Winslow Vacation Rentals

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Check prices for these dates

In two weeks
Jan 23 - Jan 25
In two months
Mar 6 - Mar 8
In three months
Apr 3 - Apr 5
In four months
May 1 - May 3

Our top choices for Winslow vacation rentals

Exterior
Cozy getaway: farmhouse with wood stove & jacuzzi tub

Cozy getaway: farmhouse with wood stove & jacuzzi tub

Cozy getaway: farmhouse with wood stove & jacuzzi tub
Oakland
10.0 out of 10, Exceptional, (8)
"It was that was said to be The host was very nice and helpful . I enjoyed my stay "
United States
Andrea C.
The price is ￥28,990
￥55,562 total
includes taxes & fees
Jan 9 - Jan 10
Cozy getaway: farmhouse with wood stove & jacuzzi tub
Exterior
Discover Oakland charm near Colby College 10 min

Discover Oakland charm near Colby College 10 min

Discover Oakland charm near Colby College 10 min
2.0 star property
Oakland
10.0 out of 10, Exceptional, (6)
"New, clean and had everything we needed. "
United States
Lara B.
The price is ￥14,729
￥39,953 total
includes taxes & fees
Jan 11 - Jan 12
Discover Oakland charm near Colby College 10 min
Terrace/patio
Family's Paradise: 3BR/2BA,Game Room & Lake Access

Family's Paradise: 3BR/2BA,Game Room & Lake Access

Family's Paradise: 3BR/2BA,Game Room & Lake Access
2.0 star property
Belgrade
9.8 out of 10, Exceptional, (8)
"We enjoyed our stay."
United States
Tyson W.
The price is ￥32,888
￥125,980 total
includes taxes & fees
Jan 9 - Jan 10
Family's Paradise: 3BR/2BA,Game Room & Lake Access
Exterior
The Cabin Skowhegan

The Cabin Skowhegan

The Cabin Skowhegan
Skowhegan
9.8 out of 10, Exceptional, (50)
"Great place to stay. Highly recommend. Owner was very kind and helpful. Cabin was worth the money."
United States
Sue
The price is ￥15,661
￥32,775 total
includes taxes & fees
Jan 11 - Jan 12
The Cabin Skowhegan
Exterior detail
3350 Middle Road

3350 Middle Road

3350 Middle Road
Sidney
8.0 out of 10, Very Good, (3)
"A great spot for all 7 of us. Nice house with zones for everyone. Lovely backyard. Big kitchen and dining table"
United States
Pat D.
The price is ￥42,426
￥52,902 total
includes taxes & fees
Jan 11 - Jan 12
3350 Middle Road
Microwave, oven, stovetop
Superb 2-bedroom Home with AC in Detroit

Superb 2-bedroom Home with AC in Detroit

Superb 2-bedroom Home with AC in Detroit
2.0 star property
Detroit
The price is ￥18,668
￥32,298 total
includes taxes & fees
Jan 9 - Jan 10
Superb 2-bedroom Home with AC in Detroit
Fridge, microwave, oven, stovetop
Pine Tree Trail Lodge

Pine Tree Trail Lodge

Pine Tree Trail Lodge
2.0 star property
Pittsfield
10.0 out of 10, Exceptional, (1)
"Great place. The host so helpful. I would definitely stay here again. "
United States
Amber G.
The price is ￥21,432
￥41,545 total
includes taxes & fees
Jan 12 - Jan 13
Pine Tree Trail Lodge
Terrace/patio
The Cozy Home- New, Comfortable, Centrally located

The Cozy Home- New, Comfortable, Centrally located

The Cozy Home- New, Comfortable, Centrally located
2.0 star property
Pittsfield
10.0 out of 10, Exceptional, (1)
"Great host great stay"
United States
thomas v.
The price is ￥23,257
￥43,104 total
includes taxes & fees
Jan 9 - Jan 10
The Cozy Home- New, Comfortable, Centrally located
Exterior
Angel Mist Retreat Garage Apartment

Angel Mist Retreat Garage Apartment

Angel Mist Retreat Garage Apartment
Pittsfield
10.0 out of 10, Exceptional, (14)
"Great stay. Very comfortable, roomy, clean and good overall value."
United States
Rob K.
The price is ￥21,988
￥48,378 total
includes taxes & fees
Jan 9 - Jan 10
Angel Mist Retreat Garage Apartment
Outdoor dining
Lighthouse Lane

Lighthouse Lane

Lighthouse Lane
Manchester
10.0 out of 10, Exceptional, (70)
"Great location. Large comfy house and beds!! The back patio with bar seating ingenious! "
United States
Barbara C.
The price is ￥35,237
￥48,821 total
includes taxes & fees
Jan 12 - Jan 13
Lighthouse Lane
Interior
Cute, new, modern duplex in renovated schoolhouse

Cute, new, modern duplex in renovated schoolhouse

Cute, new, modern duplex in renovated schoolhouse
2.0 star property
Skowhegan
The price is ￥12,529
￥17,071 total
includes taxes & fees
Jan 18 - Jan 19
Cute, new, modern duplex in renovated schoolhouse
2 bedrooms, WiFi, bed sheets
The heart of the Belgrade Lakes

The heart of the Belgrade Lakes

The heart of the Belgrade Lakes
Oakland
9.0 out of 10, Wonderful, (9)
"Host was very accommodating "
United States
Maureen
The price is ￥18,010
￥36,701 total
includes taxes & fees
Feb 1 - Feb 2
The heart of the Belgrade Lakes
Interior
High End Apartment in Downtown Hallowell

