
House vacation rentals in Wellesley
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Top-rated house rentals in Wellesley
Guests agree: these houses are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Wellesley house rentals
House rentals with a pool

Nana-tucket Inn
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!

Villa with private Pool in Boston's Elite Enclave
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.

Hopkinton Mass 3+ Bedrooms - Great location!
Brad was very friendly and helpful. Beautiful home!

Courtyard Garden | Pool | BBQ+Fire Tbl | Fireplace
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.

Beautiful Spacious 4BRM House!
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 🙏👏🏽

the house of id; vintage shop, accessible space
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!

Spacious vacation unit in premium suburban town
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!

Hidden Gem near Boston w/ Private lake access
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

Spacious 4 bedroom home with large yard
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!!

Entire House: Home Away Home
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.

Large House KingBed European Look near MoodySt 4BR
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!

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

Victorian fully renovated! T station-Boston 20'!
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.

Very nice home close to Boston
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.

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

Lake Cochituate Waterfront Home
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

sweet little house
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.

Our Pondside Cabin
A lovely home for a group of 9! Beautiful area and just what we needed for a weekend trip.

Explore Stoneham
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!

Historic Victorian Home - Family + Pet Friendly
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!

Brookline Carriage House, Longwood, Fresh Eggs!
Beautiful house in a beautiful neighborhood. We loved staying here!

Upscale Boston 2 BR w/ Off Street Parking
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!

Pvt Bedrm/Bathrm/Kitch'ette on Quiet Tree Lined St
Beautiful space in a beautiful neighborhood! Close to local restaurants and shops, but the noise of those spaces didn’t affect sleep.

Quaint neighborhood near Boston!
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
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- Hampton Beach
- Boston Common
- Fenway Park
- Revere Beach
- TD Garden
- Harvard University
- Lynn Beach
- Brown University
- Duxbury Beach
- New England Aquarium
- Faneuil Hall Marketplace
- Freedom Trail
- Canobie Lake Park
- Crane Beach
- Good Harbor Beach
- Prudential Center
- Oakland Beach
- MIT Museum
- Roger Williams Park Zoo
- Museum of Fine Arts, Boston
- Isabella Stewart Gardner Museum
- Quincy Market
- Bunker Hill Monument
- Franklin Park Zoo