House vacation rentals in Wellesley

Find and book unique houses on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for Wellesley house rentals

House rentals with a pool

Guest favorite
A vibrant garden is visible, featuring a variety of colorful flowers, including pink roses and white blooms. A white picket fence lines the path, complemented by lush greenery and tall trees in the background, creating a serene and inviting atmosphere.
Home in North Andover
4.94 out of 5 average rating, 158 reviews

Nana-tucket Inn

SamRating, 5 stars3 weeks ago
We had a great time - beautiful house in a terrific location. Super convenient for Phillips Academy if that's why you're in the area. Nancy was very attentive (and actually lives in an apartment downstairs) so was able to do lots of nice things for us like bake us a coffee cake and make floral centerpieces. Thank you!
Top guest favorite
A private heated pool is surrounded by lush greenery, providing a tranquil setting. Loungers are positioned nearby, and a blue lane divider is visible across the pool. Sunlight reflects off the water, enhancing the serene atmosphere.
Home in Newton
5 out of 5 average rating, 19 reviews

Villa with private Pool in Boston's Elite Enclave

JonRating, 5 stars3 weeks ago
Great option when staying in Newton and right down the street from an incredible entrance to a hiking trail. Serge was a great host and kept us informed the entire trip.
Guest favorite
An outdoor swimming pool is surrounded by a spacious patio and lush greenery. Sun loungers are arranged around the pool, with a shaded seating area nearby. The house features a multi-level deck overlooking the pool, creating a relaxing outdoor space for guests.
Home in Hopkinton
4.95 out of 5 average rating, 155 reviews

Hopkinton Mass 3+ Bedrooms - Great location!

DeanneRating, 5 stars1 week ago
Brad was very friendly and helpful. Beautiful home!
Guest favorite
A clear blue pool reflects the surrounding area, framed by a patio with lounge chairs. A shaded seating area is visible next to the pool, enhancing outdoor relaxation options.
Home in Worcester
4.96 out of 5 average rating, 102 reviews

Courtyard Garden | Pool | BBQ+Fire Tbl | Fireplace

ChristinaRating, 5 stars4 days ago
We were in town for my daughter’s wedding and I was looking for a place that had outdoor space to enjoy and this house did not disappoint. Everything was spectacular! It was lovely to have the pool, we enjoyed our coffee in the morning and wine at night surrounded by peaceful lighting. The kitchen is beautiful (exactly) like the pictures and so many extras. The host who lives downstairs was very helpful and thoughtful. We appreciated all the special touches and look forward to finding a reason to return.
Top guest favorite
The exterior of a two-story house is displayed, featuring white siding and red shutters. A well-maintained front yard is visible, showcasing green grass and shrubs. A brick pathway leads to the front door, framed by two planters with greenery.
Home in Arlington
4.94 out of 5 average rating, 34 reviews

Beautiful Spacious 4BRM House!

NicholasRating, 5 stars2 weeks ago
I loved everything Maxine said and how she helped navigate around every even in the house, everything was so clean, very quite place good for professional working, everything was just beyond, amazing & lovely place you feel right at home with so much space to move around the house. Being free having your privacy. Thank you Maxine 🙏👏🏽
Top guest favorite
An inviting bedroom features wood-paneled ceilings and soft lighting. A spacious bed is situated near a window with light filtering through. A vintage-style chair and a wooden bench add to the room's charm, complemented by a decorative area rug underfoot.
Home in Norwood
4.95 out of 5 average rating, 44 reviews

the house of id; vintage shop, accessible space

JasonRating, 5 stars1 week ago
Super fun and eclectic house! What really made the stay were the owners, they are thoughtful and very responsive, they clearly care a lot about their guests!
Guest favorite
The backyard features a shared pool surrounded by a brick patio, reflecting the greenery of nearby trees. The area is enclosed by a fence, providing a sense of privacy. A wooden bench is visible nearby, offering a spot to relax by the water.
Home in Weston
4.97 out of 5 average rating, 95 reviews

Spacious vacation unit in premium suburban town

LucyRating, 5 stars3 weeks ago
Scott was very easy to communicate with, and he was very nice. They were so thoughtful and even left us a dozen eggs from their backyard chickens! The place was spacious and peaceful. Check in and checkout process was very easy!
Superhost
A welcoming entrance is displayed with a polished brick pathway leading to a well-maintained white house. The front features large black-framed windows and a pair of bold red doors flanked by pots of colorful flowers, complemented by lush green landscaping.
Home in Canton
4.88 out of 5 average rating, 26 reviews

Hidden Gem near Boston w/ Private lake access

MeganRating, 5 stars3 days ago
This property was one of the best airbnbs we have stayed at. Clean and cozy and felt right at home. There was plenty for the kids to do so we didn’t have to limit screen time because they wanted to be enjoying the amenities available! Jody was quick to respond with any/all questions or concerns we had. We would highly recommend to everyone especially those with children!

