
Vacation rentals in Wellesley
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Top-rated vacation rentals in Wellesley
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for Wellesley vacation rentals
Other great vacation rentals in Wellesley

Clear Pond Pet Friendly Inn
Friendly host! Allowed us to bring our 4 little dogs! Hard to find a host that will allow this. Clean and peaceful property.

White Pine Cottage
Great older lake house vibe. We liked it very much. It worked great for our family of five.

Every room a water view updated kitchen & bath
Excellent experience. Easy check in and the place was perfect, she even had some snacks waiting for us upon arrival. Easy walk to the ferry into Boston, and easy parking. It was winter, but there were plenty of outdoor activities so we'd love to come back during the summer. Older house but so charming and great location. Overall great communication before, during, and after; she even offered to ship a shoe my niece left behind to us. Would love to come back and would absolutely recommend to anyone looking for a great place in Hull.

The Curie-Perfect for Monthly Stays
This apartment is a great find! The location is perfect, not far from Boston, near every colleges for those who come visiting! This apartment building is indeed very new, built in 2021; but also blended in with history, the leasing office/lobby was converted from an old day chapel, pristine, elegant. Very unique Airbnb experience indeed. The small town is full of vibe with various kinds of cuisines, very good for families, young or old. Melissa, the host is super, giving us very detailed information and instructions from parking to checking in, every tiny details she thoughtfully considered. We couldn’t be happier to stay in this apartment. Highly recommended!

Stagehill Beach House
Loved this rental! Katie was so nice and very accommodating! This house was great! Pictures didn’t do it justice! Plenty of room and amazing views. My favorite room was the sitting room upstairs with views from every window! Lots of clean linens and super comfy beds! Check in and check out were a breeze. Easy to follow instructions on how to close up. Only complaint was on me! Wish we booked “in season” to take advantage of the beach! We will definitely be back! Thank you again, Katie! Your place and you, were top notch!

COMFORTABLE 2ND FLOOR, FULL EQUIPPED&PET FRIENDLY
Dilsia is a great host. She provided lot of things thoughtfully which were extremely useful for us. We enjoyed our stay. She is very responsive and kind. Thank you for making our stay so nice.

Gloucester Beach House, near Good Harbor Beach!
Our stay at the Gloucester Beach House was great. It is a nice walk down to Good Harbor Beach, The Common Place Market and the neighborhood is peaceful. Its about a 10-minute drive to anywhere you want to go in Gloucester. Diane was responsive with any communication we had with her, and stayed in contact with us throughout the trip. We were grateful to be able to check in early after traveling all night to rest before beginning our trip adventures. For anyone interested, the Rhumb Line currently offers live music every night and its a variety of music. We went there several times and the musician's were top notch, and this is a place where the locals gather. We ended up visiting with friends and family and looking forward to another trip out to explore more of North Shore! Thank you so much for the wonderful home and stay.

SplashLanding Private Beach Getaway in Gloucester
Exceptional hosts and exceptional accommodations, with an exceptional location adjacent to an exceptional ocean-front beach in an exceptionally private neighborhood. There’s nothing to say but the word repeated 5 times above. But it’s worth saying once more — exceptional!
Quick stats about vacation rentals in Wellesley
Total rentals
60 properties
Total number of reviews
3.3K reviews
Family-friendly rentals
10 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Wifi availability
60 properties include access to wifi
Frequently Asked Questions
Where should I stay in Wellesley?
Make yourself at home in Wellesley by choosing from our most frequently booked neighborhoods. We have over 370 vacation rentals in Wellesley Hills, over 330 vacation rentals in Waban, and over 50 vacation rentals in Wellesley Square.
Are there house rentals with a dedicated workspace in Wellesley?
Yes! Work meets play with ease at over 20 house rentals in Wellesley featuring dedicated workspaces. Stay connected and productive in your home away from home.
What are the most popular amenities for House Rentals in Wellesley?
Enhance your stay in our House Rentals with the most popular amenities: over 20 homes with self check-in, over 10 homes with a bbq area, and more. Indulge in the ultimate retreat, tailored to your preferences.
Are there pet-friendly vacation rentals in Wellesley?
Four-legged friends are welcome in Wellesley. Choose from more than 10 vacation rentals for guests traveling with pets.
Do house rentals in Wellesley have self check-in?
Absolutely! We offer over 20 house rentals with self check-in in Wellesley. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Wellesley have a bbq area?
Absolutely! We offer over 10 house rentals with a bbq area in Wellesley. Enjoy a tailored experience with all the comforts you desire.
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- Hampton Beach
- Boston Common
- TD Garden
- Fenway Park
- Harvard University
- Brown University
- New England Aquarium
- Faneuil Hall Marketplace
- Freedom Trail
- Prudential Center
- Symphony Hall
- Roger Williams Park Zoo
- Oakland Beach
- Boston Public Library
- Crane Beach
- Pinehills Golf Club
- Aaronap Cellars
- John Hancock Tower
- Boston Children's Museum
- Quincy Market
- Pavilion Beach
- Museum of Fine Arts, Boston
- Manchester Country Club - NH
- Canobie Lake Park
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