
House holiday rentals in Wellesley
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Top-rated house rentals in Wellesley
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Popular amenities for house rentals in Wellesley
House rentals with a pool

Nana-tucket Inn
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.

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
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! 💛

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
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!

Quiet/Private Neighborhood
Hands down one of the best Airbnbs my family and I have stayed in! We didn't want to leave this place. To top it off, Michelle is a great host. 5/5 rating for sure!
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
The house very clean and communication was prompt.

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

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
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.

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.

Lake Cochituate Waterfront Home
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!
Private house rentals

Peaceful lakeside retreat
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.

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!

The Cozy Colonial - 4 BDRM house with parking
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!

Upscale Boston 2 BR w/ Off Street Parking
Pristine clean, great beds, comfortable, onsite parking, safe

4 bd Ocean View, Dual Deck, Beach Front Retreat
Great location, spacious open floor plan, and beautiful views

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

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!

Last-Minute Deal: Spacious, Deluxe and Cozy Stay!
⭐️⭐️⭐️⭐️⭐️ 5/5 – A Perfect Stay with a Wonderful Host! I had an outstanding experience staying at Joe’s Airbnb on Herrod Ave in Brockton. From the moment I arrived, it was clear that Joe is a thoughtful and attentive host who genuinely cares about her guests' comfort and experience. The home was spotless, beautifully maintained, and exactly as described, if not better. Every detail was thoughtfully arranged, from the cozy linens and fully stocked kitchen to the fast Wi-Fi and quiet surroundings. The neighborhood is peaceful and safe, and it's conveniently located near shops, restaurants, and major routes. Joe was incredibly welcoming and responsive throughout my stay. She made sure I had everything I needed, offered great local tips, and went above and beyond to ensure I felt right at home. Whether you're visiting Brockton for business or leisure, I can't recommend this place enough. If you’re lucky enough to find availability here, don’t hesitate, book it! Thank you again, Joe?
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
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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
- Roger Williams Park Zoo
- MIT Museum
- Museum of Fine Arts, Boston
- Oakland Beach
- Quincy Market
- Bunker Hill Monument
- Pinehills Golf Club
- Pawtucket Country Club