Holiday rentals in Windsor

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Top-rated holiday rentals in Windsor

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

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Top guest favourite

A large blue house with multiple sections is pictured beside a clear lake. A private dock extends into the water, and outdoor seating in the form of two chairs is visible on the lawn, surrounded by lush trees.

Home in Augusta

Lakefront: Private Hot Tub, Sauna & 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!

4.96 out of 5 average rating, 237 reviews

Guest favourite

Cabin in Whitefield

Maybelle the Tiny Cabin on 100 acres

Maybelle is an 8x18 cabin with a full-size loft bed, a Cubic Mini Woodstove (wood provided), Natures Head Composting Toilet and Jetsetter massaging hot tub. Kayaks, paddle board, & canoe included . Walking trails surround your cabin. Outside there’s a fire pit and a quick path to the water. Maybelle's kitchen has all the cooking essentials and there's a small propane grill outside & the fire pit for cooking. Cell reception is okay in the cabin, wifi is from a Starlink booster & Window A/C

5.0 out of 5 average rating, 136 reviews

Top guest favourite

Cabin in Chesterville

Off-Grid Cabin with Wood Fired Hot Tub. 4 Kayaks

Relax at this off-grid modern A-Frame cabin on 90 acres in Maine's Lakes Region. The cabin is tucked deep in the woods, far away from everything. 4 kayaks and firewood included. Separate bunk cabin increases sleeping capacity to 10 Wood-Fired Cedar Hot Tub - a relaxing, very unique experience 5+ lakes nearby- beautiful swimming and kayaking Cedar throughout cabin, concrete countertops, cedar/concrete shower. Outdoor firepit. Hiking trails. Beaver Pond. Property has private airstrip (51ME)

5.0 out of 5 average rating, 213 reviews

Guest favourite

A serene lakeside view is framed by trees as dusk approaches, showcasing calm waters reflecting soft evening light. A small table and comfortable chairs sit on a stone patio, while a dock is visible nearby, perfect for relaxing by the water.

Cottage in China

Lake House on Three Mile Pond with Amazing views

Enjoy Three Mile Pond from a private cottage with amazing views, Quiet and private to enjoy Maine the way it should be, deck, dock, kayaks are available, grill, fire pit and wood for the fire. Sleeps 6, 2 Queen size beds in loft and a queen size sleeper sofa on the main floor. Second floor deck with seating Wake up in the morning and walk directly outside to enjoy coffee and breakfast while enjoying the loons. Linens, towels, pillows and blankets supplied, groceries, laundry, restaurants nearby.

4.98 out of 5 average rating, 91 reviews

Top guest favourite

A circle of white Adirondack chairs is arranged around a fire pit on a manicured lawn. Tall trees provide shade, and a serene lake is visible in the background, reflecting the soft light of the evening. The scene conveys a peaceful outdoor gathering space.

Home in Oakland

Lakefront 3 bedroom pet friendly on Messalonski

Make memories of a lifetime at this unique and cozy family-pet-friendly private lakefront on Messalonskee. Beautifully manicured lawn/gardens with a fire pit surrounded by the peaceful sounds of nature. A large dock to take in the spectacular views of bald eagles, loons, and blue herons. Owners boat is attached for occasional boat rides. This guesthouse is newly built with a covered porch overlooking the serene lake. Comes w/3 kayaks, 2 paddle boards, a paddle boat, life jackets, and a canoe

4.99 out of 5 average rating, 100 reviews

Guest favourite

A charming cottage exterior is framed by lush greenery, featuring a welcoming front porch with white railings. Large windows allow natural light to fill the interior, while the gabled roof adds character. A few steps lead to the entrance, bordered by a rock and trees.

Cottage in Whitefield

Ollie's Cottage on the Sheepscot River

Lovingly restored riverfront cottage in the small village of Coopers Mills. 20 minutes from midcoast Maine (Camden, Rockland, Damariscotta) in the heart of a rural farming community in Lincoln County. This 100+ year old home, once owned by the host's great Aunt Ollie, is fully outfitted to accommodate up to 7 guests and always delivered sparkling clean. Explore the Sheepscot River, eat locally at Swallowtail Farm and Sheepscot General, treasure hunt at Elmer's Barn, and enjoy the quiet.

4.97 out of 5 average rating, 96 reviews

Top guest favourite

The tranquil water reflects a colorful sky at dawn, with soft pinks and blues blending above a tree-lined shore. Gentle ripples disrupt the mirrored surface, enhancing the serene ambiance of the scene.

