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Check prices for these dates

Next weekend
21 Mar - 23 Mar
In two weeks
28 Mar - 30 Mar
In one month
11 Apr - 13 Apr
In two months
9 May - 11 May

Compare Cottages in Windsor with updated reviews, rates, and availability.

A Charming Waterfront Cottage with Touches of Elegance
Miscellaneous

A Charming Waterfront Cottage with Touches of Elegance

10.0 out of 10, Exceptional, (102)
"My friend and I are writers, and we came to this cottage to work on our books. It was the perfect location with the sunrise views over the water from the magnificent porch. The cottage was exceptionally clean, cozy, and beautiful. We had one small hiccup with the heat, but the manager, David, showed up immediately and the problem was rectified promptly. I loved it and we would absolutely stay there again."
A Charming Waterfront Cottage with Touches of Elegance
April Special, Lake Great Pond, Dog Friendly
Outdoor dining

April Special, Lake Great Pond, Dog Friendly

10.0 out of 10, Exceptional, (34)
"The host could not of been better very tentative in answering questions and requests we will come again in summer or.fall when weather is at it's best "
The price is AED 427
AED 969 total
includes taxes & fees
16 Mar - 17 Mar
April Special, Lake Great Pond, Dog Friendly
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

9.6 out of 10, Exceptional, (10)
"We spent a beautiful fall weekend at Cedar Estates, the house was clean and very well equipped, as described in the listing. We enjoyed a nice campfire on Saturday night at the fire pit. Our 2 dogs really enjoyed exploring and running outside as well! Clean sheets and towels, hot water - lovely overall!"
Belgrade Lakes Cottage w/ Long Pond beach access close to Augusta, Colby College
Cottage on Cobbosseecontee Lake. Dates available.
Fridge, microwave, oven, stovetop

Cottage on Cobbosseecontee Lake. Dates available.

10.0 out of 10, Exceptional, (161)
"Brought my son fishing for the weekend ! Property was great- right on the lake and was perfect for a weekend away. Very clean and had everything we needed! We will be staying here again for sure "
Cottage on Cobbosseecontee Lake. Dates available.
Lighthouse Lane
Outdoor dining

Lighthouse Lane

10.0 out of 10, Exceptional, (53)
"The property offered easy access to the lake and was very clean. Our group had a great time ice fishing and relaxing."
The price is AED 735
AED 1,009 total
includes taxes & fees
20 Mar - 21 Mar
Lighthouse Lane
Waterfront 2br/2ba cottage
Fridge, microwave, oven, stovetop

Waterfront 2br/2ba cottage

9.8 out of 10, Exceptional, (11)
"This property was wonderful. It had everything renters could ever need including an instant pot pressure cooker and excellent coffee machine that was stocked and ready to make good coffee. The cleanliness of the property was exceptional. The beds were very comfortable. We were in the area for cross country ski races and had a great stay. "
The price is AED 569
AED 1,489 total
includes taxes & fees
3 Apr - 4 Apr
Waterfront 2br/2ba cottage
Quiet & Lovely Lakefront Cottage for Families!
TV, books

Quiet & Lovely Lakefront Cottage for Families!

9.6 out of 10, Exceptional, (13)
"Our family loved the access to the water! We had a blast playing and fishing on the lake. We also appreciated the ease of check in and the quick response from the host to any questions or issues we had. We knew that this was a cottage or camp so did not expect something fancy or super modern. It fit our needs very well."
Quiet & Lovely Lakefront Cottage for Families!
"Not-A-Pine Lane COTTAGE" is a family treasure enjoyed by generations
Beach towels

"Not-A-Pine Lane COTTAGE" is a family treasure enjoyed by generations

9.6 out of 10, Exceptional, (56)
"Great location. fishing was awesome!! Tiffany was so nice and accommodating We had a nice few days! very nice getaway!"
"Not-A-Pine Lane COTTAGE" is a family treasure enjoyed by generations
Maine Waterfront Cottage: Nestled on an acre of land, with 500ft of shore front
Miscellaneous

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

10.0 out of 10, Exceptional, (55)
"We loved our stay at this cottage. It had a beautiful waterfront, location, with bright big windows and a gorgeous view from everyone. The decor and comfort of the home is the best we’ve ever stayed in. There are many luxuries to enjoy and comforts everywhere you turn. The owner, David, is very accommodating and even offered us an early check-in and a late check out so we could extend our stay. He was gracious and helpful, but also respected our privacy. A nice touch was every morning when we...
Maine Waterfront Cottage: Nestled on an acre of land, with 500ft of shore front
Charming 2-bedroom lake front cottage on serene Cobbosseeconte with kayaks, ac
Property grounds

Charming 2-bedroom lake front cottage on serene Cobbosseeconte with kayaks, ac

2.0 star property
Charming 2-bedroom lake front cottage on serene Cobbosseeconte with kayaks, ac
Quiet - Romantic - Secluded Cottage on Lake
Exterior

Quiet - Romantic - Secluded Cottage on Lake

9.8 out of 10, Exceptional, (25)
"Very lovely."
Quiet - Romantic - Secluded Cottage on Lake
Cozy Cottage with Beach & Dock on Woodbury Pond.
Interior

Cozy Cottage with Beach & Dock on Woodbury Pond.

