A wooden signpost with 'WINTHROP' written on it, surrounded by greenery and trees.

Winthrop Vacation Rentals

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Winthrop vacation rentals

A covered porch with wicker furniture, a white door, and a welcome mat.

1. Cozy cottage in the Winthrop Lakes Area

Cozy cottage in the Winthrop Lakes Area
Winthrop
9.8 out of 10, Exceptional, (9 reviews)
"The property was lovely, and the host was wonderful!"
United States
Treseanne A.
The price is AED 382
AED 677 total
includes taxes & fees
9 Nov - 10 Nov
Cozy cottage in the Winthrop Lakes Area
A spacious room with a wooden floor, a striped rug, a black chair, and a dining table.

2. Jill's Place, new construction, lake access Cobbosee, 1 mile from Cabin Masters

Jill's Place, new construction, lake access Cobbosee, 1 mile from Cabin Masters
Winthrop
9.0 out of 10, Wonderful, (4 reviews)
"Very nice property, great location, nice decor, pet friendly, and good kitchen area."
United States
Laura M.
The price is AED 643
AED 1,137 total
includes taxes & fees
19 Oct - 20 Oct
Jill's Place, new construction, lake access Cobbosee, 1 mile from Cabin Masters
A two-story house with a red roof, located by a lake surrounded by dense green trees.

3. July 7 to 14 Available: Big Porches w/ Scenic Views, Kayaks & Room to Gather

July 7 to 14 Available: Big Porches w/ Scenic Views, Kayaks & Room to Gather
Winthrop
9.6 out of 10, Exceptional, (5 reviews)
"Nice place to stay"
United States
Michael Y.
The price is AED 1,194
AED 3,315 total
includes taxes & fees
26 Oct - 27 Oct
July 7 to 14 Available: Big Porches w/ Scenic Views, Kayaks & Room to Gather
A wooden interior with a radial wooden ceiling design and a central skylight.

4. Island Tree House Glamping

Island Tree House Glamping
Monmouth
10.0 out of 10, Exceptional, (11 reviews)
"Sunset/rise were so perfect, and we got a special appearance of a double rainbow during our stay!"
United States
Desiree L.
The price is AED 40
AED 813 total
includes taxes & fees
28 Oct - 29 Oct
Island Tree House Glamping
A wooden cabin with a porch, a rocking chair, and a table with a lantern.

5. Naughty Dog Private Island Log Cabin

Naughty Dog Private Island Log Cabin
Monmouth
10.0 out of 10, Exceptional, (13 reviews)
"Honestly, this property and the whole experience exceeded all my expectations (which were already pretty high). Kent and the team were so accommodating, making sure that we had everything that we needed and were available at any time. They made special plans to accommodate some friends for a day visit and were so kind and helpful. The property itself was so perfect for what we wanted and the dog so enjoyed the freedom that only a private island can bring! Thanks, Kent, for a very memorable stay....
United States
Peter O.
The price is AED 426
AED 1,401 total
includes taxes & fees
21 Oct - 22 Oct
Naughty Dog Private Island Log Cabin
A living room with a fireplace, a glass of white wine, a cutting board with cheese, and a remote control.

6. High End Apartment in Downtown Hallowell

High End Apartment in Downtown Hallowell
Hallowell
10.0 out of 10, Exceptional, (113 reviews)
"Bigger than I expected and one of the homier properties I have been to in a while. Great location to walk around town and minutes to Augusta. Will book again"
United States
Shawn
The price is AED 437
AED 789 total
includes taxes & fees
2 Nov - 3 Nov
High End Apartment in Downtown Hallowell
A tent with a bed, two chairs, and a table.

7. Get in touch with nature.

Get in touch with nature.
Richmond
10.0 out of 10, Exceptional, (52 reviews)
"Perfect place to reset your soul! Loved it!"
United States
Vincent
The price is AED 397
AED 633 total
includes taxes & fees
18 Oct - 19 Oct
Get in touch with nature.
A compact RV interior with a bed, seating area, and a small kitchenette.

