Family-friendly holiday rentals in Marlborough

4.98 out of 5 average rating, 132 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

KitchenFamilyWi-Fi

4.97 out of 5 average rating, 156 reviews

Home in Framingham

1BR Loft | 25 Mins to Boston | Quiet Neighborhood

Welcome to The Loft! 100% Private 1-Bedroom Place Queen Bed — Pillowtop Mattress Full Kitchen — Stove, Fridge, Dishwasher, Pots/Pans, Utensils & Essentials Dining Area — Table & Chairs Living Room — Leather Sofa 49" SmartTV — Netflix + Sling Live TV Bathroom — Shower, Plush Towels & Natural Bath Products Private 2nd Floor Entrance Heated Outdoor Stairs Your Own Driveway Quiet & Safe Neighborhood Deep Cleaned & Sanitized 2 Min Walk to Park 25 Mins to Boston Easy Access —Route 9 & 90-Mass Pike

KitchenIndoor spacesLaundry

4.96 out of 5 average rating, 444 reviews

A colorful treehouse stands elevated among the trees, featuring a wooden deck with railings. The exterior showcases a playful combination of purple, yellow, and red, with multiple windows inviting natural light. The surrounding foliage adds to the charming, secluded atmosphere.

Treehouse in Thompson

The Tree House at Underhill Hollow

The Treehouse is a place where magic happens. Whether you’re looking for a romantic getaway, a family vacation or both. Sleep amongst the trees on a 7 acre 1825 farm. Meet Whirly, Gig and Belle. Find all 7, fairy houses. Go on a treasure hunt. Poke about our paths or explore the Airline trail, just off the property. S’mores, campfires, ghost stories and more. Meet our chickens. Spot deer, ducks or “Blue”, our resident blue heron. Adventure is in the air at the Hollow. Or nap in the hammock.

KitchenIndoor spacesRiver

4.98 out of 5 average rating, 136 reviews

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

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.

KitchenIndoor spacesBiking

4.99 out of 5 average rating, 232 reviews

A quaint cabin is positioned among trees, softly lit at night. An illuminated entrance is framed by colorful pots and surrounded by a cozy seating area with an Adirondack chair. Flickering firelight adds warmth to the inviting outdoor space.

Cabin in Littleton

Private & Remote, Enjoy Outdoors, Sleep in Luxury

Bit of a wonderland (57 Acres, 100+ 5-star reviews). A place you won't soon forget. Complimentary firewood, 1/2 hour from Boston, camp but sleep in luxury. This cabin is privately located on a retired Christmas tree farm, about a one-quarter mile off the public road. Listen to the water flow, and watch the sunset over the wetlands. This site is ideally suited for a couple looking for an outdoor experience retiring to the comfort and security of a luxury tiny house. Everything is solar-powered.

KitchenFamilyTV

4.95 out of 5 average rating, 421 reviews

A spacious yard is surrounded by tall trees, showcasing a playground with a slide and swings. A garden area is interspersed with colorful flowers and is set against the backdrop of lush greenery. A trampoline is visible in the distance, along with a greenhouse.

Farm stay in Rutland

Farm Living

We offer a quiet country setting on a small working farm, with cows, horses, pigs, goats, donkeys, peacocks, emu, rabbits, dogs, chickens, ducks and wildlife strolling now and then. There’s opportunity to interact with the animals. Pack n play available for little ones upon request and another twin fold up bed. We truly want all of our guest to enjoy all the farm has to offer and enjoy the peacefulness. Please inquire about kayak rentals. We also have a game room available to rent. See photos

Indoor spacesFamilyLocation

4.97 out of 5 average rating, 247 reviews

Cottage in Stow

White Pine Cottage – Cozy 3BR w/ Fireplace

Welcome to White Pine Cottage - a cozy 1930s cottage in Stow, MA with modern amenities. Great landing pad if you are coming to the area to visit family, work or a weekend getaway. Located in quiet wooded neighborhood with very little traffic. Relax by the fireplace and enjoy a soak in the whirlpool tub. Convenient to local farms, orchards, golfing, wooded trails and more. Hudson, Sudbury and Maynard's restaurants and shops 15 minutes away and big city Boston / Cambridge only 40 minutes.