10.0 out of 10, Exceptional, (5)
"We loved staying here. The home was clean and the perfectly equipped with everything you need. The pond was great and my girls enjoyed swimming! It was a great value. Sasha was a great communicator. "
Cozy Cottage with Beach & Dock on Woodbury Pond.
Cheerful Cottage Close to Everything 13
Outdoor dining

Cheerful Cottage Close to Everything 13

9.6 out of 10, Exceptional, (9)
"Cozy, clean, and conveniently located for accessing many peninsulas. Just off Rt 1- noise not a problem."
Cheerful Cottage Close to Everything 13
Waterfront Nobleboro Cottage w/ Kayaks & Boat Dock
2 bedrooms, desk, iron/ironing board, internet

Waterfront Nobleboro Cottage w/ Kayaks & Boat Dock

7.4 out of 10, Good, (3)
"We had a great stay at Depatsy’s camp with our 10mo old son and pup. The house was cozy, spacious and had everything we needed. The house was in a perfect location with access to the water and kayaks/paddle boards. We spent a lot of time on the patio enjoying the view and using the fire pit. Would definitely return for another trip! "
Waterfront Nobleboro Cottage w/ Kayaks & Boat Dock
Spacious 1 Bedroom Cottage Close to Everything 5
Fridge, microwave, stovetop, coffee/tea maker

Spacious 1 Bedroom Cottage Close to Everything 5

10.0 out of 10, Exceptional, (6)
"Everything was great. We had a minor ‘blip’ when the morning of our arrival, the hot water went out in our cabin. Our host reached out and offered an alternative. No biggie and everything went well. We appreciated Jeff's willingness to find a solution. "
Spacious 1 Bedroom Cottage Close to Everything 5
2 BR Lakefront Cottage in Belgrade Lakes Region
Beach

2 BR Lakefront Cottage in Belgrade Lakes Region

10.0 out of 10, Exceptional, (23)
"If you are considering this cabin, do not hesitate to book it. It is absolutely beautiful, perfect spot on the lake and still close to many local venues. We enjoyed a beautiful fall weekend and cannot wait to go back. Denise was the most gracious host and made us feel at home. We were able to fish off the dock which is just steps from the front porch. Beautiful sunsets and listening for the loons was a favorite. Wish we could give more than 5 stars! "
2 BR Lakefront Cottage in Belgrade Lakes Region
Springvale Farm: Freedom Home With Hiking Trail!
House (4 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

Springvale Farm: Freedom Home With Hiking Trail!

3.0 star property
Springvale Farm: Freedom Home With Hiking Trail!
Lakeside Cottage On Tacoma lakes
Aerial view

Lakeside Cottage On Tacoma lakes

Lakeside Cottage On Tacoma lakes
Private Dock on Messalonskee Lake: Cozy Cottage!
TV, fireplace, books

Private Dock on Messalonskee Lake: Cozy Cottage!

2.0 star property
9.6 out of 10, Exceptional, (4)
"Great, simple lakeside cabin with privacy. "
Private Dock on Messalonskee Lake: Cozy Cottage!
Weekly discounts avail. Get away from it all on the start of The Belgrade Lakes
Miscellaneous

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

9.6 out of 10, Exceptional, (49)
"It was OK."
Weekly discounts avail. Get away from it all on the start of The Belgrade 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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Other property types in Windsor

Warm & Inviting Lakeside Retreat, Private, Tranquil Picture Perfect Setting
Fridge, microwave, oven, dishwasher

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

Warm & Inviting Lakeside Retreat, Private, Tranquil Picture Perfect Setting
A Charming Waterfront Cottage with Touches of Elegance
Miscellaneous

A Charming Waterfront Cottage with Touches of Elegance

10.0 out of 10, Exceptional, (102)
"My friend and I are writers, and we came to this cottage to work on our books. It was the perfect location with the sunrise views over the water from the magnificent porch. The cottage was exceptionally clean, cozy, and beautiful. We had one small hiccup with the heat, but the manager, David, showed up immediately and the problem was rectified promptly. I loved it and we would absolutely stay there again."
A Charming Waterfront Cottage with Touches of Elegance
High End Apartment in Downtown Hallowell
Interior

High End Apartment in Downtown Hallowell

10.0 out of 10, Exceptional, (76)
"It was so nice to have family visit us and stay just down the road "
The price is AED 386
AED 721 total
includes taxes & fees
18 Mar - 19 Mar
High End Apartment in Downtown Hallowell
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.

Frequently asked questions

How much do cottages in Windsor cost?
Prices for cottages in Windsor range between and 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 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 vacay 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.
How can I find cheap cottages in Windsor?
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