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Check prices for these dates

Next weekend
25 Apr - 27 Apr
In two weeks
2 May - 4 May
In one month
16 May - 18 May
In two months
13 Jun - 15 Jun

Compare 111 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, (107)
"Beautiful cottage with an amazing view of the bay. Great porch where we spent most of our time. Very convenient to Damariscotta. Great setting for two couples. "
A Charming Waterfront Cottage with Touches of Elegance
Little Beans Cottage on Great Pond, Belgrade ME
Smart TV

Little Beans Cottage on Great Pond, Belgrade ME

10.0 out of 10, Exceptional, (38)
"This is our second time here. The cabin has everything you need. We love the old-timey feel, the choice of stream or lake, and the incredible peace."
Little Beans Cottage on Great Pond, Belgrade ME
Lighthouse Lane
Outdoor dining

Lighthouse Lane

10.0 out of 10, Exceptional, (54)
"Excellent, beautiful location next to the lake."
The price is AED 1,469
AED 1,946 total
includes taxes & fees
15 May - 16 May
Lighthouse Lane
Lazy Days - Sunny Dock - Great Swimming & Fishing - close to Camden
Property grounds

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

10.0 out of 10, Exceptional, (75)
"Scenic, remote location that’s perfectly located close to Camden, Rockport, Rockland, and Acadia. Very comfortable and had everything I needed. Highly recommend!"
Lazy Days - Sunny Dock - Great Swimming & Fishing - close to Camden
April Special, Lake Great Pond, Dog Friendly
Outdoor dining

April Special, Lake Great Pond, Dog Friendly

10.0 out of 10, Exceptional, (35)
"Really enjoyed our stay, will come back. "
The price is AED 638
AED 1,252 total
includes taxes & fees
1 May - 2 May
April Special, Lake Great Pond, Dog Friendly
"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
Cottage on Cobbosseecontee Lake. Dates available.
Fridge, microwave, oven, stovetop

Cottage on Cobbosseecontee Lake. Dates available.

10.0 out of 10, Exceptional, (163)
"Incredible location, perfect choice for a small group to spend a little time on the lake shore."
Cottage on Cobbosseecontee Lake. Dates available.
One Of Belgrade Lakes Best Kept Secrets, Very Private & 10 Feet From Waters Edge
TV, fireplace, DVD player, video library

One Of Belgrade Lakes Best Kept Secrets, Very Private & 10 Feet From Waters Edge

10.0 out of 10, Exceptional, (63)
"Our stay at the cottage was peaceful and relaxing. The entire area is beautiful and has many outdoor activities. The owners are very welcoming and clearly take a lot of pride in the property."
One Of Belgrade Lakes Best Kept Secrets, Very Private & 10 Feet From Waters Edge
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)
"Fabulous we will definitely be going back."
Maine Waterfront Cottage: Nestled on an acre of land, with 500ft of shore front
Steps to Your Private 100 Feet of Lake Front -
Interior

Steps to Your Private 100 Feet of Lake Front -

8.4 out of 10, Very Good, (16)
"It is a quiet, relaxing, cozy cabin with great views and fishing. Close to town. Would stay again!"
Steps to Your Private 100 Feet of Lake Front -
Updated Tiny House: Walk to Wiscasset Village
Exterior

Updated Tiny House: Walk to Wiscasset Village

8.0 out of 10, Very Good, (5)
"Great location, easy to get to lots of coastal regions. Property is clean and cozy."
Updated Tiny House: Walk to Wiscasset Village
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
The price is AED 735
AED 2,286 total
includes taxes & fees
1 May - 2 May
Charming 2-bedroom lake front cottage on serene Cobbosseeconte with kayaks, ac
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.
Historic Waldoboro House Near Lakes, Boating, Etc!
Interior

Historic Waldoboro House Near Lakes, Boating, Etc!

3.0 star property
10.0 out of 10, Exceptional, (2)
"Arrived late but the lights were on making it easy to find and get into. Cindy, the owner was excellent in responses and question we had and wanted to make sure that we were comfortable. Fair warning to those that have difficulty with steps. The upstairs bedrooms have very steep stairs going up to them. Otherwise would happily go back to this location again"
Historic Waldoboro House Near Lakes, Boating, Etc!
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
2 BR Lakefront Cottage in Belgrade Lakes Region
Beach

2 BR Lakefront Cottage in Belgrade Lakes Region

10.0 out of 10, Exceptional, (23)
"Nice Cabin Great Views Very Relaxing Great Location You won’t want to leave."
2 BR Lakefront Cottage in Belgrade Lakes Region
Lakeside Cottage On Tacoma lakes
Aerial view

Lakeside Cottage On Tacoma lakes

Lakeside Cottage On Tacoma lakes
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!
Waterfront 2br/2ba cottage
Fridge, microwave, oven, stovetop

Waterfront 2br/2ba cottage

9.8 out of 10, Exceptional, (11)
"Clean house"
The price is AED 698
AED 1,649 total
includes taxes & fees
5 May - 6 May
Waterfront 2br/2ba 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)
"Ideal for kayaking and fishing. Beautiful spot."
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

Downtown! Views! Dining! King & Queen beds!
Fridge, microwave, oven, stovetop

Downtown! Views! Dining! King & Queen beds!

2.0 star property
10.0 out of 10, Exceptional, (8)
"My daughter and I came to Maine for my birthday. The VRBO rental located on Water Street was flawless and exceeded our expectations. Beautifully appointed, Spotlessly clean, cozy and wonderful beds, bedding and pillows. Fun being right on the main street and walkable to most everything. The hosts were so accommodating, wish they had places all over the world. One recommendation is a tv on the kitchen level, I like tv. But the tv area upstairs is simply wonderful, so cozy. Views are delightful...
Downtown! Views! Dining! King & Queen beds!
April Special, Lake Great Pond, Dog Friendly
Outdoor dining

April Special, Lake Great Pond, Dog Friendly

10.0 out of 10, Exceptional, (35)
"Really enjoyed our stay, will come back. "
The price is AED 638
AED 1,252 total
includes taxes & fees
1 May - 2 May
April Special, Lake Great Pond, Dog Friendly
Spacious 5-bedroom lakefront home on pristine Lower Narrows Pond in Winthrop
Fridge, microwave, oven, stovetop

Spacious 5-bedroom lakefront home on pristine Lower Narrows Pond in Winthrop

Spacious 5-bedroom lakefront home on pristine Lower Narrows Pond in Winthrop
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.