Family-friendly holiday rentals in Worcester

4.96 out of 5 average rating, 407 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.

4.99 out of 5 average rating, 376 reviews

The exterior of a charming wooden structure features light brown shingle siding and a welcoming entrance. Two windows flank a set of double black doors, accentuated by decorative lanterns. A stone pathway leads to the entrance, bordered by manicured greenery.

Guest suite in Uxbridge

Beautiful, Unique, & Cozy Cedar Flat

Come enjoy this new and beautifully designed space in historic Uxbridge, MA. Set up like a tiny house, it is the most cozy and clean place you will visit. A ship’s ladder will take you to the queen loft bed or use a new PotteryBarn sleeper sofa. The Frame TV will act as a beautiful painting if you prefer to "unplug." Climate control and a hammock chair are a perfect combo! Located on a quiet street, it is an easy 25 min. drive to Providence or Worcester, and only 50 min. to downtown Boston.

5 out of 5 average rating, 215 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

Relax and rejuvenate at this unique getaway on 20 acres in CT’s Quiet Corner. Just an hour from Boston, Providence, & Hartford, enjoy this private in-law studio with beautiful forest views. Lounge in bath robes & soak in the hot tub, take a walk along the trails, enjoy local vineyards, or explore antiques. Folks from all backgrounds and identities are welcome at The Farmette. Ideal for couples, solo travelers, or a family with a young kid. Please include all individuals (&pets) in your booking.

4.88 out of 5 average rating, 176 reviews

A living area is presented with a blue sectional sofa adorned with colorful cushions. A round coffee table is situated in front. A large wall-mounted TV is visible, complemented by a wooden side table and a clock on the wall. Natural light enters through a window with patterned curtains.

Flat in Worcester

Lovely 1BR APT, close to colleges

INNER CITY GEM 🔸🔹!! Centrally located in the heart of the city. Just a few minutes drive to anything in the city. A few blocks from the campus of Clark, Becker, & Assumption University. This unit boasts a large bedroom with a queen bed, dedicated workspace, a full closet, and a wall-mounted TV. There is an all-in-one kitchen, Dining Area with a fold-away table to optimize space, and a living room with a big-screen TV and a pull-out sofa bed. A full bathroom with all the necessary amenities!

4.88 out of 5 average rating, 459 reviews

A two-story grey house with white trim is visible, featuring large windows and a front porch. A white car is parked in the driveway, leading to a closed garage door. Lush trees provide greenery around the property.

Guest suite in Worcester

Private Suite with separate entrance in Worcester

The suite allows maximum of two pets per reservation for $50 per a pet. Our guests privacy starts from check in to check out with private entrance. The living room has mini library for guests, a 65 inch smart TV with high speed Internet and complimentary YouTubeTV local channels. The suite has a mini kitchen with mini refrigerator, freezer, microwave, air fryer, and coffee maker. It also has stocked cabinet utensils, cleaning supplies, linen closet and electric pump air mattress if necessary.

4.83 out of 5 average rating, 301 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.

Guest house in Worcester

Carriage house apartment

We have a one bedroom apartment at our historic home, Liberty Farm, which is the 2nd oldest house in Worcester Massachusetts and known as the Abby Kelley Foster house to the locals. Recent furniture upgrade in living room, see pictures. Kitchen has all of the amenities: stove, microwave, fridge, disposal and stack-able washer/dryer. Guests may enjoy the grounds in the quiet Tatnuck Square neighborhood, minutes from the Worcester Airport, restaurants, and hiking. House tours upon request.

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.

4.97 out of 5 average rating, 159 reviews

In-law Apartment, Full Kitchen, Near Mt Wachusetts

Your home away from home is a spacious & newly renovated basement/in-law apartment (approx 1100 sq feet) located below the main house, with its own private entrance, dedicated parking & in walkable neighborhood. The unit has a bathroom, full kitchen, living room & bedroom w/queen bed & extra tv. Hubbardston is a quaint little town with no stop-lights yet conveniently located to many beautiful hiking trails, fishing spots and lakes. 10 minutes from route 2 and 15 minutes from Mt Wachusetts.

