Holiday rentals in Sterling

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Top-rated holiday rentals in Sterling

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

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Top guest favourite
A cozy living area is accompanied by a comfortable sofa with accent pillows. A television is placed on a side table. The kitchenette features a refrigerator, coffee maker, and essential cooking appliances, while sunlight filters through the window, illuminating the warm wood flooring.
Flat in Groton
4.96 out of 5 average rating, 136 reviews

Cute & Cozy Groton apartment w/private patio

Cozy apartment with your own private patio; 5-min walk to downtown, shops, cafes, library & restaurants; hop on the Nashua River Rail trail where you can walk/bike to neighboring towns. Enjoy all Groton has to offer, miles of hiking trails, rent a canoe or kayak, golf, horse riding, fishing, apple, pumpkin & berry picking; walk up to Bancroft Castle on Gibbet Hill where “Little Women" was filmed & enjoy the view. Don’t miss a visit to Groton Hill Music, our world class music performance venue 🎶

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, 230 reviews

Peaceful Mill with Waterfall - Top 1% 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 remote workspace

Top guest favourite
The sun sets over the calm waters of Cedar Lake, casting a golden glow across the surface. Fluffy clouds are visible in the sky, reflecting the warm colors of the sunset. A serene atmosphere is created by the natural surroundings.
Cottage in Sturbridge
4.97 out of 5 average rating, 164 reviews

Cedar Sunrise

Welcome to Cedar Lake. Come enjoy the lake and all it has to offer while staying in this cottage at the waters edge. This home may be small, but it offers a full kitchen with microwave, gas stove, Keurig and full size refrigerator. Open concept living, dining and kitchen. One bedroom with queen size bed, an open loft with a twin size bunk bed with trundle and a pullout couch in the living room. Full size bathroom with tub, washer & dryer on site. Enjoy grilling on the deck and soaking up the sun

Guest favourite
Home in Westminster
4.89 out of 5 average rating, 218 reviews

Lakefront, view of ski mtn, fireplace, sauna

Direct lakefront with panoramic views of Wachusett Mountain (#1 skiing in MA). In the summer, enjoy the kayaks, canoe, paddle-boards, motor boat. In the winter, cozy up next to the fireplace and enjoy a complimentary bottle of wine. In the fall, gaze upon the breathtaking foliage from the sunroom. Outdoor shower, dock, firepit, hammock, bike, washer/dryer, desk, sauna, dishwasher, linens, kitchen amenities. Our other lakefront house is down the road: www.airbnb.com/h/lakefrontmountainview

Top guest favourite
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 Nobscot
4.97 out of 5 average rating, 110 reviews

Cozy en suite w/ high ceilings

 Relax in this peaceful private en suite with breathtaking backyard views of the tall pine forest. Lots of natural light fills the space with room darkening shades to sleep in. Enjoy cozy nights by the fireplace and a well stocked granite kitchen. Great location only minutes to the Mass Pike. 25 min to Boston. 30 min. to Foxboro Stadium. Enjoy shopping at the Natick Mall, AMC movies, tons of diverse dining & grocery options. Backyard has firepit for outdoor eves. Safe walkable neighborhood.

Top guest favourite
A comfortable sofa is positioned near a window with sheer curtains, allowing natural light to illuminate the space. A decorative pillow with text is placed on the sofa, while a glass of wine rests on a wooden table outside, visible through the window.
Cabin in Winchendon
4.96 out of 5 average rating, 103 reviews

The little house on Mirror Pond

Escape to our fully renovated tiny pond house on the serene Mirror Pond. Perfect for up to 4 guests, enjoy swimming, kayaking, or floating on tubes. Unwind by the fire pit, barbecue on the deck, or cozy up by the fireplace (our apologize but it is currently not working) with board games on cooler days. With great WiFi, it’s also ideal for a peaceful work retreat. Whether you're here to relax, or get some work done, this tranquil hideaway offers the perfect blend of adventure and relaxation.

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, 186 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
The studio features a spacious bed with white linens, accented by decorative throw pillows. A vibrant piece of art adorns the wall above the bed. A modern vanity area with a sink is visible, along with natural light filtering through windows that offer views of the surrounding woods.
Guest suite in Milford
5 out of 5 average rating, 162 reviews

New England Village Luxury Studio

Kick back and relax in this stylish studio! Our house is in a quiet neighborhood of older homes surrounded by woodlands yet conveniently located downtown, a half mile from our village green (Milford Oval). A short stroll over the river will take you to cafes, restaurants, pubs with live music, post office, library, shops & useful stores such as CVS. Whatever brings you…business, skiing, hiking, antiques, a family celebration or a romantic weekend away…we are looking forward to hosting you!

Top guest favourite
The exterior of a charming residence is showcased, featuring light green siding and multiple windows adorned with white trim. A wooden front door with a welcoming wreath is visible, complemented by steps leading to the entrance and surrounding natural greenery.
Guest suite in Ashburnham
4.95 out of 5 average rating, 187 reviews

The Ginger Bed King and Queen Suite

Come for the lovely country setting, snow, amenities, neighborhood, convenience, privacy, spaciousness, the comfortable beds. Close to many wonderful hiking/biking paths, rail trails, Wachusett ski area, Jewel Hill, Lake Wampanoag, Kirby area. WI-FI, TV ( Hulu and Netflix), refrigerator, microwave, coffee/tea maker, (kitchenette, not a full kitchen) reading lights, table area, continental breakfast, parking... For couples, families with older children, and friends. Everyone is welcome!

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
4.98 out of 5 average rating, 196 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.

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.
Guest house in Westminster
4.98 out of 5 average rating, 471 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
4.89 out of 5 average rating, 513 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.

Popular amenities for Sterling holiday rentals