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Family-friendly vacation rentals in Wellesley

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Quick stats about vacation rentals that are family-friendly in Wellesley

  • Total vacation rentals

    Explore 30 vacation rentals in Wellesley

  • Nightly prices starting at

    Wellesley vacation rentals start at ﺩ.ﺇ 184 per night before taxes and fees

  • Verified guest reviews

    Over 1,010 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    30 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!

Top-rated family-friendly rentals in Wellesley

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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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

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

KitchenIndoor spacesWifi

4.98 out of 5 average rating, 145 reviews
Top guest favorite
A charming farmhouse stands amidst a lush garden, surrounded by vibrant purple irises. The white exterior of the house contrasts beautifully with the greenery, providing a serene atmosphere. Tall trees and a manicured lawn enhance the inviting landscape of the property.
Guest suite in Weston

Flower Farm Getaway 2BR, 20 Min To Boston

Spacious two-bedroom in-law suite attached to 1700’s 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 “D” subway stop into Boston (parking available), or commuter rail stops (Auburndale, Wellesley & Kendal Green Stations). It's a 20-minute drive to Amtrak's "Route 128" station to NYC and points south.

Indoor spacesFamilyAmenities

5.0 out of 5 average rating, 211 reviews
Top guest favorite
Guest suite in Dover

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.

FamilyKitchenDecor

4.98 out of 5 average rating, 346 reviews
Superhost
A spacious living area features two gray sofas with yellow accent pillows, arranged around a circular wooden coffee table. A gas fireplace is centered against a white mantel, complemented by large windows allowing natural light and views of greenery.
Townhouse in Waltham

Boston's Luxury Home: Pet-Friendly, 4BR, Sleeps 10

Luxury, modern, bright townhouse offering a gourmet kitchen is available for your next getaway. Just 1 min walk to Waltham Rail Station (some ambient rail sounds possible), buses to downtown, famous Moody street & Main street with 50+ restaurants, grocery, ALL WITHIN WALKING DISTANCE. Easy commute to anywhere within Waltham, Boston, Cambridge, Watertown. Ideal place for working professionals, families, or someone visiting Boston for the weekend. ATTACHED GARAGE PARKING INCLUDED for 2 cars.

KitchenFamilyBackyard

4.93 out of 5 average rating, 162 reviews
Superhost
A spacious bedroom features two neatly made beds, one larger and one smaller, adorned with white bedding. A bedside table holds a lamp, and a window with light curtains allows natural light to enter, complemented by warm LED ceiling lights.
Condo in Waltham

Lovely one bedroom apartment condo, with parking

The whole group will enjoy easy access to everything from this centrally located place. Entire unit. In the heart of Waltham Large and comfortable one bedroom apartment in quite condominium style place. Great location 5 minutes walk to train or bus to Boston, 6 minutes walk to Moody street where all the restaurants and attractions are currently open. Also 7 minutes drive from Brandeis university or Bentley College . We are located near everything you would need to do in Waltham. The

Indoor spacesFamilyComfort

4.84 out of 5 average rating, 153 reviews
Top guest favorite
A living area features a large wall adorned with natural-themed artwork, complemented by two windows allowing ample light. A flat-screen TV is mounted on the wall opposite a small table with a woven texture. A plush gray sofa enhances the inviting space.
Apartment in Newton

Inn at Newton Highlands, Suite 2, Apartment-Hotel

This gorgeous 1,800 sq. ft. 3 bedroom, 2 1/2 bathroom suite at The Inn at Newton Highlands is impeccably designed and decorated. It occupies the second and third floors of the building and immerses you in luxury and style. Its private 800 sq. ft. deck offers stunning views of the village. The space comes with a bonus room. This suite is one of several luxury suites in a small boutique Inn located in the heart of Newton Highlands in a beautiful , fully remodeled historic building.

FamilyIndoor spacesSleep quality

5.0 out of 5 average rating, 121 reviews
Guest favorite
A cozy living area is presented with a comfortable gray sofa and a dark wooden coffee table. A small dining table with two chairs is positioned near the patio doors, which are flanked by light curtains. A patterned area rug adds warmth to the hardwood floor.
Apartment in Newton

Conveniently Located Private Garden Apartment

Garden-level apartment next to public park, yet convenient to Newton Centre, Chestnut Hill, Boston College, Longwood Medical Area, and public transit. Easy access to Boston area attractions. Sleep late in a comfy bedroom with blackout shades, relax in front of the 55" HDTV, whip up a quick meal in the kitchenette, or enjoy the outdoors sitting on the patio. Come and go as you please with a private entry. Great for quick visits or extended stay. Newton Short Term Rental - STRA-23

FamilyIndoor spacesBackyard

4.92 out of 5 average rating, 416 reviews
Guest favorite
Home in Wayland

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.

