House vacation rentals in Wellesley

Find and book unique houses on Airbnb

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Popular amenities for Wellesley house rentals

House rentals with a pool

Guest favourite
Home in North Andover
4.93 out of 5 average rating, 153 reviews

Nana-tucket Inn

JeremyRating, 5 stars5 months ago
We had an absolutely wonderful experience staying at this Airbnb! The home was impeccably clean, cozy, and well-stocked with everything we could possibly need. The host's attention to detail was evident in every corner, from the kids' toys to the thoughtful touches like snacks, coffee, and local guidebooks. The location was perfect—peaceful and quiet but still close to shops and restaurants. I especially loved relaxing in front of the fire and enjoying the serene surroundings. The host was incredibly responsive and went above and beyond to ensure our stay was seamless, offering great tips about the area and checking in (without being intrusive). I highly recommend this spot to anyone visiting North Andover or the greater Boston area.
Top guest favourite
Home in Lakeside Marblehead
5 out of 5 average rating, 13 reviews

Large Pool, Nature Trails, Redd's Pond, 4-Bed

ChristopherRating, 5 stars2 weeks ago
Everything was as listed and very responsive and great host. The property was in a very nice and in a great town. We enjoyed our time there.
Guest favourite
Home in Hopkinton
4.95 out of 5 average rating, 153 reviews

Hopkinton Mass 3+ Bedrooms - Great location!

RenaeRating, 5 stars2 weeks ago
Six of us stayed over the weekend. We were very comfortable and Brad was very helpful and responsive. House had everything that we needed. Brad is a great host. Would 100% recommend a stay.
Top guest favourite
Home in Plymouth
4.96 out of 5 average rating, 55 reviews

Our families slice of heaven

MarkRating, 5 stars6 months ago
Marla's vacation home was very lovely. We liked the pictures of her place, but once we arrived we realized that she had remodeled a number of rooms. Each room was updated, very clean and cozy. Marla has made sure that her place is stocked with all of the large and small conveniences that guests would want in a home away from home. The location and the surroundings are stunning, especially with the Fall foliage. One can tell that Marla takes great pride in her beautiful rental. -Mark & Susan G
Guest favourite
Home in Worcester
4.96 out of 5 average rating, 98 reviews

Courtyard Garden | Pool | BBQ+Fire Tbl | Fireplace

AyannaRating, 5 stars6 months ago
booked this charming property in Worcester as a convenient spot to visit my son, who attends college nearby, and for family weekend at Boston University, where my daughter just started school. Hotels in Boston were priced from $600 to $1,200 per night, so finding this home was ideal. I brought along my elderly mother, who is in the early stages of Alzheimer’s, and I was hoping for a place that would feel like a true home—a space where we could spend quality time together in the evenings and early mornings. This home exceeded our expectations. The description was spot on, and the space was everything we needed and more. I especially enjoyed sitting outside by the fireplace each morning for my prayers and reflections. The rooms were fantastic, and watching our football game on Sunday night on the "big screen wall" was a highlight. Many thanks to the hosts for providing such a welcoming and memorable place for our family.
Guest favourite
Home in Woodstock
4.94 out of 5 average rating, 235 reviews

Cedar Ridge: House or House+Apartment

SuzanneRating, 5 stars1 month ago
We love the house! It’s spotless (very clean), very comfortable and super peaceful in a beautiful location! Highly recommend!
Top guest favourite
Home in Plymouth
4.97 out of 5 average rating, 32 reviews

Getaway with pool

JoanneRating, 5 stars5 months ago
We absolutely loved our stay at this rental! The space was incredibly well-equipped, providing everything we needed and more. The rooms were spacious and comfortable, making it easy for us to relax and enjoy our vacation. The attention to detail in the amenities was impressive, from the fully stocked kitchen to the cozy living areas. We felt right at home and appreciated all the thoughtful touches that made our stay so enjoyable. Highly recommend to anyone looking for a wonderful and well-appointed place to stay!
Guest favourite
Home in Plymouth
4.9 out of 5 average rating, 115 reviews

Seaview Summit | Ocean Views, Indoor Pool, Beach

BenRating, 5 stars1 week ago
We had a great stay. The house is new and is exactly as it appears in the pictures. The views are stunning. There are a total of five bedrooms and four bathrooms, which was perfect for our family vacation with 7 adults and 3 kids. Only suggestion is if you have little ones bring a gate because there is no door to the basement stairs. Speaking of kids, the pool is SO awesome to have if you happen to get a rainy or cold day. Plenty of space/seating to eat inside or outside. We would definitely come back!

