A steel bridge over a river with lush greenery on both sides.

Winslow Holiday Rentals

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Check prices for these dates

In two weeks
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

Our top choices for Winslow holiday rentals

Exterior

1. Sister A-Frame in Woods B

Sister A-Frame in Woods B
Oakland
10.0 out of 10, 12, (12 reviews)
"Very cute. Clean. Good location for an event at Bowl in the Pines."
United States
Lisa
The price is HK$946
HK$2,031 total
includes taxes & fees
15 Sept - 16 Sept
Sister A-Frame in Woods B
Outdoor dining

2. Minutes to Colby

Minutes to Colby
Waterville
8.8 out of 10, 26, (26 reviews)
"Close to our event, great communication, clean, comfortable & cozy"
United States
Shelly B.
The price is HK$1,247
HK$1,966 total
includes taxes & fees
15 Sept - 16 Sept
Minutes to Colby
Private kitchen

3. Fabulous 3-bedroom RV with direct access to the Sebasticook River!

Fabulous 3-bedroom RV with direct access to the Sebasticook River!
Benton
9.4 out of 10, 3, (3 reviews)
"Beautiful camper and property! We loved it!"
United States
Tracy D.
The price is HK$706
HK$1,111 total
includes taxes & fees
27 Sept - 28 Sept
Fabulous 3-bedroom RV with direct access to the Sebasticook River!
Living area

4. Charming cabin in the birches right on the atv trail!

Charming cabin in the birches right on the atv trail!
Fairfield
8.6 out of 10, 9, (9 reviews)
"The Host was great, I highly recommend this spot, everything was super smooth and the cabin was beautiful. "
United States
Jason B.
The price is HK$882
HK$1,346 total
includes taxes & fees
15 Sept - 16 Sept
Charming cabin in the birches right on the atv trail!
Room

5. The heart of the Belgrade Lakes

The heart of the Belgrade Lakes
Oakland
9.0 out of 10, 10, (10 reviews)
"Host was very accommodating "
United States
Maureen
The price is HK$902
HK$1,795 total
includes taxes & fees
15 Sept - 16 Sept
The heart of the Belgrade Lakes
Property grounds

6. Central Maine Apartment offering 4 Seasons of Fun.

Central Maine Apartment offering 4 Seasons of Fun.
Oakland
10.0 out of 10, 48, (48 reviews)
"Apartment was comfortable and as described. I had a nice stay."
United States
kathy e.
The price is HK$887
HK$2,043 total
includes taxes & fees
28 Sept - 29 Sept
Central Maine Apartment offering 4 Seasons of Fun.
Front of property

7. Private Dock on Messalonskee Lake: Cozy Cottage!

Private Dock on Messalonskee Lake: Cozy Cottage!
3.0 star property
Augusta
10.0 out of 10, 1, (1 review)
"Great little lake cabin. Had everything we needed. Clean, comfortable, quite. Beautiful area and views. We had a wonderful stay and would stay again."
United States
John
The price is HK$894
HK$2,543 total
includes taxes & fees
16 Sept - 17 Sept
Private Dock on Messalonskee Lake: Cozy Cottage!
Exterior

8. Discover Oakland charm near Colby College 10 min

Discover Oakland charm near Colby College 10 min
Oakland
9.8 out of 10, 17, (17 reviews)
"House very clean and convenient location for what we had going on. "
United States
Tammy W.
The price is HK$1,341
HK$2,325 total
includes taxes & fees
17 Sept - 18 Sept
Discover Oakland charm near Colby College 10 min
Private kitchen

9. Cozy newly built 1-bedroom unit 2 Kentucky Bay in charming Smithfield Maine

Cozy newly built 1-bedroom unit 2 Kentucky Bay in charming Smithfield Maine
Smithfield
10.0 out of 10, 3, (3 reviews)
"WE were delighted in our accommodations. The apartment was lovely and very clean. Lynne was very responsive to my numerous questions. The location was centralized to hiking and biking trails and a quick jaunt to Augusta for the triathlon. I have to say that I slept like a baby too which is not a normal occurence for me. The mattress was so very comfortable. We would not hesitate to book here again. Thank you for a lovely visit."
United States
Cheri A.
The price is HK$941
HK$1,197 total
includes taxes & fees
15 Sept - 16 Sept
Cozy newly built 1-bedroom unit 2 Kentucky Bay in charming Smithfield Maine
Interior

10. Boat launch and Trailer parking, Dog Friendly, Lake Great Pond

Boat launch and Trailer parking, Dog Friendly, Lake Great Pond
Belgrade
10.0 out of 10, 56, (56 reviews)
"Great place, quiet neighborhood off the lake, very comfortable. Would definitely stay again!"
United States
Steve C.
The price is HK$940
HK$2,581 total
includes taxes & fees
15 Sept - 16 Sept
Boat launch and Trailer parking, Dog Friendly, Lake Great Pond
Outdoor dining

