Holiday houses in Boylston

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Top-rated holiday rentals in Boylston

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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, 232 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 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 Greendale
5 out of 5 average rating, 100 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.

Top Guest favourite
Cabin in Princeton
5 out of 5 average rating, 17 reviews

The Cottage at Allen Hill Farm

Escape to our newly renovated wooden COTTAGE at the idyllic Allen Hill Farm in Princeton, MA. Wake up to breathtaking views, old stone walls, and peaceful farm life with our dog, cats, and chickens — soon joined by our majestic and stunning Shirehorses. Just 4 minutes to Wachusett Mountain skiing, hiking trails, and lakes, yet far enough for true tranquility. Cozy interiors, stargazing nights, and nature all around make this the perfect retreat for couples, skiers, and nature lovers.

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, 509 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.

A bright bedroom features two twin beds dressed in soft pink bedding. A textured area rug with floral patterns lies beneath. A wooden nightstand holds a small fan, and a sheer curtain allows natural light to gently fill the space.
Apartment in Worcester
4.83 out of 5 average rating, 53 reviews

Hollywood Bungalow 4

This cute apartment has a microwave, toaster and small fridge in the kitchen area with a table for two. Beautiful brand new bathroom in classic black and white. Air conditioning and tv in the bedroom. This apartment is on the 2nd floor. Wifi-the internet connection works pretty well most of the time. However spectrum, the only internet provider for this area has periodic issues. No smoking in the building or anywhere on the building grounds.

Guest favourite
An inviting living area features a large blue sectional sofa, accented by various cushions in warm tones. A wooden coffee table sits in the center, with a potted plant in the corner. Two pieces of artwork are displayed on the wall, complemented by natural light from the windows.
Guest suite in Shrewsbury
4.92 out of 5 average rating, 12 reviews

Stylish, clean, new 1 bedroom apartment

This is a spacious, stylish, clean, newly renovated, private one bedroom unit in the lower level of a quiet, home. The home is surrounded by mature trees in a very quiet neighborhood. You will NOT share any space with the rest of the home. Guest only occupied home. The upper level is occupied by travel healthcare workers who work most of the time so it tends to be very quiet. Parking in the driveway, own washer/dryer, bathroom etc.

Superhost
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
4.92 out of 5 average rating, 562 reviews

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!

Guest favourite
A well-lit sleeping area features a spacious bed covered with a light-colored blanket. A desk and chair are positioned near a window with blinds. A decorative plant sits in a pot beside a wooden dresser, adding a touch of greenery to the neutral palette.
Guest suite in Marlborough
4.86 out of 5 average rating, 303 reviews

Professional Accommodations!

Across from Lake Williams near 20 and 495, completely separate entrance and parking, all newly renovated, central air, high speed fios internet, 43 inch smart tv, desk, mini fridge, microwave in separate eating area, walk to Dunkin Donuts, Your completely private space! Walk to restaurant with indoor and outdoor seating. For your safety during Covid I keep 72 hours Between guests and have unit professionally cleaned!

Guest favourite
A bright living area is highlighted by large windows offering expansive views. A comfortable sofa and a futon are arranged around a round coffee table. Light-colored walls and hardwood flooring contribute to the serene ambiance of the space.
Guesthouse in Shrewsbury
4.74 out of 5 average rating, 242 reviews

A Comfy Hilltop Home

Nice and comfy home with spectacular views and sunset! This house overlooks the rolling Worcester hills for miles and miles. Convenient location, quiet neighborhood, big backyard, expansive deck, and nearby scenic hiking trails. The house has 2 bedrooms, 1 kitchen, 1 full bathroom, washer & dryer, big deck, and lots of parking space. Beautiful and comfortable, with everything you'd need for cooking and relaxing.

Guest favourite
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
4.77 out of 5 average rating, 174 reviews

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.

Guest favourite
A spacious living area features a dark sofa and a black coffee table with a decorative plant. A kitchenette is visible in the background, equipped with essential appliances. Soft lighting enhances the clean, minimal aesthetic, while an adjacent sleeping area is partially seen.
Guesthouse in Shrewsbury
4.96 out of 5 average rating, 25 reviews

New Private Apartment

Enjoy your privacy and comfort in this calm, meticulously created walkout guest suite. Featuring a completely separate entrance, a full bathroom, queen bed, a well equipped kitchenette, and all the basic amenities to allow you to unwind in a clean, minimal aesthetic. With easy access to local hospitals, highways, shops, and restaurants, it's a perfect central location for any of your travels.

A bright and open living area features a comfortable gray sofa and contemporary glass coffee table. Two decorative stools add a stylish touch. The adjacent kitchen area is equipped with modern appliances, and large windows allow natural light to fill the space.
Apartment in Shrewsbury
4.53 out of 5 average rating, 19 reviews

Private 2BR Retreat + Office

Unwind in this serene and stylish 2-bedroom suite nestled among trees — private, peaceful, and fully equipped. With a dedicated office space, full kitchen, and two free parking spots, it's perfect for work trips, family stays, or extended visits. Enjoy the best of both worlds: tucked away in nature yet just a short walk to supermarkets, cafés, and restaurants. Your perfect home base in town!

Popular amenities for Boylston holiday rentals