House vacation rentals in Wellesley

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Top-rated house rentals in Wellesley

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Top guest favorite
The exterior of a two-level home is depicted, surrounded by lush green lawns and mature trees. A pathway leads to the welcoming entrance, flanked by garden beds featuring various plants. The house features a traditional design with large windows allowing for ample natural light.
Home in Holliston
4.97 out of 5 average rating, 112 reviews

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.

Guest favorite
A stone fireplace is framed by a slate hearth and topped with a white shelf displaying framed photographs. Adjacent, a small black table stands with a decorative plant. Light wood flooring extends into the background, leading to a room with a radiator and a sideboard.
Home in Dedham
4.93 out of 5 average rating, 118 reviews

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.

Top guest favorite
A welcoming living area features a gray sofa and a green couch, complemented by a patterned area rug. A television sits on a stand against the wall, while indoor plants add a touch of greenery. Natural light illuminates the space from well-placed ceiling lights.
Home in Newtonville
4.95 out of 5 average rating, 147 reviews

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.

Top guest favorite
A comfortable seating area is highlighted by two stylish armchairs and a soft sofa. Natural light filters through large windows that overlook the greenery outside. A modern rug is placed on the wooden floor, complementing the decor, while a lamp and coat rack add functional touches.
Home in Framingham
4.97 out of 5 average rating, 103 reviews

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.

Guest favorite
A cozy living room is highlighted by wood paneling and exposed beams. Plush seating includes a sofa and two armchairs. A coffee table is centered in the space, with a television displaying programming. Natural light fills the room through multiple windows adorned with soft curtains.
Home in Brighton
4.93 out of 5 average rating, 351 reviews

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.

Superhost
A modern living room features a sleek fireplace beneath a wall-mounted television. Two stylish blue armchairs complement a sectional sofa adorned with textured cushions. A geometric rug anchors the space, and natural light flows in through large sliding doors that lead to a balcony.
Home in Watertown
4.88 out of 5 average rating, 116 reviews

Luxury large house minutes to Cambridge and Boston

Whether you looking for a vacation house or just work from home, call this perfect luxury house your home! Wonderfully located, spacious and comfortable house for all. The house has fully equipped kitchen, chef grade appliances, TV/Game room. There are four bedrooms, two full baths and two half baths, TV room and work from home desk setup. The home also has a beautiful backyard with outdoor furniture for you to relax and enjoy. FREE PARKING driveway for 2 cars, and inbuilt with Tesla charger

Top guest favorite
The living room features two dark leather sofas arranged around a circular glass coffee table. Natural light enters through large windows adorned with light-colored drapes. A mirror on the wall complements the warm beige walls, enhancing the space's cozy atmosphere.
Home in Wayland
4.93 out of 5 average rating, 170 reviews

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

Guest favorite
A modern kitchen area is presented with wooden cabinetry and black appliances, including a refrigerator and microwave. A dining table with place settings is visible, alongside a cozy living area featuring a leather sofa and a ceiling fan overhead.
Home in Framingham
4.97 out of 5 average rating, 146 reviews

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

Top guest favorite
The kitchen area features a modern design with a sleek, round dining table surrounded by four transparent chairs. Stainless steel appliances, including a refrigerator and stove, are present, complemented by wooden cabinetry. Natural light enters through a window, illuminating the polished hardwood floor.
Home in Brighton
4.87 out of 5 average rating, 226 reviews

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.

Superhost
Home in Cochituate
4.89 out of 5 average rating, 115 reviews

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.

Guest favorite
A single-story home is nestled among green trees, featuring a light-colored exterior with red shutters. The driveway leads to the front door, surrounded by well-maintained landscaping and a grassy lawn.
Home in Framingham
4.95 out of 5 average rating, 101 reviews

Quiet Northside Home in Framingham

This quiet three bedroom home with 1.5 baths has a full kitchen. You can enjoy breakfast in the kitchen nook and more substantial meals in the dining room. Two separate living spaces—a living room and a large family room with Smart TV and office area—allow group members to pursue different activities. The main bedroom has an attached half bath for privacy. The quiet residential neighborhood has two parks and hiking trails just a few blocks away.

Top guest favorite
A two-story white house features a welcoming front porch and black shutters. Lush greenery surrounds the property, with a well-kept lawn and flower beds. A pathway leads from the road to the entrance, and a driveway is visible beside the house.
Home in Dedham
4.98 out of 5 average rating, 274 reviews

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 Wellesley house rentals

When is the best time to visit Wellesley?

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Avg. priceG$19,053 GYDG$19,053 GYDG$29,312 GYDG$29,312 GYDG$31,406 GYDG$29,312 GYDG$29,312 GYDG$19,053 GYDG$19,053 GYDG$29,312 GYDG$29,312 GYDG$19,053 GYD
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Quick stats about house rentals in Wellesley

  • Total vacation rentals

    Explore 40 vacation rentals in Wellesley

  • Nightly prices starting at

    Wellesley vacation rentals start at G$6,281 GYD per night before taxes and fees

  • Verified guest reviews

    Over 1,880 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space & kid-friendly amenities

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    40 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!