Winslow Holiday Rentals

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Check prices for these dates

In two weeks
27 Feb - 1 Mar
In two months
10 Apr - 12 Apr
In three months
8 May - 10 May
In four months
5 Jun - 7 Jun

Our top choices for Winslow holiday rentals

Exterior

The Cabin Skowhegan

The Cabin Skowhegan
Skowhegan
9.8 out of 10, Exceptional, (51 reviews)
"Very quiet and relaxing - just what we wanted."
United States
Mary D.
The price is HK$782
HK$1,653 total
includes taxes & fees
1 Mar - 2 Mar
The Cabin Skowhegan
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, (82 reviews)
"Great apartment, close to town, very clean, comfortable beds. Loved the little extras too.. coffee, creamer, etc! Will definitely stay again. "
United States
Rebekah B.
The price is HK$938
HK$1,797 total
includes taxes & fees
18 Feb - 19 Feb
Two bedroom Mid Century Modern apartment in Downtown Hallowell
Interior

Ice Fishing, Dog Friendly, Lake Great Pond

Ice Fishing, Dog Friendly, Lake Great Pond
Belgrade
10.0 out of 10, Exceptional, (49 reviews)
"All was exactly as we hoped it would be, perfect for a family and added benefit of pet friendly."
United States
Jonathan I.
The price is HK$829
HK$2,225 total
includes taxes & fees
12 Feb - 13 Feb
Ice Fishing, Dog Friendly, Lake Great Pond
Exterior

Sister A-Frame in Woods B

Sister A-Frame in Woods B
Oakland
10.0 out of 10, Exceptional, (9 reviews)
"Great stay. Would stay here again if in the area."
United States
Amanda M.
The price is HK$1,048
HK$1,917 total
includes taxes & fees
3 Mar - 4 Mar
Sister A-Frame in Woods B
2 bedrooms, WiFi, bed sheets

The heart of the Belgrade Lakes

The heart of the Belgrade Lakes
Oakland
9.0 out of 10, Wonderful, (9 reviews)
"Host was very accommodating "
United States
Maureen
The price is HK$629
HK$1,496 total
includes taxes & fees
16 Feb - 17 Feb
The heart of the Belgrade Lakes
Smart TV

Charming cabin in the birches right on the atv trail!

Charming cabin in the birches right on the atv trail!
Fairfield
9.0 out of 10, Wonderful, (6 reviews)
"Very neat cabin. Spacious all utilities and a fire pit"
United States
Lisa O.
The price is HK$1,055
HK$1,551 total
includes taxes & fees
12 Feb - 13 Feb
Charming cabin in the birches right on the atv trail!
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 reviews)
"Great hiking - nice views."
United States
Norbert A.
The price is HK$790
HK$1,883 total
includes taxes & fees
12 Feb - 13 Feb
Central Maine Apartment offering 4 Seasons of Fun.
On the beach

The Retreat- A Relaxing Beachside Bungalow

The Retreat- A Relaxing Beachside Bungalow
Burnham
10.0 out of 10, Exceptional, (3 reviews)
"Great cabin and location "
United States
John V.
The price is HK$1,296
HK$3,198 total
includes taxes & fees
12 Feb - 13 Feb
The Retreat- A Relaxing Beachside Bungalow
Exterior

Angel Mist Retreat Garage Apartment

Angel Mist Retreat Garage Apartment
Pittsfield
10.0 out of 10, Exceptional, (14 reviews)
"Great stay. Very comfortable, roomy, clean and good overall value."
United States
Rob K.
The price is HK$1,098
HK$2,415 total
includes taxes & fees
13 Feb - 14 Feb
Angel Mist Retreat Garage Apartment
Microwave, oven, stovetop

Superb 2-bedroom Home with AC in Detroit

Superb 2-bedroom Home with AC in Detroit
Detroit
The price is HK$763
HK$1,428 total
includes taxes & fees
2 Mar - 3 Mar
Superb 2-bedroom Home with AC in Detroit
Terrace/patio

Family's Paradise: 3BR/2BA,Game Room & Lake Access

Family's Paradise: 3BR/2BA,Game Room & Lake Access
Belgrade
9.8 out of 10, Exceptional, (9 reviews)
"We enjoyed our stay."
United States
Tyson W.
The price is HK$1,641
HK$6,568 total
includes taxes & fees
12 Feb - 13 Feb
Family's Paradise: 3BR/2BA,Game Room & Lake Access
Fireplace

Forest Cabin with Wall of Windows

Forest Cabin with Wall of Windows
Jackson
The price is HK$1,079
HK$1,806 total
includes taxes & fees
3 Mar - 4 Mar
Forest Cabin with Wall of Windows
TV

NEW Cozy Cabin located in Oakland tucked away in a peaceful wooded scene.

