House holiday rentals in Wellesley

Find and book unique houses on Airbnb

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 $67 NZD per night before taxes and fees

  • Verified guest reviews

    Over 1,880 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space and kid-friendly amenities

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    50 of Wellesley holiday 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!

Top-rated house rentals in Wellesley

Guests agree: These houses are highly rated for location, cleanliness and more.

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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
4.98 out of 5 average rating, 138 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.

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
4.98 out of 5 average rating, 135 reviews

Cozy en suite w/ high ceilings

 Relax in this peaceful private en-suite with breathtaking backyard views of the tall pine forest. 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. Just 25 min to Boston, 40 min. to Gillette Stadium. Enjoy shopping at the Natick Mall, AMC movies, tons of diverse dining & grocery options. Backyard has firepit for outdoor eves. Very safe walkable neighborhood

Guest favourite
A welcoming entryway showcases a wooden staircase leading to the upper levels. The space is enhanced by decorative topiary arrangements and features light-colored flooring providing a bright ambiance. Natural light emanates from a nearby doorway, revealing glimpses of the outdoor area.
Home in Stoughton
4.93 out of 5 average rating, 156 reviews

Modern home 22 min Boston, 20 min Gillette Stadium

Experience New England charm in this luxury home, with over 3,500 sq. feet of living space. This home has many unique characteristics that includes a Koi pond, a majestic backyard and an indoor sauna to make your short term or long term stay more comfortable. It's located in a quiet neighborhood that is walking distance to Glen Echo Park, where hiking, and fishing is available. It's 2 min away from shops, major highways, and has a 6-car driveway and abundance on-street parking. Pet friendly!

Top Guest favourite
A view of the calm water on Mirror Lake is framed by a flower-lined, stone patio leading to a wooden dock. The water reflects the greenery from the surrounding trees under a clear blue sky.
Home in Wrentham
4.96 out of 5 average rating, 106 reviews

Relaxing Waterfront Lakehouse, 10 min to Gillette

Relax at this peaceful, family-friendly lake house on Mirror Lake. Fully renovated 3-bedroom, 2 full bath getaway directly on the water with private deck, dock, patio area, propane grill, paddle boards, kayak, fishing, and more. Located nearby Gillette Stadium, Patriot Place, Wrentham Premium Outlets, Plainridge Park Casino, an abundance of restaurants, wedding venues, walking trails and central to Boston or Providence, this is a great location for many activities or just lounging by the water.

Superhost
A spacious living room features a large flat-screen TV mounted on the wall, set against light-colored walls. A glass-top coffee table sits on a decorative rug, and a white leather sofa is positioned nearby. Soft natural light enters through large windows, enhancing the inviting atmosphere.
Home in Framingham
4.78 out of 5 average rating, 100 reviews

Newly Renovated 3 Bed 2 Bath Easy Access Boston

Welcome to our newly renovated beautiful home in Greater Boston Designed for comfort and convenience, this home is perfect for families, business travelers and groups looking for a retreat ✔Sleeps 8 : 3 Queens + 2 Sofa beds (correct # of people & pets are enforced) ✔5m Stop & Shop + LifeTime Fitness ✔15m Wellesley College ✔25m --> Downtown ✔10 m--> Remote Logan Terminal ✔27 m--> BOS Airport ✔New appliances + smart TV, bluetooth speaker ✔Private patio ✔Garden ✔Driveway parking ✔Pet friendly

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 Newton
4.95 out of 5 average rating, 174 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
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, 184 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

Top Guest favourite
A bright yellow two-family home is positioned amidst greenery, featuring a welcoming entry with a red door. A small flowering tree adds a splash of color in front, while a large deck is visible in the background, perfect for outdoor gatherings.
Home in Chelmsford
5.0 out of 5 average rating, 259 reviews

Newly renovated, spacious, clean, 3 bedroom home.

Whether traveling for business or pleasure, this ideally located, pet-friendly home in North Chelmsford, Massachusetts, is accessible to major highways and commuter rails. The home is close to major hospitals, universities, and concert venues. The area is rich in America’s history and is surrounded by historical sites to visit all within minutes. The beautiful, light, airy living space boasts all the comforts of home. Our goal is to give you the best travel experience possible.

Top Guest favourite
A charming Victorian-style home is surrounded by lush greenery and well-maintained landscaping. The blue exterior features decorative trim near the porch, which is equipped with seating. Pathways lead through the front yard, adding to the welcoming ambiance of the property.
Home in Hyde Park
4.94 out of 5 average rating, 150 reviews

BEAUTIFUL SINGLE FAMILY VICTORIAN in Hyde Park!

Meticulously renovated 1873 Victorian on a sheltered street in the Hyde Park area of Boston. Enjoy over 2000 sq ft, as well as a grill and patio in the private backyard! Our cats will NOT be home during your stay. However, even though it is professionally cleaned before every stay, it's important for people with allergies to know that this is a cat house. Our home is professionally cleaned before every stay. We are completely committed to following Airbnb's Cleaning Protocol.

Guest favourite
Home in Wayland
4.9 out of 5 average rating, 132 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
The exterior of a Victorian-era home is surrounded by lush greenery, with vibrant flowers lining the pathway. A spacious porch is visible, framed by tall trees, inviting guests to enjoy the natural setting. A gravel driveway leads to the welcoming entrance.
Home in Waltham
4.94 out of 5 average rating, 108 reviews

Harvard House-The Gathering Place.

HARVARD HOUSE - The Gathering Place--- Winter Specials for single rooms Jan-March-20% off A magical atmosphere ideal for small weddings, birthdays, graduations, celebrations of life. team building "Harvard House is an amazing place, it helped our family renew the ties that bind." "The team created a shared vision, conflicts got ironed out, we built a rallying momentum." "Our wedding at Harvard House was amazing." "Our group split the costs which made it affordable."

Guest favourite
The living area is furnished with a soft sofa and decorative throw pillows, complemented by a patterned area rug. Natural light enters through sheer curtains, creating a bright and welcoming ambiance. A dining table with wooden chairs is visible in the adjoining space.
Home in Waltham
4.78 out of 5 average rating, 493 reviews

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 Wellesley house rentals

When is the best time to visit Wellesley?

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Avg. price$152 NZD$114 NZD$152 NZD$154 NZD$161 NZD$278 NZD$234 NZD$152 NZD$152 NZD$167 NZD$222 NZD$152 NZD
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