Vacation rentals in Wellesley

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Top-rated holiday rentals in Wellesley

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favourite
Apartment in Framingham
Spacious 2 Br with All The Comforts Of Home
This a quaint apartment . Not your typical hotel room. In a country setting but 5-10 minutes from great shopping, restaurants, parks, colleges and major highways. Boston is 22.5 miles away. Fenway Park is 20 miles. Worcester is 17 miles. Private location overlooking conservation land. Walk to great hiking and biking trails but car needed for other activities. Full kitchen, laundry room and living room in addition to 2 br and bath. It has the comfort of a home away from home. Please NO PETS.
24 – 31 Dec
4.91 out of 5 average rating, 256 reviews
Guest favourite
Guest suite in Weston
FLOWER FARM GETAWAY 2BR 15MIN TO BOSTON
Spacious two-bedroom in-law suite attached to 1700’s farmhouse, situated on our small flower farm and garden co-op just 15 minutes from Boston. Only a mile from the Mass Pike & Rt. 128 (I-95). Centrally located to all Rt. 128 businesses, colleges & hospitals. A 7-min drive to Riverside Green line “D” subway stop into Boston (parking available), or commuter rail stops (Auburndale, Wellesley & Kendal Green Stations). It's a 15-minute drive to Amtrak's "Route 128" station to NYC and points south.
2 – 9 Feb
5.0 out of 5 average rating, 110 reviews
Guest favourite
Guest suite in Newton
Sunny 3rd floor Studio - Near Boston
Spacious 3rd floor in-law studio in New England Colonial. NOTE: ACCESS TO STUDIO IS THRU OUR 2nd FLOOR CONDO, WHERE WE LIVE. Studio includes bedroom, bathroom, & living room with sofa bed & work area with large desk. Located in a safe residential neighborhood. A 5 min walk to the Express Bus to Boston City Center, 5 min walk to Whole Foods, Village Cafe, Marty's Wines, & CVS. Close to many Boston universities & colleges. A 20 min drive to Fenway Park. Centrally located for day trip to Cape Cod.
21 – 28 Mar
4.92 out of 5 average rating, 126 reviews

Popular amenities for Wellesley holiday rentals

Stay near Wellesley's top sights

Babson College18 locals recommend
Whole Foods Market84 locals recommend
Wellesley College16 locals recommend
Papa Razzi Wellesley8 locals recommend
The Local Wellesley7 locals recommend
Juniper12 locals recommend

Other great holiday rentals in Wellesley

Guest favourite
Guest suite in Watertown
Private 1BR Pied-a-terre
13 – 20 Nov
4.92 out of 5 average rating, 261 reviews
Guest favourite
Apartment in Hudson
Private Mother-In-Law apartment on the lake!
26 May – 2 June
4.86 out of 5 average rating, 290 reviews
Guest favourite
Home in Framingham
2BR—Charming 1900s Home—1st Floor—25min to Boston
10 – 17 Apr
4.96 out of 5 average rating, 130 reviews
Guest favourite
Guest suite in Newton
Private 1 Bedroom suite In West Newton
1 – 8 May
4.92 out of 5 average rating, 198 reviews
Guest favourite
Apartment in Framingham
Comfortable apartment in Framingham
31 May – 7 June
4.95 out of 5 average rating, 182 reviews
Guest favourite
Home in Dedham
The Gatehouse, Cheerful 3 bedroom 3 bathroom house
4 – 11 Aug
5.0 out of 5 average rating, 141 reviews
Guest favourite
Home in Dedham
Private apartment close the city!
17 – 24 Apr
4.85 out of 5 average rating, 484 reviews
Superhost
Apartment in Newton
Entire Apartment in Newton, Close to Boston!
19 – 26 Aug
4.85 out of 5 average rating, 123 reviews
Guest favourite
Home in Newton
Modern, warm & inviting home!
23 – 30 July
4.95 out of 5 average rating, 171 reviews
Guest favourite
Apartment in Waltham
Cozy Private Studio Unit w/ Laundry and Parking!
2 – 9 Feb
4.98 out of 5 average rating, 209 reviews
Guest favourite
Guest suite in Arlington
Modern and comfortable studio apartment
28 Dec – 4 Jan
4.92 out of 5 average rating, 192 reviews
Guest favourite
Condo in Wellesley
Lovely studio walk to Wellesley and Babson College
29 Nov – 6 Dec
4.96 out of 5 average rating, 55 reviews

Quick stats about holiday rentals in Wellesley

Total rentals

60 properties

Wi-Fi availability

60 properties include access to Wi-Fi

Rentals with dedicated workspaces

40 properties have a dedicated workspace

Pet-friendly rentals

10 properties allow pets

Family-friendly rentals

20 properties are a good fit for families

Total number of reviews

2.6K reviews

Destinations to explore