Holiday rentals in Windsor

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Top-rated holiday rentals in Windsor

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Guest favourite

Home in Augusta

4.97 out of 5 average rating, 117 reviews

Lakefront Trifecta w/ Hot Tub & Free Massages!

Make memories at our updated, 2500 sq. ft., lakefront home. Use our kayaks, canoes & peddle boats for the family! Great fishing - 648 acre lake. We offer many outside games, range of indoor games & arcade systems. Amazing 4-seasons room with outdoor dining setup viewing the lake. Enjoy our new hot tub, and grilling deck right outside master bedroom. Lavish soaking tub in master bath. Only 4 minutes to golf, 10 minutes to capital city, Augusta, and 45 minutes to skiing as well as Atlantic Ocean!

Guest favourite

Guest house in Washington

4.96 out of 5 average rating, 142 reviews

Fox and Bird Retreat on Davis Stream

Our off-the-grid, solar-powered cottage is nestled within our 18 acres in the town of Washington, Maine. The cottage borders a beautiful stream, is surrounded by tall pines and is several hundred feet away from our home, providing a very private and serene experience. Guests can wander or snowshoe on our property, relax in the screen house next to the cottage or hang by the accessible fire pit. We are close to many local lakes and hiking trails and only 30 minutes from Camden & Rockland.

Guest favourite

Loft in West Gardiner

4.97 out of 5 average rating, 153 reviews

Cozy, Efficiency Apartment with Hot Tub

Keep it simple at this peaceful, centrally-located efficiency apartment. 15 minutes to Gardiner and Augusta, 15 minutes to I95/295. Less than one hour from Portland. Walk along the stream, listen to the loons or enjoy relaxing in the hot tub. If you want to paddle in a kayak, you can do that too! Eagles regularly soar overhead. Queen size bed, love seat and room enough for a pack and pay or twin air mattress. A/C, full kitchen, Keurig, microwave, toaster, dishes. Wifi and cable. Roomy parking.

Guest favourite

Home in Pittston

4.99 out of 5 average rating, 142 reviews

Riverside

Overlooking Kennebec River, Riverside is a perfect setting. Open 365 days per year; 2BR, 1 BA, kitchen, DR/common area. Situates 6 comfortably, 8 with use of floor mattresses. Renovated, open concept, our home is wheelchair accessible with a wide range of amenities for disabled. We accept Service dogs and will consider family dogs and other pets on a case-by-case; please ask. Owners reside on property in separate building. Outdoor trail cameras in use to monitor exterior of residence only.

Guest favourite

Loft in Hallowell

4.91 out of 5 average rating, 185 reviews

Priivate hot tub & no cleaning fees

The Widow Avery House is a historic Georgian Federal located within two blocks of downtown Hallowell. There is a spacious bedroom with two twin beds and desk with desktop computer available for use, a sitting area with couch and large roku TV, dining area with fridge, microwave, toaster oven and keurig with complimentary coffee and private bathroom with shower. During the season complimentary bikes and kayaks are available. If the guest has a service dog, the pet deposit is $1500.

Guest favourite

Cottage in Boothbay Harbor

4.98 out of 5 average rating, 374 reviews

The Cottage at the McCobb House

Freshly renovated inside and out, the cottage is your private Maine camp. Located on an acre and a half of wooded grounds, and surrounded by forest, the cottage feels secluded, but it’s only a mile to the restaurants, shops, and waterfront attractions of bustling Boothbay Harbor. With hiking trails in the Pine Tree Preserve that adjoins the property and the Lobster Cove Meadow Preserve a five minute walk up the road, you can also explore nature and enjoy the solitude of the woods.

Guest favourite

Yurt in Appleton

4.96 out of 5 average rating, 216 reviews

SILVER MOON, a Yurt for All Seasons

Silver Moon at The Appleton Retreat is quite private, check out the Trail Map. This contemporary yurt features a private therapeutic hot tub on the wrap around deck, a fire pit, and fast wifi. Silver Moon is located in a wooded area close to a bog that attracts a variety of wildlife. The Appleton Retreat encompasses 120 acres hosting six unique retreats. To the south is the Pettengill Stream, a resource protected area. To the north is the Nature Conservancy's 1300 acre reserve.

Guest favourite

Home in Appleton

4.96 out of 5 average rating, 162 reviews

The Barn

I call my place "The Barn" because as I was finishing it it took the shape and feel of a barn. It's not a barn. It's a quiet post and beam open concept building (a Jamaica Cottages kit) set among the fields of Appleton Maine. You'll sleep in the loft or on a futon on the main floor. The bathroom is huge, 10X10, with a heated floor. It's an open concept kitchen and living space. From Appleton you are 20 miles away from the tourist destinations of Camden, Rockland, and Belfast.

Guest favourite

Guest suite in Oakland

4.98 out of 5 average rating, 117 reviews

Cozy Studio Flat, Belgrade Lakes Region

Kick back and relax in this calm, stylish, newly renovated second floor space over the garage. Enjoy four seasons in the Belgrade Lakes region of Central Maine. Hunting, fishing, hiking, biking, skiing, and snowmobiling, to name a few of the many activities available. We are 2 miles from Oakland Waterfront Park on Messalonskee Lake and just over an hour drive from both beaches and ski resorts.

Guest favourite

Home in Lisbon

4.93 out of 5 average rating, 389 reviews

Unplug at a Beachy Bolthole with Classic New England Style

Chill on the porch after exploring a scenic local walking trail and soak up the serenity of this breezy blue and white hideaway. Striped oars, starfish, smooth shells, and ocean scenes blend with shades of teal and aqua for a thoroughly calm space. There are EV chargers behind the post office. It’s around a block and a half.

Guest favourite

Place to stay in Owls Head

4.98 out of 5 average rating, 210 reviews

A comforting sweet off grid cabin near the beach!

Get away from it all when you stay at our sweet little off grid cabin in the woods. A place where sleep and peace meet! Surrounded by 15 acres of woods and fields and within walking distance to Birch Point State Park, you'll have a perfect little getaway - all while being only a few minutes away from Rockland.

Guest favourite

Rental unit in Searsmont

4.98 out of 5 average rating, 133 reviews

Searsmont Studio

Entire studio efficiency apartment w/ private entrance above our garage. Fully furnished, including washer and dryer. Country setting on quiet road. Starlink High Speed WiFi/Satellite TV. Gardens, lawns and picnic table. Close to Camden, Rockport and Belfast, but in the country.