Holiday houses in Wellesley

Find and book unique accommodation on Airbnb

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Popular amenities for Wellesley holiday rentals

Stay near Wellesley's top sights

Whole Foods Market84 locals recommend
CVS55 locals recommend
Babson College3 locals recommend
Starbucks26 locals recommend
Riverside Station15 locals recommend
Sweet Basil12 locals recommend

Other great holiday rentals in Wellesley

Guest favourite
Home in Westminster
4.94 out of 5 average rating, 127 reviews

Wachusett Mountain Get-Away

DaeshaRating, 5 stars3 months ago
It was a pleasure staying here ! Everything is clean and the house is such a nice size !
Guest favourite
Cottage in Stow
4.95 out of 5 average rating, 173 reviews

White Pine Cottage

KunhoRating, 5 stars1 week ago
The place was very cozy, and we were able to relax in a peaceful atmosphere. Everything we needed was provided and easy to use. The bedding was clean, and we enjoyed using the grill in the backyard. One minor issue was that the hot water seemed to run out quickly while filling the bathtub, possibly due to a limited tank capacity. When we turned on the fireplace, smoke filled the house because of a chimney issue, but Bill responded quickly and resolved it right away. He was very kind and even offered us a late checkout to make up for the inconvenience. Overall, it was a wonderful experience staying here, and we’d love to visit again sometime.
Top Guest favourite
Apartment in North End
5 out of 5 average rating, 7 reviews

Beautiful and spacious lovely home

ChrisRating, 5 stars1 month ago
Place worked out perfect
Top Guest favourite
Home in Hull
4.95 out of 5 average rating, 21 reviews

Every room a water view updated kitchen & bath

JohnRating, 5 stars4 months ago
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.
Superhost
Apartment in Brighton
4.84 out of 5 average rating, 32 reviews

The Curie-Perfect for Monthly Stays

XuemeiRating, 5 stars2 weeks ago
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!
Superhost
Home in Worcester
4.85 out of 5 average rating, 121 reviews

COMFORTABLE 2ND FLOOR, FULL EQUIPPED&PET FRIENDLY

AlexanderRating, 5 stars6 days ago
We had a bit of trouble checking in, but the host responded immediately and we didn't have any more trouble. The house was the best stocked of any rental we've been to; the kitchen had everything you could need, the bathroom had all kinds of toiletries, and the host even left a welcome basket with fresh fruit and snacks. The house felt very "homey", and everything was clean and comfortable. The stairs were a bit steep and our 15 year old dog struggled a little, so if you need a more accessible place this may not be for you. Aside from that, it was a great place to stay.
Guest favourite
Cottage in Newburyport
4.99 out of 5 average rating, 165 reviews

True North Cottage*Ocean side of Boat Basin!*

ErikRating, 5 stars7 months ago
Located just a short walk to the beach this charming cottage offered the perfect blend of comfort and convenience for my whole family. The spacious cottage was clean and very well designed with everything we needed for a relaxing stay, including a fully equipped kitchen and cozy living area with modern amenities. The hosts, Elia and Rob, were incredibly welcoming and accommodating and we hope to visit again soon. I would highly recommend True North Cottage to anyone looking for a peaceful getaway near the beach and scenic, downtown Newburyport.
Guest favourite
Guest suite in Rockport
4.97 out of 5 average rating, 111 reviews

8 Bells by the Sea - Private Suite-On the Beach!

AlisonRating, 5 stars7 months ago
My stay at 8 Bells by the Sea was peaceful, fun, and unique. It was a delight living mere feet from the water and feeling so connected to the tides. Robin was very helpful before and during the trip, providing me with recommendations and advice about the area. The apartment is located on a small street, filled with adorable beachy stores, restaurants, art galleries, jewelry shops, and more. The room is charmingly decorated in aquatic tones of blue and green, with thoughtful art and trinkets. There are many windows which look out onto a beautiful view of the water. The bathroom is large and was very clean. I appreciated and utilized the small refrigerator and freezer, as well as the silverware and glassware. My favorite part was mudlarking right outside the room on the beach when the tide was low. I found many pieces of ceramics, and enjoyed hanging out with the ducks and watching other birds. Highly recommend 8 Bells by the Sea for those who enjoy a cute small town by the water.

Quick stats about holiday 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

  • Wi-Fi availability

    60 properties include access to Wi-Fi

Destinations to explore