Winslow Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In one month
In two months
In three months

Holiday Rentals in Winslow

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

10.0 out of 10, Exceptional, (64)
"Great location! Amy is a fantastic host and she has provided everything for a relaxing stay on East Pond. "
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

9.4 out of 10, Exceptional, (61)
"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!"
Weekly discounts avail. Get away from it all on the start of The Belgrade Lakes

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)"
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, (28)
"This house has everything for a weekend family vacay; you can spend the whole weekend enjoying the house & amenities such as the hot tub!"
Spacious Country Home w/ Hot Tub, near Colby/Thomas

Cozy House in the heart of Waterville Maine.

9.6 out of 10, Exceptional, (44)
"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. "
Cozy House in the heart of Waterville Maine.

Cozy Long Pond Cottage: private mooring & shared dock

9.8 out of 10, Exceptional, (19)
"Very nice weekend and great host- very responsive!"
Cozy Long Pond Cottage: private mooring & shared dock

Large New Lakeside Cottage Central Air

8.4 out of 10, Very good, (36)
"We loved the cabin, even in rainy weather. "
Large New Lakeside Cottage Central Air

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

9.8 out of 10, Exceptional, (37)
"Cute house with deck overlooking the pond with almost daily sightings of eagles, loons and ducks. We loved it here and would stay here again if we come back this way again. I hated to leave this cute home. "
Weekly discounts avail. Get away at this New house on Lovejoy Pond in Albion

Sister A-Frame in Woods B

10.0 out of 10, Exceptional, (5)
"Great stay. Would stay here again if in the area."
The price is NZ$400
includes taxes & fees
30 Sept - 1 Oct
Sister A-Frame in Woods B

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

10.0 out of 10, Exceptional, (15)
"Beautiful property, had everything that was needed. Would definitely book again!"
Warm & Inviting Lakeside Retreat, Private, Tranquil Picture Perfect Setting

The Maine Experience: Where expansive nature meets modern comfort...

10.0 out of 10, Exceptional, (1)
"A great spot for all 7 of us. Nice house with zones for everyone. Lovely backyard. Big kitchen and dining table"
The price is NZ$637
includes taxes & fees
7 Oct - 8 Oct
The Maine Experience: Where expansive nature meets modern comfort...

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

9.8 out of 10, Exceptional, (27)
"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! "
The price is NZ$389
includes taxes & fees
7 Oct - 8 Oct
Tiny Cabin with Private Hot Tub on 100 Acres Kayaks, Canoes & Paddleboards

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!"
Lakefront Cabin

Lighthouse Lane

10.0 out of 10, Exceptional, (64)
"Had another great time at Jenn and Brian's property. Exactly as advertised and Jenn is quick to respond to any questions. "
The price is NZ$929
includes taxes & fees
30 Sept - 1 Oct
Lighthouse Lane

Sunset Chalet Lakefront Hot Tub Game Room

10.0 out of 10, Exceptional, (26)
"Great location, beautiful view, we've already talked about wanting to go back!"
Sunset Chalet Lakefront Hot Tub Game Room

Beachfront Cottage Nestled in a Cove

10.0 out of 10, Exceptional, (2)
"Enjoyed our stay in the cottage. Loved the view of the lake. Nice to get away from it all and enjoy a relaxing few days on the water."
Beachfront Cottage Nestled in a Cove

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"
The price is NZ$431
includes taxes & fees
30 Sept - 1 Oct
Central Maine Apartment offering 4 Seasons of Fun.

Mountainside cabin "Sasquatch Haven"

9.4 out of 10, Exceptional, (24)
"Wonderful stay!"
Mountainside cabin "Sasquatch Haven"

Near Golfcourse, Dog Friendly, Lake Great Pond

10.0 out of 10, Exceptional, (45)
"Very clean and comfortable."
The price is NZ$611
includes taxes & fees
3 Oct - 4 Oct
Near Golfcourse, Dog Friendly, Lake Great Pond

Cabin China Lake

9.6 out of 10, Exceptional, (15)
"Beautiful and relaxing "
Cabin China Lake
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Winslow Hotel Reviews

Find out more about Winslow

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 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 NZ$389 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.