8. Lemon Balm - Kut Away Campground

Lemon Balm - Kut Away Campground
Livermore Falls
The price is AED 198
AED 396 total
includes taxes & fees
17 Oct - 18 Oct
Lemon Balm - Kut Away Campground
A bathroom with a white sink, wooden paneling, a mirror with a bead trim, and a view of a house through a window.

9. 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 512
AED 639 total
includes taxes & fees
19 Oct - 20 Oct
River View Retreat, Hot Tub, Balcony, Kayaks & Bikes
A wooden cabin with a porch, a door, and a green chair.

10. Sister A-Frame in Woods B

Sister A-Frame in Woods B
Oakland
10.0 out of 10, Exceptional, (13 reviews)
"Great stay. Would stay here again if in the area."
United States
Amanda M.
The price is AED 367
AED 861 total
includes taxes & fees
3 Nov - 4 Nov
Sister A-Frame in Woods B
A covered outdoor seating area with wicker furniture, a ceiling fan, and a view of a lake.

11. Pocasset Lake Cottage, Screened Porch, Canoes and Kayaks

Pocasset Lake Cottage, Screened Porch, Canoes and Kayaks
Wayne
10.0 out of 10, Exceptional, (2 reviews)
"This is a beautiful, quiet location, and the cabin is well maintained. The grill worked well, the kitchen had everything we needed, and lots of towels were provided, even swim towels, which we didn't expect. There are three bedrooms with doors, though the last is a single pull out that was fine for our 20 year old daughter. The water at the end of the dock is about 3 feet deep, so it'd be a good spot for small children. With 2 kayaks and a canoe, we explored the coastline and saw loons and...
United States
Julie D.
The price is AED 613
AED 1,893 total
includes taxes & fees
20 Oct - 21 Oct
Pocasset Lake Cottage, Screened Porch, Canoes and Kayaks
A modern kitchen with stainless steel appliances, wooden cabinets, and a dining area with a table and chairs.

12. Renovated Year-Round Lake Retreat on Annabessacook Lake

Renovated Year-Round Lake Retreat on Annabessacook Lake
Monmouth
The price is AED 678
AED 1,231 total
includes taxes & fees
19 Oct - 20 Oct
Renovated Year-Round Lake Retreat on Annabessacook Lake
A two-story house with a front porch, a small tree, and a brick pathway.

13. Perfectly Located 1 Bedroom, newly remodeled

Perfectly Located 1 Bedroom, newly remodeled
Augusta
10.0 out of 10, Exceptional, (6 reviews)
"The area is so convenient for any business you have in the Augusta area- right off the main thoroughfare yet far enough away to be private. Check in was as simple as getting the lock code from vrbo check in emails. The apartment is even more lovely than the pictures- almost too clean and comfortable to be real! Bedtime was silent so I got a great night sleep. I only wish we would have had more time to enjoy :) Highly recommend!! "
United States
w c.
The price is AED 591
AED 1,021 total
includes taxes & fees
19 Oct - 20 Oct
Perfectly Located 1 Bedroom, newly remodeled
A bedroom with a bed, a bedside table, a lamp, and a window with curtains.

14. The heart of the Belgrade Lakes

The heart of the Belgrade Lakes
Oakland
9.2 out of 10, Wonderful, (11 reviews)
"It was amazing! Shawna was great! I forgot to add our pet on the original booking and she was so responsive and we got everything sorted out. The apartment was so comfortable and decorated beautifully! Great space from kids room with things to entertain them to calm adult bedroom. The kitchen was well stocked and had everything you could think of. We loved “the fluffy butt hut” chicken coop!!! This is a dream place, from veggie garden, pool, tree house, chicken coop. Love it! Will definitely...
United States
Tri C.
The price is AED 422
AED 861 total
includes taxes & fees
17 Oct - 18 Oct
The heart of the Belgrade Lakes
A wooden deck with picnic tables overlooking a calm lake, surrounded by dense greenery.