4.93 out of 5 average rating, 107 reviews

The living area features a light gray sectional sofa adorned with decorative cushions, positioned next to a soft ottoman. A blue area rug covers the hardwood floor, while large windows are draped with sheer curtains, allowing light to fill the space. A desk is visible in the background.

Flat in Shrewsbury

Clean & Cozy 2BR Across from Quinsigamond Lake

Unwind in our comfy 2-bedroom apartment with all the essentials for a comfortable stay. Work remotely while facing the lakeview. Super close to UMass Memorial, UMass campus, and just minutes away from Starbucks, Whole Foods, TraderJoe's and many more. Surrounded by many restaurants with great variety of taste. Easy access to the highway. Escape the ordinary and make this homy lakeview apartment your home away from home. Book now for a delightful experience!

4.89 out of 5 average rating, 493 reviews

The stone barn building is framed by vibrant lavender fields in the foreground. Evening light illuminates the windows, while a calm sunset creates a soft gradient in the sky, transitioning from warm hues to deep blues.

Barn in Holden

Farm stay in a Historic Ski Lodge turned Barn

Once a ski lodge, then a horse barn, the hayloft in this unique stone barn has been converted to a comfortable & peaceful getaway. Enjoy a tranquil farm stay on a working Lavender farm. Help feed (if you wish) the sheep and see the horses and chickens. Enjoy the serene views and take in a sunrise or sunset or the stunning evening stars and moon on the back patio, stroll around the farm and hike our 1 mile nature walk. Convenient to local skiing & golfing.

4.92 out of 5 average rating, 557 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.

Flat 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!

4.85 out of 5 average rating, 361 reviews

A welcoming living area features a green sofa and a comfortable armchair. A wooden coffee table sits in the center, accompanied by a table lamp. Natural light enters through a window dressed with sheer curtains, while a decorative wall sign adds a friendly touch.

Flat in Shrewsbury

One Bedroom Apartment with Separate Bunk Bed Area

Located in the Town of Shrewsbury, Massachusetts and less than one mile from UMass Memorial Health- University Campus and UMass Chan Medical School, our tastefully designed fully furnished second floor apartment combines luxury with comfort and has its own private entrance. Our apartment has a bright, airy floor plan, gourmet kitchen, stainless steel appliances, hardwood floors, central A/C, and washer/dryer in-unit.

4.76 out of 5 average rating, 170 reviews

A spacious bedroom is featured, with warm wood paneling and ample natural light. A queen bed is dressed in white linens, topped with neatly folded green towels. Soft lighting from a small bedside lamp creates a relaxing ambiance. Framed artwork adorns the walls.

Guest suite in Holden

Private Guest Room, Kitchenette, Office, & BR

Private downstairs with large bedroom, bathroom & small kitchen, beautiful pond view. Double Bed & Pull-Out Couch, parking in driveway, outdoor fire pit, charcoal grill and outdoor smoking area, 420 friendly. Wifi, 200+ channels HD cable & Apple TV for streaming. Work space with desk chair, small kitchen with coffee maker, mini-fridge, microwave, and toaster. Washer & dryer, shower and bathtub.

Popular amenities for Worcester 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, 218 reviews

Guest suite in Mansfield

Cozy private apt 8 mins from UCONN - solar powered

4.98 out of 5 average rating, 151 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 Elmwood

Tiny house get-away with a Yellow Door

4.95 out of 5 average rating, 163 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!

4.93 out of 5 average rating, 178 reviews

A private outdoor area features a spacious hot tub surrounded by wooden walls and deck flooring. Soft lighting is provided by string lights overhead. A small table sits nearby for convenience, and a patterned rug adds a touch of comfort to the space.

Flat in Woburn

Your Cozy 1 BR Apt & Relaxing Retreat

4.95 out of 5 average rating, 173 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

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.

4.95 out of 5 average rating, 272 reviews

Winery Studio w/ Private Hot Tub,Fireplace,Tasting

4.95 out of 5 average rating, 115 reviews

An outdoor seating area features a round table set with fruit and beverages, surrounded by four chairs. A fire pit with seating is positioned nearby, offering views of the lake under a clear blue sky with scattered clouds.

