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Compare 117 Vacation Homes in Winslow with updated reviews, rates, and availability.

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

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

Private and Calming Waterfront to the Rescue!

9.6 out of 10, Exceptional, (77)
"clean place listed accordingly "
Private and Calming Waterfront to the Rescue!

Idyllic Washington Retreat w/ Fire Pit & Yard

9.2 out of 10, Wonderful, (12)
"We stayed here because it was outside of Augusta and centered between the coast line, Moosehead Lake, and the scenic NatIonal Park."
Idyllic Washington Retreat w/ Fire Pit & Yard

The Modern Maine Retreat

9.0 out of 10, Wonderful, (4)
"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

Brand New Waterfront Lake House (completed July 2021)

10.0 out of 10, Exceptional, (22)
"We had an amazing week at this property. House was spacious, clean and had everything that we needed. We plan to stay here again next summer! "
Brand New Waterfront Lake House (completed July 2021)

Charming 4-bedroom log home with WiFi and AC in pleasant Liberty

Charming 4-bedroom log home with WiFi and AC in pleasant Liberty

Cozy House in the heart of Waterville Maine.

9.6 out of 10, Exceptional, (39)
"Very clean nice home, close to restaurants and shops. The owner was easily accessible if needed. "
Cozy House in the heart of Waterville Maine.

Spectacular Location Reasonably Priced

9.6 out of 10, Exceptional, (29)
"This is the quintessential cabin rental which provides good modern facilities with the vintage Maine camp feel we have always looked for. We will return to our 3rd rental at this property next year. Very satisfied with our experience."
Spectacular Location Reasonably Priced

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

8.2 out of 10, Very Good, (16)
"Great location! Very nice place"
Dog-friendly lakefront home with dock, fireplace, firepit, lake views, & 1 kayak

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.

Cozy Long Pond Cottage: private mooring & shared dock

9.8 out of 10, Exceptional, (13)
" Cute place"
Cozy Long Pond Cottage: private mooring & shared dock

Modern 4 BR Waterfront Lake House, beautiful Belgrade Lakes Area, Mt. Vernon, ME

10.0 out of 10, Exceptional, (16)
"We were a group of 6 men on our annual fishing trip. The rental did not disappoint, Owners were very attentive to our needs leading up to our visit. Home was well appointed, clean and came as advertised. Great Lake for fishing, caught trout, bass, cusk and perch. The eagle that hung around while we fished was an added bonus. Overall a great trip!!!"
Modern 4 BR Waterfront Lake House, beautiful Belgrade Lakes Area, Mt. Vernon, ME

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

9.8 out of 10, Exceptional, (18)
"We had an awesome time playing in the snow in the backyard and enjoying the relaxing hot tub. The house accommodated our large family and the host was very responsive and came quickly when we needed help. Will definitely come back "
Spacious Country Home w/ Hot Tub, near Colby/Thomas

Big Pines Cabin: A Waterfront Retreat Open 4 Seasons, with Private Dock

2.0 star property
10.0 out of 10, Exceptional, (5)
"Did not want to leave. So thankful work took me to this beautiful property. The views did not disappoint. Alyssa and Mike were such a pleasure to work with. Thank you for opening your home away from home for me. My family and I will definitely be back. "
Big Pines Cabin: A Waterfront Retreat Open 4 Seasons, with Private Dock

Perfect Maine Getaway in a Recently 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 Recently Renovated Cabin!

Find Your Bliss at this Private and Captivating Lakeside Retreat

10.0 out of 10, Exceptional, (20)
"We decided to book this beautiful property to bring our family together for a long weekend to celebrate Thanksgiving together for our first holiday since the passing of our father. This was the perfect spot! The house accommodated all 12 of us easily with plenty of space for more! The hope décor is perfection and the views are priceless! The days we spent there with filled with tears and laughter and reliving fond memories while making new memories. Dan was absolutely wonderful to deal with...
Find Your Bliss at this Private and Captivating Lakeside Retreat

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

8.8 out of 10, Excellent, (19)
"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

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

9.2 out of 10, Wonderful, (19)
"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

3 Bedroom year round lakefront home on Three Mile Pond in South China, ME

9.8 out of 10, Exceptional, (81)
"Great property, third tine here, excellent stocked kitchen"
3 Bedroom year round lakefront home on Three Mile Pond in South China, ME

Great Pond Waterfront: Dog-friendly Home Near Colby College

9.6 out of 10, Exceptional, (30)
"This was our third year in a row spending most of August at the wonderful Loons nest! Brent and Sarah are great and responsive hosts. The views and water are incomparable and the cabin itself has all of the modern conveniences while maintaining a rustic charm. It is one of our favorite places in the world and hope to be back next year!"
Great Pond Waterfront: Dog-friendly Home Near Colby College
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

9.8 out of 10, Exceptional, (39)
"This is a wonderful, cozy little cabin that is remote enough to be private and peaceful, but close enough to town to be convenient as well. Highly recommended!"
The price is SAR 375
SAR 695 total
includes taxes & fees
27 Apr - 28 Apr
The Cabin Skowhegan

Downtown! Views! Dining! King & Queen beds!

2.0 star property
10.0 out of 10, Exceptional, (8)
"Great location, we traveled up to Bangor and down to Portland from this central location.The apartment was beautiful and clean with a great view of the river on one side, and the main road (which was quiet) on the other.Check in and out was seamless and Drew was very communicative before and during our stay. They even cleared the balcony and steps of snow."
Downtown! Views! Dining! King & Queen beds!

April Special, Lake Great Pond, Dog Friendly

10.0 out of 10, Exceptional, (36)
"With one kid already in college locally and the other on their way there in August we have got to know this neck of the woods quite well in recent years. Driftwood Cottage provides a perfect base for visits to the area with great access to Augusta and Waterville while sitting in the idyllic Belgrade Lakes region.We don’t visit Maine for fancy, we want practical, comfortable, clean and convenient and this house that in spades. We also greatly appreciated the dog-friendliness!Hosts could not...
The price is SAR 572
SAR 1,180 total
includes taxes & fees
27 Apr - 28 Apr
April Special, Lake Great Pond, Dog Friendly
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.