The house is also centrally located, being 50 minutes away from New York City, 20 minutes away from the town of Yale and is also very close to the sea.
Westport, Connecticut, United States
6.82 km (4.3 mi) from Sherwood Island State ParkAccommodates: 5
Top guest reviews
Amenities & Room:
the three of us were very comfortable with ample space and enzo & jennifer were great hostsCleanliness:
hospitable hosts clean and comfortable houseHost:
host provided quick and courteous responsesgreat place and great hostlorenzo was an amazing host to our friendslorenzo was the perfect host and was very quick with responding to my questionslorenzo is an awesome host and we would highly recommended his place to othersRead more reviewsLocation:
lorenzo’s place is super comfortable and close to everythingreally enjoyed the location and the spacegreat location easy access to merrit parkway local stores and amenities
12. Conveniently located home with a garden patio
Make yourself at home with this accommodation that has very welcoming vibes. From the outside, it may not look like much, but on the inside, it is equipped with anything a traveller might need on their stay. The kitchen area is clean and has a stove so you can do all your cooking and a fridge to store food in. The living room has a comfy sofa, only rivalled by the fluffy bed in the bedroom. The outside patio is the best place for you to catch some fresh air.
Situated away from the train station by a 15-minute walk, this accommodation is an affordable choice to connect yourself with the city around you.
Westport, Connecticut, United States
3.31 km (2.1 mi) from Sherwood Island State ParkAccommodates: 1
Top guest reviews
Amenities & Room:
nice comfortable place to stayCleanliness:
if that doesn't bother you the room is otherwise clean comfortable quiet and the host very pleasantHost:
janette was a great hosthumble nice and kind hostgreat experience host makes an effort to make you feel like you have the place to yourselfjanette is very welcoming and friendlyRead more reviewsLocation:
nice quiet room walking distance to lots of stores bus trainthe house is in a safe locationgreat access to shops and restaurants nearby
Plan your next trip to Westport, Connecticut now
With sandy shores, peaceful grasslands and tranquil rivers and lakes, Westport is the perfect town for any sort of traveller. Whether you’re with your family, friends or significant other, there’s plenty to enjoy in this small town on the coast of the United States. From barns and farmhouses to Victorian-era studios and cosy apartments, use this list to find the best Airbnb vacation rentals in Westport, Connecticut!
When in Westport, make sure to explore the nearby areas for a wholesome experience. You can even make a pit stop in one of the hotels near Westport, Connecticut, or Airbnb vacation rentals in Bridgeport, Easton, and other surrounding towns and cities, as well, if you want to truly imbibe the local lifestyle.
Frequently asked questions about Airbnb vacation rentals in Westport
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