A steel bridge over a river with lush greenery on both sides.

Winslow Vacation Rentals

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Winslow vacation rentals

A wooden cabin with a porch, a door, and a green chair.

1. Sister A-Frame in Woods B

Sister A-Frame in Woods B
Oakland
10.0 out of 10, Exceptional, (13 reviews)
"Great stay. Would stay here again if in the area."
United States
Amanda M.
The price is AED 331
AED 777 total
includes taxes & fees
15 Nov - 16 Nov
Sister A-Frame in Woods B
A modern RV kitchen with a built-in stove, sink, and refrigerator, a seating area, and a large window.

2. Fabulous 3-bedroom RV with direct access to the Sebasticook River!

Fabulous 3-bedroom RV with direct access to the Sebasticook River!
Benton
9.6 out of 10, Exceptional, (8 reviews)
"Beautiful camper and property! We loved it!"
United States
Tracy D.
The price is AED 281
AED 434 total
includes taxes & fees
30 Nov - 1 Dec
Fabulous 3-bedroom RV with direct access to the Sebasticook River!
A living room with a sectional sofa, a coffee table, and a patterned rug. There are two paintings on the walls, a lamp, and a potted plant.

3. Cozy House in the heart of Waterville Maine.

Cozy House in the heart of Waterville Maine.
Waterville
9.6 out of 10, Exceptional, (65 reviews)
"Clean and Cozy! Always perfect for our stay "
United States
Rebecca B.
The price is AED 580
AED 889 total
includes taxes & fees
15 Nov - 16 Nov
Cozy House in the heart of Waterville Maine.
A cozy cabin interior with a wooden floor, a sofa, a table, and a television mounted on the wall.

4. Charming cabin in the birches right on the atv trail!

Charming cabin in the birches right on the atv trail!
Fairfield
8.6 out of 10, Excellent, (9 reviews)
"The cabin was perfect for our two night stay. It was very clean and it felt just like being at home. Misty was a responsive host and I would definitely rent here again."
United States
Tonilynne D.
The price is AED 314
AED 490 total
includes taxes & fees
19 Nov - 20 Nov
Charming cabin in the birches right on the atv trail!
Property grounds

5. Central Maine Apartment offering 4 Seasons of Fun.

Central Maine Apartment offering 4 Seasons of Fun.
Oakland
10.0 out of 10, Exceptional, (50 reviews)
"Apartment was comfortable and as described. I had a nice stay."
United States
kathy e.
The price is AED 386
AED 889 total
includes taxes & fees
13 Nov - 14 Nov
Central Maine Apartment offering 4 Seasons of Fun.
A bedroom with a bed, a bedside table, a lamp, and a window with curtains.

6. The heart of the Belgrade Lakes

The heart of the Belgrade Lakes
Oakland
9.2 out of 10, Wonderful, (11 reviews)
"Host was very accommodating "
United States
Maureen
The price is AED 422
AED 825 total
includes taxes & fees
23 Nov - 24 Nov
The heart of the Belgrade Lakes
A modern kitchen with a black refrigerator, dark cabinets, and a wooden dining table with a bench.

7. Cozy newly built 1-bedroom unit 2 Kentucky Bay in charming Smithfield Maine

Cozy newly built 1-bedroom unit 2 Kentucky Bay in charming Smithfield Maine
Smithfield
10.0 out of 10, Exceptional, (4 reviews)
"A lovely spot. It is extremely clean. The hostess has thought of everything! There are plenty of nice towels and facecloths and bedding. The bed is very comfortable. We have enjoyed our stay"
Canada
Sherrie
The price is AED 441
AED 528 total
includes taxes & fees
13 Nov - 14 Nov
Cozy newly built 1-bedroom unit 2 Kentucky Bay in charming Smithfield Maine
A wooden deck with outdoor furniture, a large potted plant, and string lights.

8. Fall Getaway at My Valhalla Farm- close to Waterville and minutes to lakes

Fall Getaway at My Valhalla Farm- close to Waterville and minutes to lakes
Oakland
10.0 out of 10, Exceptional, (18 reviews)
"We loved staying at the farm! My kids enjoyed meeting the horse and donkey on property. It was perfect for our family!"
United States
Shana S.
Fall Getaway at My Valhalla Farm- close to Waterville and minutes to lakes
A room with a sliding glass door leading to a deck, a wooden table, and a chair.

9. Boat launch and Trailer parking, Dog Friendly, Lake Great Pond

Boat launch and Trailer parking, Dog Friendly, Lake Great Pond
Belgrade
10.0 out of 10, Exceptional, (58 reviews)
"Great place, quiet neighborhood off the lake, very comfortable. Would definitely stay again!"
United States
Steve C.
The price is AED 694
AED 1,472 total
includes taxes & fees
15 Nov - 16 Nov
Boat launch and Trailer parking, Dog Friendly, Lake Great Pond
A living room with a sofa, a coffee table, a rug, and a painting on the wall.

10. Country setting close to lake 1 bedroom queen bed sofa, full kitchens and bath

Country setting close to lake 1 bedroom queen bed sofa, full kitchens and bath
Smithfield
The price is AED 441
AED 500 total
includes taxes & fees
1 Dec - 2 Dec
Country setting close to lake 1 bedroom queen bed sofa, full kitchens and bath
A modern living room with a flat-screen TV, a yellow armchair, a beige sofa, and a coffee table.

