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

Winslow Vacation Rentals

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Check prices for these dates

In two weeks
18 Sep - 20 Sep
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Winslow vacation rentals

Outdoor dining

1. Minutes to Colby

Minutes to Colby
Waterville
8.8 out of 10, Excellent, (25 reviews)
"Close to our event, great communication, clean, comfortable & cozy"
United States
Shelly B.
The price is AED 584
AED 933 total
includes taxes & fees
2 Sep - 3 Sep
Minutes to Colby
Exterior

2. Sister A-Frame in Woods B

Sister A-Frame in Woods B
Oakland
10.0 out of 10, Exceptional, (11 reviews)
"Great stay. Would stay here again if in the area."
United States
Amanda M.
The price is AED 443
AED 963 total
includes taxes & fees
3 Sep - 4 Sep
Sister A-Frame in Woods B
Interior

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, Exceptional, (3 reviews)
"Beautiful camper and property! We loved it!"
United States
Tracy D.
The price is AED 331
AED 520 total
includes taxes & fees
7 Sep - 8 Sep
Fabulous 3-bedroom RV with direct access to the Sebasticook River!
Smart TV

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, Excellent, (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 AED 413
AED 631 total
includes taxes & fees
3 Sep - 4 Sep
Charming cabin in the birches right on the atv trail!
2 bedrooms, WiFi, bed sheets

5. The heart of the Belgrade Lakes

The heart of the Belgrade Lakes
Oakland
9.0 out of 10, Wonderful, (10 reviews)
"Host was very accommodating "
United States
Maureen
The price is AED 422
AED 841 total
includes taxes & fees
3 Sep - 4 Sep
The heart of the Belgrade Lakes
Exterior

6. Discover Oakland charm near Colby College 10 min

Discover Oakland charm near Colby College 10 min
Oakland
9.8 out of 10, Exceptional, (16 reviews)
"House very clean and convenient location for what we had going on. "
United States
Tammy W.
The price is AED 646
AED 1,125 total
includes taxes & fees
28 Sep - 29 Sep
Discover Oakland charm near Colby College 10 min
TV, fireplace, books

7. Private Dock on Messalonskee Lake: Cozy Cottage!

Private Dock on Messalonskee Lake: Cozy Cottage!
Sidney
9.0 out of 10, Wonderful, (12 reviews)
"Great place to stay for our annual fishing weekend in the Belgrade Lakes region! "
United States
Shawn H.
The price is AED 283
AED 1,221 total
includes taxes & fees
16 Sep - 17 Sep
Private Dock on Messalonskee Lake: Cozy Cottage!
Paper towels

8. 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, Exceptional, (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 AED 441
AED 561 total
includes taxes & fees
7 Sep - 8 Sep
Cozy newly built 1-bedroom unit 2 Kentucky Bay in charming Smithfield Maine
Outdoor dining

9. 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, Exceptional, (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 AED 771
AED 1,600 total
includes taxes & fees
3 Sep - 4 Sep
Fall Getaway at My Valhalla Farm- close to Waterville and minutes to lakes
Cottage (2 Bedrooms) | Front of property

10. Private Dock on Messalonskee Lake: Cozy Cottage!

Private Dock on Messalonskee Lake: Cozy Cottage!
3.0 star property
Augusta
10.0 out of 10, Exceptional, (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 AED 419
AED 1,191 total
includes taxes & fees
16 Sep - 17 Sep
Private Dock on Messalonskee Lake: Cozy Cottage!
TV

11. 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, (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 AED 390
AED 806 total
includes taxes & fees
2 Sep - 3 Sep
Two bedroom Mid Century Modern apartment in Downtown Hallowell
Coffee/tea maker, fridge, microwave, oven

12. Cozy new 1 bedroom, queen bed, and queen sofa bed, washer/dryers. Radiant heat.

Cozy new 1 bedroom, queen bed, and queen sofa bed, washer/dryers. Radiant heat.
Smithfield
10.0 out of 10, Exceptional, (1 review)
"Clean and new."
United States
erik s.
The price is AED 441
AED 561 total
includes taxes & fees
7 Sep - 8 Sep
Cozy new 1 bedroom, queen bed, and queen sofa bed, washer/dryers. Radiant heat.
Terrace/patio

