Family-friendly vacation rentals in Westwood

4.98 out of 5 average rating, 145 reviews

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

FamilyIndoor spacesShared spaces

4.98 out of 5 average rating, 346 reviews

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.

Indoor spacesFamilyAccuracy

4.92 out of 5 average rating, 160 reviews

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

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 limited on-street parking. Pet friendly!

KitchenIndoor spacesWalkability

4.96 out of 5 average rating, 235 reviews

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

Stunning CLG with private entrance, deck, & parking. •Bedroom #1 ground floor (2 guests only) has a Queen bed & smart TV with deck access. •Bedroom #2 upstairs is ONLY AVAILABLE FOR BOOKINGS OF 3–4 GUESTS and includes a Queen bed, smart TV, mini gym & office. •Living room with lake view & smart TV. •Bathroom with tub and sitting shower bench. •Fully equipped kitchen with stainless steel appliances. •Internet Access, You Tube, and Netflix. •Summer lake access.

Indoor spacesFamilyNearby

4.95 out of 5 average rating, 224 reviews

The exterior of a red house is framed by a well-maintained garden comprising various flowers and greenery. The house features a welcoming entryway, a chimney, and a grassy area. Sunlight illuminates the scene, highlighting the vibrant colors of the surrounding landscape.

Apartment in Dedham

Two bedrooms, full bathroom, and breakfast room

We offer the entire second floor of our home: two bedrooms, each with a queen-size bed, a full bathroom, and a well-stocked breakfast / snack room. We are located literally seconds off Rt. 128 / I-95, in a quiet, secluded area. Our deck, gardens and grounds (which include a pond, birdfeeders, and, perhaps, wildlife sightings) are available for your enjoyment. You will have complete privacy in your quarters, but we will be close at hand should you need advice or service. Gretje and Bob

FamilyIndoor spacesBackyard

5.0 out of 5 average rating, 121 reviews

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.

KitchenIndoor spacesLayout

Guesthouse in West Roxbury

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.

Country Cottage in the City

This poolside cottage is a country retreat in the city. We are nestled into a small bit of woods on top of the "hill" as it is called locally. The cottage is a studio apartment that has a microwave and mini-fridge as well as sitting area and table. It has a lovely view of the pool and gardens. Besides the pool, there are two garden ponds where we keep ornamental fish. Outside the garden fence there is often a parade of various types of birds, bunnies and even wild turkeys and deer.

Indoor spacesFamilyOutdoor spaces

4.95 out of 5 average rating, 218 reviews

Place to stay in Sherborn

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.

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!

Indoor spacesFamilyHospitality

4.98 out of 5 average rating, 360 reviews

4.95 out of 5 average rating, 160 reviews

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

FamilyIndoor spacesCheckout

4.95 out of 5 average rating, 112 reviews

A spacious bedroom features a large bed with a light-colored comforter and decorative pillows. Two lamps provide soft lighting. Mirrored closet doors reflect the room, and artwork hangs on the wall, adding a touch of character. Warm wooden flooring complements the neutral decor.

Home in Canton

Gorgeous 2nd Floor Home with Private Entry

Welcome to your home away from home! This beautiful second-floor 2 BR unit keyless self check in offers a private entrance and private stairs. Features: · Newly Installed AC · Fully Kitchen: Equipped with smart utilities, including an oven, microwave, dishwasher, washer, and dryer. · High-speed internet. · Comfortable Sleeping Arrangements: 2 beds & a sofa bed, perfect for accommodating up to 4 guests.

FamilyKitchenCleanliness

4.98 out of 5 average rating, 306 reviews

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.

KitchenFamilyBreakfast

4.98 out of 5 average rating, 147 reviews

The cottage features a white exterior with blue shutters and a sloped gray roof. A gravel pathway leads to the entrance, bordered by well-maintained shrubs. In the background, a barn is visible among the trees, and grassy areas surround the home.

Cottage in Millis

Windy Knob Farm Cottage - stay on a working farm

A former caretaker's cottage located on a 92-acre historic farm just 40 minutes from Boston. Home to abundant wildlife and farm animals, spectacular sunsets, lush pastures, rolling hills and meadows, woodlands, a pond and bogs. Walking trails nearby on property, and farmstand produce/eggs are produced onsite. Come stay to enjoy a change of scenery!

KitchenIndoor spacesOutdoor spaces

Popular amenities for Westwood family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.96 out of 5 average rating, 166 reviews

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

KitchenIndoor spacesNearby

4.96 out of 5 average rating, 156 reviews

Cottage in Mendon

Cozy Lake Cottage: Hot Tub, Gym & Waterfront Views

KitchenIndoor spacesHospitality

4.98 out of 5 average rating, 221 reviews

Apartment in Arlington

Lakeside apartment, patio, hot tub, outside shower

Indoor spacesFamilyQuiet

4.95 out of 5 average rating, 180 reviews

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!

