Winslow Holiday Rentals

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Check prices for these dates

Tonight
27 Dec - 28 Dec
Tomorrow
28 Dec - 29 Dec
Next weekend
2 Jan - 4 Jan
In two weeks
9 Jan - 11 Jan

Our top choices for Winslow holiday rentals

Terrace/patio
The Cabin Skowhegan

The Cabin Skowhegan

The Cabin Skowhegan
Skowhegan
9.8 out of 10, Exceptional, (50)
"Great place to stay. Highly recommend. Owner was very kind and helpful. Cabin was worth the money."
United States
Sue
The price is HK$777
HK$1,626 total
includes taxes & fees
29 Dec - 30 Dec
The Cabin Skowhegan
TV
Two bedroom Mid Century Modern apartment in Downtown Hallowell

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, (81)
"Great location and excellent accommodations. Just what we needed for this quick stay. We would definitely stay here again!"
United States
J K.
The price is HK$971
HK$1,838 total
includes taxes & fees
29 Dec - 30 Dec
Two bedroom Mid Century Modern apartment in Downtown Hallowell
Fridge, oven, stovetop, dishwasher
No bookings after 8/15/2024. Property sold. VRBO Thank you.

No bookings after 8/15/2024. Property sold. VRBO Thank you.

No bookings after 8/15/2024. Property sold. VRBO Thank you.
Searsmont
10.0 out of 10, Exceptional, (5)
"Love the cottage and very clean and quiet."
United States
Jeanne
The price is HK$769
HK$1,093 total
includes taxes & fees
28 Dec - 29 Dec
No bookings after 8/15/2024. Property sold. VRBO Thank you.
Fridge, microwave, oven, stovetop
Angel Mist Retreat Garage Apartment

Angel Mist Retreat Garage Apartment

Angel Mist Retreat Garage Apartment
Pittsfield
10.0 out of 10, Exceptional, (14)
"Great stay. Very comfortable, roomy, clean and good overall value."
United States
Rob K.
The price is HK$1,091
HK$2,401 total
includes taxes & fees
28 Dec - 29 Dec
Angel Mist Retreat Garage Apartment
Exterior
Sister A-Frame in Woods B

Sister A-Frame in Woods B

Sister A-Frame in Woods B
Oakland
10.0 out of 10, Exceptional, (9)
"Great stay. Would stay here again if in the area."
United States
Amanda M.
The price is HK$937
HK$1,775 total
includes taxes & fees
1 Jan - 2 Jan 2026
Sister A-Frame in Woods B
Outdoor dining
Lighthouse Lane

Lighthouse Lane

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 HK$2,798
HK$3,727 total
includes taxes & fees
28 Dec - 29 Dec
Lighthouse Lane
Property grounds
Central Maine Apartment offering 4 Seasons of Fun.

Central Maine Apartment offering 4 Seasons of Fun.

Central Maine Apartment offering 4 Seasons of Fun.
Oakland
10.0 out of 10, Exceptional, (43)
"Great hiking - nice views."
United States
Norbert A.
The price is HK$785
HK$1,872 total
includes taxes & fees
8 Jan - 9 Jan 2026
Central Maine Apartment offering 4 Seasons of Fun.
On the beach
The Getaway- A Cozy Lakeside Cabin

The Getaway- A Cozy Lakeside Cabin

The Getaway- A Cozy Lakeside Cabin
Burnham
10.0 out of 10, Exceptional, (6)
"Such a great cabin and location. Super clean and a perfect getaway, we can’t wait to go back!"
United States
Sara D.
The price is HK$1,288
HK$3,426 total
includes taxes & fees
28 Dec - 29 Dec
The Getaway- A Cozy Lakeside Cabin
Property grounds
Tiny Cabin with Private Hot Tub on 100 Acres Kayaks, Canoes & Paddleboards

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

Tiny Cabin with Private Hot Tub on 100 Acres Kayaks, Canoes & Paddleboards
Whitefield
9.8 out of 10, Exceptional, (30)
"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 HK$1,166
HK$1,745 total
includes taxes & fees
11 Jan - 12 Jan 2026
Tiny Cabin with Private Hot Tub on 100 Acres Kayaks, Canoes & Paddleboards
Outdoor dining
Minutes to Colby

Minutes to Colby

Minutes to Colby
Waterville
8.8 out of 10, Excellent, (22)
"Close to our event, great communication, clean, comfortable & cozy"
United States
Shelly B.
The price is HK$847
HK$1,474 total
includes taxes & fees
8 Jan - 9 Jan 2026
Minutes to Colby
Living area
The heart of the Belgrade Lakes

The heart of the Belgrade Lakes

The heart of the Belgrade Lakes
Oakland
9.0 out of 10, Wonderful, (9)
"Host was very accommodating "
United States
Maureen
The price is HK$626
HK$1,488 total
includes taxes & fees
4 Jan - 5 Jan 2026
The heart of the Belgrade Lakes
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

