Windsor Vacation Rentals

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Check prices for these dates

In two weeks
Oct 10 - Oct 12
In one month
Oct 24 - Oct 26
In two months
Nov 21 - Nov 23
In three months
Dec 19 - Dec 21

Vacation Rentals in Windsor

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

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

9.8 out of 10, Exceptional, (28)
"This house has everything for a weekend family vacay; you can spend the whole weekend enjoying the house & amenities such as the hot tub!"
Spacious Country Home w/ Hot Tub, near Colby/Thomas
“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage
Property grounds

“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage

9.8 out of 10, Exceptional, (35)
"This a gem of a place. Quiet, cozy spots, beautiful proximity to the lake. We really enjoyed our night, and were sorry we did not have a longer stay."
The price is ￥22,274
￥46,439 total
includes taxes & fees
Oct 18 - Oct 19
“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage
Weekly discounts avail. Get away from it all on the start of The Belgrade Lakes
Exterior

Weekly discounts avail. Get away from it all on the start of The Belgrade Lakes

9.4 out of 10, Exceptional, (61)
"Great family camp right on the water with great views and paddle boats to play and fish the lake. Nice host, it was a peaceful stay!"
Weekly discounts avail. Get away from it all on the start of The Belgrade Lakes
Blue Loon Camp on Pleasant Pond in Litchfield
Property grounds

Blue Loon Camp on Pleasant Pond in Litchfield

9.4 out of 10, Exceptional, (6)
"This comfy cabin can sleep 6 people no problem! With a close quarters experience made staying more the fun! EasyAccess to kayaks and canoes was awesome. Had a couple Beavers going back n forth in front of the cabin as well! Bailey the Neighbor dog stopped by to say hi in the yard along with Chancellor and Lous minutes prior. Thanks again for your accommodations. We would love to visit again in the future! "
Blue Loon Camp on Pleasant Pond in Litchfield
Peaceful.... Lakefront Cottage... Kayakers Paradise....
Exterior

Peaceful.... Lakefront Cottage... Kayakers Paradise....

10.0 out of 10, Exceptional, (59)
"Beautiful, peaceful location. Great fishing. Comfortable, immaculate cabin."
Peaceful.... Lakefront Cottage... Kayakers Paradise....
Cheerful Cottage Close to Everything 13
Marina

Cheerful Cottage Close to Everything 13

9.0 out of 10, Wonderful, (12)
"Nice and quiet even though it was right next to major travel routes "
Cheerful Cottage Close to Everything 13
Mountainside cabin "Sasquatch Haven"
Interior

Mountainside cabin "Sasquatch Haven"

9.4 out of 10, Exceptional, (24)
"Wonderful stay!"
Mountainside cabin "Sasquatch Haven"
Cozy Long Pond Cottage: private mooring & shared dock
Outdoor dining

Cozy Long Pond Cottage: private mooring & shared dock

9.8 out of 10, Exceptional, (19)
"Very nice weekend and great host- very responsive!"
Cozy Long Pond Cottage: private mooring & shared dock
Come Spring Farm Glamping Dome 2
WiFi

Come Spring Farm Glamping Dome 2

10.0 out of 10, Exceptional, (1)
"My friends and I had a great time at Come Spring Farm! We got hit with a lot of rain as soon as we arrived and it was really cool to watch the storm through the windows in the dome. We were impressed with the bathroom/shower facilities and the Coop hang out space, and I was thrilled to help feed the animals in the morning. We hope to return soon!"
The price is ￥26,161
￥37,888 total
includes taxes & fees
Oct 23 - Oct 24
Come Spring Farm Glamping Dome 2
Spectacular Cobbossee Lakefront with Hot Tub&Dog Friendly
Outdoor spa tub

Spectacular Cobbossee Lakefront with Hot Tub&Dog Friendly

10.0 out of 10, Exceptional, (251)
"Spacious, clean comfortable. Beautiful views. Right on lake."
Spectacular Cobbossee Lakefront with Hot Tub&Dog Friendly
Peaceful home with forest views & great yard - minutes to town
TV, fireplace

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

8.0 out of 10, Very Good, (8)
"Fit our needs perfectly!"
Peaceful home with forest views & great yard - minutes to town
Dome 3 at Come Spring Farm Glamping - Alpaca Farm
Living area

Dome 3 at Come Spring Farm Glamping - Alpaca Farm

9.0 out of 10, Wonderful, (7)
"Beautiful location and a unique stay."
The price is ￥29,898
￥42,451 total
includes taxes & fees
Sep 28 - Sep 29
Dome 3 at Come Spring Farm Glamping - Alpaca Farm
Spacious 1 Bedroom Close to Everything 4
Marina