15. Maine river escape: free kayaks, paddle boards, tennis, cute rabbits and fun!

Maine river escape: free kayaks, paddle boards, tennis, cute rabbits and fun!
West Gardiner
9.8 out of 10, Exceptional, (22 reviews)
"This was the ideal Maine spot."
United States
Lisa W.
The price is AED 698
AED 1,589 total
includes taxes & fees
20 Oct - 21 Oct
Maine river escape: free kayaks, paddle boards, tennis, cute rabbits and fun!
Property grounds

16. Central Maine Apartment offering 4 Seasons of Fun.

Central Maine Apartment offering 4 Seasons of Fun.
Oakland
10.0 out of 10, Exceptional, (50 reviews)
"Apartment was comfortable and as described. I had a nice stay."
United States
kathy e.
The price is AED 382
AED 917 total
includes taxes & fees
1 Nov - 2 Nov
Central Maine Apartment offering 4 Seasons of Fun.
A bedroom with a bed, wooden ceiling, a window with blinds, a nightstand, and a framed picture on the wall.

17. An Authentic Clean & Cozy Maine Homestay

An Authentic Clean & Cozy Maine Homestay
Buckfield
9.8 out of 10, Exceptional, (69 reviews)
"Host was very accommodating and helpful! Was a great space to stay and felt homey! In a good area with plenty of amenities nearby."
United States
Autumn M.
The price is AED 456
AED 741 total
includes taxes & fees
19 Oct - 20 Oct
An Authentic Clean & Cozy Maine Homestay
A room with a sliding glass door leading to a deck, a wooden table, and a chair.

18. 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, (58 reviews)
"Great place, quiet neighborhood off the lake, very comfortable. Would definitely stay again!"
United States
Steve C.
The price is AED 595
AED 1,405 total
includes taxes & fees
18 Oct - 19 Oct
Boat launch and Trailer parking, Dog Friendly, Lake Great Pond
A kitchen with built-in appliances, wooden shelves, and a window with a view.

19. Heated Bathroom Floors, Steps from Bates College, Quiet & Beautiful Cottage!

Heated Bathroom Floors, Steps from Bates College, Quiet & Beautiful Cottage!
Lewiston
10.0 out of 10, Exceptional, (6 reviews)
"Great little spot with easy access to the college. Host was great and included some very thoughtful touches, which were much appreciated."
United States
Joseph D.
Heated Bathroom Floors, Steps from Bates College, Quiet & Beautiful Cottage!
A campsite with two wooden cabins, a dirt path, and string lights.

20. Old Apple Orchard Yurt 2

Old Apple Orchard Yurt 2
Buckfield
The price is AED 408
AED 892 total
includes taxes & fees
23 Oct - 24 Oct
Old Apple Orchard Yurt 2
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 Winthrop Hotel Reviews

The Elmwood

The Elmwood

8/10 Good
"Very clean hotel. Nice array of food for breakfast A little too close to the highway for me"
Stefanie 1-night trip
Posted 1 hour ago
The Elmwood

Frequently asked questions

Can I find a vacation rental in Winthrop?

Yes, we offer vacation rentals close to popular sights in Winthrop, or you can choose a secluded option if you want a relaxing place to stay.

What are some of the best vacation rentals in Winthrop?

Stunning Belgrade Lakes Waterfront Retreat – Dock, Kayaks & Breathtaking Views!: You might want to consider this vacation rental near Winthrop, which offers a patio, a garden, and air-conditioning to help you feel perfectly comfortable in your new surroundings.

How many vacation rentals are there in Winthrop?

Expedia has 15 vacation rentals for your stay in Winthrop.

What can I see and do in Winthrop?

Maranacook Lake and Cobbosseecontee Lake are a couple of lovely local spots to get outside and enjoy nature. While here, Annabessacook Lake and Wilson Pond are other places worth a visit.

What are vacation rentals like in Winthrop?

Vacation rentals are private accommodations you can book for a few days or a quick weekend in Winthrop. Vacation rentals provide amenities such as patios, hot tubs, and fire pits so you'll have all the conveniences of home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of privacy away from public hotel elevators and busy reception areas while still allowing you to travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive choice for families.