Rated as one of the best places where you can live thanks to its quiet and secured neighborhood and welcoming locals, Winchester is a sublime town located in the suburb of downtown Boston. One interesting fact about this place is that it used to be dubbed as the ‘Black Horse Village’ for its bustling tavern. Today, it has become a thriving ‘bedroom’ community for out-of-towners who come here to stay for work, which is why visitors will likely meet people from different regions of the state. This charming town is lauded for its boatload of ponds and meandering rivers. Getting to Winchester is pretty easy. Simply head to the Lowell Commuter Rail Line out of North Station and you will stop at Winchester Center and Wedgemere. If you’re planning to visit this town, then do check out our list of the best Airbnb vacation rentals in Winchester, 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. Modern one-bedroom apartment near a lake (from USD 135)
Conveniently located close to downtown Winchester and universities, this modern one-bedroom apartment is ideal for couples planning to stay for a few days in Winchester. The property is immaculately set and has a snug bedroom decked with a vintage touch, a fully equipped kitchen, and a living room. It is located in a serene area on a tree-lined street not far from a beautiful lake inhabited by gorgeous swans.
Top guest reviews
Amenities & Room:
cozy place with a full kitchen large closet and nice bathroommany thoughtful touches throughout from the ceiling fans to the keurig with coffee podsexcellent and spacious apartment with full kitchen private entrance and full bathi stayed in the "harry potter" bedroom under the stairs and it was super cozynicely appointed with a beautiful bathroomCleanliness:
beautiful and extremely clean cute placethe apartment is carefully prepared and and cleanedwhole place sparkling cleanthe place itself is clean cozy and very well appointedthe apartment is clean and comfortable with every space usefulHost:
extremely cozy and the owners were very responsivehosts were super responsive- would certainly recommend to anyonegreat place nice hosts that were very tolerant of my two cheeky children’s and myselfthis was our second stay in this great apartment and donna and gary are very caring and responsive hoststhe lodging couldn't be more comfortable and hosts more welcoming and helpfulRead more reviewsLocation:
location was amazing quiet but close to everythinggreat place in an awesome location for a great pricewonderful location walking distance to main street in a charming and safe neighborhoodwe loved this cozy perfectly located space with easy walking distance to the center of town it was perfectgood place to stay if you want to be close to town
2. Deluxe two-bedroom apartment
Located close to downtown Winchester, this deluxe apartment is ideal for people looking for two bedrooms, a fully equipped kitchen, and a comfortable office desk. Some of its best amenities include a washing machine, a wardrobe, kitchenwares and cupboards, and a free parking area. Enjoy the coziness of your bedroom and feel the smoothness of the bed linens. If facilities such as restaurants, transportation, and cafes are what you’re looking for, then this accommodation is located within close proximity to those places.
Winchester, Massachusetts, United States
2.66 km (1.7 mi) from Middlesex Fells ReservationAccommodates: 2
Top guest reviews
Host:
darcy and julio are some of the best hosts anyone could ask forthey are very kind warm and welcomingRead more reviewsLocation:
the train station is just a 3 minute drive from their house and parking there is very easy
3. Luxury apartment close to facilities (from USD 125)
Are you looking for a luxurious one-bedroom apartment close to facilities such as cafes, restaurants, and shops? Then this place is just for you. Located in downtown Winchester, this property is styled in opulent interior decor. It has a plush bedroom, a living room equipped with upholstered sofas where you can relax, and an immaculate bathroom fitted with bathing amenities. There is also a modern kitchen outfitted with kitchenware and cupboards for guests’ use.
Top guest reviews
Amenities & Room:
there is plenty of natural light in the kitchen and living spacethe apartment is immaculate and very well equipped with a complete kitchengreat place with what seemed the most comfortable bed/pillow selection everthe bed is very comfortable and bedroom has a black out shade so controlling morning light is easyCleanliness:
suzanne's place is just as advertised modern and cleanplace was sparkling cleanthe apartment was clean and exactly what we were looking foreverything was new and very cleanthe listing is very accurate and the place was very cleanHost:
she was a wonderful host and even let us take our time checking out the last morningthis is a lovely apartment with an excellent hostthoughtful host charming and modern lodgingssuzanne was a great host and genuinely concerned that her guests have a good visitsuzanne was also super responsive to any inquiry i had and was a thoughtful hostRead more reviewsLocation:
great location just outside of bostonsuch a great locationthe area is quiet and cutevery friendly host thanks so much for the stay super close to supermarket and restaurantssuzanne's place was cute and wonderful she made us feel welcome and comfortable
4. Convenient one-bedroom apartment
This convenient one-bedroom apartment is ideally located within close proximity to a commuter rail and downtown Winchester. The accommodation is perfect for those seeking an affordable and decent place where they can bed down for a few days. The place is equipped with a small bedroom, a clean bathroom, and essential amenities such as a washing machine and a free parking lot. If you’re looking for tranquility and some excellent amenities, then this might just be your kind of place. One guest will be staying in a bedroom that comes with hot water and internet access.