11. Two bedroom Mid Century Modern apartment in Downtown Hallowell

Two bedroom Mid Century Modern apartment in Downtown Hallowell
Hallowell
10.0 out of 10, Exceptional, (97 reviews)
"Cute place, quiet neighborhood close to downtown."
United States
Melissa F.
The price is AED 413
AED 759 total
includes taxes & fees
16 Nov - 17 Nov
Two bedroom Mid Century Modern apartment in Downtown Hallowell
A deck with two Adirondack chairs, a metal fire pit, and a view of a lake surrounded by trees.

12. China Lake, Dog Friendly, Lots of space for family gatherings

China Lake, Dog Friendly, Lots of space for family gatherings
China
10.0 out of 10, Exceptional, (5 reviews)
"Perfect for family gatherings Home was very clean and well stocked Host responded quickly to all messages Love that it is pet friendly"
United States
Anne S.
The price is AED 818
AED 2,241 total
includes taxes & fees
15 Nov - 16 Nov
China Lake, Dog Friendly, Lots of space for family gatherings
A modern kitchen with dark blue cabinets, a black refrigerator, and a wooden table with black cushioned benches.

13. Cozy new 1 bedroom, queen bed, and queen sofa bed, washer/dryers. Radiant heat.

Cozy new 1 bedroom, queen bed, and queen sofa bed, washer/dryers. Radiant heat.
Smithfield
9.4 out of 10, Exceptional, (3 reviews)
"The stay was nice, it was cute place and priced reasonably. The horses across the street were a fun surprise in the morning."
United States
Hailey M.
The price is AED 441
AED 528 total
includes taxes & fees
13 Nov - 14 Nov
Cozy new 1 bedroom, queen bed, and queen sofa bed, washer/dryers. Radiant heat.
A spacious kitchen with wooden cabinets, a microwave, and a stove.

14. The Libby House – Fast WiFi, Parking & Full Kitchen

The Libby House – Fast WiFi, Parking & Full Kitchen
Pittsfield
10.0 out of 10, Exceptional, (1 review)
"Great place!"
United States
mary jane c.
The price is AED 375
AED 528 total
includes taxes & fees
16 Nov - 17 Nov
The Libby House – Fast WiFi, Parking & Full Kitchen
A modern kitchen with dark cabinets, a black refrigerator, and a wooden dining table with bar stools.

15. Whitsendsport unit 4 1 bedroom & queen pull out couch on 50 acres Smithfield

Whitsendsport unit 4 1 bedroom & queen pull out couch on 50 acres Smithfield
Smithfield
8.0 out of 10, Very good, (1 review)
"Very clean and centrally located for the Belgrade Lakes. Nice people and I will definitely stay again."
United States
Mike F.
The price is AED 441
AED 528 total
includes taxes & fees
13 Nov - 14 Nov
Whitsendsport unit 4 1 bedroom & queen pull out couch on 50 acres Smithfield
Terrace/patio

16. Quiet Maine Retreat- Fast Wi-Fi - Long Stays Welcome- close to I95

Quiet Maine Retreat- Fast Wi-Fi - Long Stays Welcome- close to I95
Pittsfield
9.8 out of 10, Exceptional, (10 reviews)
"I recommend this property to anyone staying in the Pittsfield area. I’ve already suggested it to our friends who live there as great option for guests. Very clean and comfortable and a good value."
United States
Anonymous traveler
The price is AED 437
AED 681 total
includes taxes & fees
13 Nov - 14 Nov
Quiet Maine Retreat- Fast Wi-Fi - Long Stays Welcome- close to I95
A wooden deck with a railing and steps leading to a house.

17. Home Away From Home. Family friendly, comfortable- centrally located in Augusta

Home Away From Home. Family friendly, comfortable- centrally located in Augusta
Augusta
The price is AED 562
AED 901 total
includes taxes & fees
13 Nov - 14 Nov
Home Away From Home. Family friendly, comfortable- centrally located in Augusta
A large, red, two-story house with a balcony and a tower, surrounded by a fence and trees.

18. Angel Mist Retreat Garage Apartment

Angel Mist Retreat Garage Apartment
Pittsfield
10.0 out of 10, Exceptional, (15 reviews)
"Very quiet and lovely apartment. The host was very accommodating and attentive to my questions."
United States
Ruth W.
The price is AED 516
AED 1,039 total
includes taxes & fees
13 Nov - 14 Nov
Angel Mist Retreat Garage Apartment
A large, two-story house with a well-lit front porch and multiple windows.

19. Elizabeth Cottage

Elizabeth Cottage
Mount Vernon
The price is AED 771
AED 1,519 total
includes taxes & fees
15 Nov - 16 Nov
Elizabeth Cottage
A living room with a fireplace, a glass of white wine, a cutting board with cheese, and a remote control.

20. High End Apartment in Downtown Hallowell

High End Apartment in Downtown Hallowell
Hallowell
10.0 out of 10, Exceptional, (115 reviews)
"Bigger than I expected and one of the homier properties I have been to in a while. Great location to walk around town and minutes to Augusta. Will book again"
United States
Shawn
The price is AED 437
AED 725 total
includes taxes & fees
6 Dec - 7 Dec
High End Apartment in Downtown Hallowell
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

Lockwood Hotel

Lockwood Hotel

10/10 Excellent
"Had a wonderful stay at the Lockwood. The room, hotel and staff were all top shelf!"
Jeanne 1-night trip
Posted 2 days ago
Lockwood Hotel

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?

Stunning Belgrade Lakes Waterfront Retreat – Dock, Kayaks & Breathtaking Views!: This vacation home rental near Winslow offers a patio, a garden, and air-conditioning to help you feel perfectly comfortable in your new surroundings.

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.