Holiday houses in Sterling

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Top-rated holiday rentals in Sterling

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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, 223 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

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, 128 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. ~

Guest favourite
A charming lake house is depicted by the water, showcasing a light blue exterior and a welcoming front porch. The reflection in the calm lake adds depth to the scene, surrounded by lush greenery and hints of fall colors in the trees.
Home in Westminster
4.83 out of 5 average rating, 173 reviews

Lakefront, view of ski mtn, firepit, kayaks, dock

A charming lake house with a magnificent view of a ski mountain — Wachusett Ski Resort (voted #1 in MA). Newly-renovated, 650 square foot cabin with a wall unit AC, fire pit, grill, smart TVs, kayaks, paddle board, and all the amenities you’ll need. (FYI: We also own another lakefront Airbnb right down the street that accommodates 10 guests. Ask for link.) *A brand new retaining wall and dock will be installed May 2024. This will extend and even out the lawn for nights around the firepit!

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
4.97 out of 5 average rating, 157 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
An inviting open living space showcases warm brick walls and original timber beams. A spacious seating area features a brown leather couch and wooden coffee table, while a grand piano occupies one corner. Large windows with serene views of the outdoors offer natural light.
Loft in Peterborough
5 out of 5 average rating, 209 reviews

Peaceful Mill on the Water - Home Away from Home

Immerse in tranquility at our serene mill retreat in Southern NH. This historic space, adorned with original timber, rustic brickwork, and lofty 11 ft ceilings, offers a spacious 2,650 sq ft sanctuary. Relax in the soaking tub, or savor the calming waterfall views from the deck. Conveniently near downtown, but distant enough for undisturbed peace. Welcome to your soothing retreat for rest and rejuvenation. A remote worker's dream office with high speed connectivity and dedicated workspace.

Top 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.
Guesthouse in Westminster
4.98 out of 5 average rating, 439 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 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.
Apartment in Shrewsbury
4.93 out of 5 average rating, 107 reviews

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!

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, 442 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, 490 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
A naturally lit living room is featured with hardwood flooring and warm-toned walls. A comfortable sofa and a sofa bed are positioned near a coffee table, with a decorative bowl placed on top. A brick fireplace serves as a focal point across from a large television.
Home in Shrewsbury
4.85 out of 5 average rating, 230 reviews

A Fabulous House with Beautiful Views

Gorgeous home with spectacular views and sunset! This big 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 3 bedrooms, 1 kitchen, 3.5 bathrooms, washer & dryer, enclosed porch, and lots of parking space. Great place for large group gatherings. Beautiful and comfortable, with everything you'd need for cooking and relaxing.

Guest favourite
An aerial view captures the farmhouse in a vibrant red hue, surrounded by lush greenery and autumn foliage. The expansive yard includes several parked vehicles, while the mountains rise in the background under a clear blue sky.
Home in Sterling
4.94 out of 5 average rating, 220 reviews

Quiet country retreat with modern conveniences

Our mountain-view farmhouse sits on a 5 acre knoll, 300' from a quiet country road, surrounded by the sights and sounds of quintessential New England. The location of the property strikes a perfect balance between seclusion and convenience with access to hiking, kayaking, biking, parks, restaurants, grocery, and shopping close by. Restaurant food delivery of local favorites for Japanese (including sushi), Chinese, pizza, sub, salads, etc is available.

Guest favourite
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, 556 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!

Popular amenities for Sterling holiday rentals