Windsor Vacation Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Browse Select Windsor Vacation Homes

“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage

10.0 out of 10, Exceptional, (27)
"The owners were ver accommodating and the place is a quiet, pretty location "
The price is CA $249
CA $481 total
includes taxes & fees
Aug 18 - Aug 19
“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage

Peaceful home with forest views & great yard - minutes to town

8.8 out of 10, Excellent, (5)
"Your home is beautiful!! Love all the windows, very comfortable!!"
Peaceful home with forest views & great yard - minutes to town

3 Bedroom year round lakefront home on Three Mile Pond with private dock

9.8 out of 10, Exceptional, (88)
"Great location. Very peaceful with beautiful view too. Would stay here again!"
3 Bedroom year round lakefront home on Three Mile Pond with private dock

Lakefront home on Long Pond with private dock, firepit & woodstove- dog-friendly

9.2 out of 10, Wonderful, (20)
"The house & deck were very nice with beautiful view of the lake. It could use some typical amenities like tissues, hair dryer, etc. The main problem is getting to the house. It’s a 3/4 mile drive down a narrow stone road riddled with potholes and bumps. I was afraid I was going to do damage to the rental car and that’s driving at or lower than the 15mph speed limit! "
Lakefront home on Long Pond with private dock, firepit & woodstove- dog-friendly

Cozy Cottage on water's edge of Lake Cobbosseecontee

8.8 out of 10, Excellent, (12)
"Great little getaway, sitting right by the water. We loved our time there. Alarice is a great hot and responded quickly to any needs or questions."
The price is CA $179
CA $438 total
includes taxes & fees
Aug 17 - Aug 18
Cozy Cottage on water's edge of Lake Cobbosseecontee

Weekly discounts avail. Get away at this New house on Lovejoy Pond in Albion

9.8 out of 10, Exceptional, (31)
"This place was perfect for our 3-night stay. Inside, it hits the sweet spot between well-equipped but uncluttered. The bird-watching overlooking the water was fantastic - from huge bald eagles to petite hummingbirds. "
Weekly discounts avail. Get away at this New house on Lovejoy Pond in Albion

Dog-friendly lakefront home with dock, fireplace, firepit, lake views, & 1 kayak

7.6 out of 10, Good, (21)
"We enjoyed this place and will definitely come back again."
Dog-friendly lakefront home with dock, fireplace, firepit, lake views, & 1 kayak

Spacious Country Home w/ Hot Tub, near Colby/Thomas

9.8 out of 10, Exceptional, (26)
"This house has everything for a weekend family vacay; you can spend the whole weekend enjoying the house & amenities such as the hot tub!"
The price is CA $327
CA $645 total
includes taxes & fees
Sep 6 - Sep 7
Spacious Country Home w/ Hot Tub, near Colby/Thomas

Tree-lined home with screened porch & perfect Midcoast location

8.8 out of 10, Excellent, (10)
"Very nice and private home that has everything you’ll need on your trip."
Tree-lined home with screened porch & perfect Midcoast location

Spectacular Location Reasonably Priced

9.6 out of 10, Exceptional, (29)
"Peaceful and scenic location"
Spectacular Location Reasonably Priced

Warm & Inviting Lakeside Retreat, Private, Tranquil Picture Perfect Setting

10.0 out of 10, Exceptional, (11)
Warm & Inviting Lakeside Retreat, Private, Tranquil Picture Perfect Setting

Spectacular Cobbossee Lakefront with Hot Tub&Dog Friendly

10.0 out of 10, Exceptional, (248)
"Had another great fishing trip with this as our home base! Always clean and comfortable! "
Spectacular Cobbossee Lakefront with Hot Tub&Dog Friendly

Find Your Bliss at this Private and Captivating Lakeside Retreat

10.0 out of 10, Exceptional, (25)
"Great stay, amazing house and property!"
Find Your Bliss at this Private and Captivating Lakeside Retreat

The Modern Maine Retreat

8.8 out of 10, Excellent, (8)
"Multi generation family in town to visit other family. Kitchen adequate for meal prep, "
The Modern Maine Retreat

Elegant home with a cozy living area, Wifi, backyard, and washer/dryer

8.0 out of 10, Very good, (3)
"This house is so cute. It had everything we needed and the hosts were easy to work with. "
Elegant home with a cozy living area, Wifi, backyard, and washer/dryer

Coastal Farmhouse in historic Sheepscot Village

10.0 out of 10, Exceptional, (2)
"Lovely updated older home. Excellent kitchens (yes - two!!), comfortable bedrooms, nice bathrooms - one with charming claw foot tub/shower. Very comfortable couch, sitting from and dining area for six. Marvelous screened in porch with ceiling fan. On a dead end street perfect for walking dogs. Close to Damariscotta. Responsive host. Clean charcoal Weber grill. Dishwasher, free laundry machines."
Coastal Farmhouse in historic Sheepscot Village

Sunfish Cove is the perfect year round getaway.

10.0 out of 10, Exceptional, (47)
"We had a wonderful stay. Everything was clean and the amenities were perfect. The kids had fun with all the games. The hosts responded quickly to all questions and had great suggestions for activities in the area. When we return we will be sure to stay again. "
Sunfish Cove is the perfect year round getaway.

Perfect Maine Getaway in a Recently Renovated Cabin!

9.6 out of 10, Exceptional, (15)
"Had a great time at the cabin, just steps from town. Would recommend if you want to close to everything."
Perfect Maine Getaway in a Recently Renovated Cabin!

Located directly in central downtown and beach area, fish or kayak from backyard

8.0 out of 10, Very good, (6)
"Enjoyed our stay. House was clean and well equipped. However, access to Lake Annabessacook is limited. Will consider staying there again in the future."
Located directly in central downtown and beach area, fish or kayak from backyard

Damariscotta Lakefront 3BR+

6.0 out of 10, (1)
"The house has good size rooms. The house is hot on hot days - definitely needs more ceiling fans or some AC units and/or box fans for air circulation. Screened in porch is very nice. Not our definition of lake front (would call it lake house) and the water at dock very shallow so not boat friendly other than kayaks/canoes. Lots of lily pads and water weeds. Quiet cove except when nearby camp going on but happy noises with that but louder. "
Damariscotta Lakefront 3BR+
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in

Top Windsor Hotel Reviews