Search Holiday Rentals in Winslow

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Tonight
May 14 - May 15
Tomorrow
May 15 - May 16
This weekend
May 17 - May 19
Next weekend
May 24 - May 26

Top Holiday Rentals in Winslow

Interior
High End Apartment in Downtown Hallowell
10.0 out of 10, Exceptional, (60)
"The property was as described and exactly what we needed. Downtown was a block away. Several restaurants and shops. We are originally from the area and selected this location because it was near downtown and central to places in Augusta and Gardiner that we wanted to visit. The house is a wonderfully updated old home."
High End Apartment in Downtown Hallowell
On the beach
Three waterfront cottages with private sandy beach - Family Getaway
10.0 out of 10, Exceptional, (20)
"WE HAD AN AMAZING STAY! MOST ENJOYABLE AND BEAUTIFUL PROPERTY"
Three waterfront cottages with private sandy beach - Family Getaway
Fridge, microwave, stovetop, coffee/tea maker
Sunset Chalet- Stylish Waterfront Gem
10.0 out of 10, Exceptional, (20)
"This is by far one of the best places we’ve stayed. From the beautiful decor, exposed wood and cozy fireplace. It was the attention to detail and small little extras that made this an extra special visit. The serene music playing as you enter the home to the specialized note and picnic basket! They are very accommodating to any situation that may arise and communicate on a five star level. An amazing stay and will be visiting again!"
The price is £732
per night
15 May - 16 May
Sunset Chalet- Stylish Waterfront Gem
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Exterior
Light-Filled Log Home, 4 Wooded Acres, & Lake Access. The water is 0.4 mi away.
10.0 out of 10, Exceptional, (51)
"The property was just as described and we enjoyed the peace and quiet. The cabin is beautiful and very well appointed. I would definitely recommend it to friends."
Light-Filled Log Home, 4 Wooded Acres, & Lake Access. The water is 0.4 mi away.
Property grounds
MAGICAL 97 yr. old Mayflower Lodge Waterfront Cabin Silver Lake, Swim SUNSETS
10.0 out of 10, Exceptional, (7)
"This cabin is a perfect retreat in the Maine woods. We had a wonderful time enjoying the lake's crystal clear water especially with all the watertoys . The cabin was good sized and super clean. Roy was so friendly and easy to deal with it made the whole vacation a pleasure. We will be back next summer."
MAGICAL 97 yr. old Mayflower Lodge Waterfront Cabin Silver Lake, Swim SUNSETS
Terrace/patio
Lake Great Pond, Dog Friendly, Golfing
10.0 out of 10, Exceptional, (22)
"Everything you could possibly need for a short to medium term stay in a VERY good location for the region."
The price is £270
per night
27 May - 28 May
Lake Great Pond, Dog Friendly, Golfing
Interior
MoonLight Treehouse- Luxury Waterfront Escape
10.0 out of 10, Exceptional, (10)
"My husband and I have 4 kids together and 7 pets, to say we needed this little trip is an understatement. It was peaceful, beautiful and so relaxing."
The price is £684
per night
15 May - 16 May
MoonLight Treehouse- Luxury Waterfront Escape
Property grounds
Lakefront Cottage - sleeps 6 - 2 baths
10.0 out of 10, Exceptional, (2)
"Great size, very clean. The posted pictures do not do this camp justice! Lots of upgrades and Beth is very responsive. Beautiful cove with little traffic. Sounds of loons day and night. Great bass fishing too! There is a wonderful dock but be sure to bring your own water toys. Great place for children with neighbors that encourage lots of kid play, exploring/adventuring, and boisterous fun."
Lakefront Cottage - sleeps 6 - 2 baths
Property grounds
Modern 4 BR Waterfront Lake House, beautiful Belgrade Lakes Area, Mt. Vernon, ME
10.0 out of 10, Exceptional, (2)
"We spent a lovely long weekend in this beautiful spot on the lake. Even with snow outside it was cozy and comfy and the perfect spot to relax between our Maine adventures. The hosts were great about keeping us up to date on weather conditions and other updates. Would highly recommend!"
Modern 4 BR Waterfront Lake House, beautiful Belgrade Lakes Area, Mt. Vernon, ME
On the beach
The Hideout - Just Steps to the Beach!
10.0 out of 10, Exceptional, (4)
"Let me start with the view: oh what is it beautiful! A little regret that we came when the temperatures were still chilly, so we only took it in from the windows. But still! Just a lovely setting! The house was simple, but so well maintained. The kitchen had even more gear than I expected. Everything about it was comfortable. My college daughter liked having “her space” in the loft. The property owners were very responsive. For an individual, a couple or a small family looking for peace and...
The price is £358
per night
17 May - 18 May
The Hideout - Just Steps to the Beach!
Interior
Quintessential Maine cabin w/ private waterfront
10.0 out of 10, Exceptional, (4)
"The place was exactly as described but even more beautiful than the photos show. It served as a perfect home base to explore different parts of Maine and we can’t wait to be back."
Quintessential Maine cabin w/ private waterfront
Property grounds
5 BED HOUSE + HOT TUB, SAUNA AND 600’ OF PRIVATE SHORELINE.
10.0 out of 10, Exceptional, (2)
"We spent our stay in awe of their clean, peaceful atmosphere. Whether we were sitting by the fireplace, playing endless rounds of pool, relaxing in the hot tub or enjoying the private, spacious yard, it was exactly what we needed for a spring getaway! We had everything we needed, and then some. A great stay for anyone lucky enough to snag it."
5 BED HOUSE + HOT TUB, SAUNA AND 600’ OF PRIVATE SHORELINE.
Outdoor dining
Cozy Lake House on Cobbosseeconte Lake
10.0 out of 10, Exceptional, (38)
"Despite our travel plans getting interrupted the host was great emito work with looking forward to next year"
The price is £378
per night
15 May - 16 May
Cozy Lake House on Cobbosseeconte Lake
Exterior
Tiny House on 100 Acres Kayaks/Canoes/Paddleboards
9.8 out of 10, Exceptional, (20)
"I was offered Stella which is a beautiful little apartment due to a mistake I made when applying to stay in Roxie. I didn't realize Roxie was solar and I really needed electricity for this stay. It was a more a business trip not a camping trip.Sherri very graciously let me stay in Stella which was wonderful . Very clean, bright , everything you could need . I would definitely stay there again.."
The price is £129
per night
19 May - 20 May
Tiny House on 100 Acres Kayaks/Canoes/Paddleboards
Property grounds
Spacious Country Home, Hot Tub, near Colby/Thomas
9.8 out of 10, Exceptional, (13)
"We had a great time meeting up with family. The house was well stocked, plenty of stores nearby for shopping. The hot tub was a hit! The property is beautiful and the host was very helpful. They came and dug us out from a snow storm!"
Spacious Country Home, Hot Tub, near Colby/Thomas
Fridge, microwave, oven, stovetop
Belgrade Lakes getaway with private swim dock, outdoor living, & canoe/kayaks
9.8 out of 10, Exceptional, (7)
"The cabin was very nice and comfortable. Nicely decorated and very serene. Had all amenities that were needed. We enjoyed the peacefulness."
Belgrade Lakes getaway with private swim dock, outdoor living, & canoe/kayaks
Property grounds
The Cabin - Skowhegan
9.6 out of 10, Exceptional, (24)
"I liked everything about this cabin and the large yard to walk my dog . "
The price is £138
per night
15 May - 16 May
The Cabin - Skowhegan
Exterior
Weekly discounts avail. Get away from it all on the start of The Belgrade Lakes
9.6 out of 10, Exceptional, (42)
"The picture you show was the owners 1st property and we could not access the property with my elderly family. When I called the owner, he offered me a second option of another property. That is the property I rated. It was very kind of the owner to accomodate us. It was a lit more driving than we intended but the accommodstions were much better for us."
Weekly discounts avail. Get away from it all on the start of The Belgrade Lakes
Aerial view
Secluded escape with three beaches, lake access, grill & fast WiFi - dogs OK
9.4 out of 10, Exceptional, (13)
"House was very comfortable and had everything needed for our stay."
Secluded escape with three beaches, lake access, grill & fast WiFi - dogs OK
2 bedrooms, WiFi, bed sheets
Mountainside cabin "Sasquatch Haven"
9.4 out of 10, Exceptional, (17)
"The view was AMAZING. The cabin was very neat and tidy, had everything that we needed. We received a nice email with all the information necessary a few days in advance. Check-in was super easy. The location is quiet and secluded which was just what we were looking for. Already thinking about going back."
Mountainside cabin "Sasquatch Haven"
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See all available properties in Winslow
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.

