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

Winslow Vacation Rentals

Check prices for these dates

In two weeks
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

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, (11 reviews)
"Great stay. Would stay here again if in the area."
United States
Amanda M.
$238 nightly
The price is $259
Sep 14 - Sep 15
Total with taxes and fees
Sister A-Frame in Woods B
A wooden deck with a table and chairs, a view of a house, and a tree.

2. Minutes to Colby

Minutes to Colby
Waterville
8.8 out of 10, Excellent, (25 reviews)
"Close to our event, great communication, clean, comfortable & cozy"
United States
Shelly B.
$230 nightly
The price is $251
Sep 14 - Sep 15
Total with taxes and fees
Minutes to Colby
A modern RV kitchen with a built-in stove, sink, and refrigerator, a seating area, and a large window.

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

Fabulous 3-bedroom RV with direct access to the Sebasticook River!
Benton
9.4 out of 10, Exceptional, (3 reviews)
"Beautiful camper and property! We loved it!"
United States
Tracy D.
$130 nightly
The price is $142
Sep 27 - Sep 28
Total with taxes and fees
Fabulous 3-bedroom RV with direct access to the Sebasticook River!
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 Host was great, I highly recommend this spot, everything was super smooth and the cabin was beautiful. "
United States
Jason B.
$158 nightly
The price is $172
Sep 12 - Sep 13
Total with taxes and fees
Charming cabin in the birches right on the atv trail!
A bedroom with a bed, a bedside table, a lamp, and a window with curtains.

5. The heart of the Belgrade Lakes

The heart of the Belgrade Lakes
Oakland
9.0 out of 10, Wonderful, (10 reviews)
"Host was very accommodating "
United States
Maureen
$215 nightly
The price is $234
Sep 12 - Sep 13
Total with taxes and fees
The heart of the Belgrade Lakes

6. Central Maine Apartment offering 4 Seasons of Fun.

Central Maine Apartment offering 4 Seasons of Fun.
Oakland
10.0 out of 10, Exceptional, (48 reviews)
"Apartment was comfortable and as described. I had a nice stay."
United States
kathy e.
$238 nightly
The price is $260
Sep 13 - Sep 14
Total with taxes and fees
Central Maine Apartment offering 4 Seasons of Fun.
A cozy cabin interior with a wooden ceiling, a sofa, two chairs, a TV, and a fireplace.

7. Private Dock on Messalonskee Lake: Cozy Cottage!

Private Dock on Messalonskee Lake: Cozy Cottage!
Sidney
9.0 out of 10, Wonderful, (12 reviews)
"Great place to stay for our annual fishing weekend in the Belgrade Lakes region! "
United States
Shawn H.
$303 nightly
The price is $330
Sep 16 - Sep 17
Total with taxes and fees
Private Dock on Messalonskee Lake: Cozy Cottage!
A modern kitchen with a black refrigerator, dark cabinets, and a wooden dining table with a bench.

8. 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, (3 reviews)
"WE were delighted in our accommodations. The apartment was lovely and very clean. Lynne was very responsive to my numerous questions. The location was centralized to hiking and biking trails and a quick jaunt to Augusta for the triathlon. I have to say that I slept like a baby too which is not a normal occurence for me. The mattress was so very comfortable. We would not hesitate to book here again. Thank you for a lovely visit."
United States
Cheri A.
$140 nightly
The price is $153
Sep 13 - Sep 14
Total with taxes and fees
Cozy newly built 1-bedroom unit 2 Kentucky Bay in charming Smithfield Maine
A single-story house with a gray siding exterior, a white front door, and two flower planters on either side of the entrance.

9. Discover Oakland charm near Colby College 10 min

Discover Oakland charm near Colby College 10 min
Oakland
9.8 out of 10, Exceptional, (16 reviews)
"House very clean and convenient location for what we had going on. "
United States
Tammy W.
$253 nightly
The price is $276
Sep 14 - Sep 15
Total with taxes and fees
Discover Oakland charm near Colby College 10 min
A wooden deck with outdoor furniture, a large potted plant, and string lights.

10. 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, (16 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
$351 nightly
The price is $374
Sep 14 - Sep 15
Total with taxes and fees
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.

11. 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, (56 reviews)
"Great place, quiet neighborhood off the lake, very comfortable. Would definitely stay again!"
United States
Steve C.
$407 nightly
The price is $444
Sep 20 - Sep 21
Total with taxes and fees
Boat launch and Trailer parking, Dog Friendly, Lake Great Pond
A cozy cabin interior with a wooden ceiling, a sofa, two chairs, a TV, and a fireplace.

12. Private Dock on Messalonskee Lake: Cozy Cottage!

Private Dock on Messalonskee Lake: Cozy Cottage!
3.0 star property
Augusta
10.0 out of 10, Exceptional, (1 review)
"Great little lake cabin. Had everything we needed. Clean, comfortable, quite. Beautiful area and views. We had a wonderful stay and would stay again."
United States
John
$298 nightly
The price is $324
Sep 16 - Sep 17
Total with taxes and fees
Private Dock on Messalonskee Lake: Cozy Cottage!
A living room with a sofa, a coffee table, a rug, and a painting on the wall.

13. 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
$150 nightly
The price is $164
Oct 1 - Oct 2
Total with taxes and fees
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.

14. 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, (92 reviews)
"House and community was amazing love the vibe of house experience was far and above expectations "
United States
Mike W.
$212 nightly
The price is $231
Sep 16 - Sep 17
Total with taxes and fees
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.

15. 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, (3 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.
$584 nightly
The price is $636
Sep 16 - Sep 17
Total with taxes and fees
China Lake, Dog Friendly, Lots of space for family gatherings

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, (8 reviews)
"Great host great stay"
United States
thomas v.
$208 nightly
The price is $227
Sep 12 - Sep 13
Total with taxes and fees
Quiet Maine Retreat- Fast Wi-Fi - Long Stays Welcome- close to I95
A large, red, two-story house with a balcony and a tower, surrounded by a fence and trees.

17. 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.
$282 nightly
The price is $308
Sep 13 - Sep 14
Total with taxes and fees
Angel Mist Retreat Garage Apartment
A bathroom with a white sink, wooden paneling, a mirror with a bead trim, and a view of a house through a window.

18. 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.
$160 nightly
The price is $174
Sep 14 - Sep 15
Total with taxes and fees
River View Retreat, Hot Tub, Balcony, Kayaks & Bikes
A wooden cabin interior with a sofa, dining table, and a chair with a woven seat.

19. Once Upon a Time — A Peaceful Maine Escape

Once Upon a Time — A Peaceful Maine Escape
Freedom
$385 nightly
The price is $420
Sep 12 - Sep 13
Total with taxes and fees
Once Upon a Time — A Peaceful Maine Escape
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

The Elmwood

The Elmwood

10/10 Excellent
"Very clean"
Terrance 2-night trip
Posted 15 hours ago
The Elmwood

Find out more about Winslow

Everything you need to know about Winslow vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winslow vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winslow vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winslow vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winslow. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Winslow in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $142 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winslow rentals

At Expedia, we put the best Winslow vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Winslow rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winslow vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winslow. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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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?

Great Pond Waterfront: Dog-friendly Home Near Colby College: Located near Winslow, this vacation home rental is located on a lake and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 3 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.