House holiday rentals in Wellesley

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Top-rated house rentals in Wellesley

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Top Guest favourite
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, 111 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 favourite
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 favourite
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 favourite
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 favourite
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.

Top Guest favourite
A fully equipped kitchen is shown, featuring stainless steel appliances including a refrigerator, microwave, and dishwasher. Granite countertops provide ample workspace, while natural light filters through the two windows above the sink. A coffee maker sits on the counter, adding to the amenities.
Home in Framingham
4.9 out of 5 average rating, 253 reviews

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

Top Guest favourite
A cozy living area is presented, featuring a modern black sofa and two soft pink ottomans. Natural light streams in through the window, illuminating the space. Decorative shelves with plants and artwork add a touch of greenery and charm to the room.
Home in Stoneham
4.93 out of 5 average rating, 308 reviews

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.

Superhost
Home in Cochituate
4.89 out of 5 average rating, 114 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 favourite
A spacious living area features a mix of comfortable seating, including a large sofa and a cozy armchair. Natural light streams through multiple windows covered with woven shades. Shelves filled with books and decorative items line one wall, while a light-colored rug adds warmth to the concrete floor.
Home in Brookline Village
4.92 out of 5 average rating, 151 reviews

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!

Top Guest favourite
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.

Guest favourite
A dining area is shown with a long wooden table set with neutral placemats. Four tan chairs surround the table, and a decorative flower arrangement is placed at its center. Natural light filters through three large windows, framed by soft gray shades.
Home in West Newton
4.91 out of 5 average rating, 175 reviews

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.

Top Guest favourite
A modern living area is furnished with a sectional couch and a vibrant red chair. A large television is mounted on the wall above a dark wood entertainment unit, which holds decorative items. Wooden floors and recessed lighting contribute to a bright and welcoming environment.
Home in Watertown
4.96 out of 5 average rating, 138 reviews

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

When is the best time to visit Wellesley?

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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
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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!