If you have plans of staying in Massachusetts for quite some time, then you should consider staying in a house in this oceanside neighborhood of Winthrop. Since it’s located near a harbor, you’ll get to see wonderful views of the skyline. Not to mention, it’s easy to head to the nearest beach where you can play with the sand or go for a swim. The close proximity to the majestic waters gives the place a serene atmosphere, along with the calming ocean breeze. Additionally, public transportation in Winthrop is convenient, for those who want to branch out to other places such as Boston. Luckily, we have provided you with possible homes in the area. Go through this list of the top Airbnb vacation rentals in Winthrop, Massachusetts.
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 09, 2024.
1. Chic studio apartment with a garden (from USD 123)
This apartment is the perfect resting place for the weekend. Come inside through the private entryway and you’ll be greeted by the sight of the stylish and spotless living room. There’s a window that overlooks the backyard and allows an ample amount of sunlight to brighten the room. You can also get some Vitamin D while lounging in the garden. Take beautiful pictures of the pond or simply just watch it for some peace of mind. If you’re planning to stay for more than just a few days, you’ll be allowed to have access to laundry facilities. Since it’s located 10 minutes from the airport, this is the ideal place to come home to after a long and tiring flight.
Top guest reviews
Amenities & Room:
beautiful little studio with a beyond comfy bednice hosts providing cozy room with free snacks and drinks and introduction of sightseeings and restaurants in winthropit is extremely well put together and beyond comfortableCleanliness:
this place was clean and comfortablevery clean comfortable convenient private great placeclean as always love it thereclean well finished comfortable bedroom was very clean quiet and comfortableHost:
the host was amazing and top level serviceshost was friendly and answered promptlynice place with great hostsvery welcoming and responsive hostgreat attention from hostsRead more reviewsLocation:
super close to the airportsuper close to the beachgreat location for airport travel or boston visitsvery accommodating - great location with easy access to airport and downtownalso a fantastic location
Superhost
2. Modern bungalow near the beach (from USD 110)
Go on a relaxing vacation in this seaside bungalow. Start your day by waking up on a soft queen-size bed covered by high-quality linens. Make a cup of coffee and drink it while watching the television. However, the highlight of this lodging is the parks and beaches located a few steps away. Enjoy the sand and the sea whenever you want, and watch the sunset on the horizon.
Top guest reviews
Amenities & Room:
very clean room with the amenities i neededcomfortable and clean with many amenities and thoughtful touchesthe room was very clean and the space was utilized well with appliances and amenitiesthe bed was extremely comfortable and added to the overall homey feel of the roomCleanliness:
clean and cozy spaceexceptionally clean and well-presentedvery clean and comfortableplace was really clean and comfortablethe room was clean cozy and beautifulHost:
these hosts were super accommodatingwould recommend great hoststhank you so much for being amazing hosts john and arturo) hosts are quick to respond and very kindfantastic stay and great hostsRead more reviewsLocation:
location is beautiful and close to the airport toogreat location near the baythe location was ideal for being close to the airport which was only a 20 minute drive awayreally cute and comfortable apartment in such a beautiful locationloved the location and scenery around deer island
3. Grand apartment with luxurious bathroom (from USD 179)
Book this spacious and classy apartment with a couple of your friends for your next getaway. After an exciting day spent swimming at the beach, you can retire to your magnificent home for the weekend. Make the most out of the large bathroom by treating yourself to a nice soak in the bathtub. Try different cuisines at the nearby restaurants or take them home where you can keep it in the refrigerator. If you don’t feel like going to the beach, you can cool yourself in the shared swimming pool. Everything you need for a fun and fulfilling holiday is just a couple of steps away.
Top guest reviews
Amenities & Room:
the place and location were also great the pool and grill were among the great amenitieslocation is amazing and the heated pool was perfect even for a colder nightthe pool was bath water and the neighborhood was so quite it was the best place to relaxfrank & kathy’s apartment was very comfy (i love the big bathtubthis place was great frank and kathy were very helpful and went above and beyond to make us comfortableCleanliness:
house was clean comfy bedsit was a clean placeit was clean and well decoratedit was clean and well decoratedexcellent stay very clean place close walk to ocean and beachHost:
they were amazing hoststhey were amazing hoststhe hosts were so generous and accommodating and kindsuper nice host very comfortablefrankie was a wonderful hostRead more reviewsLocation:
location was very beautifulsuper close to revere beach and very close to the airportnice space at a great locationgreat place nice location; everything exactly as advertisedperfect space for our group of 4 located within walking distance of the beach
4. Tranquil spot with two outdoor porches (from USD 161)
If you’re in need of a breather from your daily routine, you might want to hide in this bright apartment. Relish in the peaceful atmosphere that you won’t find in any busy city streets. There are multiple rooms meant for different activities. Prepare a hearty feast in the kitchen and enjoy them in the dining room. There’s a room with large windows dedicated to those who love feeling the sun on their skin. You can also hang out on the front porch or the back porch. The front porch is the best spot to sit if you want to see the stars at night. Meanwhile, the back porch has a cover, making it a cool spot during rainy days. You can sip on a warm drink while admiring the majestic trees.