Cabin Style Studio Apt with Private Hot tub on 100 Acres Kayaks, Canoes & SUP
Whitefield
10.0 out of 10, Exceptional, (6)
"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$1,438
HK$2,296 total
includes taxes & fees
4 Jan - 5 Jan 2026
Cabin Style Studio Apt with Private Hot tub on 100 Acres Kayaks, Canoes & SUP
Outdoor dining
Ice Fishing, Dog Friendly, Lake Great Pond

Ice Fishing, Dog Friendly, Lake Great Pond

Ice Fishing, Dog Friendly, Lake Great Pond
Belgrade
10.0 out of 10, Exceptional, (48)
"Great place for us to get in 2 days of golf and 2 days of fishing. House was clean and communication with host prior to arrival and during our stay was excellent. "
United States
Thomas B.
The price is HK$1,578
HK$3,177 total
includes taxes & fees
4 Jan - 5 Jan 2026
Ice Fishing, Dog Friendly, Lake Great Pond
Fridge, microwave, oven, stovetop
The Hideout Cabin | Steps to the Beach

The Hideout Cabin | Steps to the Beach

The Hideout Cabin | Steps to the Beach
Burnham
10.0 out of 10, Exceptional, (9)
"Amenities were great. Property was clean and quiet. Perfect for teens. Great view of the lake. Updated kitchen and grill was great for making family meals. Enjoyed making s'mores in the fire pit. Kayaks were so much fun. "
United States
Jamie M.
The price is HK$1,288
HK$3,417 total
includes taxes & fees
31 Dec - 1 Jan 2026
The Hideout Cabin | Steps to the Beach
Interior
High End Apartment in Downtown Hallowell

High End Apartment in Downtown Hallowell

High End Apartment in Downtown Hallowell
Hallowell
10.0 out of 10, Exceptional, (96)
"Beautiful place to stay. Having coffee with all the fixings already there along with snacks was great! Would definitely stay here again!"
United States
John H.
The price is HK$870
HK$1,601 total
includes taxes & fees
2 Jan - 3 Jan 2026
High End Apartment in Downtown Hallowell
Exterior
Cozy Farmhouse -minutes to town, miles from stress

Cozy Farmhouse -minutes to town, miles from stress

Cozy Farmhouse -minutes to town, miles from stress
Oakland
10.0 out of 10, Exceptional, (7)
"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$1,749
HK$3,120 total
includes taxes & fees
11 Jan - 12 Jan 2026
Cozy Farmhouse -minutes to town, miles from stress
Exterior
The Maine Lake House with an Amazing Sand 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)
"Great stay, property was a great fit for a few day stay to visit family."
United States
Amy M.
The price is HK$1,543
HK$4,002 total
includes taxes & fees
28 Dec - 29 Dec
The Maine Lake House with an Amazing Sand Beach!
Property grounds
Pine Tree Trail Lodge

Pine Tree Trail Lodge

Pine Tree Trail Lodge
2.0 star property
Pittsfield
10.0 out of 10, Exceptional, (1)
"Great place. The host so helpful. I would definitely stay here again. "
United States
Amber G.
The price is HK$1,118
HK$2,125 total
includes taxes & fees
8 Jan - 9 Jan 2026
Pine Tree Trail Lodge
Fridge, microwave, oven, stovetop
Discover Oakland charm near Colby College 10 min

Discover Oakland charm near Colby College 10 min

Discover Oakland charm near Colby College 10 min
2.0 star property
Oakland
10.0 out of 10, Exceptional, (6)
"New, clean and had everything we needed. "
United States
Lara B.
The price is HK$769
HK$2,067 total
includes taxes & fees
11 Jan - 12 Jan 2026
Discover Oakland charm near Colby College 10 min
Exterior
A soul soothing escape. Artistically built and lovingly maintained.

A soul soothing escape. Artistically built and lovingly maintained.

A soul soothing escape. Artistically built and lovingly maintained.
New Sharon
10.0 out of 10, Exceptional, (30)
"This is the nicest place we have ever stayed in as a couple. "
United States
Orran K.
The price is HK$1,853
HK$3,054 total
includes taxes & fees
5 Jan - 6 Jan 2026
A soul soothing escape. Artistically built and lovingly maintained.
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

The Skowhegan By Kasa

The Skowhegan By Kasa

10/10 Excellent
"Great place to stay!"
Kelly 1-night trip
Posted 5 days ago
The Skowhegan By Kasa

Find out more about Winslow

Search for holiday rentals in Winslow on Expedia! You can easily find your home rentals, villas, holiday apartments in Winslow using one of the methods below:

  • View our selection of featured holiday rentals in Winslow
  • Use the map to find apartments and other holiday homes in the Winslow neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Winslow while they last

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?

My Valhalla Farm: This holiday home rental outside of Winslow is located in a rural location, and has a garden, a BBQ and free WiFi to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

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.