Cottage in Augusta

Super cute waterfront cottage

Beautiful four-season waterfront cottage located on the outskirts of Augusta. The main living space has a full kitchen, living room/dining space, bathroom with laundry, and bedroom (queen bed). The walk-out basement, with its own bathroom, offers a cabin-style space to lounge in or as a second bedroom. Or stay outside and enjoy the water views from the second-story deck or ground-level fire pit. Either spot is an amazing place to enjoy the night sky and listen to the loons and eagles!

4.93 out of 5 average rating, 99 reviews

Guest favourite

A serene view of a lake at sunset is presented, showcasing soft hues of orange, pink, and purple reflected on the water. Silhouettes of trees line the shore, while the calm surface creates gentle ripples, inviting relaxation and contemplation.

Home in Manchester

Lakeside retreat on quiet cove on Cobbessee Lake!

Nothing beats summer days on the lake in Maine. Not only is this lake home situated on a quiet cove on central Maine's Cobbossee Lake, but it is near amenities in Augusta and close to I-95! Enjoy two large docks, a large lawn and gently sloping swimming area, and a newly renovated five bedroom house with two full bathrooms. This is the Maine vacation home you are looking for! Two of the bedrooms and one bathroom are in the basement, which is still under some small construction.

4.84 out of 5 average rating, 115 reviews

Guest favourite

A wooden deck is positioned among trees, offering views of a calm lake. A dining table with chairs is visible on the deck. Two kayaks are moored at a nearby dock, surrounded by lush greenery and reflections of the sky on the water.

Cabin in Augusta

Quintessential Maine cabin w/ private waterfront

Experience the historic Fox Glen Cabin with all the 1930s charm, updated with everything you need for a restful lakeside vacation! Enjoy your coffee on the screened-in porch overlooking the water or watch the sunset during a leisurely kayak. 15 minutes from the historic downtown, a microbrewery & local restaurants. This cozy cabin is pet friendly and perfect for up to 7 people, includes a full kitchen, beautiful stone hearth & gas fireplace, washer/dryer, fire pit, & 2 kayaks.

4.98 out of 5 average rating, 46 reviews

Guest favourite

A spacious living area with high ceilings is highlighted by wooden flooring and contrasting brick walls. A comfortable sofa faces a wooden coffee table, and two distinct entrances are visible. The kitchen features modern appliances, seamlessly integrated within the open layout.

Flat in Augusta

Loft - Downtown Augusta - 1 Bedroom

Welcome to Riverview Terrace Loft 7, located in the heart of Augusta, ME. This charming 1-bed, 1-bath apartment offers a full kitchen. The apartment boasts 12' high ceilings, creating an open and airy atmosphere. The stunning granite and brick walls add a touch of elegance to the space. Situated in the heart of downtown Augusta, you'll have easy access to all the amenities the city has to offer. The Kennebec River Rail trail, Restaurants, local shops are all just steps away.

4.89 out of 5 average rating, 101 reviews

Top guest favourite

The treehouse structure is illuminated at dusk, highlighting its elevated design among tall trees. Soft lighting from the windows enhances its cozy appearance. A spacious deck can be seen extending from the building, inviting relaxation amidst the surrounding forest.

Treehouse in Appleton

BREEZE, in a tree The Appleton Retreat

BREEZE Treehouse, at The Appleton Retreat is located on 120 acres of private land, bordered by 1,300 acres of a protected nature conservancy. To the south is the Pettengill Stream a resource protected area and to the north a large secluded pond. BREEZE does not have a hot tub but guests may reserve the sauna, which is close by and private. The Appleton Retreat is less than a 30 minute drive to Belfast, Rockport, Camden and Rockland, charming downeast seaside towns.

4.97 out of 5 average rating, 464 reviews

Top guest favourite

Home in Augusta

Cozy Lakefront Cabin on a Pond in Augusta, Maine

Escape to a private waterfront getaway on Three Cornered Pond. Watch fall color light up the shoreline, walk the pines, or unwind by one of two fire pits. This pet-friendly home blends Maine's rustic charm with modern comfort: a gourmet kitchen, arcade games, fast WiFi, warm heat pumps, and spa-like heated bidets. Ideal for families, friends, couples, or a quiet work retreat. Create precious memories in a warm, welcoming home designed for good times together.

4.96 out of 5 average rating, 27 reviews