Winslow Vacation Rentals

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Check prices for these dates

In two weeks
Apr 24 - Apr 26
In two months
Jun 5 - Jun 7
In three months
Jul 3 - Jul 5
In four months
Jul 31 - Aug 2

Our top choices for Winslow vacation rentals

Exterior

The Cabin Skowhegan

The Cabin Skowhegan
Skowhegan
9.8 out of 10, Exceptional, (52 reviews)
"Very quiet and relaxing - just what we wanted."
United States
Mary D.
$181 nightly
The price is $197
Apr 10 - Apr 11
Total with taxes and fees
The Cabin Skowhegan
Interior

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, (52 reviews)
"Great location!"
United States
Gail D.
$266 nightly
The price is $290
Apr 9 - Apr 10
Total with taxes and fees
Boat launch and Trailer parking, Dog Friendly, Lake Great Pond
Fireplace

Forest Cabin with Wall of Windows

Forest Cabin with Wall of Windows
Jackson
10.0 out of 10, Exceptional, (1 review)
"The space was warm and clean and had everything we needed. The hosts were incredibly friendly and helpful. "
United States
Ally L.
$189 nightly
The price is $206
Apr 9 - Apr 10
Total with taxes and fees
Forest Cabin with Wall of Windows
Exterior

Sister A-Frame in Woods B

Sister A-Frame in Woods B
Oakland
10.0 out of 10, Exceptional, (9 reviews)
"Great stay. Would stay here again if in the area."
United States
Amanda M.
$210 nightly
The price is $228
Apr 10 - Apr 11
Total with taxes and fees
Sister A-Frame in Woods B
TV

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, (83 reviews)
"Great apartment, close to town, very clean, comfortable beds. Loved the little extras too.. coffee, creamer, etc! Will definitely stay again. "
United States
Rebekah B.
$223 nightly
The price is $243
Apr 12 - Apr 13
Total with taxes and fees
Two bedroom Mid Century Modern apartment in Downtown Hallowell
Terrace/patio

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

Family's Paradise: 3BR/2BA,Game Room & Lake Access
Belgrade
9.8 out of 10, Exceptional, (9 reviews)
"We enjoyed our stay."
United States
Tyson W.
$730 nightly
The price is $796
Apr 9 - Apr 10
Total with taxes and fees
Family's Paradise: 3BR/2BA,Game Room & Lake Access
Microwave, oven, stovetop

Superb 2-bedroom Home with AC in Detroit

Superb 2-bedroom Home with AC in Detroit
Detroit
$164 nightly
The price is $178
Apr 12 - Apr 13
Total with taxes and fees
Superb 2-bedroom Home with AC in Detroit
Smart TV

Charming cabin in the birches right on the atv trail!

Charming cabin in the birches right on the atv trail!
Fairfield
9.2 out of 10, Wonderful, (7 reviews)
"Very neat cabin. Spacious all utilities and a fire pit"
United States
Lisa O.
$158 nightly
The price is $172
Apr 16 - Apr 17
Total with taxes and fees
Charming cabin in the birches right on the atv trail!
Exterior

Angel Mist Retreat Garage Apartment

Angel Mist Retreat Garage Apartment
Pittsfield
10.0 out of 10, Exceptional, (14 reviews)
"Great stay. Very comfortable, roomy, clean and good overall value."
United States
Rob K.
$285 nightly
The price is $311
Apr 9 - Apr 10
Total with taxes and fees
Angel Mist Retreat Garage Apartment
Exterior

Discover Oakland charm near Colby College 10 min

Discover Oakland charm near Colby College 10 min
Oakland
10.0 out of 10, Exceptional, (6 reviews)
"Very clean and comfy. A pleasure to stay there. "
United States
Vicki W.
$180 nightly
The price is $196
Apr 19 - Apr 20
Total with taxes and fees
Discover Oakland charm near Colby College 10 min
2 bedrooms, WiFi, bed sheets

The heart of the Belgrade Lakes

The heart of the Belgrade Lakes
Oakland
9.0 out of 10, Wonderful, (9 reviews)
"Host was very accommodating "
United States
Maureen
$214 nightly
The price is $233
Apr 12 - Apr 13
Total with taxes and fees
The heart of the Belgrade Lakes
Terrace/patio

