Winslow Vacation Rentals

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Nov 16 - Nov 17
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Vacation Rentals in Winslow

Terrace/patio
The Cabin Skowhegan

The Cabin Skowhegan

Skowhegan
9.8 out of 10, Exceptional, (50)
"Great place to stay. Highly recommend. Owner was very kind and helpful. Cabin was worth the money."
United States
Sue
$192 nightly
The price is $209
Nov 19 - Nov 20
Total with taxes and fees
The Cabin Skowhegan
Fridge, oven, stovetop, dishwasher
No bookings after 8/15/2024. Property sold. VRBO Thank you.

No bookings after 8/15/2024. Property sold. VRBO Thank you.

Searsmont
10.0 out of 10, Exceptional, (5)
"Perfect fit for our trip. Everything we needed in this cute little home."
United States
Carol F.
$129 nightly
The price is $141
Nov 17 - Nov 18
Total with taxes and fees
No bookings after 8/15/2024. Property sold. VRBO Thank you.
Fridge, microwave, oven, stovetop
Discover Oakland charm near Colby College 10 min

Discover Oakland charm near Colby College 10 min

2.0 star property
Oakland
10.0 out of 10, Exceptional, (6)
"I would highly recommend this beautiful rental to anyone. Brand new, super clean , all necessities ( down to complimentary shampoo/ conditioner)A lot of bang for your buck! Host was absolutely amazing to work with . "
United States
Mary G.
$238 nightly
The price is $260
Dec 2 - Dec 3
Total with taxes and fees
Discover Oakland charm near Colby College 10 min
Property grounds
3350 Middle Road

3350 Middle Road

Sidney
8.0 out of 10, Very Good, (3)
"The house was clean a nice place to stay. We were there in September, and the pool was not heated, so be aware of that. That didn't matter to my group. My only comment is that they had several plug in scent units around the first floor, and that smell was a bit too much for some of us, so we unplugged them while we were there. Problem solved. "
United States
Donald A.
$308 nightly
The price is $336
Dec 2 - Dec 3
Total with taxes and fees
3350 Middle Road
Living area
The heart of the Belgrade Lakes

The heart of the Belgrade Lakes

Oakland
9.0 out of 10, Wonderful, (9)
"your attention to details and the care you've put into the space - it really stood out to us!!! 5 stars it is not enough. "
United States
Anna D.
$176 nightly
The price is $191
Nov 17 - Nov 18
Total with taxes and fees
The heart of the Belgrade Lakes
Interior
Ice fishing, king size beds, dog friendly

Ice fishing, king size beds, dog friendly

Canaan
10.0 out of 10, Exceptional, (3)
"This is the PERFECT place to truly disconnect and relax! The house is clean, spacious, and has everything you need! Being steps away from the lake was very convenient and having the kayaks available for use was awesome. Being able to wake up to a sunrise, and hang in the porch watching the sunset was amazing. "
United States
Brianna P.
$292 nightly
The price is $318
Nov 23 - Nov 24
Total with taxes and fees
Ice fishing, king size beds, dog friendly
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)
"Amazing stay loved how clean everything was"
United States
Britney A.
$226 nightly
The price is $246
Nov 17 - Nov 18
Total with taxes and fees
Central Maine Apartment offering 4 Seasons of Fun.
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, (80)
"We had a lovely stay at this apartment. Very clean, accommodating and inviting. Comfortable beds and available hosts! Pam suggested The Liberal Cup for dinner when we asked and it was a perfect way to wrap up our evening in lovely Hallowell! Highly recommend this rental!"
United States
carlin o.
$217 nightly
The price is $237
Nov 29 - Nov 30
Total with taxes and fees
Two bedroom Mid Century Modern apartment in Downtown Hallowell
Fridge, microwave, oven, stovetop
The Beach Bum | Modern Cabin on the Sand

The Beach Bum | Modern Cabin on the Sand

Burnham
10.0 out of 10, Exceptional, (2)
"It was great. Just what we were looking for. Very quiet and peaceful."
United States
Kaye S.
$373 nightly
The price is $407
Nov 17 - Nov 18
Total with taxes and fees
The Beach Bum | Modern Cabin on the Sand
Outdoor dining
Minutes to Colby

Minutes to Colby

Waterville
8.8 out of 10, Excellent, (22)
"This was such a wonderful option. Location, clean, and adorable. "
United States
Laurie L.
$175 nightly
The price is $191
Nov 17 - Nov 18
Total with taxes and fees
Minutes to Colby
Microwave, oven, stovetop, dishwasher
The Cozy Home- New, Comfortable, Centrally located

