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Vacation rentals in Wellesley

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Wellesley

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

Guest favorite

Apartment in Framingham

4.91 out of 5 average rating, 256 reviews

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.

Jan 6 – 13

R2,926 ZAR per night
Guest favorite

Guest suite in Weston

5.0 out of 5 average rating, 113 reviews

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.

Jan 16 – 23

R4,265 ZAR per night
Guest favorite

Guest suite in Newton

4.92 out of 5 average rating, 126 reviews

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.

Jun 5 – 12

R2,053 ZAR per night

Popular amenities for Wellesley vacation 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 vacation rentals in Wellesley

Guest favorite

Apartment in Newton

4.87 out of 5 average rating, 103 reviews

Newton Decorator's Guest Suite

Aug 28 – Sep 4

R3,058 ZAR per night
Guest favorite

Apartment in Framingham

4.95 out of 5 average rating, 181 reviews

Comfortable apartment in Framingham

Jun 15 – 22

R1,792 ZAR per night
Guest favorite

Home in Framingham

4.89 out of 5 average rating, 246 reviews

1BR—Bright & Cozy 2-Level Home — 25 Min to Boston

May 1 – 8

R3,478 ZAR per night
Guest favorite

Guest suite in Newton

4.93 out of 5 average rating, 200 reviews

Private 1 Bedroom suite In West Newton

Nov 12 – 19

R2,370 ZAR per night
Guest favorite

Guest suite in Sherborn

4.97 out of 5 average rating, 235 reviews

Entire Historic Carriage House with Fireplace & AC

Jun 9 – 16

R3,551 ZAR per night
Guest favorite

Home in Newton

4.95 out of 5 average rating, 172 reviews

Modern, warm & inviting home!

Nov 11 – 18

R9,744 ZAR per night
Superhost

Guest suite in Wayland

4.86 out of 5 average rating, 117 reviews

Private and Clean 2 Bedroom Apartment

Nov 18 – 25

R2,801 ZAR per night
Superhost

Apartment in Newton

4.85 out of 5 average rating, 123 reviews

Entire Apartment in Newton, Close to Boston!

Jul 8 – 15

R2,500 ZAR per night
Guest favorite

Apartment in Hudson

4.86 out of 5 average rating, 291 reviews

Private Mother-In-Law apartment on the lake!

Oct 6 – 13

R1,745 ZAR per night
Guest favorite

Home in Dedham

5.0 out of 5 average rating, 143 reviews

The Gatehouse, Cheerful 3 bedroom 3 bathroom house

Aug 10 – 17

R9,800 ZAR per night
Guest favorite

Apartment in Waltham

4.98 out of 5 average rating, 209 reviews

Cozy Private Studio Unit w/ Laundry and Parking!

Nov 18 – 25

R2,365 ZAR per night
Guest favorite

Apartment in Holliston

4.95 out of 5 average rating, 110 reviews

Lake Link

Nov 12 – 19

R3,008 ZAR per night

Quick stats about vacation rentals in Wellesley

Total rentals

60 properties

Wifi availability

60 properties include access to wifi

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

Frequently Asked Questions

  • Do house rentals in Wellesley have free parking?

    Absolutely! We offer over 50 house rentals with free parking in Wellesley. Enjoy a tailored experience with all the comforts you desire.

  • Where should I stay in Wellesley?

    Make yourself at home in Wellesley by choosing from our most frequently booked neighborhoods. We have over 310 vacation rentals in Waban, over 360 vacation rentals in Wellesley Hills, and over 50 vacation rentals in Wellesley Square.

  • What are the most popular amenities for House Rentals in Wellesley?

    Enhance your stay in our House Rentals with the most popular amenities: over 50 homes with wifi, over 50 homes with free parking, over 50 homes with air conditioning, over 40 homes with a kitchen, 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.

  • Are there vacation rentals with a dedicated workspace in Wellesley?

    Yes! Work meets play with ease at over 40 vacation rentals in Wellesley featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do house rentals in Wellesley have air conditioning?

    Absolutely! We offer over 50 house rentals with air conditioning in Wellesley. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Wellesley have wifi?

    Absolutely! We offer over 50 house rentals with wifi in Wellesley. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Wellesley have a kitchen?

    Absolutely! We offer over 40 house rentals with a kitchen in Wellesley. Enjoy a tailored experience with all the comforts you desire.

Destinations to explore