Top guest reviews
Amenities & Room:
however there is wi-fi and a smart tv with hulu netflix etcthe space was also huge we had tons of roomit has 2 big bedrooms comfortable living areas and a quirky layout with original hardwood floors & featuresthe apartment was super easy to get into and there is off-street parkingthe apartment is a second floor rental and is very welcomingCleanliness:
clean luxurious linens and toiletriesthe apartment was spotless and extremely invitingthe place was so clean and beautifulfrank's house is extremely clean and quietgreat place to stay at very clean and very spaciousHost:
super attentive host with quick response timesthe host is outstanding makes you feel like homefrankie the host was very responsive and a great helpthanks franckie great hostamazing place and wonderful hostRead more reviewsLocation:
perfect location to bostongreat location for bostongreat place close to the citycozy apartment in great location and virtually no hustle bustleeasy check in great location would stay here again
5. Oceanfront sanctuary with pool (from USD 239)
Summer may be all fun and games but sometimes, the heat can be too much. When it’s blistering hot outside, you can stay cool inside your private apartment and enjoy the air conditioning. You can also swim in the saltwater pool and refresh yourself while looking at breathtaking ocean views. If you want a closer view of the sunset, head on over to the beach. Stay in this delightful summer vacation home and you’re guaranteed to have a refreshing experience.
Top guest reviews
Amenities & Room:
there’s a full kitchen a grille and fun patio furniture toofantastic apartment with lovely pool and beach viewsthe patio and the pool was great to relax insetting - wake up to the waves amazing ocean view beach access and pool at the housewe really enjoyed the pool and ocean viewCleanliness:
everything was clean and comfortable and a lot of personal touchesthe apartment was sparkling clean and exactly as advertisedeverything was exceptionally clean and readily available to usthe towels and hot shower were fabulous and we appreciated how clean everything wasthe apartment itself was very clean and comfortableHost:
she’s what i call a super hosthosts were so nice and hospitableamazing place and fantastic hoststhey are both super kind people and easy to speak withcarol and john were perfect hostsRead more reviewsLocation:
the location was perfectwonderful location close to transportation into boston (recommended)the location was fantastic a short 9 minute drive right to downtown bostoncarol and john’s place was incredible the location is great easy to get everywherea great place to relax just a minutes walk from the beach
6. Private rental with parking (from USD 172)
Looking for a place where you can spend time with your partner? This newly renovated crib is the one for you. There are tons of attractions you can visit without straying too far away from your lodging. Take a short walk to Yirrell Beach, where you can play with the sand, or go for a surf. Deer Island Park, a park filled with jogging and hiking trails, is just a few minutes away. Treat yourself to dinner at one of the many surrounding restaurants, and finish it off with some ice cream. Once you’re tired, you can head home and have a good night’s sleep on the king-size bed.
Top guest reviews
Amenities & Room:
and the cottage was neat cozy and comfortableCleanliness:
the unit is clean well equipped and beautiful situatedit's very nicely furnished clean and tastefulthe space was clean and bright and the bathroom was well equippedvery clean and well presented and everything operated perfectlythe cottage was immaculately clean the grounds are very well keptHost:
john & nok were wonderful attentive hostsjohn & nok were excellent hosts & easy to communicate withwonderful hosts with a beautiful placejohn & nok's place was amazing and they were wonderful hostsjohn and nok were friendly and helpfulRead more reviewsLocation:
great location when visiting bostongreat location easy access and parkingsuper close walk to the beachnice cozy place in a fun locationand the location at the very tio of winthrop is quite remarkable and unique
7. Heavenly hideaway near the beach (from USD 111)
Escape from the city and hide in this private attic apartment. It has its own living room equipped with a television for your entertainment. However, the best room to relax in is the bedroom. There’s a window on top of the bed where you can peek at the horizon and watch the sky change colors. Despite its rural setting, the apartment is close to a number of public transportation options, including a bus stop. Explore the rest of Winthrop whenever you feel like going outside. Drop by Aquarium Station and go on a boat tour or a shopping spree.