11. Fall Getaway at My Valhalla Farm- close to Waterville and minutes to lakes

Fall Getaway at My Valhalla Farm- close to Waterville and minutes to lakes
Oakland
10.0 out of 10, 16, (16 reviews)
"Kathleen was a wonderful host. My family and I found the property welcoming and relaxing. Great place to stay if you are looking for a laid back atmosphere and peaceful time in the country."
United States
Jared
The price is HK$1,647
HK$2,930 total
includes taxes & fees
15 Sept - 16 Sept
Fall Getaway at My Valhalla Farm- close to Waterville and minutes to lakes
Living area

12. Private Dock on Messalonskee Lake: Cozy Cottage!

Private Dock on Messalonskee Lake: Cozy Cottage!
Sidney
8.8 out of 10, 13, (13 reviews)
"Great place to stay for our annual fishing weekend in the Belgrade Lakes region! "
United States
Shawn H.
The price is HK$604
HK$2,590 total
includes taxes & fees
16 Sept - 17 Sept
Private Dock on Messalonskee Lake: Cozy Cottage!
Living area

13. Two bedroom Mid Century Modern apartment in Downtown Hallowell

Two bedroom Mid Century Modern apartment in Downtown Hallowell
Hallowell
10.0 out of 10, 92, (92 reviews)
"House and community was amazing love the vibe of house experience was far and above expectations "
United States
Mike W.
The price is HK$953
HK$1,859 total
includes taxes & fees
16 Sept - 17 Sept
Two bedroom Mid Century Modern apartment in Downtown Hallowell
Exterior

14. Angel Mist Retreat Garage Apartment

Angel Mist Retreat Garage Apartment
Pittsfield
10.0 out of 10, 15, (15 reviews)
"Great stay. Very comfortable, roomy, clean and good overall value."
United States
Rob K.
The price is HK$1,101
HK$2,414 total
includes taxes & fees
15 Sept - 16 Sept
Angel Mist Retreat Garage Apartment
Terrace/patio

15. China Lake, Dog Friendly, Lots of space for family gatherings

China Lake, Dog Friendly, Lots of space for family gatherings
China
10.0 out of 10, 3, (3 reviews)
"Perfect for family gatherings Home was very clean and well stocked Host responded quickly to all messages Love that it is pet friendly"
United States
Anne S.
The price is HK$2,202
HK$4,640 total
includes taxes & fees
16 Sept - 17 Sept
China Lake, Dog Friendly, Lots of space for family gatherings
Interior

16. River View Retreat, Hot Tub, Balcony, Kayaks & Bikes

River View Retreat, Hot Tub, Balcony, Kayaks & Bikes
Hallowell
10.0 out of 10, 2, (2 reviews)
"Great place and great host. Right in the water and close to New York and Canada"
United States
Anthony R.
The price is HK$1,094
HK$1,363 total
includes taxes & fees
15 Sept - 16 Sept
River View Retreat, Hot Tub, Balcony, Kayaks & Bikes
Exterior

17. Perfectly Located 1 Bedroom, newly remodeled

Perfectly Located 1 Bedroom, newly remodeled
Augusta
10.0 out of 10, 4, (4 reviews)
"I’ve stayed in many rental properties and this one is by far the cleanest and nicest. Everything was exactly as described and there was even a second ac unit in the bedroom. It’s on a nice quiet street and convenient to many things. You truly can’t go wrong choosing to stay here."
United States
Lisa G.
The price is HK$1,255
HK$2,188 total
includes taxes & fees
15 Sept - 16 Sept
Perfectly Located 1 Bedroom, newly remodeled
Terrace/patio

18. Quiet Maine Retreat- Fast Wi-Fi - Long Stays Welcome- close to I95

Quiet Maine Retreat- Fast Wi-Fi - Long Stays Welcome- close to I95
Pittsfield
9.8 out of 10, 9, (9 reviews)
"Great host great stay"
United States
thomas v.
The price is HK$933
HK$1,778 total
includes taxes & fees
23 Sept - 24 Sept
Quiet Maine Retreat- Fast Wi-Fi - Long Stays Welcome- close to I95
Property grounds

19. Glamping at Maine Water Buffalo Farm

Glamping at Maine Water Buffalo Farm
Appleton
9.0 out of 10, 7, (7 reviews)
"Very quite and private and beautiful surroundings"
United States
Gary
The price is HK$1,012
HK$1,274 total
includes taxes & fees
16 Sept - 17 Sept
Glamping at Maine Water Buffalo Farm
Living area

20. Salt water hot tub, king size beds, dog friendly, lake front, dock, boat launch

Salt water hot tub, king size beds, dog friendly, lake front, dock, boat launch
Canaan
9.8 out of 10, 8, (8 reviews)
"Awesome stay right on the water. "
United States
Timothy S.
The price is HK$1,364
HK$3,333 total
includes taxes & fees
17 Sept - 18 Sept
Salt water hot tub, king size beds, dog friendly, lake front, dock, boat launch
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 Towne Motel

The Towne Motel

8/10 Good
"The toilet was very low and we are elderly. It was difficult for us to use."
Howard 1-night trip
Posted 1 hour ago
The Towne Motel

Find out more about Winslow

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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?

Stunning Belgrade Lakes Waterfront Retreat – Dock, Kayaks & Breathtaking Views!: This holiday home rental outside of Winslow offers a patio, a garden and air conditioning to help you feel perfectly comfortable in your new surroundings.

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.