House holiday rentals in Wellesley

Find and book unique houses on Airbnb

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Popular amenities for Wellesley house rentals

House rentals with a pool

Guest favourite
Home in North Andover
4.94 out of 5 average rating, 157 reviews

Nana-tucket Inn

AdamRating, 5 stars3 weeks ago
The Nana-Tucket Inn is an absolutely gorgeous and pristine property with everything a family could need! It was perfect for our family while we were visiting New England. It was a great space for family time and our teenagers had plenty to do. Nancy and Joe are the perfect hosts! They are kind and extremely helpful while they maintain the beautiful property. They are not intrusive at all but are there if you need anything. During our stay, a huge storm blew through Massachusetts with extremely strong winds and tons of rain. Nancy and Joe had the mess made by the storm was cleaned up immediately by a professional crew the next morning so that we did not miss a single moment of the property amenities! Nancy also made us a blueberry crumble cake that was delicious and so kind. We thoroughly enjoyed our stay and we cannot wait to return during our next New England trip.
Top Guest favourite
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 favourite
Home in Hopkinton
4.95 out of 5 average rating, 155 reviews

Hopkinton Mass 3+ Bedrooms - Great location!

DeanneRating, 5 stars4 days ago
Brad was very friendly and helpful. Beautiful home!
Guest favourite
Home in Worcester
4.96 out of 5 average rating, 101 reviews

Courtyard Garden | Pool | BBQ+Fire Tbl | Fireplace

XufengRating, 5 stars3 weeks ago
From the moment we arrived, we felt completely at home thanks to the incredibly warm and welcoming hosts, Tania and Glenn. They went above and beyond to make our stay comfortable, offering great local tips and always greeting us with a smile. Their hospitality truly made a difference. The home itself is absolutely stunning—beautifully designed, impeccably clean, and filled with thoughtful touches that made it feel extra special. Whether we were enjoying a quiet morning coffee or relaxing in the cozy living area after a day of exploring, everything was perfect. This was one of the best Airbnb experiences we've ever had. If you're lucky enough to find availability here—book it! You won't regret it. Thank you, Tania and Glenn, for a truly unforgettable stay! 💛
Guest favourite
Home in Woodstock
4.94 out of 5 average rating, 239 reviews

Cedar Ridge: House or House+Apartment

AlissaRating, 5 stars4 days ago
We LOVED: 1) The location! The driveway is long & sand/gravel but you could drive it in a sedan fine. 2) The amenities! The pack n play was a HUGE lifesaver! 3) This location is mostly child friendly. 4) The view is phenomenal! When we woke up & opened the curtains for the first time, we were in awe! 5) The host was extremely helpful. The hot water went out once, but she was over in 5 minutes to fix it. Some feedback: 1) The windows in the ceiling in the master bed! They're HUGE and BRIGHT. 2) The bugs. Ants. Spiders. It was a struggle. NOW I WILL SAY - I brought this up to the host on day 3 and they were more than willing to come help how they could. The house is located in the middle of the forest, but it was a lot. If it weren't for an m&m left under the nightstand in the bedroom by a previous guest, it probably wouldn't have been so bad. 3) the coffee maker was pretty rough when we got there.. a simple over site by the crew. Overall, I would definitely consider this location again
Top Guest favourite
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 favourite
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
Home in Canton
4.88 out of 5 average rating, 25 reviews

Hidden Gem near Boston w/ Private lake access

RachaelRating, 5 stars1 month ago
Absolutely incredible stay. The host was very helpful. The house is absolutely beautiful, and the lake is stunning. The basement was so so fun- darts, ping pong, billiards, and more games. We miss the house already!

Weekly house rentals

Guest favourite
Home in Wayland
4.95 out of 5 average rating, 92 reviews

Spacious 4 bedroom home with large yard

NicoleRating, 5 stars1 week 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 favourite
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 favourite
Home in Waltham
4.97 out of 5 average rating, 39 reviews

Large House KingBed European Look near MoodySt 4BR

DianeRating, 5 stars4 days ago
The house very clean and communication was prompt.
Top Guest favourite
Home in Holliston
4.97 out of 5 average rating, 87 reviews