Weekly house rentals

Superhost
Home in Rindge
5 out of 5 average rating, 3 reviews

Secluded lakefront vacation home

ClaudiaRating, 5 stars2 months ago
Beautiful home. Well kept. Hosts super accessible and very friendly. We felt like home and house is super cozy
Guest favourite
Home in Salisbury
4.88 out of 5 average rating, 213 reviews

Spacious waterfront free parking &Wi-fi

PamRating, 5 stars3 days ago
We had a wonderfully relaxing ladies weekend to celebrate my retirement. Diana's place was extremely clean and comfortable with a spectacular view from the private covered porch. We had everything we needed and felt right at home. Thank-you for sharing your lovely home with us!
Guest favourite
Home in South Weymouth
4.93 out of 5 average rating, 118 reviews

Entire House Near South Shore Hospital/Whole Foods

ChloeRating, 5 stars1 month ago
My groups stayed at Trang’s home for 2 night and our stay was perfect. The home was exactly as pictured in the listing and was very clean and spacious. Check-in instructions were straight forward and easy to understand. Would definitely stay again in the future if we ever find ourselves in the area.
Top guest favourite
Home in Newburyport
4.99 out of 5 average rating, 131 reviews

“Salty Girl” Plum Island, MA

KathleenRating, 5 stars3 days ago
Every 6 months or so, my close friend from college and I meet somewhere between our houses (ME & NY). We loved meeting at Erin’s place this time around. The location was unique, walkable, and easy to find (10 minute drive to NBP). The house was very clean and has a beautiful, spacious layout with the pitched roof. Erin was quick to communicate when she noticed the WIFI was switched off. We really enjoyed the quiet, peaceful environment and Plum Island wasn’t busy at all in May, which was just what we were looking for.
Guest favourite
Home in Lexington
4.92 out of 5 average rating, 119 reviews

Mid-Century Modern in Historic Lexington

MichaelRating, 5 stars1 month ago
Great place for our coaches to meet up and sleep after a full day of coaching in Boston area. Very comfortable space. Highly recommend this home.
Top guest favourite
Home in Wrentham
4.88 out of 5 average rating, 105 reviews

Backyard Oasis with Hot Tub

AndresRating, 5 stars2 months ago
A wonderful place that felt even larger than in the pictures, surrounded by beautiful scenery, offering complete privacy, and the perfect touch of a delicious hot tub experience under a snowy night.
Guest favourite
Home in Shrewsbury
4.91 out of 5 average rating, 151 reviews

Scenic House on Hilltop

BarbaraRating, 5 stars1 week ago
We come to this large house to Quilt and knit twice a year. On a nice day the back deck is a great place to sit and enjoy the trees and view. It's a comfortable place to be.
Guest favourite
Home in Dorchester
4.96 out of 5 average rating, 114 reviews

LargeDuplex10Beds w/prkg near Downton

RyanRating, 5 stars1 month ago
Fatima's place was welcoming, clean, and well-equipped. She was extremely accommodating and helpful. I enjoyed the amount of space we had for a large group. The transit nearby was down but they still had busses to accommodate. Definitely an amazing value for what we paid. I'd definitely recommend it for a bachelor party or any large group outing. We couldn't have had a better time!

Private house rentals

Guest favourite
Home in Annisquam
4.96 out of 5 average rating, 25 reviews

Beach House on a Private Beach!