KitchenIndoor spacesHeating

4.89 out of 5 average rating, 133 reviews
Top guest favorite
A spacious living area features a vaulted ceiling, large windows allowing natural light, and a comfortable sofa. A wooden coffee table sits at the center, complemented by patterned armchairs. Adjacent, a farmhouse dining table accommodates six, enhancing the open layout.
Place to stay in Sherborn

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. NEW in 2022: Mini-split AC!

FamilyIndoor spacesLocation

4.98 out of 5 average rating, 360 reviews
Top guest favorite
A dining area with a dark wooden table is set for four, featuring a colorful table runner. Natural light filters through windows adorned with light curtains, illuminating a cozy living room space beyond, furnished with a sectional couch, decorative pillows, and houseplants.
Guest suite in Newton

New Markdown! Lovely 3 Bedroom Unit with Garage

Planning your World Cup trip? Boston host of 7 World Cup matches. Enjoy the comfort of a fully equipped home perfect for watching every game This beautiful sunlit second floor unit with private garage has 3 bedrooms, full bathroom, splendid modern kitchen, gracious dining room, an elegant living room and a dedicated pleasant office room . Enjoy the shared backyard with a patio and playground for the kids. Registration: STR - 24 - 12

Indoor spacesKitchenParks

4.95 out of 5 average rating, 161 reviews
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

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.

KitchenFamilyCondition

4.98 out of 5 average rating, 306 reviews
Top guest favorite
A spacious studio features natural wood beams overhead and a combination of seating areas. A comfortable bed is positioned alongside a decorative side table. A dining table with chairs is visible, and light streams in through the windows, enhancing the bright and inviting atmosphere.
Guesthouse in Chestnut Hill

Private Carriage House near Newton Center and BC

Large studio above garage with private entrance located on famous Heartbreak Hill. Kitchenette with Fridge, Microwave, Keurig and full bathroom. Less than 1 mile to Boston College and just minutes to Cambridge and Boston. Easy walk to public transportation and Newton Center with great restaurants, bars, parks, and shopping. Free off-street parking.

Indoor spacesKitchenBathroom

4.95 out of 5 average rating, 154 reviews

Popular amenities for Wellesley family-friendly rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

Top guest favorite
A historic stone farmhouse is set on a spacious green lawn, complemented by a vibrant red barn in the background. Tall trees provide shade, and a carefully arranged stone border outlines the lush garden area, creating a tranquil outdoor setting.
Farm stay in Hopkinton

1790 Stone Manor Farm

FamilyKitchenLocation

4.96 out of 5 average rating, 166 reviews
Top guest favorite
Apartment in Arlington

Lakeside apartment, patio, hot tub, outside shower

KitchenIndoor spacesHiking

4.98 out of 5 average rating, 221 reviews
Top guest favorite
An outdoor swimming pool is surrounded by a spacious patio and lush greenery. Sun loungers are arranged around the pool, with a shaded seating area nearby. The house features a multi-level deck overlooking the pool, creating a relaxing outdoor space for guests.
Home in Hopkinton

Hopkinton Mass 3+ Bedrooms - Great location!

Indoor spacesKitchenShared spaces

4.95 out of 5 average rating, 180 reviews
Top guest favorite
Cottage in Mendon

Cozy Lake Cottage: Hot Tub, Gym & Waterfront Views

KitchenIndoor spacesCleanliness

4.96 out of 5 average rating, 157 reviews
Top guest favorite
The exterior of a rustic wooden house is surrounded by lush greenery and trees. A small fenced area is visible near the entrance, where a welcoming front door can be seen. The building features windows and a gabled roof, set in a tranquil natural environment.
Farm stay in Thompson

Rustic Farmette Studio w/yearround Hot Tub

FamilyKitchenBreakfast

5.0 out of 5 average rating, 266 reviews
Guest favorite
Apartment in Woburn

Romantic Getaway w/private Jacuzzi• Fire Pit•

Indoor spacesKitchenSolo travel

4.93 out of 5 average rating, 242 reviews
Guest favorite
A spacious bedroom features a large bed adorned with a patterned green and white quilt. Natural light floods the room through multiple windows, highlighting a small desk and ergonomic chair. Soft lighting is provided by sconces on the walls.
Guesthouse in Worcester

Quiet Oasis In The City

KitchenIndoor spacesWifi

4.83 out of 5 average rating, 121 reviews
Top guest favorite
The lakefront home features a modern exterior with a stone chimney and expansive deck. A shaded outdoor seating area is visible, surrounded by lush greenery. Adjacent, a garage completes the picturesque setting, set against a clear blue sky.
Home in Burrillville

Lakefront Beauty with Hot Tub

KitchenIndoor spacesOutdoor spaces

4.96 out of 5 average rating, 109 reviews

Family- and pet-friendly home rentals

Top guest favorite
A cozy sleeping area is separated by wooden bookshelves, showcasing an array of books. A queen size bed is placed against a wall, complemented by warm lighting. A small dining table with two chairs is situated nearby, enhancing the functional layout.
Apartment in Natick

