Search Cottages in Winslow

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

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 62 Cottages in Winslow with updated reviews, rates, and availability.

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
2 bedroom cottage house at Pond Hill Farms
2 bedrooms, iron/ironing board, free WiFi, bed sheets

2 bedroom cottage house at Pond Hill Farms

10.0 out of 10, Exceptional, (5)
"Excellent host"
2 bedroom cottage house at Pond Hill Farms
Summer Getaway on North Pond - Hidden Harlow Lane Retreat
Exterior

Summer Getaway on North Pond - Hidden Harlow Lane Retreat

9.6 out of 10, Exceptional, (25)
"Beautiful property and very nice host"
Summer Getaway on North Pond - Hidden Harlow Lane Retreat
Lighthouse Lane
Terrace/patio

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
April Special, Lake Great Pond, Dog Friendly
Exterior

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 427
AED 969 total
includes taxes & fees
29 Apr - 30 Apr
April Special, Lake Great Pond, Dog Friendly
"Not-A-Pine Lane COTTAGE" is a family treasure enjoyed by generations
Smart TV, fireplace, books

"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
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
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
Timeless Lakefront Cottage with private dock- East Pond Belgrade Lakes Region
Property grounds

Timeless Lakefront Cottage with private dock- East Pond Belgrade Lakes Region

10.0 out of 10, Exceptional, (31)
"Great spot right on quiet East Pond. Cottage is perfect and had everything and more than we needed. Owner was easy to communicate with and very pleasant. Highly recommended rental. "
Timeless Lakefront Cottage with private dock- East Pond Belgrade Lakes Region
2 BR Lakefront Cottage in Belgrade Lakes Region
Property grounds

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
Springvale Farm: Freedom Home With Hiking Trail!
Interior

Springvale Farm: Freedom Home With Hiking Trail!

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

9.6 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
Private Dock on Messalonskee Lake: Cozy Cottage!
Interior

Private Dock on Messalonskee Lake: Cozy Cottage!

2.0 star property
9.6 out of 10, Exceptional, (4)
"Great spot right on the lake, True to what was listed. The beds weren’t very comfortable but otherwise everything was great."
Private Dock on Messalonskee Lake: Cozy Cottage!
Belgrade Lakes Cottage w/ Long Pond beach access close to Augusta, Colby College
Terrace/patio

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

9.6 out of 10, Exceptional, (10)
"House was spacious and had all the necessities. The location was nice. Good for a relaxing trip near the water "
Belgrade Lakes Cottage w/ Long Pond beach access close to Augusta, Colby College
Beachfront Cottage Nestled in a Cove
Terrace/patio

Beachfront Cottage Nestled in a Cove

Beachfront Cottage Nestled in a Cove
Screen Porch with see thru roof, BQ, 30' from sandy beach, canoe and 3 kayaks
Exterior

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

7.6 out of 10, Good, (22)
"Our stay was great. Kids enjoyed the water and there was plenty of lawn space to play games."
Screen Porch with see thru roof, BQ, 30' from sandy beach, canoe and 3 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

7.0 out of 10, Good, (4)
"The listing stated there were upstairs tenants. Long story short, on Thanksgiving when they arrived home to me enjoying an outdoor fire, the accused me of using their firewood, I had brought my own. Then another night I left to do an activity with my kids and returned to not being able to park, due to them taking up three spaces with their truck. They were noisy every night until midnight and up every morning by 7a. In have no living family besides my kids and I was looking for a relaxing...
Lakefront Home on Togus Pond with 2 Decks, Great View & Shared Canoe/Firepit
Cozy 1 BR Maine lakeside cottage getaway with WiFi, laundry, and full kitchen.
Exterior

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

2.0 star property
10.0 out of 10, Exceptional, (6)
"Great place, would certainly rent again the future "
Cozy 1 BR Maine lakeside cottage getaway with WiFi, laundry, and full kitchen.
Unique Cottage
Exterior

Unique Cottage

10.0 out of 10, Exceptional, (25)
"The property was very nice meeting all our needs. The view of the lake from the gorgeous screened porch and the gas fire log were great! A highly recommed cottage! "
Unique Cottage
Maine Summer Lake House on Bald Head Island
Exterior

Maine Summer Lake House on Bald Head Island

10.0 out of 10, Exceptional, (25)
"“8 is Enough” was well furnished and had comfortable beds and was well appointed and felt “homey”. It is well located on the lake with a wonderful swim platform and dock. There are multiple fire pits and a perfect screened in porch. The Gleason’s were very accommodating and communicative owners and our trip was perfect."
Maine Summer Lake House on Bald Head Island
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.
Don't see what you're looking for?
See all available properties in Winslow
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Winslow

April Special, Lake Great Pond, Dog Friendly
Exterior

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 427
AED 969 total
includes taxes & fees
29 Apr - 30 Apr
April Special, Lake Great Pond, Dog Friendly
The Cabin Skowhegan
Terrace/patio

The Cabin Skowhegan

9.8 out of 10, Exceptional, (39)
"The location was great! Close enough to town to be convenient and far enough out to have a remote country feeling. We most likely will return. The cabin was rustic, which had it's charm."
The price is AED 367
AED 681 total
includes taxes & fees
20 Apr - 21 Apr
The Cabin Skowhegan
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!
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.