Cottage in Mendon

Cozy Lake Cottage: Hot Tub, Gym & Waterfront Views

4.96 out of 5 average rating, 144 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

Family- and pet-friendly home rentals

4.93 out of 5 average rating, 207 reviews

A modern kitchen features white cabinetry and granite countertops, equipped with a refrigerator, microwave, and stove. A small dining table is set with white chairs, and a potted plant adds a fresh touch. Natural light enters through a nearby window.

Guest suite in Brooklyn

Affordable In-Law Apartment in Brooklyn, CT

4.94 out of 5 average rating, 121 reviews

An open-concept living area is highlighted by hardwood floors and a vaulted ceiling. A maintenance-free reef tank with ambient lighting is displayed on the wall. Modern seating options include a sectional sofa and chairs arranged around a coffee table, with large windows providing natural light.

Flat in Westford

Large One Bedroom Apartment

4.89 out of 5 average rating, 206 reviews

A lakefront cottage is positioned among trees, with a spacious lawn leading down to the water. A newly installed dock extends into the lake, while various colorful kayaks and paddle boards are neatly arranged on the grass. The sun sets, casting a warm glow over the scene.

Home in Westminster

Lakefront, view of ski mtn, fireplace, sauna

4.88 out of 5 average rating, 445 reviews

An open living area features a cozy striped sofa and a bright red pub table. A winding black staircase leads to the upper sleeping area. Natural light enters through a nearby door. A flat-screen TV is mounted on the wall, enhancing the space's functionality.

Barn in Carlisle

Private Studio w/ Loft Center Historic Carlisle

4.97 out of 5 average rating, 188 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

Guest suite in Coventry Lake

A cozy living space is presented, featuring a blue couch, a small wooden dining table with four chairs, and access to a bedroom and kitchen. Natural light enters through multiple windows, while neutral walls and beige carpet enhance the inviting atmosphere.

4.91 out of 5 average rating, 311 reviews

Country retreat 25min to Hartford/15min to UCONN

4.89 out of 5 average rating, 128 reviews

The cottage is framed by vibrant flower beds featuring a variety of colorful blooms. Tall trees provide shade, complementing the lush greenery of the surrounding yard. The structure includes large windows, showcasing a welcoming façade with a gently sloped roof and a detached garage.

Cottage in Worcester

Unique and Private Cottage in Worcester

4.95 out of 5 average rating, 116 reviews

A warm kitchen area features wooden paneling and a round dining table set for two. A small, cozy electric stove is situated near the table. The space is complemented by a full-size refrigerator and a microwave, with decorative touches on the walls.

Flat in New Ipswich

Quiet country apartment in farmland setting.

Family-friendly home rentals with a pool

4.96 out of 5 average rating, 106 reviews

A well-lit living area features a cozy white sectional sofa and a stylish floor lamp. Light from large windows illuminates the space, highlighting the warm wooden wall design. A round mirror complements the room, while a small table is adorned with decorative plants.

Flat in Brighton

Peaceful suite in Boston with city views

4.93 out of 5 average rating, 258 reviews

The renovated house is situated amidst lush greenery, surrounded by trees and a well-maintained lawn. A small swimming pool is visible within a fenced area, complemented by several umbrellas for shade, enhancing the outdoor ambiance on a sunny day.

Home in Woodstock

Cedar Ridge: House

4.95 out of 5 average rating, 169 reviews

A majestic moose stands partially submerged in the calm waters of a pond, showcasing its prominent antlers. Lush greenery surrounds the area, creating a serene and natural atmosphere.

Cabin in Hubbardston

Triggers Cabin

Guest house 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, 205 reviews

Country Cottage in the City

4.97 out of 5 average rating, 371 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.

Flat in Waltham

Cozy Private Studio Unit w/ Laundry and Parking!

4.89 out of 5 average rating, 109 reviews

A rustic cabin with a stone chimney is set against a backdrop of lush trees and a warm sunset. The wraparound porch features wooden railings and is complemented by neatly landscaped areas. A stone wall borders the driveway, leading to the cabin's entrance.

Cabin in Glocester

Get comfy in the country!

4.97 out of 5 average rating, 152 reviews

An expansive aerial view reveals a private pool surrounded by lush green grass and trees. A small pond is visible nearby, with vibrant foliage framing the scene. Open fields stretch into the distance, highlighting the rural setting on the property.

Home in Windham

mid century ranch style house on farmland