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Check prices for these dates

In two weeks
Sep 5 - Sep 7
In two months
Oct 17 - Oct 19
In three months
Nov 14 - Nov 16
In four months
Dec 12 - Dec 14

Browse Select Windsor Vacation Homes

Our top choices for Windsor vacation homes

Sister A-Frame in Woods B
Exterior

Sister A-Frame in Woods B

10.0 out of 10, Exceptional, (3)
"Great stay. Would stay here again if in the area."
The price is CA $167
CA $317 total
includes taxes & fees
Aug 25 - Aug 26
Sister A-Frame in Woods B
Cozy Cottage on water's edge of Lake Cobbosseecontee
Property grounds

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 $180
CA $441 total
includes taxes & fees
Aug 25 - Aug 26
Cozy Cottage on water's edge of Lake Cobbosseecontee
Little Landing Cottage-gorgeous View BBQ Wi-fi
Suite

Little Landing Cottage-gorgeous View BBQ Wi-fi

3.5 star property
10.0 out of 10, Exceptional, (1)
"I love this little cottage. I will definitely be staying again. Thank you.!!!!!"
The price is CA $520
CA $974 total
includes taxes & fees
Sep 1 - Sep 2
Little Landing Cottage-gorgeous View BBQ Wi-fi
Dome 1 - Luxury Dome at Come Spring Farm
Exterior

Dome 1 - Luxury Dome at Come Spring Farm

9.8 out of 10, Exceptional, (11)
"We had a great experience with our stay Everything was nice the owner was very helpful and friendly "
The price is CA $277
CA $409 total
includes taxes & fees
Aug 25 - Aug 26
Dome 1 - Luxury Dome at Come Spring Farm
Sunset Chalet-amazing Views Private hot tub
Suite

Sunset Chalet-amazing Views Private hot tub

3.0 star property
10.0 out of 10, Exceptional, (1)
"Easy to find, amenties were great for kitchen, bathroom, and game room. We look forward to going again but try one of the treehouses. "
The price is CA $668
CA $1,136 total
includes taxes & fees
Aug 26 - Aug 27
Sunset Chalet-amazing Views Private hot tub
NEW Cozy Cabin located in Oakland tucked away in a peaceful wooded scene.
Fridge, microwave, stovetop, coffee/tea maker

NEW Cozy Cabin located in Oakland tucked away in a peaceful wooded scene.

The price is CA $215
CA $432 total
includes taxes & fees
Aug 30 - Aug 31
NEW Cozy Cabin located in Oakland tucked away in a peaceful wooded scene.
Red Cedar Haven in Sidney
House

Red Cedar Haven in Sidney

2.0 star property
The price is CA $917
CA $1,486 total
includes taxes & fees
Sep 3 - Sep 4
Red Cedar Haven in Sidney
Island Tree House: Lake Front, Kayaks, & Fire Pit
Interior

Island Tree House: Lake Front, Kayaks, & Fire Pit

10.0 out of 10, Exceptional, (7)
"The place was great and secluded. Kent and Heather were amazing hosts "
The price is CA $118
CA $521 total
includes taxes & fees
Sep 4 - Sep 5
Island Tree House: Lake Front, Kayaks, & Fire Pit
Cozy Keyes Cottage-family-friendly Amazing Views
Suite

Cozy Keyes Cottage-family-friendly Amazing Views

3.5 star property
The price is CA $594
CA $1,055 total
includes taxes & fees
Sep 1 - Sep 2
Cozy Keyes Cottage-family-friendly Amazing Views
Charming Guest House on Farm - Near lakes and trails
TV

Charming Guest House on Farm - Near lakes and trails

10.0 out of 10, Exceptional, (4)
"Enjoyed a 2 night stay at this quiet country retreat. Our host was friendly and took time to visit. The kitchen was well stocked and it's a charming historic structure, equipped with modern conveniences. What more could you want! "
The price is CA $286
CA $476 total
includes taxes & fees
Sep 3 - Sep 4
Charming Guest House on Farm - Near lakes and trails
Dome 3 at Come Spring Farm Glamping - Alpaca Farm
Living area

