
Family-friendly vacation rentals in Wellesley
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Wellesley
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

Cozy Private Studio Unit w/ Laundry and Parking!
Almost every guest describes my place as cozy, which was the feeling I was going for when I designed the space! You'll love this good sized 300 sq. ft PRIVATE 1 bedroom studio. This unit has its own entrance w/ punch code door, full bathroom, large walk-in closet, mini fridge, freezer and microwave. It has one parking spot in the driveway and a washer /dryer. The backyard is shared but the unit has a private patio. Rental is attached to a single family home. (Please note: No full kitchen)

Flower Farm Getaway 2BR, 20 Min To Boston
Spacious two-bedroom in-law suite attached to 1700âs farmhouse, situated on our small flower farm and garden co-op just 20 minutes from Boston. Only a mile from the Mass Pike & Rt. 128 (I-95). Centrally located to all Rt. 128 businesses, colleges & hospitals. A 7-min drive to Riverside Green line âDâ subway stop into Boston (parking available), or commuter rail stops (Auburndale, Wellesley & Kendal Green Stations). It's a 15-minute drive to Amtrak's "Route 128" station to NYC and points south.

Peaceful Country Home, Dover, Ma: Private Entrance
Graceful country oasis in a renovated 125 year old historic home, 35 minutes driving time from downtown Boston. (Important-stair climbing required to reach bedroom suite.) I welcome quiet, mature guests as this is a very peaceful (non-party)environment. We are located on a scenic road in sophisticated Dover, Ma, a commuter/country setting, with miles of hiking trails and roads ideal for cycling. I have owned and loved this home for 35 years and take great joy in its charm and outdoor spaces.

Country Charm minutes from the Hub - 1st Floor Apt
Private, smoke/pet-free 1st floor efficiency apartment with independent access for ONE PERSON ONLY at back of family home. Includes full bathroom, refrigerator, microwave, coffee maker + WiFi. All basic supplies provided. Driveway parking. Mins from MBTA transit including commuter rail. Laundry-room access for rentals of 7 nights ore more. Sorry, no vaping and no smokers - even if you smoke outside - because smoke odor on you or your clothes can be left in your wake in the room. No open flame.

Entire Historic Carriage House with Fireplace & AC
Escape to our charming Carriage House in the Historic District of Sherborn which offers the feel of a country retreat without being far from civilization. Great for travelers looking for a peaceful getaway, checking out nearby colleges or attending a celebration like a wedding or graduation. You will love the feel of the Carriage House, its spacious living and dining room, well-equipped kitchen, and the beautiful grounds. Check us out on IG @carriagehousema. NEW in 2022: Mini-split AC!

New Super Modern 2 bed in Waltham
A tastefully decorated unit on the 1st floor. Just across from the Waltham Watch Factory. 10-min walk to Moody St. and Charles River path. Built in 2014, open living, dining, and kitchen areas are ideal for working or entertaining. Stainless steel appliances and high class kitchenware. Spacious 2 bedrooms and 1 bathroom. Private deck. In unit washer/dryer. Baby friendly. Parking spot#1. Tax of 11.7% starts 7/1/19. Open and no-contact fire stairway is accessible from the parking lot.

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.

Comfortable apartment in Framingham
Newly renovated basement apartment. Private entrance and living space which includes a kitchen, bedroom, hallway and bathroom. The kitchen has a microwave and refrigerator, but no stove. Very clean and well maintained. Comfortable queen size bed. Driveway space for 1 car and plenty of street parking. Great location. Walking distance to Dunkin' Donuts, Domino's Pizza, and local shops. Less than 2 miles from the Mass Pike. No Pets / No Smoking inside

Modern Farmhouse Suite in Historic Lexington
Enjoy a modern farmhouse themed private suite in a peaceful setting in historic Lexington. Our home is perfect for : -Travelers visiting Boston and surrounding historical sites -Visitors seeking to stay in close proximity to family and friends in Lexington or surrounding communities -Locals in need of temporary housing -Business professionals needing accommodations within commuting distance to Boston -Families with kids, couples, or solo guests

