Vacation rentals in Wellesley

Book unique vacation rentals, houses, and more on Airbnb

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Popular amenities for Wellesley vacation rentals

Stay near Wellesley's top sights

Whole Foods Market84 locals recommend
CVS55 locals recommend
Babson College18 locals recommend
Wellesley College16 locals recommend
Starbucks26 locals recommend
Riverside Station15 locals recommend

Other great vacation rentals in Wellesley

Superhost
Condo in Plymouth
4.77 out of 5 average rating, 154 reviews

Clear Pond Pet Friendly Inn

NicklausRating, 5 stars5 months ago
Friendly host! Allowed us to bring our 4 little dogs! Hard to find a host that will allow this. Clean and peaceful property.
Guest favorite
Cottage in Stow
4.95 out of 5 average rating, 171 reviews

White Pine Cottage

NickRating, 5 stars1 week ago
Great older lake house vibe. We liked it very much. It worked great for our family of five.
Top guest favorite
Home in Hull
4.95 out of 5 average rating, 21 reviews

Every room a water view updated kitchen & bath

JohnRating, 5 stars3 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, 31 reviews

The Curie-Perfect for Monthly Stays

XuemeiRating, 5 stars1 week 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!
Top guest favorite
Home in Ipswich
4.98 out of 5 average rating, 194 reviews

Stagehill Beach House

PaulaRating, 5 stars6 months ago
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!
Superhost
Home in Worcester
4.85 out of 5 average rating, 119 reviews

COMFORTABLE 2ND FLOOR, FULL EQUIPPED&PET FRIENDLY

AnanthRating, 5 stars1 week ago
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.
Guest favorite
Home in Gloucester
4.91 out of 5 average rating, 121 reviews

Gloucester Beach House, near Good Harbor Beach!

TashaRating, 5 stars3 months ago
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.
Top guest favorite
Guest suite in Gloucester
4.98 out of 5 average rating, 424 reviews

SplashLanding Private Beach Getaway in Gloucester

MichaelRating, 5 stars2 weeks ago
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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