Holiday Homes in Windsor

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Check prices for these dates

In two weeks
5 Sept - 7 Sept
In one month
19 Sept - 21 Sept
In two months
17 Oct - 19 Oct
In three months
14 Nov - 16 Nov

Featured Holiday Homes in Windsor

Our top choices for Windsor holiday homes

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 AU$500
includes taxes & fees
25 Aug - 26 Aug
Cozy Cottage on water's edge of Lake Cobbosseecontee
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 AU$363
includes taxes & fees
25 Aug - 26 Aug
Sister A-Frame in Woods B
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 AU$514
includes taxes & fees
1 Sept - 2 Sept
Dome 1 - Luxury Dome at Come Spring Farm
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 AU$1,374
includes taxes & fees
6 Sept - 7 Sept
Little Landing Cottage-gorgeous View BBQ Wi-fi
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 AU$1,377
includes taxes & fees
6 Sept - 7 Sept
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 AU$491
includes taxes & fees
22 Aug - 23 Aug
NEW Cozy Cabin located in Oakland tucked away in a peaceful wooded scene.
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 AU$541
includes taxes & fees
2 Sept - 3 Sept
Charming Guest House on Farm - Near lakes and trails
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 AU$611
includes taxes & fees
4 Sept - 5 Sept
Island Tree House: Lake Front, Kayaks, & Fire Pit
Red Cedar Haven in Sidney
House

Red Cedar Haven in Sidney

2.0 star property
The price is AU$1,671
includes taxes & fees
3 Sept - 4 Sept
Red Cedar Haven in Sidney
Cozy Keyes Cottage-family-friendly Amazing Views
Suite

Cozy Keyes Cottage-family-friendly Amazing Views

3.5 star property
Cozy Keyes Cottage-family-friendly Amazing Views
Come Spring Farm Glamping Dome 2
WiFi

Come Spring Farm Glamping Dome 2

The price is AU$446
includes taxes & fees
25 Aug - 26 Aug
Come Spring Farm Glamping Dome 2
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 AU$446
includes taxes & fees
1 Sept - 2 Sept
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. "
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 AU$537
includes taxes & fees
26 Aug - 27 Aug
“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage
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 AU$1,063
includes taxes & fees
31 Aug - 1 Sept
Charming Lakefront Home: Big Porches, Kayaks & Room to Gather
The Entire Waldoboro Inn
Exterior detail

The Entire Waldoboro Inn

The price is AU$2,012
includes taxes & fees
24 Aug - 25 Aug
The Entire Waldoboro Inn
THE NOOK Apartment
Game room

THE NOOK Apartment

The price is AU$500
includes taxes & fees
8 Sept - 9 Sept
THE NOOK Apartment
Little Landing Cottage | Lakefront · Dock · Kayaks
Terrace/patio

Little Landing Cottage | Lakefront · Dock · Kayaks

9.8 out of 10, Exceptional, (9)
"Great location! "
The price is AU$1,208
includes taxes & fees
1 Sept - 2 Sept
Little Landing Cottage | Lakefront · Dock · Kayaks
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 AU$1,414
includes taxes & fees
1 Sept - 2 Sept
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 AU$970
includes taxes & fees
27 Aug - 28 Aug
Camp Lintonia on Tacoma Lakes
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

Holiday Inn Express & Suites Waterville - North by IHG

Holiday Inn Express & Suites Waterville - North by IHG

10/10 Excellent
"My stay was great, the breakfast buffet was excellent"
Patrick 5-night trip
Posted 2 days ago
Holiday Inn Express & Suites Waterville - North by IHG