Family-friendly holiday rentals in Worcester County

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Top-rated family-friendly rentals in Worcester County

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

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Top guest favourite
A serene pond reflects the white cottage and surrounding trees, creating a tranquil scene. Wildflowers and grasses frame the water's edge, while lush greenery enhances the natural beauty of the area. The peaceful environment is ideal for relaxation and outdoor exploration.
Cottage in Petersham
4.99 out of 5 average rating, 231 reviews

Cider House Cottage

Antique guest cottage on a becountry farm property with acres of fields, ponds, forests and streams, adjoining Quabbin Reservoir domain. Ideal for hikers, bird watchers, and bicyclists, this quiet country retreat offers trails and terrain to explore, only 3 miles away from small historic New England town. Make yourself at home in the comfortably furnished post and beam home with terrace and pond views, adventure in the surroundings, dip in fresh water streams, and relax in the claw foot bathtub

Top guest favourite
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
4.99 out of 5 average rating, 385 reviews

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.

Superhost
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
4.88 out of 5 average rating, 181 reviews

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!

Top guest favourite
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
4.89 out of 5 average rating, 130 reviews

Unique and Private Cottage in Worcester

Unique and private - your own cottage in the desirable West Side of Worcester. The carriage house of a larger property, the cottage is situated in lush gardens, with on-street parking on your doorstep. 5 minute walk to WPI, 5 minute drive to city center and 15 mins to UMass Med. Furnished tastefully and simply with antiques and original art works; brand-new bathroom with shower; washer and dryer; fully-equipped kitchen. An ideal retreat or longer professional let - fast Eero mesh wifi network.

Top guest favourite
A single-story farmhouse features a covered front porch adorned with hanging plants. A well-maintained lawn surrounds the home, complemented by landscaped bushes. An American flag is displayed, and tall trees line the background, providing a natural setting.
Guest suite in Thompson
4.98 out of 5 average rating, 179 reviews

Meadowside: Perfect Location w/ Endless Recreation

Perfect location, great value, & tons of privacy! Come stay at Meadowside! You'll be in a beautifully appointed and completely private 620 sq ft in-law suite. We're a quarter mile away from Webster Lake and an easy drive to all area attractions! Bring your boat, as we have plenty of room for your trailer in our parking lot-sized driveway! Room to sleep up to 4, king bed in the master, 1.5 baths, kitchen, laundry, front farmer's porch, and garden dining! You name it, it's here at Meadowside!

Guest favourite
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
4.88 out of 5 average rating, 462 reviews

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.

Superhost
A serene waterfront view reveals a calm lake reflecting clear blue skies. A grassy area leads to a sandy beach, with an American flag gently waving nearby. The scene is framed by trees and manicured foliage, providing a peaceful outdoor retreat.
Home in Worcester
4.75 out of 5 average rating, 159 reviews

Private waterfront home!

“La Casita” is a private waterfront home near Umass medical! Modern 1-2 bedroom home with a Master Bedroom on the 2nd floor and a multi use room that can be used as a 2nd bedroom with a full size futon. There is a 3 season porch with a dining nook which leads out to a big outdoor deck. There are multiple ceiling fans and water toys for renters use. No pets or smokers. This is a quiet, family oriented neighborhood with another home on the lot with small children so calm renters only please.

Guest favourite
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
4.82 out of 5 average rating, 309 reviews

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.

Top guest favourite
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.
Guest suite in Hubbardston
4.98 out of 5 average rating, 175 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.

Top guest favourite
A spacious loft area features a queen-sized bed with a cozy comforter and decorative pillows, alongside a daybed for seating or lounging. Wooden beams and a rustic brick hearth enhance the charm. Light enters through multiple windows, illuminating the inviting space.
Guest suite in Littleton
4.91 out of 5 average rating, 448 reviews

Historic Loft with bathroom & kitchenette

A beautiful 1840s barn loft steps away from miles of hiking trails. Fully separate and private entrance, bathroom, and kitchenette. Enjoy a serene, rustic cabin atmosphere with a historic brick hearth and exposed beams. Southeast facing windows overlook patio, garden and ruins. Off the beaten path but only 5 min. to Rte 2, Rte 495, and Boston commuter rail. Drive times w/o traffic: 45 min. Boston, 20 min. Lowell/ Rte 3, Burlington, Bedford, Nashua 30 min.

Guest favourite
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
4.89 out of 5 average rating, 506 reviews

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.

Superhost
The cozy cottage is nestled among trees, featuring a welcoming wooden deck. Reflections of the structure can be seen in the calm water of the pond, surrounded by lush greenery. A kayak is positioned in the foreground, pointing towards the entrance.
Tiny home in Orange
4.91 out of 5 average rating, 411 reviews

The Writer's Retreat: A Sweetwater Stay

Located on the shore of Tully Pond, The Writers Retreat is a newly designed 325sqft lake side cottage with breathtaking views of Tully Mountain. This 4-season cottage is built with salvaged barn wood; up-cycled maple floors and custom built furniture and lighting. It's the little sister to The Fishing Cottage. You'll find this intimate home has everything you need to relax, write the next Great American Novel, connect with a lover, or just plain chill.

Popular amenities for Worcester County family-friendly rentals