
House holiday rentals in Wellesley
Find and book unique houses on Airbnb
Quick stats about house rentals in Wellesley

Total holiday rentals
Explore 50 holiday rentals in Wellesley

Nightly prices starting at
Wellesley holiday rentals start at €35 per night before taxes and fees

Verified guest reviews
Over 1,880 verified reviews to help you choose

Family-friendly holiday rentals
20 properties offer extra space & child-friendly amenities

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wifi availability
50 of Wellesley holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Wellesley rentals

4.8 Average rating
Wellesley stays are highly rated by guests – averaging 4.8 out of 5!
Top-rated house rentals in Wellesley
Guests agree: these houses are highly rated for location, cleanliness and more.

All New Private Country Setting (2 Level-No Share)
We built this 2 level home 9 years ago and it is located on Washington St in the towns Historic district. The home is set back from street with a long country style driveway. We designed it with large windows in all rooms, welcoming the sunlight and peaceful setting. Access to clean and empty garage for storage (No parking). We have no personal items in the guest level - all closets and dressers are empty and yours for full use! Co Host reside in lower separate entrance suite. Nothing Shared.
4.97 out of 5 average rating, 144 reviews
Cozy en suite w/ high ceilings
 Relax in this peaceful private en-suite with breathtaking backyard views of the tall pine forest. Natural light fills the space with room darkening shades to sleep in. Enjoy cozy nights by the fireplace and a well stocked granite kitchen. Great location only minutes to the Mass Pike. Just 25 min to Boston, 40 min. to Gillette Stadium. Enjoy shopping at the Natick Mall, AMC movies, tons of diverse dining & grocery options. Backyard has firepit for outdoor eves. Very safe walkable neighborhood
4.98 out of 5 average rating, 141 reviews
Newly Renovated 3 Bed 2 Bath Easy Access Boston
Welcome to our newly renovated beautiful home in Greater Boston Designed for comfort and convenience, this home is perfect for families, business travelers and groups looking for a retreat ✔Sleeps 8 : 3 Queens + 2 Sofa beds (correct # of people & pets are enforced) ✔5m Stop & Shop + LifeTime Fitness ✔15m Wellesley College ✔25m --> Downtown ✔10 m--> Remote Logan Terminal ✔27 m--> BOS Airport ✔New appliances + smart TV, bluetooth speaker ✔Private patio ✔Garden ✔Driveway parking ✔Pet friendly
4.79 out of 5 average rating, 103 reviews
Newly Renovated Lovely 2 bedroom unit - Newton MA
Only a 10 minute drive to the heart of Boston's downtown area and other central Boston colleges and universities. This is a newly renovated 2 bedroom unit with 2 bathrooms on the first floor for parties up to 7 people (convertable couches) in a quiet and peaceful Irish suburban community. Driveway and street parking is always available. About an 11 minute walk to the nearest commuter rail line. Laundry access in the basement. No indoor smoke and no open flames, fines will be issued if caught.
4.95 out of 5 average rating, 176 reviews
Modern home 22 min Boston, 20 min Gillette Stadium
Experience New England charm in this luxury home, with over 3,500 sq. feet of living space. This home has many unique characteristics that includes a Koi pond, a majestic backyard and an indoor sauna to make your short term or long term stay more comfortable. It's located in a quiet neighborhood that is walking distance to Glen Echo Park, where hiking, and fishing is available. It's 2 min away from shops, major highways, and has a 6-car driveway and limited on-street parking. Pet friendly!
4.92 out of 5 average rating, 160 reviews
Entire home 3 miles from Gillette, sleeps 7.
Large yard, great for pets, this 3 BR/5 bed, well maintained home is situated 30 Minutes to Boston & Providence RI, 3 miles to Gillette Stadium & the commuter rail. Home is surrounded by many Pine trees, set back from the main road, on corner of a Cul de Sac good for walking and peace and quiet. Everything you need should be there, this was family's private residence now an Airbnb. Sit back & relax in the yard listening to the birds & enjoying nature all while being minutes to everything!
4.89 out of 5 average rating, 114 reviews
Quiet & Cozy 4 BR in Metrowest- 25 mins to Boston
Keep it simple at this peaceful and centrally-located home. Cozy, quiet & clean 4 bedroom and 2 bathroom home conveniently located in the Metrowest area- 25 minutes to Boston. Situated in a very quiet neighborhood, close to grocery stores, restaurants and shopping. Guests will have access to the entire home excluding the garage. * Free parking * Free high speed internet/WiFi * Premium Cable channels * Basic cookware & dinnerware * Access to free Washer & Dryer * Keypad Entry System
4.94 out of 5 average rating, 186 reviews
Spacious 4 bedroom home with large yard
Private and clean renovated 4 bedroom house in "Safest Town" in Massachusetts, 25 minutes from Boston. Perfect for families or travelers wanting extra space. Sleeps 8 comfortably in 4 bedrooms. Pets are completely welcome! Lots of walking trails nearby. Connected to another unit and shares the large backyard. Kids will enjoy the swingset. Lake Chochituate is near with canoe, kayak, and swimming. Close to MassPike, Rt.30 & 27, and many colleges and MetroWest office parks.
4.89 out of 5 average rating, 133 reviews
Harvard House-The Gathering Place.
HARVARD HOUSE - The Gathering Place--- Winter Specials for single rooms Jan-March-20% off A magical atmosphere ideal for small weddings, birthdays, graduations, celebrations of life. team building "Harvard House is an amazing place, it helped our family renew the ties that bind." "The team created a shared vision, conflicts got ironed out, we built a rallying momentum." "Our wedding at Harvard House was amazing." "Our group split the costs which made it affordable."
4.94 out of 5 average rating, 111 reviews
The Brickhouz at Arlington !
Just a little bit of everything for everyone to have a spectacular time in Boston, perfect for family gathering ! A funky and quirky cozy 4-bedroom brickhouse smack right in the middle of Arlington Center. 10 mins to Harvard Square, 15 minutes to Boston and Logan airport. Sleeps 8 - 2 bathrooms. Short 1 minute walk to cafes and restaurants. Discounts available for longer stays. Strictly no parties or unapproved pets.
4.99 out of 5 average rating, 118 reviews
Beautiful, Clean & Quiet 2 BR- 15 min to BOSTON
SUNNY, CLEAN 2 bedroom with updated kitchen (granite counter top) and bathroom. Minutes to vibrant Moody Street for restaurants (great selection range from good old American food to Asian), local homemade ice cream shop, shops and a movie theater. Quiet, convenient location- 15 minutes to Boston and close to Brandeis University, Regis College, Bentley College and Lasell College. FREE PARKING, WiFi and WASHER & DRYER.
4.78 out of 5 average rating, 497 reviews
Cozy, historic 3 bedroom home close to Boston!
Welcome to our cozy home. Our place blends historic charm with modern comfort. Enjoy a large, fenced yard with a grill, fire pit, and deck to relax. Inside, you'll find a well-equipped kitchen and a dining room. We offer three bedrooms with comfortable mattresses and soft bedding. The living room has a big TV with cable and streaming apps, plus high-speed Wi-Fi. Families with dogs are warmly welcomed.
4.98 out of 5 average rating, 303 reviewsPopular amenities for house rentals in Wellesley
House rentals with a pool

