Family-friendly holiday rentals in Shrewsbury

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.

4.97 out of 5 average rating, 131 reviews

Gather, Cook & Unwind, 3BR, Fireplace

A private resort — without leaving Worcester. Heated pool, fire table, garden courtyard … your own enclosed escape. ★ "Tania’s place was much more than a place….it was a full on fabulous experience." 🏊Heated Pool (to 81F) 🌿 Courtyard w. lounge + garden 🔥Patio w/ Zen fire table* 🍽️ Natural gas + charcoal grills 💧 Reverse osmosis water filter 66” smart TV projector ❄️ Central air conditioning 🔥Indoor gas fireplace 📶300+ Mbps WiFi For non-smokers. No smoking/vaping inside or outside.

Indoor spacesKitchenParking

4.95 out of 5 average rating, 424 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

KitchenFamilyGetting around

4.84 out of 5 average rating, 234 reviews

A living area invites relaxation with a large television positioned against a wall, while natural light filters through sheer curtains. A workspace is visible, featuring a desk and a plant, enhancing the room's modern and functional layout.

Apartment in Worcester

Spacious 3BR Near UMass, DCU, & Polar Park!

Welcome to your home away from home. This stylish, spacious 3-BR apartment blends comfort and convenience in a prime location. Just minutes from UMass, St. Vincent Hospital, area colleges, the DCU Center, and Polar Park. Walk to countless restaurants, cafés, and bars just six blocks away! Catch a Worcester Red Sox game or hop on the city bus right outside. Whether you’re here for business, school visits, appointments, or fun, this cozy apartment is the perfect base. We’re excited to host you!

Indoor spacesFamilyNearby

4.81 out of 5 average rating, 120 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!

KitchenIndoor spacesNearby

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!

This my home in which I am now an "empty-nester". I have 3 bedrooms available, each with a Queen bed, plus a room over the garage with 4 futons/mattresses. NOTE: I live here and will be home during your stay. You'll have access to a private bathroom and the rest of the house: kitchen, dining room, living room, etc. NO pets allowed My place is close to Boston, Worcester, Providence, state parks, etc. Good for singles, couples, business travelers and families. Great pool and hot tub!

Indoor spacesFamilyDecor

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.

5.0 out of 5 average rating, 115 reviews

Charming Large Entire Home Spacious 3 Bed 2.5 Bath

Make some memories at this unique and family-friendly place. A charming home with an eclectic style has tall ceilings, wide open spaces and just that home-sweet-home, comfy feel. Enjoy your morning coffee on the front farmers porch. A jacuzzi bath in the master bathroom. Open the windows and listen to the bird singing in the city. The sunsets are a must and can be seen from the dining room table every night. It’s unreal, really. Centrally located and only 2 minutes away from highways.

KitchenIndoor spacesTV

4.9 out of 5 average rating, 149 reviews

Apartment in Shrewsbury

Clean & Cozy 2BR | Great Central Location

Unwind in our 2nd floor apartment across from Lake Quinsigamond 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!

KitchenFamilyView

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

This historic New England farm and home is on almost 7 acres of land with mature gardens and places to hike, it is a warm and inviting place to spend lovely summer days by the pool and enjoy warm nights by the fire in the fall and winter. Kitchen and bathrooms all renovated. Located centrally in Ma- 90/495 interchange. Located 45 minutes from Boston, beach, history, mountains, lakes, & NE sports. This home is in historic Hopkinton, where the Boston Marathon starts, center of MA.

FamilyKitchenBackyard

4.9 out of 5 average rating, 544 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 horses and ponies and see the 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.

KitchenIndoor spacesBathroom

4.97 out of 5 average rating, 106 reviews

Apartment in Worcester

Spacious 1 Bedroom near Colleges, DCU+Parking

Bright and spacious second floor one bedroom apartment in Highland St / WPI area, located near WPI, Becker College, Elm Park, Highland Street, stores and restaurants, MCPHS, DCU. Huge bedroom with walk-in closet, renovated bathroom and eat-in kitchen laundry in the unit, spacious hallway, charming shared balcony, one off street parking space included. The whole group will enjoy easy access to everything from this centrally located place.

KitchenIndoor spacesAccess

4.87 out of 5 average rating, 393 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.

Apartment 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.

FamilyKitchenAccess

A charming two-story home features a green exterior with white trim and a welcoming blue front door. The expansive porch is graced by multiple seating areas, surrounded by oversized windows that invite ample natural light. Lush greenery enhances the curb appeal.

