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
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Winslow vacation rentals

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.

1. 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)
"Less than 5 minutes to Colby. We were there for a camp. AC in both bedrooms. Nice artwork and decor."
United States
Leslie G.
The price is ￥23,430
￥40,206 total
includes taxes & fees
Nov 2 - Nov 3
Cozy House in the heart of Waterville Maine.
A wooden cabin with a porch, a door, and a green chair.

2. 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 ￥15,831
￥37,100 total
includes taxes & fees
Nov 3 - Nov 4
Sister A-Frame in Woods B
A single-story house with a gray siding exterior, a white front door, and two flower planters on either side of the entrance.

3. Discover Oakland charm near Colby College 10 min

Discover Oakland charm near Colby College 10 min
Oakland
9.8 out of 10, Exceptional, (20 reviews)
"Great communication. The location was excellent for a few day trips. Very clean and well maintained. Would definitely stay here again if in the area."
United States
Patricia
The price is ￥18,878
￥36,831 total
includes taxes & fees
Oct 15 - Oct 16
Discover Oakland charm near Colby College 10 min
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 ￥17,810
￥27,179 total
includes taxes & fees
Oct 22 - Oct 23
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 ￥16,464
￥39,170 total
includes taxes & fees
Nov 1 - Nov 2
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 ￥18,206
￥37,273 total
includes taxes & fees
Oct 18 - Oct 19
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 ￥20,580
￥25,883 total
includes taxes & fees
Oct 16 - Oct 17
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)
"Kathleen was a wonderful host. My family and I found the property welcoming and relaxing. Great place to stay if you are looking for a laid back atmosphere and peaceful time in the country."
United States
Jared
The price is ￥32,414
￥56,654 total
includes taxes & fees
Oct 18 - Oct 19
Fall Getaway at My Valhalla Farm- close to Waterville and minutes to lakes
A modern kitchen with dark cabinets, a black refrigerator, and a wooden dining table with bar stools.

9. 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 ￥20,580
￥25,883 total
includes taxes & fees
Oct 31 - Nov 1
Whitsendsport unit 4 1 bedroom & queen pull out couch on 50 acres Smithfield
A room with a sliding glass door leading to a deck, a wooden table, and a chair.

10. 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 ￥26,461
￥61,697 total
includes taxes & fees
Nov 1 - Nov 2
Boat launch and Trailer parking, Dog Friendly, Lake Great Pond
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, (94 reviews)
"Cute place, quiet neighborhood close to downtown."
United States
Melissa F.
The price is ￥19,789
￥37,963 total
includes taxes & fees
Nov 2 - Nov 3
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)
"We will miss this house and would be happy to come back again. The ac in every bedroom plus the main floor made the most humid days comfortable. And China Lake is a wonderful place to have a piece of to yourself."
United States
Lisa J.
The price is ￥34,765
￥82,241 total
includes taxes & fees
Oct 14 - Oct 15
China Lake, Dog Friendly, Lots of space for family gatherings
A covered patio with a view of a lake, outdoor furniture, and a wooden deck.

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

Family's Paradise: 3BR/2BA,Game Room & Lake Access
Belgrade
10.0 out of 10, Exceptional, (12 reviews)
"We enjoyed our stay."
United States
Tyson W.
The price is ￥49,868
￥158,891 total
includes taxes & fees
Oct 28 - Oct 29
Family's Paradise: 3BR/2BA,Game Room & Lake Access
A modern kitchen with dark blue cabinets, a black refrigerator, and a wooden table with black cushioned benches.

14. 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
9.0 out of 10, Wonderful, (2 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 ￥20,580
￥25,883 total
includes taxes & fees
Oct 28 - Oct 29
Cozy new 1 bedroom, queen bed, and queen sofa bed, washer/dryers. Radiant heat.
A large, red, two-story house with a balcony and a tower, surrounded by a fence and trees.

15. Angel Mist Retreat Garage Apartment

Angel Mist Retreat Garage Apartment
Pittsfield
10.0 out of 10, Exceptional, (15 reviews)
"Great stay. Very comfortable, roomy, clean and good overall value."
United States
Rob K.
The price is ￥22,227
￥48,731 total
includes taxes & fees
Oct 18 - Oct 19
Angel Mist Retreat Garage Apartment
A living room with a sofa, a coffee table, a rug, and a painting on the wall.

16. 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 ￥20,623
￥25,937 total
includes taxes & fees
Nov 3 - Nov 4
Country setting close to lake 1 bedroom queen bed sofa, full kitchens and bath
A large, two-story house with a well-lit front porch and multiple windows.

17. Elizabeth Cottage

Elizabeth Cottage
Mount Vernon
The price is ￥33,245
￥68,765 total
includes taxes & fees
Oct 14 - Oct 15
Elizabeth Cottage
A wooden cabin interior with a sofa, dining table, and a chair with a woven seat.

18. Once Upon a Time — A Peaceful Maine Escape

Once Upon a Time — A Peaceful Maine Escape
Freedom
The price is ￥29,921
￥61,086 total
includes taxes & fees
Oct 14 - Oct 15
Once Upon a Time — A Peaceful Maine Escape
A sauna with a control panel, a bench, and a window.

19. New Lakefront Escape on Red Cedar Lane. Private Dock, Sunset Views & Family Fun

New Lakefront Escape on Red Cedar Lane. Private Dock, Sunset Views & Family Fun
Sidney
The price is ￥53,430
￥103,450 total
includes taxes & fees
Oct 14 - Oct 15
New Lakefront Escape on Red Cedar Lane. Private Dock, Sunset Views & Family Fun
A bathroom with a white sink, wooden paneling, a mirror with a bead trim, and a view of a house through a window.

20. River View Retreat, Hot Tub, Balcony, Kayaks & Bikes

River View Retreat, Hot Tub, Balcony, Kayaks & Bikes
Hallowell
10.0 out of 10, Exceptional, (2 reviews)
"Great place and great host. Right in the water and close to New York and Canada"
United States
Anthony R.
The price is ￥22,130
￥27,581 total
includes taxes & fees
Oct 19 - Oct 20
River View Retreat, Hot Tub, Balcony, Kayaks & Bikes
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

Fireside Inn & Suites Waterville

Fireside Inn & Suites Waterville

8/10 Good
"No working elevator during my stay (6–7 October). Coffee available in lobby 24/7. Ample parking, multiple entrances."
Asa 1-night trip
Posted 5 hours ago
Fireside Inn & Suites Waterville

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?

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.