Scandi-Modern Apartment

KitchenFamilySkiing

4.98 out of 5 average rating, 396 reviews
Guest favorite
Home in Framingham

Near Boston Beautiful 3 Bedroom in Framingham, MA

FamilyKitchenPets

4.83 out of 5 average rating, 134 reviews
Guest favorite
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.
Apartment in Watertown

Absolutely Gorgeous 3 Bedroom Close to Boston

FamilyIndoor spacesParking

4.95 out of 5 average rating, 161 reviews
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

Newly Renovated 3 Bed 2 Bath Easy Access Boston

FamilyIndoor spacesLocation

4.79 out of 5 average rating, 104 reviews
Guest favorite
The image displays a modern, two-story home with a brown exterior featuring horizontal siding. A unique sculpture is situated on the front lawn, surrounded by landscaped greenery. A stone pathway leads to the entrance, which is framed by tall trees and shrubs.
Guesthouse in Lexington

Unique Loft/ Studio Guesthouse (super convenient)

KitchenFamilyHeating

4.74 out of 5 average rating, 275 reviews
Guest favorite
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

Harvard House-The Gathering Place.

FamilyIndoor spacesGetting around

4.94 out of 5 average rating, 111 reviews
Top guest favorite
The exterior of a spacious guesthouse showcases a blend of siding and stone finishes. A paved driveway leads to a two-car garage. Lush greenery and flower beds enhance the inviting entrance, while multiple windows allow natural light to fill the interior.
Guest suite in Sharon

Cozy Lakeview Guesthouse Near BOS, PVD, Cape Cod

FamilyIndoor spacesValue

4.96 out of 5 average rating, 235 reviews
Top guest favorite
A stylish living room features a green sectional sofa complemented by colorful throw pillows. A round coffee table rests on a patterned area rug. Art pieces adorn the walls, and natural light enters through windows, illuminating the warm wooden flooring and brick fireplace.
Home in Arlington

The Brickhouz at Arlington !

FamilyIndoor spacesPets

4.99 out of 5 average rating, 119 reviews

Family-friendly home rentals with a pool

Guest favorite
A bright bedroom features a spacious bed with a white coverlet and colorful pillows. Natural light filters through multiple windows, enhancing the wooden accents of the walls and furniture. A television is mounted on the wall above a wooden dresser, creating a comfortable and inviting space.
Guesthouse in West Roxbury

Country Cottage in the City

Indoor spacesKitchenSleep quality

4.95 out of 5 average rating, 218 reviews
Top guest favorite
A washing machine and dryer are positioned side by side against a wall. A small dining table with white chairs is situated near a window, while a desk and chair are also present in the space. Light-colored walls and a nautical-themed clock add to the room's design.
Apartment in Waltham

Cozy Private Studio Unit w/ Laundry and Parking!

Indoor spacesKitchenQuiet

4.97 out of 5 average rating, 451 reviews
Superhost
A small seating area is presented with a pink loveseat adorned with patterned pillows, positioned beside a bedside table. A soft lamp is placed atop the table, and a tissue box is situated nearby. Light wood flooring complements the neutral color scheme.
Guest suite in Framingham

Exquisite 1 Bedroom Suite-Charming,W/Private Entry

FamilyIndoor spacesComfort

4.78 out of 5 average rating, 104 reviews
Top guest favorite
A spacious exterior view showcases a two-story light gray house with a brick chimney, set against a backdrop of lush greenery and a mix of trees. A charming barn is visible in the distance, complementing the well-maintained gardens and open lawn.
Apartment in Groton

Farmhouse Guest Apartment

FamilyIndoor spacesAmenities

5.0 out of 5 average rating, 110 reviews
Top guest favorite
Cottage in Marblehead

Steps from Harbor + Walk to Old Town + Restaurants

FamilyKitchenHospitality

4.99 out of 5 average rating, 169 reviews
Superhost
Apartment in Brighton

The Drew : Vibrant • Comfortable • W/D • City View

Indoor spacesKitchenDecor

4.8 out of 5 average rating, 124 reviews
Guest favorite
A cozy living area features a spacious daybed flanked by decorative pillows. Two armchairs are positioned across from a coffee table, enhancing the seating arrangement. A decorative vase adds charm beside the fireplace, while natural light filters through the window, illuminating the wood flooring.
Guest suite in Revere

Amazing studio

Indoor spacesKitchenQuiet

4.87 out of 5 average rating, 209 reviews
Top guest favorite
An outdoor lounge area features a circular table surrounded by curved sofas adorned with cushions. Soft curtains frame the space, while potted flowers add vibrant color. Natural light filters through the overhead structure, creating a relaxed atmosphere for gatherings.
Home in Worcester

Gather, Cook & Unwind, 3BR, Fireplace

FamilyKitchenAccuracy

4.97 out of 5 average rating, 132 reviews

Destinations to explore