NEW Cozy Cabin located in Oakland tucked away in a peaceful wooded scene.
Oakland
The price is HK$1,125
HK$2,300 total
includes taxes & fees
12 Feb - 13 Feb
NEW Cozy Cabin located in Oakland tucked away in a peaceful wooded scene.
Exterior

Discover Oakland charm near Colby College 10 min

Discover Oakland charm near Colby College 10 min
Oakland
10.0 out of 10, Exceptional, (6 reviews)
"Very clean and comfy. A pleasure to stay there. "
United States
Vicki W.
The price is HK$697
HK$2,012 total
includes taxes & fees
15 Feb - 16 Feb
Discover Oakland charm near Colby College 10 min
Exterior

Cozy getaway: farmhouse with wood stove & jacuzzi tub

Cozy getaway: farmhouse with wood stove & jacuzzi tub
Oakland
10.0 out of 10, Exceptional, (9 reviews)
"It was that was said to be The host was very nice and helpful . I enjoyed my stay "
United States
Andrea C.
The price is HK$1,525
HK$2,866 total
includes taxes & fees
15 Feb - 16 Feb
Cozy getaway: farmhouse with wood stove & jacuzzi tub
Outdoor spa tub

Cabin Style Studio Apt with Private Hot tub on 100 Acres Kayaks, Canoes & SUP

Cabin Style Studio Apt with Private Hot tub on 100 Acres Kayaks, Canoes & SUP
Whitefield
10.0 out of 10, Exceptional, (6 reviews)
"Great getaway! We loved all of the discoveries to be made both in the cabin and on the property. We stayed in Stella. It was adorable, functional, and very welcoming. We also enjoyed an outing to Kennebec Maine Cabin Masters only 20 min away! "
United States
Sandra L.
The price is HK$1,446
HK$2,181 total
includes taxes & fees
20 Feb - 21 Feb
Cabin Style Studio Apt with Private Hot tub on 100 Acres Kayaks, Canoes & SUP
On the beach

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 reviews)
"Great stay, property was a great fit for a few day stay to visit family."
United States
Amy M.
The price is HK$1,551
HK$4,033 total
includes taxes & fees
12 Feb - 13 Feb
The Maine Lake House with an Amazing Sand Beach!
Outdoor dining

Lighthouse Lane

Lighthouse Lane
Manchester
10.0 out of 10, Exceptional, (70 reviews)
"Very nice stay Beautiful lake views "
United States
Karen G.
The price is HK$1,758
HK$2,436 total
includes taxes & fees
12 Feb - 13 Feb
Lighthouse Lane
Terrace/patio

The Cozy Home- New, Comfortable, Centrally located

The Cozy Home- New, Comfortable, Centrally located
Pittsfield
10.0 out of 10, Exceptional, (1 review)
"Great host great stay"
United States
thomas v.
The price is HK$1,290
HK$2,284 total
includes taxes & fees
28 Feb - 1 Mar
The Cozy Home- New, Comfortable, Centrally located
Smart TV, books

Salt water hot tub, king size beds, dog friendly, ice fishing

Salt water hot tub, king size beds, dog friendly, ice fishing
Canaan
10.0 out of 10, Exceptional, (4 reviews)
"We had such a wonderful time here! It was so cozy during the snowstorm and had everything we needed and more. We enjoyed the hot tub and snowmobiling on the lake was awesome. The host was quick at responding and so helpful! We will definitely stay here again. "
United States
Ashley G.
The price is HK$1,288
HK$3,040 total
includes taxes & fees
12 Feb - 13 Feb
Salt water hot tub, king size beds, dog friendly, ice fishing
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

Maine Evergreen Hotel, an Ascend Collection Hotel

Maine Evergreen Hotel, an Ascend Collection Hotel

10/10 Excellent
"The Maine Evergreen was an inspiring Hotel! We travel a lot and believe that is the first time we have used that adjective to convey how we felt about any of the places we have stayed, regardless of price. The room was quite nice. The attached restaurant and lounge was quite cozy and offered high-quality fare. The hotel itself is one giant art gallery with works from dozens of Maine artists on display & for sale. It's in a very convenient location as well. But it was the staff that made our stay most rewarding. We had a very trying trip made even more difficult with car issues and the extreme weather that weekend. But the entire staff eased our anxieties and even offered assistance over and above what we expected. We will certainly choose the Maine Evergreen whenever we are in the Augusta area and give it our highest possible recommendation!"
Robert 1-night trip
Posted 3 days ago
Maine Evergreen Hotel, an Ascend Collection Hotel

Find out more about Winslow

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Look no further and take a look at our great range of rental properties in Winslow!

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?

Cozy Long Pond Cottage: community access, private mooring & shared dock.: This holiday home rental outside of Winslow is located on a lake, and has a fireplace, a patio and a BBQ 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. You and your friends and family can relax into your holiday with amenities such as a selection of games.

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.