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Check prices for these dates

In two weeks
12 Sept - 14 Sept
In one month
26 Sept - 28 Sept
In two months
24 Oct - 26 Oct
In three months
21 Nov - 23 Nov

Featured Cottages in Windsor and around

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

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

10.0 out of 10, Exceptional, (56)
"Beautiful, peaceful location. Great fishing. Comfortable, immaculate cabin."
Peaceful.... Lakefront Cottage... Kayakers Paradise....
Lighthouse Lane
Outdoor dining

Lighthouse Lane

10.0 out of 10, Exceptional, (62)
"Check in and check out was super easy. Photos are super accurate and the property is beautiful. Thank you for sharing your beautiful with us!"
The price is €470
includes taxes & fees
3 Sept - 4 Sept
Lighthouse Lane
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, (60)
"Very pretty spot. Nice lake, good for kayaking.we enjoyed the fire pit. "
Weekly discounts avail. Get away from it all on the start of The Belgrade Lakes
Private Dock on Messalonskee Lake: Cozy Cottage!
TV, fireplace, books

Private Dock on Messalonskee Lake: Cozy Cottage!

2.0 star property
9.0 out of 10, Wonderful, (6)
"We had a peaceful and relaxing stay. Nice and quiet!"
Private Dock on Messalonskee Lake: Cozy Cottage!
Happy Cottage Near Everything 11
Outdoor dining

Happy Cottage Near Everything 11

5.0 out of 10, (2)
"Very comfortable, clean small cottage. We slept great in the bed that was provided and it had a futon in the living area . We recommend that only 2 people stay there. They had a toaster oven , a full refrigerator and a coffee maker. It is very close to Route 1, Boothbay Harbor and Damariscotta. "
Happy Cottage Near Everything 11
Updated lake cottage right on Damariscotta Lake.
Property grounds

Updated lake cottage right on Damariscotta Lake.

10.0 out of 10, Exceptional, (144)
"Best location on lake. House was warm and recently updated. Fun time "
Updated lake cottage right on Damariscotta Lake.
Spacious 1 Bedroom Close to Everything 4
Marina

Spacious 1 Bedroom Close to Everything 4

9.8 out of 10, Exceptional, (19)
"This was a lovely little cabin. Everything was as described and my husband and I really enjoyed our stay."
Spacious 1 Bedroom Close to Everything 4
Driftwood Cottage with Cottages of Maine, Lake Great Pond, Dog Friendly, Kayaks
Outdoor dining

Driftwood Cottage with Cottages of Maine, Lake Great Pond, Dog Friendly, Kayaks

10.0 out of 10, Exceptional, (44)
"Very clean and comfortable."
The price is €321
includes taxes & fees
28 Aug - 29 Aug
Driftwood Cottage with Cottages of Maine, Lake Great Pond, Dog Friendly, Kayaks
Lakefront Home on Togus Pond with 2 Decks, Great View & Shared Canoe/Firepit
Terrace/patio

Lakefront Home on Togus Pond with 2 Decks, Great View & Shared Canoe/Firepit

6.4 out of 10, (7)
"First the key touch pad didn’t work , the deadbolt was hard to work the key would spin and spin when trying to lock or unlock door, the water smelled of sly, there wasn’t drinkable water the did send some, dirty areas, ants, had to use a stepping stool to get in & out of the shower, at 5ish in the morning got bit by ants in my bed, I left a day early"
Lakefront Home on Togus Pond with 2 Decks, Great View & Shared Canoe/Firepit
Maine Waterfront Cottage: Nestled on an acre of land, with 500ft of shore front
Interior

Maine Waterfront Cottage: Nestled on an acre of land, with 500ft of shore front

10.0 out of 10, Exceptional, (58)
"Fabulous we will definitely be going back."
Maine Waterfront Cottage: Nestled on an acre of land, with 500ft of shore front
Belgrade Lakes Cottage w/ Long Pond beach access close to Augusta, Colby College
Beach towels

Belgrade Lakes Cottage w/ Long Pond beach access close to Augusta, Colby College

9.0 out of 10, Wonderful, (19)
"Great location and wonderful hosts!"
Belgrade Lakes Cottage w/ Long Pond beach access close to Augusta, Colby College
Spacious 1 Bedroom Cottage Close to Everything 2
Marina