Weekly house rentals

Guest favorite
A spacious patio is equipped with a round dining table and eight wicker chairs beneath a large blue umbrella. In the background, a grassy area features a wooden playset with slides and swings, surrounded by lush trees.
Home in Wayland
4.95 out of 5 average rating, 93 reviews

Spacious 4 bedroom home with large yard

NicoleRating, 5 stars2 weeks ago
There are not very many AirBandB type places in Wayland, we wanted to stay near family and not have to stay in a hotel. as noted by others, the driveway is short and steep, so have a good parking brake. And the house is close to the road, so in warm weather with windows open there is a lot of traffic noise. The house itself is great. Well appointed with 4 bedrooms and 2 baths for a larger group. Excellent kitchen with a lot of space and the expected appliances. The Keurig machine was appreciated, and the pods that were provided. Nice picnic patio on side of house. We didn't realize the house was divided into 2 rentals (probably our fault for not reading closely), and there were other guests there the whole time, but we never heard any noise; we weren't actually at the house much except to sleep. Great option for the Wayland area!!
Guest favorite
A charming Cape house is depicted, featuring a red brick exterior and a steeper asphalt roof. The inviting front path composed of stone leads to a green door. Lush green grass surrounds the home, and small shrubs frame the entrance, creating a welcoming atmosphere.
Home in West Newton
5 out of 5 average rating, 24 reviews

Entire House: Home Away Home

JenniferRating, 5 stars1 week ago
Great location, great owner, and wonderful stay. We loved walking all around the neighborhood. The screened in porch was lovely. Wonderful backyard. Very nice sheets and towels. Excellent wi-fi and TV. We couldn't have been happier here.
Top guest favorite
The living area features a spacious leather sectional sofa, complemented by vibrant cushions and a textured green throw. A modern television is mounted on the wall, surrounded by large windows that provide ample natural light. A lush plant adds a touch of greenery to the space.
Home in Waltham
4.98 out of 5 average rating, 41 reviews

Large House KingBed European Look near MoodySt 4BR

LoriRating, 5 stars1 week ago
What a great stay! It is a beautiful, spacious and very clean home. It is in a very good location and it is complemented by private parking and an adorable, walkable city within steps. This home is a gorgeous, unique find. A classic that is beautifully renovated into a fun and modern home. It was very comfortable and we really enjoyed our stay. Our host was amazing: very professional and responsive. Not only would I highly recommend staying at Haven, but I look forward to visiting Boston and staying here again!
Top guest favorite
The exterior of a two-level home is depicted, surrounded by lush green lawns and mature trees. A pathway leads to the welcoming entrance, flanked by garden beds featuring various plants. The house features a traditional design with large windows allowing for ample natural light.
Home in Holliston
4.97 out of 5 average rating, 93 reviews

All New Private Country Setting (2 Level-No Share)

PatrickRating, 5 starstoday
This is one of the nicest Airbnbs we've stayed in and we've stay in 182 of them. This home is large, extremely well built with top quality furnishing. It is clean with great quiet HVAC and kitchen supplies. The beds are comfortable and the lighting is quite good. Outdoor seating is great and the home abuts a small forest. It is set back from the highway and road sound is minimal. There were no mosquitoes. The hosts are amazingly friendly and accommodating.
Guest favorite
The exterior of a renovated Victorian house is displayed, featuring a bright red façade with white trim. A welcoming porch with steps leads to the front door. Lush gardens with blooming flowers and well-maintained greenery surround the house, under a clear blue sky.
Home in Newton
4.98 out of 5 average rating, 42 reviews

Victorian fully renovated! T station-Boston 20'!

MitaliRating, 5 stars1 month ago
We arrived on a redeye, exhausted, and our gracious hosts had fresh bagels and coffee waiting for us. The circa 1880s home is so thoughtfully appointed and lovingly renovated that it provides a great sense of place in and historical connection to the Boston area along with all the modern conveniences. I’d stay here again in a heartbeat.
Top guest favorite
A spacious living area is presented with soft beige walls and a wooden floor. A light gray sectional sofa and a cozy armchair are arranged around a coffee table. A wall-mounted TV is positioned across from the seating, with art pieces enhancing the ambiance. Natural light floods in through two windows.
Home in Framingham
4.78 out of 5 average rating, 18 reviews

Very nice home close to Boston

ViktorRating, 5 stars1 week ago
Host was quick to respond and made sure to clearly communicate at all times. Very friendly and checked in over the phone to make sure there were no problems, we had a great stay.
Guest favorite
The exterior of a two-family house features a welcoming front porch with wooden beams. Gray stone steps lead to two separate entries, framed by black railings. Lush greenery and flower beds line the walkway, while a manicured lawn enhances the inviting curb appeal.
Home in Roslindale
5 out of 5 average rating, 14 reviews

New modern cozy 3BR condo: free parking&near train

LeighRating, 5 stars1 week ago
This is a great place in a quiet and extremely walkable neighborhood. We especially appreciated the private, off-street parking. I’d definitely stay here again!
Top guest favorite
A serene view of the clear lake is framed by bare trees and gentle foliage, reflecting the blue sky above. The calm water creates a peaceful atmosphere, inviting relaxation and tranquility.
Home in Framingham
5 out of 5 average rating, 57 reviews

Lake Cochituate Waterfront Home

BehruzRating, 5 stars1 week ago
The place was fantastic. The location and view are great. The host was proactive and responsive. My family and I would choose this place again.

