Winslow Holiday 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 holiday 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 HK$706
HK$1,599 total
includes taxes & fees
16 Nov - 17 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 HK$600
HK$928 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 HK$1,239
HK$1,898 total
includes taxes & fees
13 Dec - 14 Dec
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 HK$671
HK$1,048 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 HK$824
HK$1,881 total
includes taxes & fees
22 Nov - 23 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 HK$902
HK$1,685 total
includes taxes & fees
11 Dec - 12 Dec
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 HK$941
HK$1,129 total
includes taxes & fees
19 Nov - 20 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.
The price is HK$1,639
HK$1,924 total
includes taxes & fees
13 Nov - 14 Nov
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 HK$1,482
HK$3,143 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 HK$941
HK$1,129 total
includes taxes & fees
13 Dec - 14 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 HK$883
HK$1,621 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 HK$2,022
HK$5,153 total
includes taxes & fees
30 Nov - 1 Dec
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 HK$941
HK$1,129 total
includes taxes & fees
13 Dec - 14 Dec
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 HK$800
HK$1,129 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 HK$941
HK$1,129 total
includes taxes & fees
19 Nov - 20 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 traveller
The price is HK$934
HK$1,454 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 HK$1,200
HK$1,924 total
includes taxes & fees
13 Dec - 14 Dec
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 HK$1,101
HK$2,218 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 HK$1,647
HK$3,108 total
includes taxes & fees
22 Nov - 23 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 HK$855
HK$1,522 total
includes taxes & fees
19 Nov - 20 Nov
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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Find out more about Winslow

Search for holiday rentals in Winslow on Expedia! You can easily find your home rentals, villas, holiday apartments in Winslow using one of the methods below:

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Frequently Asked Questions

Can I find a holiday rental in Winslow?

Yes, there are holiday rentals close to the most popular sights in Winslow, or you can select a more secluded option if you're looking for a relaxing stay. Winslow is known for its riverfront.

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

Stunning Belgrade Lakes Waterfront Retreat – Dock, Kayaks & Breathtaking Views!: This holiday home rental outside of 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 wider area.

What’s a holiday rental in Winslow like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Winslow. Holiday rentals offer extras such as kitchens and laundry facilities so you'll feel right at home. If you're concerned about cleanliness, a holiday rental can provide a sense of privacy away from public hotel lifts and lobbies bustling with people while still allowing you to travel. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a great choice for families.