Vacation rentals in Windsor

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Top-rated vacation rentals in Windsor

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Guest favorite

Guesthouse in Washington

4.95 out of 5 average rating, 131 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.

Aug 12 – 19

G$26,680 GYD per night

Guest favorite

Loft in West Gardiner

4.98 out of 5 average rating, 112 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.

Apr 17 – 24

G$24,835 GYD per night

Guest favorite

Yurt in Appleton

4.96 out of 5 average rating, 227 reviews

SUMMER ROSE a Yurt for ALL Seasons

SUMMER ROSE - Overlooking the Field of Dreams pasture, and future pond, is a spacious wooden yurt with a spectacular ceiling, personal hot tub and "Hideout" a screened in sanctuary. The Appleton Retreat is situated on 120 acres of privately owned land. To the south, a short walk from Summer Rose, is the Pettengill Stream, a resource protected area where you can view wildlife or kayak; and to the north, a wooded trail leads to a secluded pond on 1,300 acres of Nature Conservancy protected land.

Jan 11 – 18

G$33,950 GYD per night

Guest favorite

Home in Augusta

5.0 out of 5 average rating, 12 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 offers a fantastic cabin-style space complete with its own bathroom) to lounge after a long day exploring. 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.

Oct 22 – 29

G$30,891 GYD per night

Guest favorite

Apartment in Nobleboro

4.89 out of 5 average rating, 137 reviews

Finding Joy

This lovely apartment is above our garage. You can come and go as you please. We have created a place for peace and solitude. Sit on the deck or look out the dining room window and see the woods and wait for the birds and wildlife that may be wonder through the yard. There is coffee and tea available, along with basic breakfast supplies, if you wish. Keyless entry allows for you to come anytime after check-in. Please note, you have to be comfortable with stairs to access the apartment.

Jul 16 – 23

G$25,481 GYD per night

Guest favorite

Guesthouse in Orland

4.99 out of 5 average rating, 103 reviews

Cozy cottage in Orland Village-Penobscot Bay area

Charming cottage in Orland Village, 2 minutes from Bucksport, a short walk away from the Orland River and its estuary on the Penobscot Bay. Nestled on 3.5 acres of wooded land, 300 ft behind an 18th-century colonial house. Completely self-contained with equipped kitchen. Fast 400 Mbs cable internet/WiFi. 45 minutes to Acadia National Park, 30 min. to Belfast, 20 min. to Castine. Perfect base for hiking, kayaking, sailing, or discovering the maritime past of the area. Pet friendly!

Dec 7 – 14

G$21,486 GYD per night

Guest favorite

Home in Appleton

4.96 out of 5 average rating, 123 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.

May 4 – 11

G$29,668 GYD per night

Guest favorite

Apartment in Hallowell

4.98 out of 5 average rating, 301 reviews

Two Bedroom Mid Century Modern Downtown Apartment

Experience this amazing two bedroom Mid-Century Modern apartment in Downtown Hallowell. This is newly renovated & steps away from a variety of restaurants & pubs. It has all the fun and funky charm of the early 1960’s with bright colors, rich woods, clean lines & shag rugs. All the modern comforts including stainless steel appliances, vessel sinks, soaker tub & new beds. A couple miles from the State Capital and centrally located between Brunswick and Waterville.

Nov 30 – Dec 7

G$27,047 GYD per night

Guest favorite

Dome in Jefferson

4.98 out of 5 average rating, 168 reviews

ComfyDome Glamping Hill-Side Site!

Situated on a cozy little hill, you'll be elevated above all the other domes, affording you a "royal" view of the landscape! With a clear view of the sprawling fields, you'll frequently be the first to spot the family of deer that visit ComfyDome. Your heart will be filled with joy at the sight of the newborn fawns walking through the grass. You'll be surrounded by stunning natural beauty on all sides and will have ample open space to enjoy your site in comfort!

Oct 13 – 20

G$26,460 GYD per night

Guest favorite

Cabin in Freedom

4.9 out of 5 average rating, 288 reviews

Cozy Lakefront Cabin in Freedom, ME

Our secluded, very quiet and private two bedroom cabin with loft features a bug-free screened-in porch on its large deck. The cabin overlooks peaceul Sandy Pond, inhabited by bald eagles, loons, and herons. Watch beautiful sunrises and sunsets, and swim, fish and kayak from our dock. We're close to coastal Belfast, Unity, MOFGA (annual Common Ground Fair), Waterville, Acadia and Camden. Eat at The Lost Kitchen, visit the Amish, hike the Hills to Sea Trail.

Dec 14 – 21

G$17,120 GYD per night

Guest favorite

Guesthouse in Unity

5.0 out of 5 average rating, 193 reviews

Modern Home on Working Farm

Modern duplex built recently across the street from a small berry and vegetable farm. This fully furnished home has a large deck with a great view. It is located 2.5 miles from Freedom village and the Lost Kitchen restaurant. It is also 8 miles from Unity College, and the Common Ground Fair fairgrounds. This single story building has a ramp, but it is slightly steeper then current standards. The inside is also laid out for wheelchair access.

Jan 16 – 23

G$20,475 GYD per night

Guest favorite

Apartment in Richmond

4.91 out of 5 average rating, 227 reviews

The Barn by Swan Island: Whimsical, Comfy, & Fun!

Welcome to the place we call "The Barn by Swan Island." Located in Richmond, ME, just a short distance from the free boat launch to Swan Island in the Kennebec River. Originally built in the mid 1800's as an attached barn to our lovely Victorian home, we have completely renovated and remade the space into a fun, comfy, and whimsical AirBnB experience. An ideal location for a trip to Midcoast Maine!

Sep 20 – 27

G$27,107 GYD per night