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

Total vacation rentals
Explore 50 vacation rentals in Wellesley

Nightly prices starting at
Wellesley vacation rentals start at $40 per night before taxes and fees

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

Family-friendly vacation rentals
20 properties offer extra space & kid-friendly amenities

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wi-Fi availability
50 of Wellesley vacation rentals include wi-fi 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.

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
ValueFamilyAmenities

All New Private Country Setting (2 Level-No Share)
We built this 2 level home 6 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.
FamilyValueOutdoor spaces

1BR Loft | 25 Mins to Boston | Quiet Neighborhood
Welcome to The Loft! 100% Private 1-Bedroom Place Queen Bed — Pillowtop Mattress Full Kitchen — Stove, Fridge, Dishwasher, Pots/Pans, Utensils & Essentials Dining Area — Table & Chairs Living Room — Leather Sofa 49" SmartTV — Netflix + Sling Live TV Bathroom — Shower, Plush Towels & Natural Bath Products Private 2nd Floor Entrance Heated Outdoor Stairs Your Own Driveway Quiet & Safe Neighborhood Deep Cleaned & Sanitized 2 Min Walk to Park 25 Mins to Boston Easy Access —Route 9 & 90-Mass Pike
LocationFamilyQuiet

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 abundance on-street parking. Pet friendly!
LocationFamilyView

Relaxing Waterfront Lakehouse, 10 min to Gillette
Relax at this peaceful, family-friendly lake house on Mirror Lake. Fully renovated 3-bedroom, 2 full bath getaway directly on the water with private deck, dock, patio area, propane grill, paddle boards, kayak, fishing, and more. Located nearby Gillette Stadium, Patriot Place, Wrentham Premium Outlets, Plainridge Park Casino, an abundance of restaurants, wedding venues, walking trails and central to Boston or Providence, this is a great location for many activities or just lounging by the water.
FamilyValueTV

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!
LocationValueWifi

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.
ValueLocationHeating

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."
FamilyLocationParking

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.
LocationValueHeating

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.
ValueLocationCheckout

Now availJamaica Plain & Arboretum 20min toBoston
Bright and sunny 2-bedroom retreat with a fully equipped kitchen, spacious bath with rain shower and tub, and TVs in each room. Enjoy fresh coffee daily with espresso maker, milk steamer, and grinder provided. Including a blender..A selection of teas .WiFi and off-street parking included. Private, peaceful, and filled with natural light—perfect for relaxing mornings and cozy evenings!
FamilyLocationBathroom

Across the Subway · TD Garden · Concerts · Games F
Escape to our stylish and comfortable home retreat, conveniently located across the street from the "T" Oak Grove Subway Station, MBTA. Here for a concert or a sports game? Only a 14 minute ride to the TD Garden, North Station! Unwind in our King Sized Primary Bedroom, and 2 cozy Queen-sized themed bedrooms.
ValueLocationGrill
Popular amenities for Wellesley house rentals
House rentals with a pool

Spacious vacation unit in premium suburban town
LocationFamilyAccess

Courtyard Garden | Pool | BBQ+Fire Tbl | Fireplace
FamilyValueQuiet

Hopkinton Mass 3+ Bedrooms - Great location!
LocationValueAmenities

Great country getaway
FamilyValueCondition

the house of id; vintage shop, accessible space
LocationFamilySleep quality

Luxury Boston Ranch –Sleeps 8|Pet+|Heated pool
ValueFamilyAmenities

Explore Boston in style! Dream home (STR-26-3)
FamilyValueCheck-in

Theatre | Arcade | Pool w. Free 3 Car Parking
LocationFamilyCleanliness
Weekly house rentals

sweet little house
ValueLocationGetting around

Newly renovated, spacious, clean, 3 bedroom home.
LocationFamilyLayout

Quiet & Cozy 4 BR in Metrowest- 25 mins to Boston
LocationValueIndoor spaces

Newly Renovated Lovely 2 bedroom unit - Newton MA
LocationFamilyParks

Gorgeous 2nd Floor Home with Private Entry
FamilyLocationAccuracy

Private apartment close the city!
LocationValueBackyard

New! 2BR Home Metro West
LocationBackyardComfort

Quiet Entire House 2Br/2Ba Walk to Train/Colleges
FamilyLocationCleanliness
Private house rentals

Spacious Victorian Home | Family + Pet Friendly
FamilyLocationBackyard

Boston Buccaneer Retreat
LocationFamilyAmenities

New modern 2bd condo: free parking/near train
FamilyLocationLong stay

Entire House:Home Away Home
LocationFamilyGetting around

Your own cottage in the city
FamilyLocationBathroom

Luxury Retreat | Theater | Game Room | Garden Spa
LocationFamilyAccuracy

Cozy Stay at the Beautiful Water Front
LocationFamilyBathroom

Luxury 4BR Near Gillette | Games + Firepit
LocationFamilyCleanliness
When is the best time to visit Wellesley?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $91 | $68 | $91 | $92 | $96 | $166 | $140 | $91 | $91 | $100 | $133 | $91 |
| Avg. temp | 27°F | 29°F | 36°F | 47°F | 57°F | 66°F | 72°F | 71°F | 64°F | 52°F | 42°F | 33°F |
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- Fenway Park
- Harvard University
- Hampton Beach
- TD Garden
- Gillette Stadium
- Boston Seaport
- Boston Common
- Revere Beach
- Brown University
- Boston University
- Boston Convention and Exhibition Center
- Freedom Trail
- New England Aquarium
- Canobie Lake Park
- Boston College
- Northeastern University
- Duxbury Beach
- MIT Museum
- Crane Beach
- Tufts University
- Quincy Market
- Harvard Square
- Roger Williams Park Zoo
- Massachusetts Institute of Technology
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