The Cozy Home- New, Comfortable, Centrally located

2.0 star property
Pittsfield
$175 nightly
The price is $191
Nov 17 - Nov 18
Total with taxes and fees
The Cozy Home- New, Comfortable, Centrally located
Terrace/patio
Sunrise Cabin - Super Clean & Solar-powered

Sunrise Cabin - Super Clean & Solar-powered

2.0 star property
Jackson
$201 nightly
The price is $219
Dec 1 - Dec 2
Total with taxes and fees
Sunrise Cabin - Super Clean & Solar-powered
Exterior
Sister A-Frame in Woods B

Sister A-Frame in Woods B

Oakland
10.0 out of 10, Exceptional, (8)
"Great stay. Would stay here again if in the area."
United States
Amanda M.
$210 nightly
The price is $228
Nov 17 - Nov 18
Total with taxes and fees
Sister A-Frame in Woods B
Outdoor dining
Ice Fishing, Dog Friendly, Lake Great Pond

Ice Fishing, Dog Friendly, Lake Great Pond

Belgrade
10.0 out of 10, Exceptional, (47)
"Perfect for our family to come into town for a graduation celebration. Loved the little extras that we did not have to buy while in town!"
United States
Jerilyn H.
$293 nightly
The price is $320
Nov 23 - Nov 24
Total with taxes and fees
Ice Fishing, Dog Friendly, Lake Great Pond
Fridge, microwave, oven, stovetop
The Hideout Cabin | Steps to the Beach

The Hideout Cabin | Steps to the Beach

Burnham
10.0 out of 10, Exceptional, (9)
"This property is completely as advertised. The beach was right outside the front door and the available kayaks made for leisurely afternoons on the water. We had issues with the shower curtain and the host came to replace it right away. Location is good to Augusta and Bar Harbour. Make time to head into Belfast and visit the town's along the coast. Our family of four had a great week here. If we ever come back to Maine I'd come back here."
Canada
m s.
$403 nightly
The price is $440
Nov 17 - Nov 18
Total with taxes and fees
The Hideout Cabin | Steps to the Beach
On the beach
The Getaway- A Cozy Lakeside Cabin

The Getaway- A Cozy Lakeside Cabin

Burnham
10.0 out of 10, Exceptional, (6)
"The cabin setting is incredible, Full Southerly view of Unity Pond with a sand beach, lawn, picnic tables and chairs. The cabin has been redone and looks to be recent with great AC, internet, comfy beds and appliances. Was quiet and clean with all modern amenities other than a dishwasher. We will rent again and again and again! Full five stars and a great host who communicates well."
United States
Robert N.
$403 nightly
The price is $440
Nov 17 - Nov 18
Total with taxes and fees
The Getaway- A Cozy Lakeside Cabin
Outdoor dining
Lighthouse Lane

Lighthouse Lane

Manchester
10.0 out of 10, Exceptional, (70)
"Excellent, beautiful location next to the lake."
United States
Sten K.
$440 nightly
The price is $480
Nov 17 - Nov 18
Total with taxes and fees
Lighthouse Lane
Fridge, microwave, oven, stovetop
Angel Mist Retreat Garage Apartment

Angel Mist Retreat Garage Apartment

Pittsfield
10.0 out of 10, Exceptional, (14)
"This was a very nice and clean place."
United States
Wilfredo S.
$283 nightly
The price is $309
Nov 17 - Nov 18
Total with taxes and fees
Angel Mist Retreat Garage Apartment
Property grounds
Pine Tree Trail Lodge

Pine Tree Trail Lodge

2.0 star property
Pittsfield
$278 nightly
The price is $281
Nov 21 - Nov 22
Total with taxes and fees
Pine Tree Trail Lodge
Exterior
The Maine Lake House with an Amazing Sand Beach!

The Maine Lake House with an Amazing Sand Beach!

Burnham
8.8 out of 10, Excellent, (6)
"Great stay, property was a great fit for a few day stay to visit family."
United States
Amy M.
$470 nightly
The price is $513
Nov 17 - Nov 18
Total with taxes and fees
The Maine Lake House with an Amazing Sand Beach!
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

10/10 Excellent
"Room was clean and tidy"
Scott 1-night trip
Posted 2 days ago
Fireside Inn & Suites Waterville

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 $228 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?

Spacious Country Home w/ Hot Tub, near Colby/Thomas: This vacation home rental near Winslow is located in a rural location and has a hot tub, a barbecue grill, and air-conditioning 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.

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.