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Compare Vacation Homes in Winslow with updated reviews, rates, and availability.

Cozy Long Pond Cottage: private mooring & shared dock
Come enjoy this warm cottage!

Cozy Long Pond Cottage: private mooring & shared dock

9.8 out of 10, Exceptional, (8)
"The stay was a very nice place and we will be coming back with the whole family next time. "
Cozy Long Pond Cottage: private mooring & shared dock
Dog-friendly lakefront home with dock, fireplace, firepit, lake views, & 1 kayak

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
Secluded escape with three beaches, lake access, grill & fast WiFi - dogs OK

Secluded escape with three beaches, lake access, grill & fast WiFi - dogs OK

9.0 out of 10, Wonderful, (18)
"Comfortable, quiet location. Appreciated the many nightlights. Both showers need grab bars. Basement shower drain not attached to shower floor."
Secluded escape with three beaches, lake access, grill & fast WiFi - dogs OK
Private and Calming Waterfront to the Rescue!
40 foot dock for boating, fishing and swimming

Private and Calming Waterfront to the Rescue!

9.6 out of 10, Exceptional, (75)
"We stayed at the property for a trade show with our team and enjoyed a comfortable clean and amazing overall stay. The house was clean kept and the owner was easy to deal with would highly recommend "
Private and Calming Waterfront to the Rescue!
Spacious Country Home w/ Hot Tub, near Colby/Thomas
Spacious dining room for your meals, game night, or remote office. (1)

Spacious Country Home w/ Hot Tub, near Colby/Thomas

9.6 out of 10, Exceptional, (15)
"The house was great in every way. "
The price is SAR 507
SAR 1,170 total
includes taxes & fees
27 Dec - 28 Dec
Spacious Country Home w/ Hot Tub, near Colby/Thomas
The Modern Maine Retreat
Room

The Modern Maine Retreat

10.0 out of 10, Exceptional, (2)
"Worked out perfectly for our needs. Owner responded immediately to assist us with minor issue. We would, and most likely will, rent this home again. Location was great for our purpose. Plenty of room."
The Modern Maine Retreat
Lake Front with Amazing Sunsets on McGrath Pond
Enjoy beautiful sunsets every night.

Lake Front with Amazing Sunsets on McGrath Pond

10.0 out of 10, Exceptional, (17)
"Very clean, cute lake house. Owner responsive, everything you need for a rental home. Lake and lake toys were so great! We really enjoyed our stay. Thank you!!! "
Lake Front with Amazing Sunsets on McGrath Pond
Small cottage house, centered on 100 acres surround by hills, lake, and cattle.
Exterior

Small cottage house, centered on 100 acres surround by hills, lake, and cattle.

2.0 star property
10.0 out of 10, Exceptional, (2)
"We only stayed for one night. Basically just slept and showered in the morning so I can not speak on how well stocked the kitchen is. However, there were plenty of pillows, blankets, and towels. Beautiful views, no trouble finding the location and the house was very clean. "
The price is SAR 1,690
SAR 2,104 total
includes taxes & fees
27 Dec - 28 Dec
Small cottage house, centered on 100 acres surround by hills, lake, and cattle.
Wildewood Haven - Charming 3-bedroom home located on Long Pond, Rome, ME
Exterior

Wildewood Haven - Charming 3-bedroom home located on Long Pond, Rome, ME

2.0 star property
Wildewood Haven - Charming 3-bedroom home located on Long Pond, Rome, ME
Charming 2-bedroom house with AC, WiFi in enchanting Skowhegan
Living area

Charming 2-bedroom house with AC, WiFi in enchanting Skowhegan

2.0 star property
10.0 out of 10, Exceptional, (2)
"This house was perfect for our stay. We could host our family for meals and meetings. We could enjoy quiet evenings by ourselves and Walmart and grocery were close enough to walk to. "
The price is SAR 559
SAR 966 total
includes taxes & fees
1 Jan - 2 January 2025
Charming 2-bedroom house with AC, WiFi in enchanting Skowhegan
Red Cedar Haven: Lakeside Tranquility
Glide across the icy expanses of Messalonskee Lake on your snowmobile, where the thrill of speed meets the serenity of snowy landscapes. An ideal getaway for winter sports aficionados.

Red Cedar Haven: Lakeside Tranquility

10.0 out of 10, Exceptional, (7)
"This is a lovely spot with expansive views of a gorgeous lake location. We enjoyed the house, the grounds, the upper and lower decks, the kayaks and SUPs provided, and dock with access to the lake. Everything was spotless and highly functional with thoughtful host details like coffee and soaps provided. A great place for family. We’d love to return. "
The price is SAR 2,440
SAR 4,164 total
includes taxes & fees
30 Dec - 31 Dec
Red Cedar Haven: Lakeside Tranquility
Light-Filled Log Home, 4 Wooded Acres, & Lake Access. The water is 0.4 mi away.
Exterior

Light-Filled Log Home, 4 Wooded Acres, & Lake Access. The water is 0.4 mi away.

