Holiday rentals in Worcester County

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Top-rated holiday rentals in Worcester County

Guests agree: these stays are highly rated for location, cleanliness and more.

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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
4.98 out of 5 average rating, 255 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
Cottage in Brimfield
4.98 out of 5 average rating, 101 reviews

Cheerful cottage by Little Alum Lake & Sturbridge

Little Alum is a gorgeous spring-fed lake in the quintessential New England town of Brimfield, MA. Brimfield is known as home to the largest flea market in the country. Little Alum is regarded as one of the cleanest lakes in Massachusetts due to its pristine water quality. The charming cottage is a one level home within close proximity to highways & downtown Sturbridge and off route 20 just a few minutes to downtown Brimfield and Antique show/flea market. Partial water views, steps to the water.

Top guest favourite
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
4.99 out of 5 average rating, 233 reviews

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.

Guest favourite
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
4.95 out of 5 average rating, 137 reviews

Private sanctuary in the city w/ patio & backyard

Enjoy much needed R&R or alone time in this elegant 500-sqft master suite. A quiet space in a nice neighborhood amidst a buzzing metropolis, accessed through a private gated entrance. Sit back in the hammock, taking in the soothing sounds of water and birds chirping under the bright sky, having a private picnic in the backyard. In the winter, a ski resort is also conveniently accessible for fun in the snow. With the sights & sounds of the city mere minutes from the property to be explored. ~

Superhost
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, 331 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.

Guest favourite
An inviting open suite features exposed wooden beams and warm, natural light. A spacious bed is positioned against a wall, framed by a colorful artwork. Comfortable seating is provided with a gray armchair nearby, complemented by bright yellow curtains covering a window.
Flat in Sturbridge
4.96 out of 5 average rating, 156 reviews

Main Street Suite

Enjoy a boutique hotel experience in a historic New England town. This private, well-equipped suite is housed in a mixed use building (with a few small businesses with daytime hours) next door to a popular craft beer pub, and across the street from a hopping neighborhood Japanese restaurant. Enjoy everything you need in a home base with quick access to Old Sturbridge Village, lakes, trails, wineries, breweries, restaurants, farmers’ markets, festivals, events, antiquing, and more!

Top guest favourite
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.
Flat in Worcester
4.96 out of 5 average rating, 112 reviews

Centrally Located Apartment in Worcester

This first-floor unit in a charming 1910 duplex offers modern comfort and unbeatable convenience. Located within half a mile of Worcester State University and a grocery store, and within walking distance of restaurants and shops, it’s perfect for any lifestyle. The updated space features lightning-fast 1 Gbps WiFi, two workspaces, off-street parking for one car, and plenty of on-street parking. Ideal for both work and relaxation, this home is fully equipped for a comfortable stay.

Top guest favourite
A bright living space features a spacious bed with light bedding and a cozy couch. A high-top dining table with teal chairs provides a dining area. The kitchen, equipped with essential appliances, is visible in the background. Natural light enters through a large window.
Flat in Brimfield
4.99 out of 5 average rating, 205 reviews

Quiet & Cozy Main Street Retreat

Skip the traffic on the way to popular seasonal tourist destination, the Brimfield Flea Market, by staying here the night prior to your visit! Or, complement an off-season stay with an abundance of hiking trails, antique shops, lakes, farms, and even a winery just a 5 minute walk from your doorstep. Enjoy the ease of a convenience store, gas station, package store, and post office across the way, combined with the peace and quiet of this private suite tucked behind the main house.

Guest favourite
A cozy living area features a large sectional sofa in gray, complemented by a bright yellow armchair. A modern black coffee table sits in the center. A flat-screen TV is mounted on the white wall, while warm string lights create a welcoming ambience.
Guest house in Westminster
4.98 out of 5 average rating, 510 reviews

Guest House - 4 miles from Wachusett Mt.

Welcome to a cozy, newly renovated semi-attached in-law unit! Nestled in a peaceful neighborhood, you’ll be just a short walk from the town center and only a 10-minute drive to the scenic Mount Wachusett. With easy access to Route 2, it’s the ideal base for your adventures. Enjoy the privacy of your own entrance and two dedicated parking spaces. Whether you’re here for a weekend getaway or a longer stay, we’re sure you’ll enjoy your time in this inviting space!

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
4.9 out of 5 average rating, 535 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 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.

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
4.89 out of 5 average rating, 435 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.

Guest favourite
An open layout is showcased, featuring a cozy living area with a light-colored sofa and a warm accent wall. A dining area with granite countertops and bar seating is visible, alongside a table suitable for work. Two windows provide natural light.
Guest suite in Worcester
4.87 out of 5 average rating, 159 reviews

Modern 2 Bedroom Basement Suite

Modern, Comfortable, Spacious 1st Floor Basement apartment; open layout concept. Located 5 minutes from Worcester State University and 15 minutes to all other Universities/Colleges (WPI, Assumption, Anna Maria, Mass College of Pharmacy, UMASS Medical and more.) 10 minutes from I-290 & 15 minutes to the Mass Pike- I-90, RT 20, RT 146, I-495, & I 395. Great alternative to local hotels, local college graduation season, or even a vacation getaway.

Popular amenities for Worcester County holiday rentals