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.

May 20 – 27

R2,329 ZAR per night

Guest favorite

Loft in West Gardiner

4.98 out of 5 average rating, 110 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.

Feb 2 – 9

R2,283 ZAR per night

Guest favorite

Home in Augusta

5.0 out of 5 average rating, 11 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.

Aug 28 – Sep 4

R3,054 ZAR per night

Guest favorite

Cabin in Whitefield

5.0 out of 5 average rating, 56 reviews

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 Jackery Solar Power generator. 2 kayaks, paddle boards or a canoe included . Hiking trails (some solar lit) surround your cabin. Outside is 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 phone reception is available in the cabin, wifi coming soon!

Feb 18 – 25

R2,585 ZAR 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.

Sep 16 – 23

R2,077 ZAR per night

Guest favorite

Cottage in Augusta

5.0 out of 5 average rating, 80 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.

Aug 24 – 31

R2,893 ZAR 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 17 – 24

R2,050 ZAR per night

Guest favorite

Home in Appleton

4.96 out of 5 average rating, 122 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 21 – 28

R2,728 ZAR per night

Guest favorite

Apartment in Hallowell

4.98 out of 5 average rating, 300 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.

Dec 13 – 20

R2,487 ZAR 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

R1,574 ZAR per night

Guest favorite

Cabin in Augusta

5.0 out of 5 average rating, 12 reviews

Price's Point - Cozy Cabin

Brand new Cozy Cabin on a small 181 acre pond. Enjoy the cabin feel of knotty pine and a big country porch overlooking the water. Walk in access to the water or ice in the winter. Kayaking, canoeing, ice fishing, snowmobiling and more depending on the time of year. A peaceful location a mile down a private road but 10 minutes away from a grocery store etc. Eagles, loons and fish will be your neighbors as you are in the moment at Price's Point.

May 11 – 18

R6,562 ZAR per night

Guest favorite

Guesthouse in Unity

5.0 out of 5 average rating, 192 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.

Oct 27 – Nov 3

R1,882 ZAR per night