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

JenRating, 5 stars2 weeks ago
If you like spacious, spotless, quiet, and comfortable homes that are stocked with all the essentials and situated in a great location, then you'll love staying at this Airbnb. It was a bit too much space for my needs and preferences as I was traveling solo, and I don't need a formal dining room or two living rooms, but the location and comfort level couldn't be beat. The hosts are very responsive. Do make sure you ask them about the heat controls, I never could figure out how to maintain the right temperature for long, but my visit was pretty short and I managed just fine. Pro tip: Don't miss a chance to sample the savory turkey pot pies and many varieties of sweet pies at nearby Out Post Farm.
Guest favourite
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.
Guest favourite
Home in Framingham
4.76 out of 5 average rating, 17 reviews

Very nice home close to Boston

AnnRating, 5 stars3 days ago
Everything went so smoothly from booking the reservation to check-in and check-out. The home had everything we needed. It was very clean. We loved the burrito restaurant and the coffee shop that we could walk to as well. We would definitely stay here again.
Top Guest favourite
Home in Framingham
5 out of 5 average rating, 56 reviews

Lake Cochituate Waterfront Home

LeahRating, 5 stars1 week ago
Beautiful private house right on the lake! The house is cozy and clean. So much to do in surrounding areas as well. Amazing hosts very accommodating, extremely friendly, helpful, generous, and respond quickly. Highly highly recommend!
Superhost
Home in Framingham
4.85 out of 5 average rating, 85 reviews

Near Boston Beautiful 3 Bedroom in Framingham, MA

ShelleyRating, 5 stars2 weeks ago
Jim is a friendly and responsive Super-Host. His home suited our needs perfectly. The neighborhood was quiet and safe and it was easy to drive to shops, train station, etc. Thanks, Jim!

Private house rentals

Top Guest favourite
Home in Bellingham
5 out of 5 average rating, 24 reviews

Peaceful lakeside retreat

JasminRating, 5 stars1 week ago
I booked the lakehouse for 4 nights to celebrate our daughter’s birthday. It was the perfect and relaxing celebration which was what we needed. The lakehouse was so beautiful, so quiet, peaceful, cozy and so relaxing. We just felt right at home. The instant we walked in and saw the view of the lake from the kitchen and living room we felt so relaxed right away. The home had everything you needed and was great place to unwind and relax. It was so clean, pristine and had all the necessities you needed. The home was decorated nicely showing their travels which we loved. The beds were so cozy, nice and comfortable, it felt like it hugged you. They had an office room that had a bed which was perfect for me to work from. We loved the lakehouse so much that we were sad to leave. But we will definitely be back. Haley was great, no wonder she is a superhost. She was so accommodating, responsive and so friendly. Thank you Haley for a great stay. We can’t wait to come back again.
Guest favourite
Home in Sudbury
4.93 out of 5 average rating, 57 reviews

Historic Victorian Home - Family + Pet Friendly

AlyssaRating, 5 stars2 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!
Top Guest favourite
Home in Norwood
4.95 out of 5 average rating, 41 reviews

The Cozy Colonial - 4 BDRM house with parking

JoanneRating, 5 stars1 month ago
This was a lovely home, and Austin did a great job making us feel welcome and answering any questions immediately. The house had everything we needed for a week’s stay. Air conditioning worked really well and especially appreciated as it was hot for a few days. Location is great, walkable to town with great restaurants and a fantastic antique market nearby. Would definitely come back!
Guest favourite
Home in Roslindale
4.99 out of 5 average rating, 76 reviews

Upscale Boston 2 BR w/ Off Street Parking

LindaRating, 5 stars2 weeks ago
Pristine clean, great beds, comfortable, onsite parking, safe
Top Guest favourite
Home in Hull
4.97 out of 5 average rating, 30 reviews

4 bd Ocean View, Dual Deck, Beach Front Retreat

ArnoldRating, 5 stars1 day ago
Great location, spacious open floor plan, and beautiful views
Top Guest favourite
Home in Cambridge
5 out of 5 average rating, 51 reviews

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

KadiaRating, 5 stars1 week ago
We loved how close the place was to the T. Easy to get into Boston in less than 20 minutes! Great place if you're looking to explore Cambridge and Boston.
Guest favourite
Home in Roslindale
5 out of 5 average rating, 14 reviews

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

LeighRating, 5 stars6 days 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!
Guest favourite
Home in Framingham
4.95 out of 5 average rating, 21 reviews

Quaint neighborhood near Boston!

ShaylaRating, 5 stars1 week 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

  • Wi-Fi availability

    40 properties include access to Wi-Fi

  • Popular amenities

    Kitchen, Wi-Fi and Pool

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