
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.

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.

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.

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 & Cooking 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 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

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.

Comfortable house w garden and parking, close to T
The house is conveniently located 15-20 mins from downtown and 25 mins from the airport by taxi. There is a train and bus stations close by and there are lots of restaurants and stores (whole foods has everything) in a walking distance. There is a driveway parking that fits 3 cars. The house offers 7 sleeping places which is perfect for families and groups however there is no living room. Great place to stay with dogs as there is a backyard and lots of walking options.

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.

Private apartment close the city!
New couch! New towels and linens! Fresh paint! New flooring coming soon. I heard the feedback and am refreshing/updating everything! My goal is happy guests and I'll do my best to make that happen. This private apartment is part of my home but has a separate entrance, full bath, living room and private bedroom. We're in a family neighborhood close to the city, and very convenient for those visiting with a car.

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 6 guests or more.

Lake home
Enjoy the lake view from the dining room, living room and bedroom! There is a deck with a BBQ, full kitchen, 1 bedroom and 1 bathroom. For 2 guests only please. No parties or gatherings allowed. The beach / dock will be shared the the tenant below. Use of kayaks, paddleboard and canoe is allowed.
Popular amenities for house rentals in Wellesley
House rentals with a pool

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

Pet-friendly 4-Bed Home w/Pool, Nature Trails

Hopkinton Mass 3+ Bedrooms - Great location!

Bauhaus Retreat in Nature Preserve

Beautiful Spacious 4BRM House!

the house of id; vintage shop, accessible space

Spacious vacation unit in premium suburban town

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

Spacious & Pet-Friendly Modern Home in Charlestown

Cozy Boston Homestead : Sleeps 8, Pet Friendly

Lux Townhouse Steps to T, Zen Patio + 4 Parking

The Cozy Colonial - 4 BDRM house with parking

The Most Stunning Leaf-peeping In The Country!

Boston Buccaneer Retreat

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

Bright mid-century modern 4 bedroom 3 bath beauty
Private house rentals

sweet little house

The Grand Residence

Charming Boston Single Fam Home Near Commuter Rail

Old Charm with Modern comfort near boston city

Charming Victorian home in desirable Boston suburb

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

Very nice home close to Boston

Gorgeous 2nd Floor Home with Private Entry
When is the best time to visit Wellesley?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $119 SGD | $119 SGD | $183 SGD | $183 SGD | $196 SGD | $183 SGD | $183 SGD | $119 SGD | $119 SGD | $183 SGD | $183 SGD | $119 SGD |
| 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 $39 SGD 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 & child-friendly amenities

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
40 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
- Fenway Park
- TD Garden
- Boston Common
- Harvard University
- Revere Beach
- Brown University
- Lynn Beach
- New England Aquarium
- MIT Museum
- Good Harbor Beach
- Duxbury Beach
- Freedom Trail
- Canobie Lake Park
- Crane Beach
- Museum of Fine Arts, Boston
- Quincy Market
- Oakland Beach
- Prudential Center
- White Horse Beach
- Roger Williams Park Zoo
- Salem Willows Park
- Franklin Park Zoo
- Symphony Hall