FamilyIndoor spacesCheckout

4.82 out of 5 average rating, 118 reviews

A spacious bedroom features a large bed with a quilted taupe cover and decorative pillows. Framed artwork hangs on the walls alongside window treatments, while warm table lamps provide gentle lighting on both sides of the bed. Soft textiles create a calming atmosphere.

Condo in Shrewsbury

Luxury Spacious 2BR • King & Queen Beds • 2 Baths

Family-Friendly 2BR Getaway! Spacious stay with a 🛏️ King & Queen bed, ☀️ outdoor patio, 👶 baby crib! 🐶 pet-friendly neighborhood! Great for 🩺 travel nurses & 💼 professionals with ⚡ high-speed WiFi, 📺 Roku TV & 🎬 Netflix. Easy access to UMASS and St Vincent Hospitals 🏥 for work or care for loved ones. Close to 👵 Southgate Shrewsbury—perfect for visiting Grandma & Grandpa! Close to beautiful Dean Park—perfect for walks, playtime, or just soaking up nature. We’d love to host you!

FamilyIndoor spacesNearby

4.98 out of 5 average rating, 128 reviews

The bedroom features a spacious bed adorned with navy bedding and accented by decorative pillows. Nightstands with lamps are positioned on either side. Natural light enters through a window, illuminating the warm wooden flooring.

Guest suite in Stow

Sisu Suite: Private one bedroom suite

Private suite with separate entrance. Locked door between suite and home. Sitting room with love seat, folding wall-mounted table/desk and chairs, tv, and kitchenette. Kitchenette includes mini fridge, microwave, coffeemaker, water kettle, and toaster. Bedroom with queen sized bed. New bathroom. 25 miles west of Boston. Minutes from pick-your-own apple orchards, winery, cider breweries, and golf courses. Backyard connects to conservation land trails. 3.3 miles from S. Acton Rail station.

Indoor spacesKitchenParking

4.82 out of 5 average rating, 107 reviews

Apartment in Framingham

Comfy Cute lovely 1 BR 1 bed APT w/Private Access.

Cozy and lovely 1 bedroom 1 bed apartment in Framingham with private access and parking. Everything nearby is perfect for solo adventures, couples, and business travelers, with groceries, restaurants, train stations, shopping centers, Natick Mall, and Framingham State University just minutes away. You can get around Boston and Providence with ease! Occupancy: Maximum 2 adults. Property type One-bedroom apartment or guest suite Property type: Entire house/apartment

FamilyIndoor spacesHospitality

4.91 out of 5 average rating, 604 reviews

A spacious living area features a dark gray futon adorned with patterned cushions, accompanied by a wooden coffee table. A rustic wooden cabinet houses a television, while natural light is invited through the glass doors leading to an exterior space.

Apartment in Hudson

Newly Renovated Apartment Near Downtown Hudson

Newly renovated private attic apartment near downtown Hudson with kitchenette, living room and bedroom/office. A warm, cozy space with plenty of natural light! Just upgraded to a new king sized bed! Free parking on site Walking distance to restaurants, cleaners, antique shops, roller skating, shopping center, gym, breweries, golf course... & lots more! Nearby there are lots of historical sites, ski areas, and areas for swimming!

Indoor spacesKitchenLocation

4.82 out of 5 average rating, 109 reviews

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

Forget your worries in this spacious and serene space. We are right in the city but you'll feel miles away. This two level guest home is surrounded by nature and very relaxing. Two bedrooms and two baths. Two king sized beds. One full bath with oversized tub downstairs. Upstairs bath with standing shower. Full kitchen and coffee and tea. Hot tub is included with BNB. Pool is a separate rental. Message for details.

Indoor spacesFamilyParking

Popular amenities for Marlborough 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, 164 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

KitchenFamilyAccess

4.95 out of 5 average rating, 153 reviews

Cottage in Mendon

Cozy Lake Cottage: Hot Tub, Gym & Waterfront Views

KitchenIndoor spacesWalkability

4.95 out of 5 average rating, 179 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!

FamilyIndoor spacesCondition

5.0 out of 5 average rating, 261 reviews

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

FamilyKitchenPool

Farm stay in North Andover

The spacious room features a king-sized bed with soft bedding and decorative pillows. Natural wood accents support a pitched ceiling, while a chandelier provides ambient lighting. A cozy gas fireplace and a flat-screen TV are visible. Large windows allow natural light and views of the surroundings.