Spacious vacation unit in premium suburban town
4.97 out of 5 average rating, 120 reviews
Hopkinton Mass 3+ Bedrooms - Great location!
4.95 out of 5 average rating, 179 reviews
Gather, Cook & Unwind, 3BR, Fireplace
4.97 out of 5 average rating, 132 reviews
Great country getaway
4.87 out of 5 average rating, 187 reviews
Luxury Boston Ranch –Sleeps 8|Pet+|Heated pool
4.84 out of 5 average rating, 56 reviews
Spacious quiet Newton Villa *Easy Boston Access!
5.0 out of 5 average rating, 42 reviews
Explore Boston in style! Dream home (STR-26-3)
4.95 out of 5 average rating, 91 reviews
Private/Quiet Single Family Home
4.94 out of 5 average rating, 84 reviewsWeekly house rentals

Gorgeous 2nd Floor Home with Private Entry
4.95 out of 5 average rating, 111 reviews
1BR Sunlit 2-Story | Boston 25 Min | Free Parking
4.9 out of 5 average rating, 268 reviews
All the comforts of home, quiet city neighborhood
4.93 out of 5 average rating, 385 reviews
The Red Door Carriage House
4.98 out of 5 average rating, 276 reviews
Now availJamaica Plain & Arboretum 20min toBoston
4.89 out of 5 average rating, 182 reviews
Arlington Playhouse: 5BR/3BA w/ Elite Game Suite
4.93 out of 5 average rating, 100 reviews
Wellesley Spacious and Modern
5.0 out of 5 average rating, 35 reviews
Quiet Entire House 2Br/2Ba Walk to Train/Colleges
4.72 out of 5 average rating, 18 reviewsPrivate house rentals

Elegant Chestnut Hill Home
4.86 out of 5 average rating, 59 reviews
Family-Friendly 4BR Near Boston, Walk to Moody St
4.94 out of 5 average rating, 17 reviews
Elegant 4BR Retreat | Yard & Parking | Dedham 94
4.97 out of 5 average rating, 29 reviews
Very nice home close to Boston
4.82 out of 5 average rating, 68 reviews
Entire House:Home Away Home
5.0 out of 5 average rating, 29 reviews
Walk to Restaurants & Park - Charming Cottage
4.95 out of 5 average rating, 64 reviews
Garden Paradise Retreat in Marlboro
5.0 out of 5 average rating, 27 reviews
Single Family Boston House Great Privacy
4.9 out of 5 average rating, 58 reviewsWhen is the best time to visit Wellesley?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | €79 | €59 | €79 | €80 | €84 | €145 | €122 | €79 | €79 | €87 | €116 | €79 |
| Avg. temp | -3°C | -2°C | 2°C | 8°C | 14°C | 19°C | 22°C | 22°C | 18°C | 11°C | 6°C | 0°C |
Destinations to explore
- Fenway Park
- Hampton Beach
- Harvard University
- TD Garden
- Boston Seaport
- Gillette Stadium
- Boston Common
- Revere Beach
- Boston University
- Boston Convention and Exhibition Center
- Freedom Trail
- New England Aquarium
- Boston College
- Northeastern University
- Canobie Lake Park
- Duxbury Beach
- MIT Museum
- Harvard Square
- Tufts University
- Crane Beach
- Quincy Market
- Snhu Arena
- Massachusetts Institute of Technology
- Saquish Beach