Other types of properties in Winslow you may be interested in

Exterior
Maine Evergreen Hotel, Ascend Hotel Collection
2.5 star property
9.2 out of 10, Wonderful, (1003)
"Nice hotel, beautiful view "
The price is £147
per night
19 May - 20 May
Maine Evergreen Hotel, Ascend Hotel Collection
Desk, laptop workspace, free WiFi, bed sheets
The Elmwood
2.5 star property
8.8 out of 10, Excellent, (260)
"Pet friendly"
The price is £129
per night
15 May - 16 May
The Elmwood
Exterior
Holiday Inn Express & Suites Waterville - North, an IHG Hotel
2.5 star property
8.6 out of 10, Excellent, (585)
"Perfect for my needs. My second stay, I will definitely be back. "
The price is £125
per night
29 May - 30 May
Holiday Inn Express & Suites Waterville - North, an IHG Hotel
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.

Everything you need to know about Winslow holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winslow holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Winslow holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winslow holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winslow holiday rentals we have selected for you start as low as £129 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Winslow rentals

At Expedia, we put the best Winslow holiday 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 holiday.

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. 

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’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.

Recent reviews of Winslow properties
Expedia verified reviews

The Elmwood

The Elmwood

5/5 Excellent
"Pet friendly"
A verified traveller stayed at The Elmwood
Posted 19 hours ago
The Elmwood