13. 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, Exceptional, (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 AED 1,529
AED 2,936 total
includes taxes & fees
7 Sep - 8 Sep
China Lake, Dog Friendly, Lots of space for family gatherings
Exterior

14. Angel Mist Retreat Garage Apartment

Angel Mist Retreat Garage Apartment
Pittsfield
10.0 out of 10, Exceptional, (15 reviews)
"Great stay. Very comfortable, roomy, clean and good overall value."
United States
Rob K.
The price is AED 516
AED 1,143 total
includes taxes & fees
4 Sep - 5 Sep
Angel Mist Retreat Garage Apartment
Interior

15. 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, Exceptional, (56 reviews)
"Great place, quiet neighborhood off the lake, very comfortable. Would definitely stay again!"
United States
Steve C.
The price is AED 890
AED 1,783 total
includes taxes & fees
20 Sep - 21 Sep
Boat launch and Trailer parking, Dog Friendly, Lake Great Pond
Exterior detail

16. Arden Cottage

Arden Cottage
Mount Vernon
The price is AED 771
AED 1,607 total
includes taxes & fees
2 Sep - 3 Sep
Arden Cottage
Interior

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

River View Retreat, Hot Tub, Balcony, Kayaks & Bikes
Hallowell
10.0 out of 10, Exceptional, (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 AED 516
AED 642 total
includes taxes & fees
8 Sep - 9 Sep
River View Retreat, Hot Tub, Balcony, Kayaks & Bikes
Exterior

18. Perfectly Located 1 Bedroom, newly remodeled

Perfectly Located 1 Bedroom, newly remodeled
Augusta
10.0 out of 10, Exceptional, (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 AED 588
AED 1,029 total
includes taxes & fees
2 Sep - 3 Sep
Perfectly Located 1 Bedroom, newly remodeled
Property grounds

19. Glamping at Maine Water Buffalo Farm

Glamping at Maine Water Buffalo Farm
Appleton
8.8 out of 10, Excellent, (6 reviews)
"Very quite and private and beautiful surroundings"
United States
Gary
The price is AED 474
AED 597 total
includes taxes & fees
2 Sep - 3 Sep
Glamping at Maine Water Buffalo Farm
Smart TV, fireplace, books

20. Rustic Mountainside Cabin: “Liberty Lodge”

Rustic Mountainside Cabin: “Liberty Lodge”
Liberty
10.0 out of 10, Exceptional, (3 reviews)
"Place was great. Beautiful area and host was great about communicating so any questions we had were answered immediately"
United States
Brenda S.
The price is AED 863
AED 2,250 total
includes taxes & fees
1 Oct - 2 Oct
Rustic Mountainside Cabin: “Liberty Lodge”
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

Fireside Inn & Suites Waterville

Fireside Inn & Suites Waterville

10/10 Excellent
"Rooms were very clean. Staff was very helpful."
Sharon 1-night trip
Posted 8 hours ago
Fireside Inn & Suites Waterville

Frequently asked questions

Can I find a vacation rental in Winslow?

Yes, you can find vacation rentals near well known sights in Winslow, or you can select a more secluded option if you're looking for relaxation. Winslow is known for its riverfront.

What are some of the best vacation home rentals that Winslow has to offer?

Warm & Inviting Lakeside Retreat, Private, Tranquil Picture Perfect Setting: This vacation home rental near Winslow is located on a lake and has a fireplace, a patio, and a barbecue grill 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 you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

What’s there to see and do in Winslow?

Explore the area and family-friendly sights such as First Congregational Church, 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 larger area.

What’s a vacation rental in Winslow like?

Vacation rentals are private properties you can book for several days or longer in Winslow. Vacation rentals provide amenities such as laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about a clean environment, a vacation rental can offer a sense of security away from shared hotel elevators and busy front desks while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive option for a small group gathering.