Private house rentals

Superhost
The exterior of a charming, two-car garage is showcased, featuring natural stone and a shingle roof. Wooden double doors with decorative hardware are visible, along with a basketball hoop attached to the side. The surrounding landscape includes lush green grass and trees.
Home in Westwood
4.83 out of 5 average rating, 86 reviews

sweet little house

WillRating, 5 stars2 months ago
This is a cute ADU within walking distance to the Route 128 station. The unit is very spacious and reasonably priced. Wuke graciously helped us out when we needed laundry detergent. We would stay here again. Only downside is that the ADU has a bit of an unfinished feel. The shower did not have a curtain, the bedroom skylight window was papered over, and there was command-strip residue leftover in a few places.
Guest favorite
The exterior of a charming log cabin retreat is displayed, featuring a welcoming porch with seating, surrounded by lush greenery. Warm light glows from the windows, highlighting the rustic stone chimney and sloped roof. A spacious driveway leads to the cabin, adding to its inviting presence.
Home in Westminster
4.96 out of 5 average rating, 72 reviews

Our Pondside Cabin

RoseRating, 5 stars3 days ago
A lovely home for a group of 9! Beautiful area and just what we needed for a weekend trip.
Guest favorite
The kitchenette features wooden cabinets and a granite countertop, equipped with a sink, stove, microwave, and coffee maker. A small dining table is set with green plates and utensils. Bright lighting illuminates the space, enhancing functionality.
Home in Stoneham
4.94 out of 5 average rating, 54 reviews

Explore Stoneham

PeterRating, 5 stars6 months ago
Stayed here for 10 days in late November. My mom was transitioning from the hospital to rehab and then to her home. I worked all day everyday getting her place ready. John's Place came to be known as My Sanctuary at the end of the day. Very comfortable and very quiet. And John is a very nice, accommodating, compassionate guy. He asked about my mom everyday. I will definitely stay here for my next trip to the Boston area. Thanks for everything, John!
Guest favorite
The charming exterior of the 1897 home features a wraparound porch adorned with flags and seasonal decorations. A well-maintained yard displays decorative stone borders, mulch, and blooming flowers, framed by lush green trees and shrubs.
Home in Sudbury
4.93 out of 5 average rating, 57 reviews

Historic Victorian Home - Family + Pet Friendly

AlyssaRating, 5 stars3 weeks ago
Matthew's place was a great spot for our big group. Excellent value for the price. Easy communication and clear instructions. We would definitely stay here again!
Superhost
The spacious dining area features a wooden table with seating for six, surrounded by comfortable chairs. A bright blue couch adds a pop of color, while warm wood paneling lines the walls. Light filters through diamond-shaped windows, enhancing the inviting ambiance.
Home in Jamaica Plain
5 out of 5 average rating, 15 reviews

Brookline Carriage House, Longwood, Fresh Eggs!

WilliamRating, 5 stars3 weeks ago
Beautiful house in a beautiful neighborhood. We loved staying here!
Guest favorite
The dining area features a round glass table surrounded by five upholstered chairs, positioned beneath a decorative light fixture. A spacious kitchen bar with four stools is visible in the background, complemented by large windows allowing natural light to fill the space.
Home in Roslindale
4.99 out of 5 average rating, 77 reviews

Upscale Boston 2 BR w/ Off Street Parking

MariaRating, 5 stars4 days ago
Great place! Spotless- everything you can possibly need including cooking oils and various kitchen gadgets. The location is within 15-20 minutes of most places. Great to have parking right there by the house also. Tim is a great communicator. Thanks for a comfortable stay!
Top guest favorite
The bedroom features a wooden bed with a light-colored blanket. A small bedside lamp emits soft light next to the bed, while a tall black dresser stands against the opposite wall. Natural light brightens the space through a nearby window.
Home in Cambridge
5 out of 5 average rating, 53 reviews

Pvt Bedrm/Bathrm/Kitch'ette on Quiet Tree Lined St

ChristaRating, 5 stars3 days ago
Beautiful space in a beautiful neighborhood! Close to local restaurants and shops, but the noise of those spaces didn’t affect sleep.
Top guest favorite
A small home is situated within a green yard, featuring a covered porch and multiple windows. Lush foliage surrounds the property, and a barbecue grill is placed on the porch. Distinct garden beds are visible, complementing the spacious lawn.
Home in Framingham
4.95 out of 5 average rating, 21 reviews

Quaint neighborhood near Boston!

ShaylaRating, 5 stars2 weeks ago
Marcia’s place was great! This is our second time staying with her and it’s so convenient. Everything we needed, Marcia is so quick to respond and helpful.

Quick stats about house rentals in Wellesley

  • Total rentals

    40 properties

  • Total number of reviews

    2K reviews

  • Family-friendly rentals

    10 properties are a good fit for families

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    40 properties include access to wifi

  • Popular amenities

    Kitchen, Wifi, and Pool

Destinations to explore