4.93 out of 5 average rating, 301 reviews

Winery Studio w/ Private Hot Tub & Wine Tasting

Indoor spacesKitchenComfort

4.95 out of 5 average rating, 183 reviews

A private backyard oasis is surrounded by lush greenery and blooming flowers. A swimming pool is featured in the foreground, reflecting blue skies. Outdoor seating areas are visible, providing space for relaxation and enjoyment.

Home in North Andover

Nana-tucket Inn

KitchenFamilyView

4.88 out of 5 average rating, 109 reviews

An inviting living area features a mix of comfortable seating options in neutral tones and stripes. A wooden coffee table sits centrally, adorned with a floral arrangement. Sunlight filters through large windows, illuminating the space and highlighting a stone fireplace in the background.

Cottage in Woodstock

Lakefront Cottage Complete with Kayaks!

FamilyKitchenGetting around

4.92 out of 5 average rating, 233 reviews

Apartment in Woburn

Romantic Getaway w/private Jacuzzi• Fire Pit•

FamilyKitchenComfort

Family- and pet-friendly home rentals

4.9 out of 5 average rating, 132 reviews

Home in Wayland

Spacious 4 bedroom home with large yard

KitchenFamilyAmenities

5.0 out of 5 average rating, 111 reviews

The charming exterior of a two-story house is showcased, featuring a gray façade with white trim and an inviting front porch. American flags adorn the porch, while well-maintained shrubs and a grassy area complement the space. A brick pathway leads toward the entrance.

Home in Worcester

Charming Large Entire Home Spacious 3 Bed 2.5 Bath

Indoor spacesFamilyHospitality

4.97 out of 5 average rating, 206 reviews

The home is nestled among trees in a wooded setting, with a deck visible in the distance. Sunlight filters through the foliage, casting dappled light on the ground, while an array of green leaves and flowering plants create a natural frame around the structure.

Guest suite in Bolton

Vaughn Hill Hideaway & Sauna

KitchenIndoor spacesBathroom

4.88 out of 5 average rating, 478 reviews

Barn in Carlisle

Private Studio w/ Loft Center Historic Carlisle

FamilyKitchenNearby

4.93 out of 5 average rating, 133 reviews

A pathway leads down to the tranquil waters of Lake Quinsig, surrounded by lush greenery. Soft clouds drift across a bright blue sky, reflecting light on the calm surface of the lake. Boat docks are visible, inviting leisurely activities.

Home in Worcester

Million-Dollar View - Great Location/Sleeps 9

Indoor spacesFamilyCheckout

4.82 out of 5 average rating, 331 reviews

A welcoming living room features light-colored sofas adorned with decorative pillows. Natural light filters through two windows, illuminating a cozy atmosphere. A lamp and a dresser add functionality, while a neutral carpet completes the space. Greeting from the entrance can be seen in the background.

Guesthouse in Worcester

Carriage house apartment

FamilyKitchenTV

4.9 out of 5 average rating, 143 reviews

Apartment in Shrewsbury

Clean & Cozy 2BR | Great Central Location

KitchenIndoor spacesOutdoor spaces

4.82 out of 5 average rating, 131 reviews

Home in Framingham

Near Boston Beautiful 3 Bedroom in Framingham, MA

Indoor spacesFamilyLaundry

Family-friendly home rentals with a pool

4.97 out of 5 average rating, 126 reviews

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

Courtyard Garden | Pool | BBQ+Fire Tbl | Fireplace

KitchenIndoor spacesDecor

Guest suite in Hubbardston

A cozy living area is featured with a brown sofa adorned with patterned cushions. A small coffee table sits on a patterned rug, and a lamp is positioned beside a side table. In the background, the kitchen is visible, showcasing stainless steel appliances and additional cabinetry.

4.98 out of 5 average rating, 218 reviews

In-law Apartment, Full Kitchen, Near Mt Wachusetts

KitchenFamilyQuiet

5.0 out of 5 average rating, 107 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 spacesFamilyHospitality

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.

4.95 out of 5 average rating, 215 reviews

Country Cottage in the City

Indoor spacesFamilyView

4.94 out of 5 average rating, 252 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

FamilyIndoor spacesWalkability

4.95 out of 5 average rating, 100 reviews

Apartment in Everett

Curated Designer Retreat • Pool • Gym • Dining

KitchenFamilyAccess

4.97 out of 5 average rating, 442 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!

FamilyKitchenParking