High End Apartment in Downtown Hallowell

High End Apartment in Downtown Hallowell
Hallowell
10.0 out of 10, Exceptional, (97)
"Beautiful place to stay. Having coffee with all the fixings already there along with snacks was great! Would definitely stay here again!"
United States
John H.
The price is ￥17,540
￥32,263 total
includes taxes & fees
Jan 9 - Jan 10
High End Apartment in Downtown Hallowell
Interior
Ice Fishing, Dog Friendly, Lake Great Pond

Ice Fishing, Dog Friendly, Lake Great Pond

Ice Fishing, Dog Friendly, Lake Great Pond
Belgrade
10.0 out of 10, Exceptional, (48)
"Great place for us to get in 2 days of golf and 2 days of fishing. House was clean and communication with host prior to arrival and during our stay was excellent. "
United States
Thomas B.
The price is ￥18,981
￥47,149 total
includes taxes & fees
Jan 11 - Jan 12
Ice Fishing, Dog Friendly, Lake Great Pond
Fireplace
Sunrise Cabin - Super Clean & Solar-powered

Sunrise Cabin - Super Clean & Solar-powered

Sunrise Cabin - Super Clean & Solar-powered
2.0 star property
Jackson
The price is ￥23,413
￥37,982 total
includes taxes & fees
Jan 11 - Jan 12
Sunrise Cabin - Super Clean & Solar-powered
On the beach
The Maine Lake House with an Amazing Sand Beach!

The Maine Lake House with an Amazing Sand Beach!

The Maine Lake House with an Amazing Sand Beach!
Burnham
8.8 out of 10, Excellent, (6)
"Great stay, property was a great fit for a few day stay to visit family."
United States
Amy M.
The price is ￥31,087
￥80,648 total
includes taxes & fees
Jan 11 - Jan 12
The Maine Lake House with an Amazing Sand Beach!
Outdoor dining
Minutes to Colby

Minutes to Colby

Minutes to Colby
Waterville
8.8 out of 10, Excellent, (22)
"Close to our event, great communication, clean, comfortable & cozy"
United States
Shelly B.
The price is ￥17,070
￥30,044 total
includes taxes & fees
Jan 12 - Jan 13
Minutes to Colby
Outdoor spa tub
Cabin Style Studio Apt with Private Hot tub on 100 Acres Kayaks, Canoes & SUP

Cabin Style Studio Apt with Private Hot tub on 100 Acres Kayaks, Canoes & SUP

Cabin Style Studio Apt with Private Hot tub on 100 Acres Kayaks, Canoes & SUP
Whitefield
10.0 out of 10, Exceptional, (6)
"Great getaway! We loved all of the discoveries to be made both in the cabin and on the property. We stayed in Stella. It was adorable, functional, and very welcoming. We also enjoyed an outing to Kennebec Maine Cabin Masters only 20 min away! "
United States
Sandra L.
The price is ￥28,973
￥46,261 total
includes taxes & fees
Jan 19 - Jan 20
Cabin Style Studio Apt with Private Hot tub on 100 Acres Kayaks, Canoes & SUP
Property grounds
Central Maine Apartment offering 4 Seasons of Fun.

Central Maine Apartment offering 4 Seasons of Fun.

Central Maine Apartment offering 4 Seasons of Fun.
Oakland
10.0 out of 10, Exceptional, (43)
"Great hiking - nice views."
United States
Norbert A.
The price is ￥15,818
￥38,068 total
includes taxes & fees
Jan 12 - Jan 13
Central Maine Apartment offering 4 Seasons of Fun.
TV
NEW Cozy Cabin located in Oakland tucked away in a peaceful wooded scene.

NEW Cozy Cabin located in Oakland tucked away in a peaceful wooded scene.

NEW Cozy Cabin located in Oakland tucked away in a peaceful wooded scene.
Oakland
The price is ￥22,552
￥45,749 total
includes taxes & fees
Jan 9 - Jan 10
NEW Cozy Cabin located in Oakland tucked away in a peaceful wooded scene.
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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Top Winslow Hotel Reviews

Hampton Inn Augusta

Hampton Inn Augusta

10/10 Excellent
"Clean, comfortable, courteous staff, great breakfast. Our stay was great!"
Vickie 4-night trip
Posted 2 days ago
Hampton Inn Augusta

Find out more about Winslow

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Frequently asked questions

Can I find a vacation rental in Winslow?

Yes, you can find vacation rentals near well known sights in Winslow, or you can select a more secluded option if you're looking for relaxation. Winslow is known for its riverfront.

What are some of the best vacation home rentals that Winslow has to offer?

Spacious Country Home w/ Hot Tub, near Colby/Thomas: This vacation home rental near Winslow is located in a rural location and has a hot tub, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

What’s there to see and do in Winslow?

Explore the area and family-friendly sights such as Maine State Museum, or get out into nature at a spot like Kennebec River. Fort Halifax and Waterville Opera House are a couple of places you'll find in the larger area.

What’s a vacation rental in Winslow like?

Vacation rentals are private properties you can book for several days or longer in Winslow. Vacation rentals provide amenities such as laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about a clean environment, a vacation rental can offer a sense of security away from shared hotel elevators and busy front desks while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive option for a small group gathering.