Holiday Rentals in Winslow

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Holiday Rentals in Winslow

Classy AF Home Steps from Colby and Trails

Oakland
10.0 out of 10, Exceptional, (48)
"Clean, comfortable and incredibly close to campus for a college visit."
United States
Patricia R.
Classy AF Home Steps from Colby and Trails

Maine Cabin Masters Camp completely redone waiting for a Lake loving family !

2.0 star property
Readfield
10.0 out of 10, Exceptional, (7)
"It was a wonderful week. The cabin is very well appointed. We lacked for nothing! Thank you "
United States
Gigi A.
Maine Cabin Masters Camp completely redone waiting for a Lake loving family !

Spacious Country Home w/ Hot Tub, near Colby/Thomas

Sidney
9.8 out of 10, Exceptional, (35)
"Very nice hot tub, quite and beautiful area! Air quality amazing and AC works fantasticly!"
United States
Nathan
Spacious Country Home w/ Hot Tub, near Colby/Thomas

Light-Filled Log Home, 4 Wooded Acres, & Lake Access. The water is 0.4 mi away.

Fayette
10.0 out of 10, Exceptional, (61)
"great accommodations and proximity to hiking trails and college tours. pond very clean and great for swimming and kayaking - even saw a couple of loons! local farms are great for fruit, produce, and eggs. "
United States
Lisa R.
Light-Filled Log Home, 4 Wooded Acres, & Lake Access. The water is 0.4 mi away.

Lakefront Cabin

China
10.0 out of 10, Exceptional, (27)
"My family and I attended a concert at the Bowl in the Pines and wanted to make a weekend out of it and found this perfect little cabin right on the lake! Kids absolutely loved swimming, fishing and canoeing! Great spot for family bonding! Thank you! "
United States
Laura L.
Lakefront Cabin

Private and Calming Waterfront to the Rescue!

Augusta
9.8 out of 10, Exceptional, (86)
"Absolutely amazing property, everything we were looking for and an amazing host too! Highly recommend! "
United States
samantha c.
Private and Calming Waterfront to the Rescue!

Large Secluded Cabin on the Lake - Now booking 2+ night stays

Smithfield
10.0 out of 10, Exceptional, (66)
"Great vacation with 3 generations of our family. House was beautiful, lake clean with great swimming and fishing. Hope to return for years to come. "
United States
David M.
Large Secluded Cabin on the Lake - Now booking 2+ night stays

Weekly discounts avail. Get away from it all on the start of The Belgrade Lakes

Oakland
9.4 out of 10, Exceptional, (66)
"Very peaceful and a great fishing spot."
United States
Chris H.
Weekly discounts avail. Get away from it all on the start of The Belgrade Lakes

Warm & Inviting Lakeside Retreat, Private, Tranquil Picture Perfect Setting

Mount Vernon
10.0 out of 10, Exceptional, (20)
"Beautiful property, had everything that was needed. Would definitely book again!"
United States
Rachel G.
Warm & Inviting Lakeside Retreat, Private, Tranquil Picture Perfect Setting

NEW! Long Pond Lake View Getaway w/HOT TUB, ME

Mount Vernon
10.0 out of 10, Exceptional, (2)
"This house was absolutely stunning! Had absolutely everything that you needed the house offered everything that one would need and plenty of space for everybody! The game room was so fun! The hot tub was a great bonus! Everyone had an amazing time while staying."
United States
Rachael L.
NEW! Long Pond Lake View Getaway w/HOT TUB, ME

Weekly discounts avail. Get away at this New house on Lovejoy Pond in Albion

Albion
9.8 out of 10, Exceptional, (37)
"Nice place, great fishing. "
United States
Bryan W.
Weekly discounts avail. Get away at this New house on Lovejoy Pond in Albion

Large New Lakeside Cottage Central Air

Belgrade
8.4 out of 10, Very good, (37)
"Totally enjoyed our trip. This is the 2nd time we've stayed here. John is a great host. "
United States
Irene D.
Large New Lakeside Cottage Central Air

Cozy Long Pond Cottage: private mooring & shared dock

Rome
9.8 out of 10, Exceptional, (20)
"We had a great time kayaking on the lake and enjoying the beach. The house had plenty of room to get together with family for dinners. The house is well equipped and very comfortable."
United States
Jim U.
Cozy Long Pond Cottage: private mooring & shared dock

Lighthouse Lane

Manchester
10.0 out of 10, Exceptional, (70)
"The house location on the lake is perfect! So beautiful and quiet:) The house was overall very nice to live in."
United States
Nathalie N.
The price is €424
includes taxes & fees
23 Nov - 24 Nov
Lighthouse Lane

Tiny Cabin with Private Hot Tub on 100 Acres Kayaks, Canoes & Paddleboards

Whitefield
9.8 out of 10, Exceptional, (29)
"We stayed in this cabin for two nights with our dog and it was very peaceful and fun! The cabin has a campfire, lots of batteries for charging, lights, battery fans, etc. There were many long walking trails with fun activities; like kayaking, axe throwing, a pizza oven… Exactly what we were looking for! Would stay again! "
United States
Ben R.
The price is €200
includes taxes & fees
23 Nov - 24 Nov
Tiny Cabin with Private Hot Tub on 100 Acres Kayaks, Canoes & Paddleboards

Ice Fishing, Dog Friendly, Lake Great Pond

Belgrade
10.0 out of 10, Exceptional, (48)
"The house was great, and the owners were very communicative and responsive. Would definitely recommend and stay again!"
United States
Jonathon R.
The price is €246
includes taxes & fees
23 Nov - 24 Nov
Ice Fishing, Dog Friendly, Lake Great Pond

Cozy House in the heart of Waterville Maine.

Waterville
9.6 out of 10, Exceptional, (49)
"Loved the cozy home! We would stay there again in a heartbeat. The only thing that we would have been nice is if there was a tv in the main bedroom, but that’s just a personal preference. "
United States
Michelle
Cozy House in the heart of Waterville Maine.

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.
The price is €203
includes taxes & fees
24 Nov - 25 Nov
Sister A-Frame in Woods B

Lakefront cabin on North Pond with private beach

Smithfield
9.6 out of 10, Exceptional, (7)
"We came to Maine to relax and decompress. This spot was perfect for that The quiet was just what we needed and the property was clean, spacious and comfortable."
United States
Michael C.
Lakefront cabin on North Pond with private beach

One Of Belgrade Lakes Best Kept Secrets, Very Private & 10 Feet From Waters Edge

Mt Vernon
10.0 out of 10, Exceptional, (74)
"The view was spectacular the cabin was beautiful hope to come back next year"
United States
Jennifer S.
One Of Belgrade Lakes Best Kept Secrets, Very Private & 10 Feet From Waters Edge
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

Find out more about Winslow

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 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 are some of the best holiday rentals that Winslow has to offer?

Spacious Country Home w/ Hot Tub, near Colby/Thomas: This holiday home rental outside of Winslow is located in a rural location, and has 1 hot tub, a BBQ 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 that 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 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.