Winchester, Massachusetts, United States
3.52 km (2.2 mi) from Middlesex Fells ReservationAccommodates: 1
Top guest reviews
Cleanliness:
room was very clean and comfortableclean cozy every need is metnice people very clean good locationeverything was relatively clean and wei's wife was very nice in all interactionsHost:
wei is a great hostwei responded fast and was a great hostthe hosts are friendly and accommodating and i loved their pet fish oscargreat place to stay wei was a fantastic hostthe hosts are humble and caring no negatives at allRead more reviewsLocation:
great place close to workgreat location in winchester centerthe sushi place downstairs is greatit’s a decent place in a nice communitya wonderful place to stay
5. Decent one-bedroom apartment with facilities
Located not far from the downtown area and universities, this decent one-bedroom apartment is packed with facilities such as sleek furniture, a parking area, complimentary internet access, heated water, and a cozy bed. The property is suited for those looking for a convenient place at an affordable price. Unwind over a glass of wine and let go of the fatigue from traveling by basking in the comfort of your apartment.
Winchester, Massachusetts, United States
3.54 km (2.2 mi) from Middlesex Fells ReservationAccommodates: 2
Top guest reviews
Amenities & Room:
excellent host it can be a bit hot in the room but there is an acCleanliness:
the room bathroom were cleanHost:
hosts are friendly and kindwei and his family were kind and courteouswei was responsive and friendlywei was kind enough to carry my bag upstairs for meRead more reviewsLocation:
very clean that coupled with close proximity to public transportation makes this the ideal place to stay ata good place to stay
Nearby options
6. Lakeside cottage with hot tub (from USD 115)
Find your blissful sanctuary at this lakeside cottage that comes with excellent amenities to make your stay as comfortable as possible. Some of the top-notch amenities here include a hot tub, an outdoor shower, a gorgeous patio, a pathway leading to the lake, and an outdoor dining area. What makes this place stand out from others is its sublime location. Here, you can rejuvenate by simply basking in the incredible view of the lake. During the summer season, you can swim and kayak for a refreshing vacation.
Top guest reviews
Amenities & Room:
the lakeside apartment has the most amazing view especially at sunset and sunrisebeautiful quiet and serene apartmentcomfortable clean and a beautiful view of the lakethe apt is charming comfortable & very private the setting is beautifulthe living area was very clean cozy and furnished with all the amenities you could wantCleanliness:
everything was clean and the apartment was comfortableapartment was clean well decorated with special touchesthe apartment is beautiful clean and well equippedthe place itself is beautiful clean and invitingvery cozy spacious and cleanHost:
the gracious hosts are wonderfulthe hosts are beyond accommodating and just lovely peoplehosts were wonderfuldouglas was a great hostwe will certainly be back thank you to the great hostsRead more reviewsLocation:
this location location location is just wonderfulthe location is just amazingit's a gorgeous locationnice location right on the waterpeaceful quiet location with everything you need
Superhost
7. Luxurious two-bedroom apartment with amenities (from USD 63)
Discerning guests will enjoy staying at this luxurious two-bedroom apartment that comes with some of the best amenities. Located close to Highway 93, the property can accommodate up to four guests in its spacious interior. There are two premium bedrooms with comfortable beds. There is also a fully equipped kitchen consisting of kitchenware and basic cooking ingredients such as oil, salt, and pepper. Other amenities guests can make use of are the common bathroom and the living area decked out with plush sofas and a smart TV with a Roku. Additionally, those who need to tend to their work can make use of an office desk and a comfortable chair in one of the bedrooms.
