
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.

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.

All the comforts of home, quiet city neighborhood
Sleep peacefully in this beautiful home above Oak Square>Brighton>Boston. Updated, comfortably furnished, well-stocked with electronics, appliances, and housewares. Driveway parking spot. Ideal for couples, solo adventurers, and business travelers with auto or use ride services. Laundry service one mile away. Newbury Street: 8 miles away, North End: 9 miles, Seaport: 9 miles, Logan airport: 11 miles. Close to BC/Harvard; 1 mile from I-90/Mass Pike in Newton Corner, restaurants, attractions.

1BR—Bright & Cozy 2-Level Place — 25 Min to Boston
800ft² 1-Bedroom, 2-Level Apartment Private Rental @ our 3-Rental Property 1st Floor: —Fully Equipped Granite Kitchen w/Dishwasher + Essentials & Cookware —Living Room w/Queen Sofa Bed + Dining Table 2nd Floor: —Bedroom - Memory Foam Queen Bed —Full Length Mirror —Desk & Chair + Dresser —Bathroom - Shower/Tub Backyard Patio Laundry Room (Basement) Driveway Parking 25 min to Boston 15 min walk to Train 5 min walk to Jack’s Abby Brewery 3 min walk to Park/Playground Deep Cleaned & 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.

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.

Pretzel Factory Loft w/Peloton
Creative loft style house that is home to a fashion designer and her family! Two floor loft like living very centrally located in Brookline MA. Very centrally located in Brookline Village. A few minutes walk to the T and very close to the hospital district. Whole house perfect for the whole family with fast Wifi and garage parking. Search for 'Everywhere Architecture' & click on 'White Place' to see more pictures!

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.

Convenient 2BR Condo W/Private Parking in Newton
This is a duplex condo that can comfortably accommodate two families. The upper level has 2 bedrooms and 1.5 bathrooms, suitable for 2–4 guests. The lower level (basement) has 1 bedroom and 1 bathroom, also suitable for 2–4 guests. If you would like to use the basement space, please let us know in advance. The basement suite will be opened for group of 5 guests or more.

Absolutely Gorgeous 3 Bedroom Close to Boston
Enjoy a stylish experience at this recently-renovated, modern 3-bedroom apartment. Centrally-located, modern, bright and located in a historic Boston suburb on a quiet, private-way with plenty of free, off-street parking and within walking distance to the town center, river walk, bike paths and dog park.
Popular amenities for Wellesley house rentals
House rentals with a pool

Nana-tucket Inn

Hopkinton Mass 3+ Bedrooms - Great location!

Bauhaus Retreat in Nature Preserve w/ Pool

Courtyard Garden | Pool | BBQ+Fire Tbl | Fireplace

the house of id; vintage shop, accessible space

Spacious vacation unit in premium suburban town

Hidden Gem near Boston w/ Private lake access

Quiet/Private Neighborhood
Weekly house rentals

Elegant Guest suite Wellesley

New modern 2bd condo: free parking/near train

Large Home•PERFECT Location for FIFA WC & Boston!

94_Elegant 4BR Home w/Yard & Ample Parking, Dedham

Bright mid-century modern 4 bedroom 3 bath beauty

Lake Cochituate Waterfront Home

Private Home

Charming Studio.
Private house rentals

Spacious & Pet-Friendly Modern Home in Charlestown

The Grand Residence

Charming Boston Single Fam Home Near Commuter Rail

Charming Victorian home in desirable Boston suburb

Sea Forever - Oceanfront Home in Nahant!

Lakefront Beauty with Hot Tub

Stylish Retreat in Historic Quincy | Pet Friendly

Very nice home close to Boston
When is the best time to visit Wellesley?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $158 NZD | $158 NZD | $243 NZD | $243 NZD | $260 NZD | $243 NZD | $243 NZD | $158 NZD | $158 NZD | $243 NZD | $243 NZD | $158 NZD |
| 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 40 holiday rentals in Wellesley

Nightly prices starting at
Wellesley holiday rentals start at $52 NZD per night before taxes and fees

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

Family-friendly holiday rentals
10 properties offer extra space and kid-friendly amenities

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
40 of Wellesley holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Wellesley rentals

4.8 Average rating
Wellesley stays are highly rated by guests—averaging 4.8 out of 5!
Destinations to explore
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- Hampton Beach
- Fenway Park
- TD Garden
- Boston Common
- Harvard University
- Revere Beach
- Brown University
- Lynn Beach
- MIT Museum
- New England Aquarium
- Freedom Trail
- Good Harbor Beach
- Canobie Lake Park
- Duxbury Beach
- Crane Beach
- Museum of Fine Arts, Boston
- Quincy Market
- Prudential Center
- Oakland Beach
- White Horse Beach
- Roger Williams Park Zoo
- Franklin Park Zoo
- Salem Willows Park
- Symphony Hall




