
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.
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Get the amount of space that is right for you
Popular amenities for Wellesley vacation rentals
Other great vacation rentals in Wellesley

Tiny house experience steps from the water!
Dean's place was amazing! I felt at peace and felt like I was really in the middle of nature. Quiet and very cozy place! I will be back again! Dean is very friendly and communication is quick and easy!

Elegant Guest suite Wellesley
It was my second stay here and the whole experience was outstanding, once again. Such a great place and hosts.

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.

Lovely & Spacious 5 Bedroom Home 20 min. to Boston
Our stay was incredible! We were in town for my daughter's graduation. The home was clean, comfortable and full of charm - a perfect blend of warmth and elegance. The neighborhood was quiet and picturesque, perfect for our family. Kim was incredibly kind, responsive and thoughtful - making sure we had everything we needed for a relaxing and stress-free visit. Every detail made if feel like a home away from home. I would highly recommend these accommodations. We couldn't have asked for better. We'd love to return again!

Very nice home close to Boston
The house was perfect. More space than needed for one person. The kitchen was beautifully updated. The mater bathroom looked like it was newly updated. Lots of space, double sinks. The shower had built in places for shampoos and body wash. The mattress in the master bedroom was amazing. The best nights sleep I have had in a long time. Private street was so quiet you could sleep like a log. Jeff checked in to make sure I got in ok and that everything was to my liking. Four Season service and comfort.

Apartment in Newton, MA
Great place, very comfortable and nicely kept. Good location, highly recommend!

Lovely studio walk to Wellesley and Babson College
I loved staying at Francisco’s Airbnb. It was walking distance to Wellesley College where I was attending my reunion. Very safe, close to a Whole Foods, I would stay there again!

Gorgeous Guest Suite in Weston
From the time we arrived we felt very at home and knew it would be a comfortable stay. The view out the large window makes the living room feel even more spacious. The large, heavy bath towels were wonderful and the home was exceptionally clean. Nicole gave us solid recommendations on some nearby restaurants and was attentive to our needs. We will definitely see if we can stay next time we are in Natick.
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 50 vacation rentals in Wellesley Square, over 330 vacation rentals in Waban, and over 370 vacation rentals in Wellesley Hills.
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 10 homes with a bbq area, over 20 homes with self check-in, 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
- Revere Beach
- Fenway Park
- TD Garden
- Harvard University
- Lynn Beach
- Duxbury Beach
- Brown University
- New England Aquarium
- Faneuil Hall Marketplace
- Freedom Trail
- Crane Beach
- Canobie Lake Park
- Roger Williams Park Zoo
- Prudential Center
- MIT Museum
- Good Harbor Beach
- Oakland Beach
- Museum of Fine Arts, Boston
- Quincy Market
- Bunker Hill Monument
- Isabella Stewart Gardner Museum
- Pinehills Golf Club