4.97 out of 5 average rating, 200 reviews

Modern & Spacious 4 Bedroom Single Family Home

Welcome to our 4-bedroom, 1.5 bathroom renovated – 2,300 sq ft home! This modern space has an open floor plan, oversized windows, high ceilings, all new appliances/fixtures, ample living space and so much more! The property is conveniently located on a side street on the West Side, close to WPI, Clark, Holy Cross, the DCU Center, Polar Park and Downtown Worcester!

FamilyKitchenLong stay

Popular amenities for Shrewsbury family-friendly rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.95 out of 5 average rating, 155 reviews

Cottage in Mendon

Cozy Lake Cottage: Hot Tub, Gym & Waterfront Views

KitchenIndoor spacesValue

4.83 out of 5 average rating, 120 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

KitchenFamilyCleanliness

5.0 out of 5 average rating, 263 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

KitchenIndoor spacesBeach

4.96 out of 5 average rating, 107 reviews

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

FamilyIndoor spacesLocation

4.95 out of 5 average rating, 140 reviews

A spacious bedroom is presented with a king-sized bed dressed in patterned bedding. A wooden bench sits at the foot of the bed, and a decorative cabinet is visible in the corner. Natural light filters through a nearby window covered by dark curtains.

Guest suite in Fitchburg

Private sanctuary in the city w/ patio & backyard

Indoor spacesFamilyCondition

4.89 out of 5 average rating, 116 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!

FamilyKitchenHiking

Townhouse in West Brookfield

An open living area features a large sectional sofa arranged around a round coffee table, with a decorative area rug below. A wall-mounted TV is present, alongside a modern electric fireplace. Natural light is allowed in through multiple windows, complemented by soft white curtains.

4.85 out of 5 average rating, 193 reviews

Luxury By The Lake

FamilyIndoor spacesOutdoor spaces

4.91 out of 5 average rating, 239 reviews

Apartment in Woburn

Romantic Getaway w/private Jacuzzi• Fire Pit•

KitchenIndoor spacesComfort

Family- and pet-friendly home rentals

4.96 out of 5 average rating, 114 reviews

A spacious living area highlights a comfortable gray sofa, complemented by a wooden coffee table at the center. A large television is mounted on the wall, and natural light enters through multiple windows adorned with white trim.

Apartment in Worcester

Centrally Located Apartment in Worcester

KitchenFamilyParking

A spacious living area is presented with a comfortable sectional sofa and a coffee table. A brick fireplace serves as a central feature, while a wall-mounted television is visible. Light streams in through nearby windows, enhancing the warm ambiance of the room.

4.94 out of 5 average rating, 120 reviews

Luxury Haven: Cozy Palace

KitchenFamilyNearby

4.98 out of 5 average rating, 141 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

Indoor spacesKitchenAmenities

4.97 out of 5 average rating, 252 reviews

Cottage in Stow

White Pine Cottage – Cozy 3BR w/ Fireplace

KitchenFamilyCondition

4.97 out of 5 average rating, 257 reviews

A stately farmhouse stands illuminated against the night sky. Warm light glows from the windows, highlighting the inviting entrance adorned with a wreath and seasonal decor. The exterior features classic architectural elements, including multiple windows and a welcoming front door.

Guest suite in Uxbridge

The 1780 Suite

KitchenFamilyOutdoor spaces

4.94 out of 5 average rating, 267 reviews

A feature wall is adorned with various steampunk elements, including gears, clocks, and unique decorative items. An intricately designed aircraft model is suspended from the ceiling, while a small table with a glass sits nearby, adding to the eclectic ambiance.

Farm stay in Thompson

SteamPunk Bunk House and Intergalactic Way Station

KitchenIndoor spacesLong stay

4.82 out of 5 average rating, 335 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

KitchenIndoor spacesLaundry

4.89 out of 5 average rating, 239 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

FamilyKitchenCheckout

Family-friendly home rentals with a pool

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, 226 reviews

In-law Apartment, Full Kitchen, Near Mt Wachusetts

KitchenFamilyLocation

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.

4.78 out of 5 average rating, 104 reviews

Exquisite 1 Bedroom Suite-Charming,W/Private Entry

Indoor spacesKitchenLocation

5.0 out of 5 average rating, 109 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 spacesKitchenHospitality

4.94 out of 5 average rating, 255 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

KitchenIndoor spacesLong stay

4.96 out of 5 average rating, 115 reviews

Apartment in Everett

Curated Designer Retreat • Pool • Gym • Dining

Indoor spacesKitchenLayout

4.92 out of 5 average rating, 278 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

Indoor spacesFamilyAmenities

4.9 out of 5 average rating, 147 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!

KitchenFamilyComfort