The Escape | Steps to the Sand

The Escape | Steps to the Sand
Burnham
$370 nightly
The price is $404
Apr 9 - Apr 10
Total with taxes and fees
The Escape | Steps to the Sand
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
Whitefield
10.0 out of 10, Exceptional, (6 reviews)
"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.
$254 nightly
The price is $277
Apr 13 - Apr 14
Total with taxes and fees
Cabin Style Studio Apt with Private Hot tub on 100 Acres Kayaks, Canoes & SUP
Smart TV, books

Salt water hot tub, king size beds, dog friendly, lake front, dock, boat launch

Salt water hot tub, king size beds, dog friendly, lake front, dock, boat launch
Canaan
10.0 out of 10, Exceptional, (5 reviews)
"Awesome stay right on the water. "
United States
Timothy S.
$326 nightly
The price is $356
Apr 9 - Apr 10
Total with taxes and fees
Salt water hot tub, king size beds, dog friendly, lake front, dock, boat launch
Property grounds

Central Maine Apartment offering 4 Seasons of Fun.

Central Maine Apartment offering 4 Seasons of Fun.
Oakland
10.0 out of 10, Exceptional, (43 reviews)
"Great hiking - nice views."
United States
Norbert A.
$223 nightly
The price is $243
May 7 - May 8
Total with taxes and fees
Central Maine Apartment offering 4 Seasons of Fun.
Outdoor dining

Minutes to Colby

Minutes to Colby
Waterville
8.8 out of 10, Excellent, (22 reviews)
"Close to our event, great communication, clean, comfortable & cozy"
United States
Shelly B.
$228 nightly
The price is $249
Apr 9 - Apr 10
Total with taxes and fees
Minutes to Colby
Interior

Jill's Place, new construction, lake access Cobbosee, 1 mile from Cabin Masters

Jill's Place, new construction, lake access Cobbosee, 1 mile from Cabin Masters
Winthrop
$268 nightly
The price is $292
Apr 11 - Apr 12
Total with taxes and fees
Jill's Place, new construction, lake access Cobbosee, 1 mile from Cabin Masters
Terrace/patio

The Cozy Home- New, Comfortable, Book Swap

The Cozy Home- New, Comfortable, Book Swap
Pittsfield
10.0 out of 10, Exceptional, (1 review)
"Great host great stay"
United States
thomas v.
$212 nightly
The price is $231
Apr 11 - Apr 12
Total with taxes and fees
The Cozy Home- New, Comfortable, Book Swap
Private kitchen

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
$124 nightly
The price is $135
Apr 10 - Apr 11
Total with taxes and fees
Cozy new 1 bedroom, queen bed, and queen sofa bed, washer/dryers. Radiant heat.
Exterior

Perfectly Located 1 Bedroom, newly remodeled

Perfectly Located 1 Bedroom, newly remodeled
Augusta
10.0 out of 10, Exceptional, (1 review)
"The area is so convenient for any business you have in the Augusta area- right off the main thoroughfare yet far enough away to be private. Check in was as simple as getting the lock code from vrbo check in emails. The apartment is even more lovely than the pictures- almost too clean and comfortable to be real! Bedtime was silent so I got a great night sleep. I only wish we would have had more time to enjoy :) Highly recommend!! "
United States
w c.
$245 nightly
The price is $267
Apr 9 - Apr 10
Total with taxes and fees
Perfectly Located 1 Bedroom, newly remodeled
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

Holiday Inn Express & Suites Waterville - North by IHG

Holiday Inn Express & Suites Waterville - North by IHG

10/10 Excellent
" Nice"
Fleming 1-night trip
Posted 11 hours ago
Holiday Inn Express & Suites Waterville - North by IHG

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 $206 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.

Explore a world of travel with Expedia

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?

Cozy Long Pond Cottage: community access, private mooring & shared dock.: This vacation home rental near Winslow is located on a lake and has a fireplace, a patio, and a barbecue grill 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. You and your friends and family can relax into your vacation with amenities like a selection of games.

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.