Dome 3 at Come Spring Farm Glamping - Alpaca Farm

8.4 out of 10, Very good, (5)
The price is CA $277
CA $393 total
includes taxes & fees
Sep 1 - Sep 2
Dome 3 at Come Spring Farm Glamping - Alpaca Farm
Modern lake front home
Fridge, microwave, oven, stovetop

Modern lake front home

9.2 out of 10, Wonderful, (10)
"Great location to stay if you're wanting to check out Portland to Bar Harbor. We loved the hot tub and the access to the water with views of wildlife and stars. The haystack trail right across the street was a great start to the day as well. "
The price is CA $324
CA $833 total
includes taxes & fees
Aug 27 - Aug 28
Modern lake front home
“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage
Property grounds

“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage

10.0 out of 10, Exceptional, (30)
"The owners were ver accommodating and the place is a quiet, pretty location "
The price is CA $243
CA $475 total
includes taxes & fees
Aug 26 - Aug 27
“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage
Come Spring Farm Glamping Dome 2
WiFi

Come Spring Farm Glamping Dome 2

The price is CA $207
CA $307 total
includes taxes & fees
Aug 25 - Aug 26
Come Spring Farm Glamping Dome 2
Charming Lakefront Home: Big Porches, Kayaks & Room to Gather
Terrace/patio

Charming Lakefront Home: Big Porches, Kayaks & Room to Gather

9.6 out of 10, Exceptional, (4)
"Wonderful stay! This is the third year in a row our group of "mature" fishermen have stayed at this lake. This was by far the best place we stayed at. Views and setting are all that we could ask for. We'll be back again."
The price is CA $407
CA $941 total
includes taxes & fees
Aug 31 - Sep 1
Charming Lakefront Home: Big Porches, Kayaks & Room to Gather
THE NOOK Apartment
Game room

THE NOOK Apartment

The price is CA $327
CA $426 total
includes taxes & fees
Sep 21 - Sep 22
THE NOOK Apartment
SkyView Treehouse Lakefront Private Hot Tub
Interior

SkyView Treehouse Lakefront Private Hot Tub

10.0 out of 10, Exceptional, (5)
"We had a fantastic stay at the sky view treehouse. It was beautiful and very clean. Feras’ attention to detail was amazing and it made our stay better than any hotel."
The price is CA $653
CA $1,243 total
includes taxes & fees
Sep 1 - Sep 2
SkyView Treehouse Lakefront Private Hot Tub
Camp Lintonia on Tacoma Lakes
Interior

Camp Lintonia on Tacoma Lakes

10.0 out of 10, Exceptional, (8)
"Comfortable, clean, good amenities. Fun home layout for family gathering."
The price is CA $684
CA $853 total
includes taxes & fees
Sep 3 - Sep 4
Camp Lintonia on Tacoma Lakes
The Entire Waldoboro Inn
Exterior detail

The Entire Waldoboro Inn

The price is CA $1,224
CA $1,763 total
includes taxes & fees
Sep 21 - Sep 22
The Entire Waldoboro Inn
Cozy Keyes Cottage | Lakefront • Dock • Kayaks
Terrace/patio

Cozy Keyes Cottage | Lakefront • Dock • Kayaks

10.0 out of 10, Exceptional, (13)
"We loved your house. You made our stay amazing. We will certainly be back in '24."
The price is CA $579
CA $1,117 total
includes taxes & fees
Sep 1 - Sep 2
Cozy Keyes Cottage | Lakefront • Dock • Kayaks
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.
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Top Windsor Hotel Reviews

Fireside Inn & Suites Waterville

Fireside Inn & Suites Waterville

10/10 Excellent
"We enjoyed our stay & we will be back"
Marilyn 1-night trip
Posted 18 hours ago
Fireside Inn & Suites Waterville