
House holiday rentals in Wellesley
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Top-rated house rentals in Wellesley
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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.

~*Pet Friendly 30min to Downtown*~ THE BOSTONIAN
Relax in the Bostonian, a stylish, pet-friendly apartment on the semi-basement level of a charming multi-family house. The apartment is air conditioned & overlooks a beautiful patio and backyard. Located in quiet Hyde Park neighborhood, a 30 minute drive into downtown Boston. Plenty of free streetside parking. Private in unit laundry. Professionally cleaned. Room 1: Queen size bed Room 2: Queen size bed Room 3: Living room couch, TV, electric fireplace Dining room: includes two wall arcades

1000sf 2 Bed Condo Near Tufts, Harvard & Train
Welcome to The University Retreat, our spacious 1,000 SqFt condo just minutes from Davis Square, Tufts, and Harvard University. This centrally-located apartment is the perfect home base for your next visit to Boston. ✔ 7-min walk to Davis Square and MBTA train stop ✔ Less than 15 mins to Tufts, Harvard University, and MIT ✔ Walk outside to some of Boston's best restaurants ✔ Focused office space with high-speed internet ✔ On-street visitor parking permit available for a fee [message host]

Cozy house close to Boston
My home is very comfortable with a casual feel. I have three bedrooms with 1.5 bathrooms. I have two queen size beds and one twin size bed. My kitchen and bathrooms are updated. I have a cozy den with a Smart TV and a living room that is a comfortable place to relax. The outdoor area has a deck leading onto a patio with a fire pit. I have an outdoor gas grill. It's a great place to unwind and relax. It is fenced in with privacy. I also have a driveway and on street parking is available.

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.

Cozy en suite w/ high ceilings
 Relax in this peaceful private en suite with breathtaking backyard views of the tall pine forest. Lots of 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. 25 min to Boston. 30 min. to Foxboro Stadium. Enjoy shopping at the Natick Mall, AMC movies, tons of diverse dining & grocery options. Backyard has firepit for outdoor eves. Safe walkable neighborhood.

2BR Lovely 1900s Home | 25 Min to Boston | 1200ft²
Welcome to our Charming 1900s House! 1200ft² 2nd/Top Floor Private Apartment @ our 3-Rental Property ⭐️Children 12+ Welcome⭐️ Granite Kitchen w/Dishwasher —Fully Equipped w/ Essentials & Cookware Tiled Bathroom w/Bath & Shower 2 Queen Bedrooms 2 Desks & Chairs Recliner Sofa & Glider Loveseat Dining Room for 6 Private Entrance Driveway Parking—2 Spots Laundry in Basement 25 Min Drive to Boston 15 Min Walk to Train 5 Min Walk to Jack's Abby 3 Min Walk to Park Deep Cleaned & Fully Sanitized

Entire Apartment in Stoneham
Welcome to our cozy, beautiful, and well-equipped home—your perfect retreat in the heart of Stoneham. Wake up in this bright and inviting apartment, just 20 minutes from the airport and the historic city of Boston. You’ll be conveniently close to shopping malls, restaurants, coffee shops, grocery stores, and the stunning nature of Middlesex Fells Reservation and Stone Zoo. Whether you’re here to explore or unwind, this charming home will make your trip both enjoyable and stress-free.

Treetop Haven in the City
This is a sweet, cozy space that is not fancy but homey. You will have everything you need for a comfortable stay including a complete kitchen with everything you will need to make your own meals. We are conveniently located, near the subway and buses, supermarkets, restaurants, and coffee shops. We are within two blocks of the jewel of the Emerald Necklace, Jamaica Pond, and other green spaces. Read our reviews so you can see what previous guests have loved about Treetop Haven.

Stunning urban hideaway nearby Harvard Square
Charming apartment in a 19th century Victorian house conserves its period architectural details in recently renovated comfort. Light streams into this en-suite guest residence through gracious windows. Beautiful cabinetry and bookcases offer some evening reading. Enjoy the marble bathroom and hardware floors and well-appointed kitchenette. A stone's throw from Porter Square, where bars, cafes, boutiques, and transportation options abound. Minutes to Harvard, MIT and Boston.

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.

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

Elegant & Spacious~Easy Boston Access! STR-25-22

Hopkinton Mass 3+ Bedrooms - Great location!

Bauhaus Retreat in Nature Preserve w/ Pool

Beautiful Spacious 4BRM House!

the house of id; vintage shop, accessible space

Spacious vacation unit in premium suburban town

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

Hidden Gem near Boston w/ Private lake access
Weekly house rentals

The Enchanted Willow Storybook Boston Escape 3BDR

Elegant Guest suite Wellesley

New modern 2bd condo: free parking/near train

3 bed, in unit laundry, central air, parking

The Cozy Colonial - 4 BDRM house with parking

Pvt Bedrm/Bathrm/Kitch'ette on Quiet Tree Lined St

Now availJamaica Plain & Arboretum 20min toBoston

Beautiful appartement - quiet location - downtown
Private house rentals

Charming Boston Single Fam Home Near Commuter Rail

Union Haus - Entire Home|2 King Suites|sleeps 12

Charming Victorian home in desirable Boston suburb

Quiet 1BR • Wi-Fi • Parking Included • In Randolph

Very nice home close to Boston

Cozy studio in calm neighborhood

The Brickhouz at Arlington !

The Salty Witches Cottage
When is the best time to visit Wellesley?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £67 | £67 | £103 | £103 | £111 | £103 | £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 |
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 £22 per night before taxes and fees

Verified guest reviews
Over 2,000 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!
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- Hampton Beach
- TD Garden
- Fenway Park
- Harvard University
- Boston Common
- Revere Beach
- Brown University
- Boston University
- Freedom Trail
- New England Aquarium
- Boston Seaport
- MIT Museum
- Boston Convention and Exhibition Center
- Canobie Lake Park
- Crane Beach
- Gillette Stadium
- Duxbury Beach
- Museum of Fine Arts
- Quincy Market
- Prudential Center
- Roxbury Crossing Station
- Roger Williams Park Zoo
- Boston Children's Museum
- Symphony Hall