Spacious Private Entrance Master Bedroom/Bath
Private entrance master bedroom w/exclusive use attached bathroom. Studio-like room; exterior staircase entrance. Walk to Wellesley College, town center, commuter rail, restaurants, grocery. Short drive to Babson. Sizable room, tasteful decor, king bed, sofa, microwave, mini-fridge (NO TV/NO KITCHEN). High-speed wifi, deck, view of treetops. Safe suburban neighborhood; good walk trails, walk to tennis/spa/gym/yoga w/reasonable day fees.

Private suite 1 BR, 1 BA, 1 LR, 1FLR
Prime location in Wellesley Hills, MA. Garden level suite offers a living room and a bedroom with a private bath. It offers a full size bed in the bedroom and a queen size pullout sofa in the living room. Private entrance with smart lock entry. Easy access to commuter rail, restaurants, post office, bank, Babson College, Wellesley College and Olin College of Engineering and so much more.

Private guest house on beautiful country road
Welcome to Grove Street Studio - our detached guest house which sits right behind our home on one of the most beautiful streets in the area. This two-room studio has everything you need for a comfortable stay including your own deck looking out to the woods behind. Perfect for for a hotel alternative for someone working temporarily at nearby businesses.
Popular amenities for Wellesley family-friendly rentals
Family-friendly home rentals with a hot tub

Hopkinton Mass 3+ Bedrooms - Great location!

Your Cozy 1 BR Apt & Relaxing Retreat

BC/BU - Beautifully Renovated Penthouse 3-BR/2-BA

Winery Studio w/ Private Hot Tub,Fireplace,Tasting

Lakeside apartment, patio, hot tub, outside shower

Cozy Lake Cottage: Hot Tub, Gym & Waterfront Views

1790 Stone Manor Farm

Modern, Spacious 1BR for 4 - Easy Marathon Access!
Family- and pet-friendly home rentals

Luxury 2B1B Apt. Amazing Location

Cozy Lakeview Guesthouse Near BOS, PVD, Cape Cod

Historic JP Brownstone with Parking. Pets Welcome!

Cozy 3BR Cottage w/ Fireplace â 40 min to Boston

Large One Bedroom Apartment

Private Studio w/ Loft Center Historic Carlisle

1 Free parking spot - 1BR/1Bath - Location - Walk!

Stylish 3-bedroom 2- bathroom townhouse
Family-friendly home rentals with a pool

Peaceful suite in Boston with city views

Nana-tucket Inn

Courtyard Garden | Pool | BBQ+Fire Tbl | Fireplace

Spacious vacation unit in premium suburban town

Stylish and Cozy at Revere Beach

Modern Space With Pool Close To Singing Beach

Ocean Side, Amazing View, close to town/beach, Spa

Oceanfront Pool. Close to Boston. Free Parking.
Quick stats about vacation rentals that are family-friendly in Wellesley
Total rentals
20 properties
Nightly prices starting at
ﺊ.ďş220 before taxes and fees
Total number of reviews
700 reviews
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
20 properties include access to wifi
Popular amenities
Kitchen, Wifi, and Pool
Destinations to explore
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- Hampton Beach
- Fenway Park
- Boston Common
- TD Garden
- Harvard University
- Revere Beach
- Brown University
- Lynn Beach
- Duxbury Beach
- New England Aquarium
- Good Harbor Beach
- Canobie Lake Park
- MIT Museum
- Freedom Trail
- Crane Beach
- Faneuil Hall Marketplace
- Museum of Fine Arts, Boston
- Oakland Beach
- Quincy Market
- Prudential Center
- White Horse Beach
- Roger Williams Park Zoo
- Salem Willows Park
- Pinehills Golf Club