Holiday rentals in Littleton

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Top-rated holiday rentals in Littleton

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

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Top guest favourite
Flat in Groton
4.96 out of 5 average rating, 141 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
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, 218 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.

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 Framingham
4.98 out of 5 average rating, 121 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, 40 min. to Gillette 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
Cottage in Stow
4.97 out of 5 average rating, 239 reviews

White Pine Cottage – Cozy 3BR w/ Fireplace

Welcome to White Pine Cottage - a cozy 1930s cottage in Stow, MA with modern amenities. Great landing pad if you are coming to the area to visit family, work or a weekend getaway. Located in quiet wooded neighborhood with very little traffic. Relax by the fireplace and enjoy a soak in the whirlpool tub. Convenient to local farms, orchards, golfing, wooded trails and more. Hudson, Sudbury and Maynard's restaurants and shops 15 minutes away and big city Boston / Cambridge only 40 minutes.

Top guest favourite
The home is nestled among trees in a wooded setting, with a deck visible in the distance. Sunlight filters through the foliage, casting dappled light on the ground, while an array of green leaves and flowering plants create a natural frame around the structure.
Guest suite in Bolton
4.97 out of 5 average rating, 202 reviews

Vaughn Hill Hideaway & Sauna

Tucked into the slope of Vaughn Hill on 3 wooded acres, the entire lower level of our home is yours to enjoy. Cozy 2-bedroom unit with “the BEST BEDS at an Air BNB ever!" to quote a guest. Visit Nashoba Valley Winery, get coffee at Harvard General Store, go apple-picking at a local orchard, or hike Vaughn Hill trails. *Wood-fired backyard sauna available by request with $20 firing fee *Well-behaved dogs (non-destructive, house-broken) welcome! Sorry - no cats, due to prior experiences.

Top guest favourite
A serene lakeside view captures a vibrant sunset with the sun partially descending behind distant hills. A lone fisherman in a boat is visible on the water, while a wooden deck features seating arrangements surrounded by lush plants.
Guest suite in Tyngsborough
4.98 out of 5 average rating, 268 reviews

Lakefront Suite Two-Room, Comfy, Tranquil

Located on a lovely small lake, the upstairs suite has a panoramic view from the bedroom, a private spa-like bathroom, cotton linens, a comfy bed, A/C and a living room - it feels like an apartment, but no kitchen. Quietly watch lake nature or boats going by, or choose to swim, kayak, or fish. Enjoy industrial history at Lowell's National Park, take a forest walk nearby, or drive 10 min. to Nashua for its many restaurants, a casino, or tax-free shopping. We are one hour from Boston.

Top guest favourite
A bright yellow two-family home is positioned amidst greenery, featuring a welcoming entry with a red door. A small flowering tree adds a splash of color in front, while a large deck is visible in the background, perfect for outdoor gatherings.
Home in Chelmsford
5 out of 5 average rating, 249 reviews

Newly renovated, spacious, clean, 3 bedroom home.

Whether traveling for business or pleasure, this ideally located, pet-friendly home in North Chelmsford, Massachusetts, is accessible to major highways and commuter rails. The home is close to major hospitals, universities, and concert venues. The area is rich in America’s history and is surrounded by historical sites to visit all within minutes. The beautiful, light, airy living space boasts all the comforts of home. Our goal is to give you the best travel experience possible.

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, 463 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.

Top guest favourite
A spacious exterior view showcases a two-story light gray house with a brick chimney, set against a backdrop of lush greenery and a mix of trees. A charming barn is visible in the distance, complementing the well-maintained gardens and open lawn.
Flat in Groton
5 out of 5 average rating, 101 reviews

Farmhouse Guest Apartment

Welcome to our quiet private guest apartment! Our property, is surrounded by fields, woods, gardens, and a pond. You will enter through a shared entrance & stairway in our home, but have an entire 725 sq. ft. guest apartment all to yourself that includes a living room, full kitchen, bathroom, and large bedroom with a desk. It has ample light with views of fields, stone walls, Christmas trees and our barn. Out back we have a pool, table & chairs you may use.

Top 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, 531 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.

Top guest favourite
A private entrance to a charming home is framed by well-maintained landscaping and a gravel driveway. Decorative flower boxes adorn the windows of the light-colored exterior, while surrounding trees provide a natural backdrop, creating a serene environment.
Flat in Concord
4.96 out of 5 average rating, 230 reviews

Mema's Place --Lovely apartment in private home

This private apartment in a lovely home in historic Concord, Massachusetts features one bedroom with queen bed, living room, kitchen, bathroom, and porch. Your apartment is locked off from the rest of the home and you have your own entrance. We are within 4 miles of Concord Academy, Middlesex School, the North Bridge, Sleepy Hollow Cemetery (where Alcott, Thoreau, Emerson, and Hawthorne are buried).

Guest favourite
An open living area features a cozy striped sofa and a bright red pub table. A winding black staircase leads to the upper sleeping area. Natural light enters through a nearby door. A flat-screen TV is mounted on the wall, enhancing the space's functionality.
Barn in Carlisle
4.88 out of 5 average rating, 460 reviews

Private Studio w/ Loft Center Historic Carlisle

Charming private studio in the heart of Carlisle, perfect for 2 adults (up to 4 guests). Completely separate with no shared spaces. Close to Routes 128, 495, 35min to Boston, 10 min to historic Concord. Outdoor lovers enjoy nearby hiking, biking, and Great Brook Farm State Park. Easy access to Lowell, Nashoba Valley Ski Area, shops, and restaurants.

Popular amenities for Littleton holiday rentals