Top guest reviews
Amenities & Room:
fantastic apartment completely accurate description of staythe beds were comfortable with lots of blanketsthe living area gives plenty of room to stretch out and there's a nice view to the gardenCleanliness:
spacious and extremely cleangalya's place was amazing very clean bigger then i thoughtclean comfortable and quiet just outside of the cityvery clean the space is perfect for four peoplegalya’s apartment is wonderful very clean spacious and comfortableHost:
the host is super nicegreat place and great hostamazing place and super hostshe is one great host fast responses and also checked up on us incase we needed anythinggalya is quick to responds and was helpful she was a great hostRead more reviewsLocation:
the location was very safenice neighborhood to walk toothe location was great as well if we return to the area we would definitely stay there againnot far from the north end and has a few great restaurants and coffee shop right in stoneham
8. Swanky one-bedroom apartment with a backyard (from USD 124)
Located in a quiet area of the Woburn neighborhood, this swanky one-bedroom apartment is perfect for a couple or a solo traveler looking for a luxurious setting where they can bed down. The property is made up of a premium bedroom and a well-equipped kitchen kitted out with some of the best amenities such as a stove, an oven, a microwave, a refrigerator, a freezer, and a toaster oven. Not to mention, there is a soaking tub in the bathroom. One of its key features is the gorgeous backyard area which is an ideal spot for relaxing.
Top guest reviews
Amenities & Room:
full kitchen was appreciatedthe bed was one of the most comfortable beds i have ever slept inCleanliness:
place was clean and the backyard was beautifulthe place was extremely clean and well equippedthe house was immaculately clean quiet safe and warmit was very clean and spacious even better than we'd expectedchildren friendly very comfterble very clean i would go back againHost:
greg is an amazing hostgreg was a wonderful hostgreg was an amazing hostgreg was also very responsive to questionsamazing greg is so helpful and his home is beautifulRead more reviewsLocation:
the location is ideal for an easy and quick commute to the city centerbeautiful place in a great neighborhoodthis is a great location with easy access (no steps)the house is located within a very safe community and is very quiet and privateextremely comfortable with great location and amenities
9. Snug one-bedroom apartment in Arlington (from USD 120)
Located in the quiet neighborhood of Arlington is this snug one-bedroom apartment that consists of a pastel-colored bedroom, a convenient kitchen equipped with essential amenities such as a toaster oven, a rice maker, and a microwave, and a comfortable living room kitted out with a queen sofa bed. Spend your time in the living area watching Netflix or stroll around the neighborhood.
Top guest reviews
Amenities & Room:
the wifi is greatwonderful apartment with wonderful amenities and furnishingdanielle was super helpful and prepared the sofa bed ahead of timevery comfortable bed complete kitchencomfortable modern apt with plenty of room and amenitiesCleanliness:
very clean and thoughtfulthe apartment was clean and newvery nice clean and cozy placeapartment was clean and well equippeddanielle's appartment was perfectly clean and very comfortableHost:
the hosts are lovely caring people and are very helpfuldanielle is a great host she made us feel like homedanielle was a great host and very responsivedanielle is a great host with a greater placethe host danielle was very communicative and gave us some great tips on boston public transportation and parkingRead more reviewsLocation:
location was great; 10 minute drive to subway station to get downtowna gorgeous neighborhood close to cambridgevery good location about 30 minutes drive to boston citygreat place and great locationclose and easy parking is available
10. Lavish studio apartment in Arlington (from USD 90)
Conveniently located close to downtown Arlington, this luxurious studio apartment is meant for discerning guests looking to stay near Winchester for some days. The property is equipped with a snug bedroom and has amenities such as a sofa bed, a fully stocked kitchen with kitchenware and electronic appliances, a private patio, a parking space, and a large deck.
Top guest reviews
Amenities & Room:
basic amenities like kitchen and bathroom stuff are availablethe place had amenities kitchen work place comfortable (website hidden by airbnb) really cleanCleanliness:
very clean and well suppliednice clean place nice neighborhoodresponsive clean and everything we neededthe apartment was clean and coolvery clean and with great peopleHost:
the hosts were very responsive to all of my concerns and made sure i felt comfortable herethey were wonderful hosts and they were easy to contact if we needed anythinggreat host place and surrounding community - recommended to professionalshosts were helpful and gave us everything we needed during our staycaroline and franck are excellent hosts that went above and beyond to make sure my stay went wellRead more reviewsLocation:
the house is really close to a park and the neighborhood is safegreat stay close to boston - would stay here againher place basement apartment is very nice in a great area very close to the cityvery well located and close to the route 2 that will bring you everywhere from boston to the suburbsits clean everything you need is close also its close to the train station like 10 mins away
Stay at the charming Winchester
Stay at the charming Winchester, which is known for its gorgeous ponds, meandering rivers, and thriving out-of-towners community. It is an ideal place for those seeking to have a small meeting with family, friends, or business associates. So, book one of the best accommodations in this quaint town for comfort and convenience.
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