Spacious 1 Bedroom Close to Everything 4

9.8 out of 10, Exceptional, (21)
"This unit fit all of our needs regarding location, cleanliness, and amenities. I would 100% recommend this property to my friends and family and will revisit this if I'm in town in the future!"
Spacious 1 Bedroom Close to Everything 4
Cozy 2-bedroom cabin in tranquil China, Maine with AC, WiFi
Microwave, oven, stovetop, dishwasher

Cozy 2-bedroom cabin in tranquil China, Maine with AC, WiFi

10.0 out of 10, Exceptional, (3)
"Lovely location, peaceful. Hosts are very communicative and quickly respond to queries."
Cozy 2-bedroom cabin in tranquil China, Maine with AC, WiFi
Maine Cabin Masters Camp completely redone waiting for a Lake loving family !
Property grounds

Maine Cabin Masters Camp completely redone waiting for a Lake loving family !

2.0 star property
10.0 out of 10, Exceptional, (7)
"Wonderful hosts, they thought of everything we might need including many nice extra touches! Beautiful quiet spot with the opportunity to paddle boat, kayak, canoe, swim, fish, enjoy campfires, outdoor grilling, observe wildlife (Osprey, Bald Eagle, Deer)"
Maine Cabin Masters Camp completely redone waiting for a Lake loving family !
Large New Lakeside Cottage Central Air
Exterior detail

Large New Lakeside Cottage Central Air

8.4 out of 10, Very Good, (36)
"We loved the cabin, even in rainy weather. "
Large New Lakeside Cottage Central Air
Lakefront Cabin
Fridge, microwave, oven, stovetop

Lakefront Cabin

10.0 out of 10, Exceptional, (27)
"Enjoyed an awesome stay on the lake!! House was super and Kennith was a great host!"
Lakefront Cabin
Lakefront Studio in the Trees with Gorgeous Views, Balcony, & Shared Canoe
Property grounds

Lakefront Studio in the Trees with Gorgeous Views, Balcony, & Shared Canoe

7.0 out of 10, Good, (8)
"Affordable and clean accommodations. View was lovely—will stay again!"
Lakefront Studio in the Trees with Gorgeous Views, Balcony, & Shared Canoe
Lighthouse Lane
Outdoor dining

Lighthouse Lane

10.0 out of 10, Exceptional, (64)
"Had another great time at Jenn and Brian's property. Exactly as advertised and Jenn is quick to respond to any questions. "
The price is ￥60,543
￥80,168 total
includes taxes & fees
Oct 3 - Oct 4
Lighthouse Lane
Cozy Lakefront Cottage with Stunning Views, Deck, BBQ Grill, and Outdoor Firepit
Terrace/patio

Cozy Lakefront Cottage with Stunning Views, Deck, BBQ Grill, and Outdoor Firepit

10.0 out of 10, Exceptional, (5)
Cozy Lakefront Cottage with Stunning Views, Deck, BBQ Grill, and Outdoor Firepit
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

Maine Evergreen Hotel, an Ascend Collection Hotel

Maine Evergreen Hotel, an Ascend Collection Hotel

10/10 Excellent
"Always use this Hotel when I'm up this way, pleasant and friendly staff at check-in and as we leave. Best place to stay."
Shawn 1-night trip
Posted 2 days ago
Maine Evergreen Hotel, an Ascend Collection Hotel

Find out more about Windsor

Find out more about Windsor

Search for holiday rentals in Windsor on Expedia! You can easily find your home rentals, villas, holiday apartments in Windsor using one of the methods below:

  • View our selection of featured holiday rentals in Windsor
  • Use the map to find apartments and other holiday homes in the Windsor neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Windsor while they last

Look no further and take a look at our great range of rental properties in Windsor!

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Frequently asked questions

Are there vacation rentals in Windsor?

Yes, we offer vacation rentals close to popular sights in Windsor, or you can go with a more secluded option if you're looking for a relaxing stay. Windsor is known for its shopping and restaurants.

What are some of the best vacation home rentals in Windsor?

“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage: This vacation home rental outside of Windsor offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the books in this rental home to help you unwind.

What can I see and do in Windsor?

While exploring the area, visit family-friendly sights like Maine State Museum, or get outside and enjoy nature at Kennebec River Rail Trail. In the larger area, you’ll find Old Fort Western and Capitol Park.

What are vacation rentals like in Windsor?

Vacation rentals are privately owned accommodations you can reserve for a short or long stay in Windsor. Vacation rentals offer amenities such as laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about a clean environment, a vacation rental can provide a sense of seclusion away from shared hotel elevators and busy front desks while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular choice for small groups.