
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 £30 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 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.

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

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

Premium Condo 2B1.5B in Newton 30+ Day
Minimum stay is 30 days. This fully furnished 2-3 beds and 2.5 bath duplex condo is ideal for comfortable extended stays. The home offers spacious living areas and flexible sleeping arrangements, suitable for families, professionals, and graduate students seeking stable monthly housing. The upper level includes 2 bedrooms and 1.5 bathrooms, with an additional bedroom and full bath on the lower level available based on occupancy. Utilities and WiFi are included for a convenient long-term stay.

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.

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

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.

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."

Gorgeous 2nd Floor Home with Private Entry
Welcome to your home away from home! This beautiful second-floor 2 BR unit keyless self check in offers a private entrance and private stairs. Features: · Newly Installed AC · Fully Kitchen: Equipped with smart utilities, including an oven, microwave, dishwasher, washer, and dryer. · High-speed internet. · Comfortable Sleeping Arrangements: 2 beds & a sofa bed, perfect for accommodating up to 4 guests.

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.

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.

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.
Popular amenities for house rentals in Wellesley
House rentals with a pool

Spacious vacation unit in premium suburban town

Hopkinton Mass 3+ Bedrooms - Great location!

Gather, Cook & Unwind, 3BR, Fireplace

Great country getaway

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

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

Spacious quiet Newton Villa *Easy Boston Access!

Metrowest Family Retreat
Weekly house rentals

All the comforts of home, quiet city neighborhood

Stone Cottage with meadow view

Entire home 3 miles from Gillette, sleeps 7.

Modern home 22 min Boston, 20 min Gillette Stadium

1BR Sunlit 2-Story | Boston 25 Min | Free Parking

Now availJamaica Plain & Arboretum 20min toBoston

Wellesley Spacious and Modern

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

Family-Friendly 4BR Near Boston, Walk to Moody St

Spacious Victorian Home | Family + Pet Friendly

Very nice home close to Boston

Elegant Chestnut Hill Home

Elegant 4BR Retreat | Yard & Parking | Dedham 94

Garden Paradise Retreat in Marlboro

Walk to Restaurants & Park - Charming Cottage

New modern cozy 3BR condo: free parking&near train
When is the best time to visit Wellesley?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £67 | £50 | £67 | £68 | £71 | £123 | £103 | £67 | £67 | £74 | £98 | £67 |
| 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
- Gillette Stadium
- Boston Seaport
- Boston Common
- Revere Beach
- Boston University
- Boston Convention and Exhibition Center
- Freedom Trail
- New England Aquarium
- Canobie Lake Park
- Boston College
- Northeastern University
- MIT Museum
- Duxbury Beach
- Crane Beach
- Tufts University
- Quincy Market
- Harvard Square
- Roger Williams Park Zoo
- Saquish Beach
- Snhu Arena





