Winslow Holiday Rentals

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Holiday Rentals in Winslow

Large Secluded Cabin on the Lake - Now booking 2+ night stays
10.0 out of 10, Exceptional, (66)
"It was a relaxing week It was fully equipped with everything we expected and more"
Leslie R.
Large Secluded Cabin on the Lake - Now booking 2+ night stays
Maine Cabin Masters Camp completely redone waiting for a Lake loving family !
2.0 star property
10.0 out of 10, Exceptional, (7)
"Wonderful hosts, they thought of everything we might need including many nice extra touches! Beautiful quiet spot with the opportunity to paddle boat, kayak, canoe, swim, fish, enjoy campfires, outdoor grilling, observe wildlife (Osprey, Bald Eagle, Deer)"
Diane S.
Maine Cabin Masters Camp completely redone waiting for a Lake loving family !
Spacious Country Home w/ Hot Tub, near Colby/Thomas
9.8 out of 10, Exceptional, (31)
"Wonderful location and beautiful property, very peaceful and convenient "
Anne M.
Spacious Country Home w/ Hot Tub, near Colby/Thomas
Lighthouse Lane
10.0 out of 10, Exceptional, (67)
"We had a wonderful stay at Lighthouse Lane! The property was perfect with every detail thought out for guests! The views were spectacular and even better than what the listing photos show. We will definitely stay again! Thank you for being amazing hosts!"
Keli H.
The price is AU$825
includes taxes & fees
13 Nov - 14 Nov
Lighthouse Lane
Weekly discounts avail. Get away from it all on the start of The Belgrade Lakes
9.4 out of 10, Exceptional, (65)
"Great family camp right on the water with great views and paddle boats to play and fish the lake. Nice host, it was a peaceful stay!"
Michael L.
Weekly discounts avail. Get away from it all on the start of The Belgrade Lakes
Cozy Long Pond Cottage: private mooring & shared dock
9.8 out of 10, Exceptional, (19)
"Very nice weekend and great host- very responsive!"
Marc W.
Cozy Long Pond Cottage: private mooring & shared dock
Warm & Inviting Lakeside Retreat, Private, Tranquil Picture Perfect Setting
10.0 out of 10, Exceptional, (18)
"Beautiful property, had everything that was needed. Would definitely book again!"
Rachel G.
Warm & Inviting Lakeside Retreat, Private, Tranquil Picture Perfect Setting
Near Golfcourse, Dog Friendly, Lake Great Pond
10.0 out of 10, Exceptional, (46)
"Very clean and comfortable."
Mark B.
The price is AU$499
includes taxes & fees
4 Nov - 5 Nov
Near Golfcourse, Dog Friendly, Lake Great Pond
Weekly discounts avail. Get away at this New house on Lovejoy Pond in Albion
9.8 out of 10, Exceptional, (37)
"House was great! Clean, bright, comfortable."
Emily C.
Weekly discounts avail. Get away at this New house on Lovejoy Pond in Albion
Lakefront Cabin
10.0 out of 10, Exceptional, (27)
"Enjoyed an awesome stay on the lake!! House was super and Kennith was a great host!"
Ned S.
Lakefront Cabin
Cozy House in the heart of Waterville Maine.
9.6 out of 10, Exceptional, (46)
"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. "
Michelle
Cozy House in the heart of Waterville Maine.
A Belgrade Lakes Destination, Very Private, Tranquil [Handicap Accessible]
10.0 out of 10, Exceptional, (50)
"The home and the host were amazing! The setting along the lake is spectacular and Roger was super-helpful at every step of the trip. We will be back!"
Nancy and Michael G.
A Belgrade Lakes Destination, Very Private, Tranquil [Handicap Accessible]
Classy AF Home Steps from Colby and Trails
10.0 out of 10, Exceptional, (48)
"Clean, comfortable and incredibly close to campus for a college visit."
Patricia R.
Classy AF Home Steps from Colby and Trails
The Cabin Skowhegan
9.8 out of 10, Exceptional, (49)
"Great place to stay. Highly recommend. Owner was very kind and helpful. Cabin was worth the money."
Sue
The price is AU$327
includes taxes & fees
19 Oct - 20 Oct
The Cabin Skowhegan
NEW! Long Pond Lake View Getaway w/HOT TUB, ME
10.0 out of 10, Exceptional, (1)
"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."
Rachael L.
NEW! Long Pond Lake View Getaway w/HOT TUB, ME
Central Maine Apartment offering 4 Seasons of Fun.
10.0 out of 10, Exceptional, (42)
"Very comfortable and clean VRBO!The hosts were very kind and easy to work with!!Great location for getting into Colby Highly recommend this location for people visiting in the area"
Paul M.
The price is AU$383
includes taxes & fees
17 Nov - 18 Nov
Central Maine Apartment offering 4 Seasons of Fun.
Spacious Newer Modern Home
7.6 out of 10, Good, (46)
"We truly enjoyed our stay. Loved the ease of check in, the porch, the water, spending time with family. Thank you!"
Laurie T.
Spacious Newer Modern Home
Tiny Cabin with Private Hot Tub on 100 Acres Kayaks, Canoes & Paddleboards
9.8 out of 10, Exceptional, (28)
"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! "
Ben R.
The price is AU$350
includes taxes & fees
15 Nov - 16 Nov
Tiny Cabin with Private Hot Tub on 100 Acres Kayaks, Canoes & Paddleboards
Private and Calming Waterfront to the Rescue!
9.6 out of 10, Exceptional, (84)
"Absolutely amazing property, everything we were looking for and an amazing host too! Highly recommend! "
samantha c.
Private and Calming Waterfront to the Rescue!
The Three Cornered Pond Retreat | House in Augusta with kayaks & dock access
9.0 out of 10, Wonderful, (7)
"I loved how close it was to our normal life so we were able to relax and not spend a lot of time traveling"
BRANDON K.
The Three Cornered Pond Retreat | House in Augusta with kayaks & dock access
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, 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 favourite 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 depend 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 AU$327 per night. Entering your travel dates in the search wizard might find you 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.