10.0 out of 10, Exceptional, (56)
"Super cozy place. Use a silver popper on the pond"
Light-Filled Log Home, 4 Wooded Acres, & Lake Access. The water is 0.4 mi away.
Groups Welcome! Sleeps 16, HotTub, Skiing, Boating, Theatre Room, ITS Trails
“On Flying Pond”, The Loons, Hot Tubs, Eagles, Wine, Coffee…

Groups Welcome! Sleeps 16, HotTub, Skiing, Boating, Theatre Room, ITS Trails

Groups Welcome! Sleeps 16, HotTub, Skiing, Boating, Theatre Room, ITS Trails
Fantastic two-level home & guest cottage with fast WiFi & lake access - dogs OK

Fantastic two-level home & guest cottage with fast WiFi & lake access - dogs OK

4.0 out of 10, (2)
"The property had enough room for 10 adults to spread out comfortably. The view was beautiful. The larger house is much nicer than smaller cabin. The smaller cabin is very rustic and smells like an old camp. The listing had a fire pit listed but none was provided. The property is steep in some parts and those with limited mobility may have a hard time accessing some of the property."
Fantastic two-level home & guest cottage with fast WiFi & lake access - dogs OK
MoonLight Treehouse- Luxury Waterfront Escape

MoonLight Treehouse- Luxury Waterfront Escape

10.0 out of 10, Exceptional, (17)
"This is a lovely spot to relax and recharge. Just steps away from the stream, which was gorgeous in the fall. Feras and family were excellent hosts. The Moonlight treehouse was thoughtfully decorated; we wish wexould have stayed longer. Excellent proactive communication. We will be going back in the future!"
The price is SAR 2,027
SAR 3,657 total
includes taxes & fees
30 Dec - 31 Dec
MoonLight Treehouse- Luxury Waterfront Escape
SkyView Treehouse- Luxury Waterfront Retreat

SkyView Treehouse- Luxury Waterfront Retreat

10.0 out of 10, Exceptional, (3)
"Absolutely stunning home and location. From all the little details in the house and the host always made sure we had everything we needed and that he was just a text away if we needed anything at all. We had use of the kayaks and I would definitely suggest that because the scenery is just beautiful. Feras and his family are great hosts and I highly recommend them. "
The price is SAR 1,874
SAR 3,467 total
includes taxes & fees
22 Jan - 23 January 2025
SkyView Treehouse- Luxury Waterfront Retreat
Perfect Maine Getaway in a Newly Renovated Cabin!
Interior

Perfect Maine Getaway in a Newly Renovated Cabin!

9.6 out of 10, Exceptional, (14)
"Had a great time at the cabin, just steps from town. Would recommend if you want to close to everything."
Perfect Maine Getaway in a Newly Renovated Cabin!
Lakefront home on Long Pond with private dock, firepit & woodstove- dog-friendly

Lakefront home on Long Pond with private dock, firepit & woodstove- dog-friendly

9.2 out of 10, Wonderful, (18)
"Absolutely beautiful house on the lake. Enjoyed this with my husband and cousins. Just as described. Responsive host."
Lakefront home on Long Pond with private dock, firepit & woodstove- dog-friendly
Weekly discounts avail. Get away at this New house on Lovejoy Pond in Albion
Exterior

Weekly discounts avail. Get away at this New house on Lovejoy Pond in Albion

10.0 out of 10, Exceptional, (26)
"As described. Beautiful location. Clean and well stocked. Very cozy, comfortable and exactly what we were hoping for. Great host, thank you!"
Weekly discounts avail. Get away at this New house on Lovejoy Pond in Albion
Lovely dog-friendly lakefront abode with firepit, swimming dock, and fast WiFi

Lovely dog-friendly lakefront abode with firepit, swimming dock, and fast WiFi

8.8 out of 10, Excellent, (13)
"The place was cool, nice and clean. The place was a safe neighborhood, the places of interest are just nearby. I love to be back again. Thanks for the lovely experienced."
Lovely dog-friendly lakefront abode with firepit, swimming dock, and fast WiFi
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 Winslow

The Cabin Skowhegan
Terrace/patio

The Cabin Skowhegan

9.8 out of 10, Exceptional, (36)
"Larry hosted us for a week with our dogs while we were on a house-hunting expedition. Larry was a perfect host; very attentive but allowed us our space. The Cabin is very cozy and while there is no kitchen sink, the property details disclose this so we were prepared. It was a wonderful stay!"
The Cabin Skowhegan
High End Apartment in Downtown Hallowell

High End Apartment in Downtown Hallowell

10.0 out of 10, Exceptional, (72)
"The place is lovely and full of everything to make one feel cared for. We especially enjoyed the deck off the kitchen. The location is great with a delightful walk to wonderful restaurants--steps from the river. Top notch in every way in my view."
The price is SAR 421
SAR 773 total
includes taxes & fees
22 Jan - 23 January 2025
High End Apartment in Downtown Hallowell
Dog-friendly lakefront home with dock, fireplace, firepit, lake views, & 1 kayak

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
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.