Vacation rentals in Windsor

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Top-rated vacation rentals in Windsor

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Top guest favorite

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

4.96 out of 5 average rating, 170 reviews

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!

Guest favorite

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

4.97 out of 5 average rating, 393 reviews

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 guests may reserve the wood fired cedar hot tub and the sauna, which are close by and private, at an additional charge. The Appleton Retreat is less than a 30 minute drive to Belfast, Rockport, Camden and Rockland, charming downeast seaside towns.

Top guest favorite

A rustic cabin features a wooden exterior with stone accents, situated on a grassy area. An open door invites guests inside, while a bright green hammock is strung nearby among the trees. A fire pit is visible in the background, surrounded by natural landscaping.

Cabin in Dresden

4.98 out of 5 average rating, 259 reviews

Merrymeeting Midcoast Cabin

RUSTIC-no running water! cabin perfect for exploring all mid-coast Maine has to offer: 3 hours from Boston or Acadia, 1 hour to Portland and Maine’s gorgeous beaches. 10-30 minute drive to Hiking, swim spots, farm-stands, nationally recognized dairy farms, breweries, restaurants. 5 minute walk from a pickleball court. Stargaze in the hammock by campfire, Grill dinner, check out local tide charts to float in canoe or kayak on the Eastern river. Wood fired oven can be rented for additional fee.

Guest favorite

A cozy blue cottage is set among snow-covered trees, with a welcoming red trim around the door and windows. Three dogs sit in the foreground, showcasing their friendly demeanor, while a small sled leans against the cottage, suggesting winter activities nearby.

Guesthouse in Washington

4.95 out of 5 average rating, 152 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 favorite

Cabin in Whitefield

4.96 out of 5 average rating, 134 reviews

Roxie the Tiny Cabin on 100 acres

If all you need is a bed and a bathroom & hot tub, Roxie is the cabin for you! A very comfortable full-size bed, a composting toilet, and a mini woodstove are here for you in this cozy 8x12 cabin in the woods. 2wd access & a parking spot near your door. Hike trails, kayak, fishing, cross-country skiing, or snowshoeing then return to your little space to relax & enjoy! A firepit with wood, an outside table, hammock chairs, and solar power lights & charging. 24/7 Guest restroom with show

Top guest favorite

An open living space features a cozy seating area with a light-colored sofa and a decorative area rug. A spacious bed is placed in one corner, accompanied by soft bedding. The kitchenette is visible in the background, along with a doorway leading to a bathroom.

Apartment in Gardiner

4.98 out of 5 average rating, 149 reviews

The Escape on Elm

Our charming Airbnb is located in the heart of Gardiner Maine. Built in 1850, our historic home combines old-world charm with modern comforts. Enjoy the creaking hardwood floors, exposed beams, and coastal accents that create a calming, seaside vibe. The open layout offers a spacious living room with a sofa bed, Smart TV, books and board games. We offer a comfortable sleeping area with a queen bed. A full bathroom. Enjoy cooking in the fully equipped kitchen that opens to a private porch.

Guest favorite

A cozy interior of the RV is displayed, featuring a black sleeper sofa adorned with two light-colored pillows. A wooden dining table is positioned nearby, complemented by a blue-green chair. A small kitchenette and bathroom area are visible in the background, with natural light filtering through the window.

Camper/RV in Palermo

4.9 out of 5 average rating, 129 reviews

Camp at Shale Creek Homestead

Stay with us at Shale Creek homestead! No cleaning fee!! Come enjoy the charm of rural Maine! Countless beautiful ponds and lakes minutes away. Spectacular views of the Milky Way on clear nights and much more! Short drives to the Belfast/costal areas and Augusta. A manageable distance from the mountains of western Maine. Beautiful Branch pond at the end of the street. Lake St. George and China Lake under 10 minutes away. A Great location to enjoy Maine Kayak rentals available on site

Guest favorite

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

4.98 out of 5 average rating, 88 reviews

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 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 are supplied, groceries, laundry, restaurants nearby.

Top guest favorite

A spacious bedroom features a large bed with blue bedding against a dark blue accent wall. Two bedside lamps provide soft lighting. A comfortable leather armchair is positioned next to a small nightstand, which holds a tissue box and a framed print.

Home in Hallowell

4.97 out of 5 average rating, 152 reviews

Hilltop Retreat with A/C, Hot Tub & Sauna

Discover this newly renovated 2-bedroom, 1-bathroom home in a quiet family-friendly neighborhood in Hallowell. This home's rustic-modern design, natural light, and all-new amenities make it a perfect getaway. Relax in the hot tub or infrared sauna, grill on the deck, enjoy the backyard or visit downtown Hallowell and explore its restaurants, cafes, live music and antique shops. This home is also minutes away from several hiking and walking trails that can all be found in our guidebook.

Top guest favorite

A charming two-story building features warm wood siding and a green metal roof. The entrance is framed by a covered porch and surrounded by well-maintained landscaping. Tall trees provide shade in the foreground, enhancing the welcoming appearance of the property.

Apartment in Washington

4.97 out of 5 average rating, 121 reviews

The Washington Suite on u-pick blueberry farm.

This unique place has a style all its own. No, he didn’t sleep here, Washington that is, but now you can. Our one-hundred-acre farm is located in the small rural village of Washington. It is located just 2/10 of a mile from the village center where the general store, library and town offices are located. Easy commute east to the coast and the must-see towns of Rockland, Rockport and Camden or west to our capitol, Augusta. One hour and forty minutes to Bar Harbor and Acadia national park.

Top guest favorite

The open-concept living area features a comfortable couch and a recliner, complemented by a dining table and modern kitchen appliances. Natural light enters through the windows, illuminating the space that is adorned with neutral tones and wood flooring.

Cottage in Augusta

5 out of 5 average rating, 107 reviews

Modern Hideaway in Augusta

Centrally located modern guest home in Augusta, access points to Portland, Midcoast Maine, and Bangor. Spacious master bedroom with closet, additional bedroom, both bedrooms with queen size beds. Handicap bathroom equipped with grab rail and also handicap accessible shower with sit down bench. Many brand new amenities. 55 inch TV has Roku with access to Netflix , Disney Plus, and more! Strong WiFi with the ability to work remotely if needed and explore Augusta and surrounding area.

Guest favorite

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

4.92 out of 5 average rating, 65 reviews

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!