KitchenIndoor spacesHospitality

4.97 out of 5 average rating, 187 reviews

A patio area features grey stone flooring with a round metal table and four stylish chairs under a large blue umbrella. Vibrant yellow flowers surround the seating arrangement, providing a cheerful touch to the outdoor space. The yellow door of the tiny house is visible in the background.

Tiny home in Providence

Tiny house get-away with a Yellow Door

KitchenIndoor spacesAccess

4.92 out of 5 average rating, 212 reviews

A charming living area features two upholstered armchairs with decorative cushions, complemented by a round coffee table. Natural light filters through large windows adorned with wooden frames, illuminating the intricate wood ceiling beams above. A fireplace is situated in the corner, adding warmth to the space.

Home in Providence

Cozy Home next to City Park

Indoor spacesKitchenHeating

4.88 out of 5 average rating, 128 reviews

Home in Somerset

Fall and Holidays, Entire Home w/ Jacuzzi PETS

KitchenIndoor spacesHospitality

Farm stay in North Andover

Winery Farmhouse w/ Private Hot Tub & Wine Tasting

KitchenFamilyBathroom

4.97 out of 5 average rating, 135 reviews

Family- and pet-friendly home rentals

4.89 out of 5 average rating, 114 reviews

A well-maintained yard sits on a spacious acre, featuring lush green grass and a variety of trees. The house is partially visible on the right, and a clear path leads to the sunroom entrance. Flower beds with blooming plants add color to the landscape.

Home in Walpole

Entire home 3 miles from Gillette, sleeps 7.

Indoor spacesKitchenAir conditioning

4.89 out of 5 average rating, 133 reviews

Home in Wayland

Spacious 4 bedroom home with large yard

KitchenIndoor spacesNearby

4.92 out of 5 average rating, 416 reviews

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

Indoor spacesKitchenDecor

4.94 out of 5 average rating, 257 reviews

A spacious outdoor area features a dining table surrounded by chairs, complemented by loungers and a hot tub. An umbrella provides shade over the seating area, while lush greenery and well-maintained landscaping create a peaceful environment. The in-ground pool is visible in the foreground.

Guesthouse in Newton

Charming 2-story private Guesthouse

Indoor spacesKitchenPets

4.98 out of 5 average rating, 396 reviews

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

Indoor spacesFamilyBiking

4.84 out of 5 average rating, 133 reviews

A well-lit dining area features a wooden table surrounded by chairs, complemented by a decorative chandelier overhead. The open layout allows for a view into the comfortable living area, where soft seating and natural light create a relaxed ambiance.

Apartment in Winthrop

Sunny 3 bedroom on beach

KitchenIndoor spacesDecor

4.96 out of 5 average rating, 105 reviews

A bright living space is displayed, featuring a brown sofa, a wooden coffee table, and a large area rug. Natural light streams through large windows, illuminating the open layout that includes a kitchenette with stainless steel appliances.

Guesthouse in Weymouth

Cozy Guesthouse Near T-Station - Family Friendly

FamilyIndoor spacesQuiet

4.85 out of 5 average rating, 198 reviews

A charming blue-gray house is framed by a well-maintained lawn and flower beds. Two skylights are visible on the roof, and a small set of stairs leads to the front door. Lush greenery and shrubs surround the property, contributing to a welcoming outdoor space.

Apartment in Avon

Welcoming and Sunny

KitchenFamilyTV

Family-friendly home rentals with a pool

4.97 out of 5 average rating, 450 reviews

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!

KitchenFamilyDecor

4.96 out of 5 average rating, 116 reviews

Apartment in Everett

Curated Designer Retreat • Pool • Gym • Dining

FamilyIndoor spacesView

4.99 out of 5 average rating, 169 reviews

Cottage in Marblehead

Steps from Harbor + Walk to Old Town + Restaurants

FamilyKitchenComfort

4.87 out of 5 average rating, 209 reviews

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

FamilyIndoor spacesOutdoor spaces

5.0 out of 5 average rating, 110 reviews

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

Indoor spacesKitchenValue

Guest suite in Framingham

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.

Exquisite 1 Bedroom Suite-Charming,W/Private Entry

KitchenFamilyAccess

4.78 out of 5 average rating, 104 reviews

4.9 out of 5 average rating, 199 reviews

A serene pool area is surrounded by lush gardens, featuring vibrant flowers in planters. A pool house is visible in the background, framed by greenery. The clear water of the pool reflects the surrounding natural beauty, inviting relaxation and enjoyment.

Home in Plymouth

The Secret Garden 4 Bedroom, 7 Bed 3 Baths

KitchenFamilyBreakfast