Spacious 1 Bedroom Cottage Close to Everything 2

9.2 out of 10, Wonderful, (15)
"Nice small older cottage that has been updated nicely. The location was perfect for exploring local State Parks and the marine area."
Spacious 1 Bedroom Cottage Close to Everything 2
Cheerful Cottage with Loft Close to Everything 6
2 bedrooms, iron/ironing board, WiFi, bed sheets

Cheerful Cottage with Loft Close to Everything 6

9.0 out of 10, Wonderful, (7)
"This is a good location to explore the Booth Bay area. The Highway is near enough for loud trucks to be heard"
Cheerful Cottage with Loft Close to Everything 6
Tiny Cottage Near Everything 10
Property grounds

Tiny Cottage Near Everything 10

10.0 out of 10, Exceptional, (1)
"We recently stayed at the Tiny Cottage in Edgecomb, Maine, and truly enjoyed our visit. Except for a small initial issue, which was promptly and professionally addressed, everything was wonderful. The location is perfect for exploring the area, and the cottage itself was spotless, comfortable, and well-maintained. A lovely and relaxing getaway spot!"
Tiny Cottage Near Everything 10
Lazy Days - Sunny Dock - Great Swimming & Fishing - close to Camden
Exterior

Lazy Days - Sunny Dock - Great Swimming & Fishing - close to Camden

10.0 out of 10, Exceptional, (80)
"Such a great place to go to , and had perfect weather all week , love it there !"
Lazy Days - Sunny Dock - Great Swimming & Fishing - close to Camden
Idyllic Washington Retreat w/ Fire Pit & Yard
TV, fireplace

Idyllic Washington Retreat w/ Fire Pit & Yard

3.0 star property
10.0 out of 10, Exceptional, (1)
"It was great. Nice property, internet connection was poor"
Idyllic Washington Retreat w/ Fire Pit & Yard
Cozy 1 BR Maine lakeside cottage getaway with WiFi, laundry, and full kitchen.
Property grounds

Cozy 1 BR Maine lakeside cottage getaway with WiFi, laundry, and full kitchen.

2.0 star property
10.0 out of 10, Exceptional, (15)
"Great cozy cabin is a great quite getaway. We enjoyed bird watching. The loon on the lake was so cool n there's chipmunks running around. My dog loved watching them. Awesome place to rebalance in life. "
Cozy 1 BR Maine lakeside cottage getaway with WiFi, laundry, and full kitchen.
Quiet - Romantic - Secluded Cottage on Lake
Exterior

Quiet - Romantic - Secluded Cottage on Lake

9.6 out of 10, Exceptional, (28)
"Great place to reconnect with yourself. "
Quiet - Romantic - Secluded Cottage on Lake
Lakeside Cottage On Tacoma lakes
Exterior

Lakeside Cottage On Tacoma lakes

Lakeside Cottage On Tacoma lakes
Spacious 1 Bedroom Cottage Close to Everything 3
Marina

Spacious 1 Bedroom Cottage Close to Everything 3

9.8 out of 10, Exceptional, (11)
"The cottage was nice, perfect for two adults. Comfortable furniture and bed "
Spacious 1 Bedroom Cottage Close to Everything 3
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

Senator Inn & Spa

Senator Inn & Spa

10/10 Excellent
"Good"
Allan 1-night trip
Posted 20 hours ago
Senator Inn & Spa

Find out more about Windsor

Find out more about Windsor

Windsor Cottages information

Number of reviews
458
Accommodation
122 Cottages
Lowest Price
€321
Highest Price
€470

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Frequently asked questions

How much do cottages in Windsor cost?
Prices for cottages in Windsor range between €321 and €470 per night. No matter your budget, you're sure to find an ideal place to reconnect with nature. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many cottages are there in Windsor?
Pack your suitcase and choose from 122 cottages in Windsor. Dreaming of a place where you can relax and connect with nature? Expedia can help you find your ideal getaway in a few simple clicks.
Why book your cottage in Windsor with Expedia?
Expedia has some superb cottages in Windsor, so start packing your bags for an unforgettable holiday on nature's doorstep. If you have a budget, click on how much you want to spend and your preferred property star rating. Or, make use of our filters to search for cottages with a kitchen or a pool. We'll help you find the perfect fit whatever your getaway looks like.