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Compare 92 Cottages in Windsor with updated reviews, rates, and availability.

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

10.0 out of 10, Exceptional, (51)
"Perfect cottage for visiting Maine's small coastal towns. Comfortable and convenient. Great bird watching. Wonderful host. All around perfect stay."
Maine Waterfront Cottage: Nestled on an acre of land, with 500ft of shore front

A Charming Waterfront Cottage with Touches of Elegance

10.0 out of 10, Exceptional, (96)
"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

Cottage on Cobbosseecontee Lake. Dates available.

10.0 out of 10, Exceptional, (158)
"Incredible location, perfect choice for a small group to spend a little time on the lake shore."
Cottage on Cobbosseecontee Lake. Dates available.

Steps to Your Private 100 Feet of Lake Front -

8.4 out of 10, Very Good, (16)
"Bill was so very nice and 100% accommodating. His place was very neat and clean. The property is very well maintained, private and peaceful. His cousin , Darcy, lives 2 doors down and is readily available should there be any questions or concerns.We enjoyed the lions at night and the stars were mesmerizing along with the fireflies. Thank you for a lovely stay and we look forward to returning next year."
Steps to Your Private 100 Feet of Lake Front -

Quiet & Lovely Lakefront Cottage for Families!

9.6 out of 10, Exceptional, (13)
"Loved this spot. The lake was beautiful. We had a wonderful time even though the weather was bad a few days. The cabin was so cute and decorated very nice. The kitchen was stocked well. We had everything we needed. Loved hearing the loons at night. It wasn't too far from Camden that we visited frequently. I hope to come back there some day."
Quiet & Lovely Lakefront Cottage for Families!

Little Beans Cottage on Great Pond, Belgrade ME

10.0 out of 10, Exceptional, (38)
"It was a delight, with beautiful Great Pond and inlet close by. The house itself is rustic, spacious and comfortable. Its L.L. Bean history added to the charm. The space heaters were welcome. The location, on a spit of land near the end of a long dirt road, but convenient to the Belgrade Lakes town center, was most enjoyable. We'd definitely recommend it."
Little Beans Cottage on Great Pond, Belgrade ME

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

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

Maine Cottage w/ Dock & Kayaks, Near Augusta!

9.6 out of 10, Exceptional, (15)
"Upon arrival was ecstatic with the way the property looked from the outside! It only got better as we entered the home. Clean, up to date, roomy and comfortable! We took a walk over to the pond and the only statement made was "WOW!". We had a great time using the all of the water toys and even took a dip in the pond. Spent plenty of time just relaxing there and enjoying the serenity. This home is incredible! I look forward to telling others about it! Our host was also exceptionally graceful as...
Maine Cottage w/ Dock & Kayaks, Near Augusta!

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

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

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!

3.0 star property
Springvale Farm: Freedom Home With Hiking Trail!

Lakeside Cottage On Tacoma lakes

Lakeside Cottage On Tacoma lakes

Cheerful Cottage with Loft 9

10.0 out of 10, Exceptional, (2)
"We had a lovely weekend stay at this cozy cabin. Super clean, all the amenities needed for our small family, 2 adults + 3 year old. Convenient location, we would book here again when we are back in the area. "
Cheerful Cottage with Loft 9

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

Close to Colby, Lake Great Pond, Dog Friendly

10.0 out of 10, Exceptional, (30)
"Accurate listing, great location (easy drive to Augusta for dinner), really peaceful and quiet. GPS had a minor problem right at the end trying to send us through a neighbor's trailer, but we figured it out (the external pictures helped). Loved our stay there, even though it was just overnight on the way to somewhere else. Next time, we'll stay for a week."
The price is SAR 565
SAR 1,168 total
includes taxes & fees
26 Nov - 27 Nov
Close to Colby, Lake Great Pond, Dog Friendly

Screen Porch with see thru roof, BQ, 30' from sandy beach, canoe and 3 kayaks

7.6 out of 10, Good, (22)
"The camp was quaint, great kitchen! Unfortunately there was confusion & communication issues with our host not being notified that we had booked property. We received a refund from the host for the nights we didn't stay due to propane running out. The host had intended to have camp closed up the week we had booked."
Screen Porch with see thru roof, BQ, 30' from sandy beach, canoe and 3 kayaks

Rustic Retreat Across from Lake; Family Friendly!

8.8 out of 10, Excellent, (13)
"It's a spcious cabin with plenty of room to spread out, and a beautiful view of Sennebec Pond in Union ME. A half hour to Camden and Rockland, and just a beautiful area. Full kitchen set up, hot showers, a nice deck and fire pit for relaxing and enjoying the view of the pond. Everything was neat, clean and well organized, and stay instructions were simple and easy to follow. The only negative, and it's a realtively small one it the grans scheme, was that the windows were't clean when we looked...
Rustic Retreat Across from Lake; Family Friendly!

Waterfront 2br/2ba cottage

9.6 out of 10, Exceptional, (9)
"The response from the host was amazing! Our internet was a little slow the first day and they came and fixed it immediately. This house would be perfect for a family with kids. Lots of fun toys and extra beds in each bedroom. 10/10 recommend!! "
The price is SAR 469
SAR 1,379 total
includes taxes & fees
2 Dec - 3 Dec
Waterfront 2br/2ba cottage
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

Sunfish Cove is the perfect year round getaway.

10.0 out of 10, Exceptional, (39)
"We had a great time staying at sunfish cove! Very spacious home with great views of the water! Really enjoyed the fire pit and the outdoor amenities!"
Sunfish Cove is the perfect year round getaway.

Dog-friendly lakefront home with dock, fireplace, firepit, lake views, & 1 kayak

8.0 out of 10, Very Good, (15)
"This house has a beautiful location. My husband and I stayed for a weekend getaway and enjoyed our stay. One issue that we had was the water pressure. It was hard to shower because the water kept going in and out. As others have stated, the inside of the house could use some TLC. Some of the decorations are falling apart on the wall. The paint on the walls in some rooms look incomplete. Overall it was a good stay. "
Dog-friendly lakefront home with dock, fireplace, firepit, lake views, & 1 kayak

A Charming Waterfront Cottage with Touches of Elegance

10.0 out of 10, Exceptional, (96)
"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
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?
Cottages in Windsor range between SAR 469 and SAR 565 per night. These properties offer a chance to soak up nature’s beauty — at a price you can afford. 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?
Choose from 92 cottages in Windsor. No matter if you’re taking a trip with the kids or organizing a weekend break with your pals, Expedia will help you find the right place to get in touch with nature.
Why book your cottage in Windsor with Expedia?
Expedia has some wonderful cottages in Windsor, so get ready for a memorable vacay close to nature. If you have a certain budget, click on how much you want to spend and the preferred star rating of your property. Or, try out our filters to search for cottages with a hot tub or free WiFi. We’ll help you find the right place whatever your plans or style of travel.
How can I find cheap cottages in Windsor?
Expedia can help you easily track down cheap cottages in Windsor. To book a fantastic stay in a couple of clicks, simply use the filter tool to refine your search results by star rating, budget and amenities.