Top guest reviews
Cleanliness:
very clean and cozy spotplace was very cleanclean sheets towels soda and etcthe place was sparkling clean when we walked in and a very comfortable spaceHost:
super friendly host with very fast answers to any questions i had - definitely recommendfrankieshades was a great host who provided great tips on the local areaour host offered helpful tips for the area including a great restauranti would highly recommend this place 100% he was a great host and very responsivehe emailed me an itinerary with all the cool things to do in boston which was helpfulRead more reviewsLocation:
it is pretty close to pictureswonderful location easy to get to boston fromgreat place great location and great valuea value place to stay in a great neighborhoodgreat place great location very spacious for an attic apartment with everything you need and great communication
8. Oceanfront apartment close to Boston (from USD 325)
Just 10 minutes away from the airport is a two-bedroom house waiting for you to come by. It’s located right across the beach, which means you have easy access to the ocean. Warm yourself up in the bathroom. It’s equipped with heated floors and a steam shower, perfect for people who spend the whole day in the water. Use the fully equipped kitchen to make your favorite food and eat it while enjoying an undisturbed view of the skyline.
Top guest reviews
Amenities & Room:
you cannot beat ashley’s place for staying in winthrop (east boston) amazing views and comfortable spacewe didn't use the upstairs bed but the downstairs bed was comfortableCleanliness:
very clean home and a well-stocked kitchenthey have a clean house and are very responsivewonderful house very clean and spaciousHost:
ashley and justin were not just great host but amazinggreat place and wonderful hostsashley and her father were great hostsashely and her father justin were wonderful hosts and very welcomingsuch a handy location and both ashley and justin were fantastic friendly and helpful hostsRead more reviewsLocation:
winthrop is a lovely spot close to the city but feels like a little beach townhighly recommend a visit to rossetti’s italian eatery which was easily within walking distancegreat local italian placelocation what an amazing stayfantastic location and very accommodating host
9. Spacious manor near golf course (from USD 221)
Indulge your family and friends on a healing retreat in this serene house. Hang out in the living room or cook a meal together in the kitchen. Eat your masterpiece in the dining room while sharing stories with one another. Play in the nearby golf course or hop on the nearest train and discover all of Boston’s charms. There are so many things that you can do as a group inside and outside of this home.
Top guest reviews
Amenities & Room:
truly comfortable for large families looking to visit the city of bostonCleanliness:
this is a great place best airbnb we have stayed in clean quite and very comfortablehouse is newly renovated and super cleanher home is newly renovated and everything is sparkling clean and beautifulHost:
emmanuelle was an amazing host from responding quickly to making sure my family was well taken care ofRead more reviewsLocation:
great location with easy access to downtowngreat space great location great communication with host
10. Cozy house with stunning views
You’ll definitely feel like you’re living in a dream-like world once you stay in this historic colonial-style house. Wake up to a vivid view of the morning sky inside your airy bedroom. Drink your morning tea or coffee on the porch while staring into the harbor. Don’t miss out on the chance to ride the Winthrop Ferry and go on a mini-adventure. If you’re looking for a laidback accommodation for the family, then the answer is right here.
Winthrop, Massachusetts, United States
6.55 km (4.1 mi) from New England AquariumTop guest reviews
Amenities & Room:
we had a comfortable stay at ron’s place the house has a spectacular view of the waterit's a small space but my family of 4 adults fit nicely the rollaway beds are surprisingly comfortableoverall great spot in winthrop slightly out of the city with beautiful water view and great walkable breakfast spotCleanliness:
the apartment was clean and as describedthe house is a little bit old but clean and cozyalthough this house is old it is clean and has charm the view is beautiful from the houseHost:
you were a great hosthe was a great hostthe host is good in responding to messagesgreat hosts with thoughtful touchesron and his wife were great hostsRead more reviewsLocation:
easy access to central bostonthe location is very close to the airport and conveniently located near great restaurants as wellnice location quiet area close to the watergreat location for a relaxing private weekendgreat location needs some tlc
The best of both worlds
Why choose between living near the ocean or living near downtown, when you can do both? Start off your mornings admiring the sight of the beautiful ocean while enjoying the light breeze. Then, explore popular attractions and discover various hidden gems in the afternoon. And finally, watch the moon and stars at night while listening to crashing waves. Here at Winthrop, you can live the best of both worlds.
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