ChelseaRating, 5 stars1 day ago
A family vacation that I will always cherish. I've stayed at a lot of air bnbs and this one was stocked the best of all I've been to with the easiest checkout process I've ever experienced as well. I agree with all other 5 star reviews but would like to add that my kids 9, 7, and 5 especially loved climbing the huge rocks surrounding the harbor. Thank you for hosting us!
Guest favourite
Home in Plymouth
5 out of 5 average rating, 18 reviews

Natural beauty garden house near beaches pets OK

MaureenRating, 5 stars4 months ago
Worked out very well for our family of 4 adults, a 1 year old & a 3 year old over the winter holiday. Spacious & open kitchen/D.R./living room area, comfortable sofas & chair in L.R. The basement bedroom with 2 twin beds was not used as it was not appealing walking through a "cellar" to get to it - & it's isolating. Love all the windows to allow light in & that show the huge front yard & wooded area of the side yard. We did not use the deck or porch because of the season.
Superhost
Home in Swampscott
4.96 out of 5 average rating, 27 reviews

Master Suite with magnificent views of the ocean

JaimeRating, 5 stars3 months ago
We had a lovely long weekend at Natasha's gorgeous home. Spotlessly clean, with modern upgrades and appliances. The layout is a bit unusual as the house has been renovated and split into at least 2 units. Located on main road into Swampscott, with a view of the ocean (across the road) out the front windows--very beautiful even in the middle of winter! We had snow 2 out of 3 nights, and on the first of these there was a gentleman outside shoveling the driveway and back steps around noon. But by our check out time (noon) on Monday, nobody had cleared the snow. Got our car out ok, and we cleared off the back steps so we could bring our luggage out. There was conflicting info between the listing and what we were told by the owner re check-in and check out times--we messaged owner (twice) to clarify check out time and never heard back from her, so called her on check out morning--she apologized and honored the original listing. Info in owner's instruction booklet at house needs updating.
Guest favourite
Home in Reading
4.95 out of 5 average rating, 61 reviews

Charming Home in Reading with a Large Yard

T.J.Rating, 5 stars3 weeks ago
We thoroughly enjoyed our stay. The location was wonderful and the hosts were extremely easy to work with
Top guest favourite
Home in Providence
4.97 out of 5 average rating, 128 reviews

Charming 3 br apartment/East side

RayaRating, 5 stars3 weeks ago
Pat is a Superhost Extraordinaire! Felt at home in charming and comfortable house. Fully equipped kitchen with snacks too! The space is super clean with towels galore. Pat has thought of everything and more .... Cannot ask for a more thoughtful and generous host! The location is walkable to Brown University and parking is convenient on premises. There is even an outdoor space to relax (weather permitting). Wifi worked great. Thank you for making our stay in Providence so enjoyable!
Guest favourite
Home in Salem
4.95 out of 5 average rating, 150 reviews

Quaint Little New Hampshire Lake House Getaway!

LindaRating, 5 stars1 week ago
My husband and I were getting married and in his mind it is customary to not see the bride until she walks down the aisle! On my mind…I didn’t just want to come home, as we live together, just like any other night. I took my mother with me the night before our wedding and fell in love with this cute, quiet place with a gorgeous view, again nothing too far from our venue. We had worked out a little confusion on communication, we were great and going to have the cutest little house overlooking a pond/lake! My mother loved it and my husband loved it as well. It was very well kept, gorgeous view out the ceiling to floor windows! Private, quaint, easy to get to, quiet….just super cute all around! My husband and I do Airbnb‘s a couple times a year….if we were to look for some place close to home, we would definitely love to stay here again! Everything was great!
Guest favourite
Home in Marshfield
5 out of 5 average rating, 37 reviews

Lovely Family House Steps Away from Sandy Beach

ChevonRating, 5 stars5 months ago
Loved my stay at this beautiful home. Very clean, and felt like home. All my friends slept well and were comfortable everywhere we gathered in the home. Dominique was wonderful and responsive. I would certainly rent this again in the future.
Guest favourite
Home in Scituate
5 out of 5 average rating, 11 reviews

Oceanfront Getaway: Private Beach and Porch Dining

KimRating, 5 stars4 months ago
Our stay at the house was everything we hoped for and more. We stayed over Christmas vacation, which is not a typical time of year to stay in this coastal community, and we loved it! We greatly appreciated the quiet peaceful surrounding of the ocean and the beautiful homes all decorated for the season. Walking on the beach, with the crisp air and sound of the waves, priceless. The home was clean, comfortable and relaxing, the fireplace adding to that special holiday feel. We were able to utilize the space the home had, with beautiful views of the marsh, as we were able to meet with old friends, and share a dinner together. Our contact, Jim, was readily available for any questions or concerns we may have had, quickly answering his phone or responding to text. We left, feeling like renting this home, was the best decision we could have made. I highly recommend this home and ITrip Boston.

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

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