Holiday Rentals in Winthrop

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Winthrop holiday 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 €159
includes taxes & fees
15 Nov - 16 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 €266
includes taxes & fees
12 Nov - 13 Nov
Jill's Place, new construction, lake access Cobbosee, 1 mile from Cabin Masters
A living room with a fireplace, a television, and a sofa.

3. High End Apartment in Downtown Hallowell

High End Apartment in Downtown Hallowell
Hallowell
10.0 out of 10, Exceptional, (115 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 €175
includes taxes & fees
19 Nov - 20 Nov
High End Apartment in Downtown Hallowell
A wooden cabin with a porch, a door, and a green chair.

4. 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 €189
includes taxes & fees
12 Nov - 13 Nov
Sister A-Frame in Woods B
A covered outdoor seating area with wicker furniture, a ceiling fan, and a view of a lake.

5. 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 €446
includes taxes & fees
15 Nov - 16 Nov
Pocasset Lake Cottage, Screened Porch, Canoes and Kayaks
A wooden porch with a door, steps, and potted plants.

6. Renovated Year-Round Lake Retreat on Annabessacook Lake

Renovated Year-Round Lake Retreat on Annabessacook Lake
Monmouth
10.0 out of 10, Exceptional, (1 review)
"We had a wonderful stay! The space was incredibly cozy, comfortable, and welcoming. Ryanne was an absolutely fantastic host. She was attentive, extremely responsive, and so accommodating throughout our stay. Her kindness and generosity really stood out, and she went above and beyond to make sure we had a great experience. The place was also thoughtfully stocked with so many toiletries and essentials, which was especially helpful since I had forgotten a few things of my own! It’s clear that...
United States
Elizabeth D.
The price is €326
includes taxes & fees
12 Nov - 13 Nov
Renovated Year-Round Lake Retreat on Annabessacook Lake
A boat docked at a pier with a calm lake and a forested hill in the background.

7. Every window has a spectacular lake view Low fees

Every window has a spectacular lake view Low fees
Wayne
9.8 out of 10, Exceptional, (53 reviews)
"The property was super clean, better than the description, and Tina was incredibly fast with responses to all our questions. I've used VRBO more than twenty times for week or two-week cabins stays and this was as easy and delightful as any of them!"
United States
Dan C.
The price is €366
includes taxes & fees
24 Nov - 25 Nov
Every window has a spectacular lake view Low fees
A modern living room with a flat-screen TV, a yellow armchair, a beige sofa, and a coffee table.

8. 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, (97 reviews)
"Cute place, quiet neighborhood close to downtown."
United States
Melissa F.
The price is €186
includes taxes & fees
16 Nov - 17 Nov
Two bedroom Mid Century Modern apartment in Downtown Hallowell
A cozy living room with a large window, a leather armchair, a beige sofa, and a wooden coffee table.

9. Readfield Retreat w/ Lake Maranacook Views!

Readfield Retreat w/ Lake Maranacook Views!
Readfield
9.4 out of 10, Exceptional, (16 reviews)
"Great spot for our family trip."
United States
Kevin P.
The price is €451
includes taxes & fees
12 Nov - 13 Nov
Readfield Retreat w/ Lake Maranacook Views!
A wooden deck with a railing and steps leading to a house.

10. Home Away From Home. Family friendly, comfortable- centrally located in Augusta

Home Away From Home. Family friendly, comfortable- centrally located in Augusta
Augusta
The price is €221
includes taxes & fees
12 Nov - 13 Nov
Home Away From Home. Family friendly, comfortable- centrally located in Augusta
A spacious log cabin interior with a large living area, a stone fireplace, and a staircase leading to an upper level.

11. Spacious Waterfront Log Home on Huge Lake in Private Cove: Host Weddings

Spacious Waterfront Log Home on Huge Lake in Private Cove: Host Weddings
Wayne
9.0 out of 10, Wonderful, (2 reviews)
"The property was very nice!"
United States
James D.
The price is €788
includes taxes & fees
16 Nov - 17 Nov
Spacious Waterfront Log Home on Huge Lake in Private Cove: Host Weddings
Property grounds

12. 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 €215
includes taxes & fees
24 Nov - 25 Nov
Central Maine Apartment offering 4 Seasons of Fun.
A wooden deck with picnic tables overlooking a calm lake, surrounded by dense greenery.

13. 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, (23 reviews)
"This was the ideal Maine spot."
United States
Lisa W.
The price is €355
includes taxes & fees
16 Nov - 17 Nov
Maine river escape: free kayaks, paddle boards, tennis, cute rabbits and fun!
A compact kitchen with a central island, a dining area with a bench, and a sofa.

14. The Cozy Apartment near Bates, St. Mary’s & CMMC

The Cozy Apartment near Bates, St. Mary’s & CMMC
Lewiston
The price is €223
includes taxes & fees
24 Nov - 25 Nov
The Cozy Apartment near Bates, St. Mary’s & CMMC
A covered outdoor seating area with a view of a lake and trees.

15. Echo Lake Retreat: Dock, Kayaks, Sunsets

Echo Lake Retreat: Dock, Kayaks, Sunsets
Mount Vernon
The price is €525
includes taxes & fees
24 Nov - 25 Nov
Echo Lake Retreat: Dock, Kayaks, Sunsets
A room with a sliding glass door leading to a deck, a wooden table, and a chair.

16. 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 €380
includes taxes & fees
18 Nov - 19 Nov
Boat launch and Trailer parking, Dog Friendly, Lake Great Pond
A covered deck with large windows overlooking a lake, a boat on the water, and a forested shoreline.

17. Camp Lintonia on Tacoma Lakes

Camp Lintonia on Tacoma Lakes
Litchfield
10.0 out of 10, Exceptional, (20 reviews)
"Loved it"
United States
Sandra R.
The price is €259
includes taxes & fees
30 Nov - 1 Dec
Camp Lintonia on Tacoma Lakes
A bedroom with a bed, a bedside table, a lamp, and a window with curtains.

18. The heart of the Belgrade Lakes

The heart of the Belgrade Lakes
Oakland
9.2 out of 10, Wonderful, (11 reviews)
"Host was very accommodating "
United States
Maureen
The price is €193
includes taxes & fees
24 Nov - 25 Nov
The heart of the Belgrade Lakes
A bedroom with a bed, wooden ceiling, a window with blinds, a nightstand, and a framed picture on the wall.

19. An Authentic Clean & Cozy Maine Homestay

An Authentic Clean & Cozy Maine Homestay
Buckfield
9.8 out of 10, Exceptional, (70 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 €196
includes taxes & fees
12 Nov - 13 Nov
An Authentic Clean & Cozy Maine Homestay
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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Find out more about Winthrop

Everything you need to know about Winthrop holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winthrop holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winthrop holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winthrop holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winthrop. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winthrop holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winthrop holiday rentals we have selected for you start as low as €158 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Winthrop rentals

At Expedia, we put the best Winthrop holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Winthrop rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winthrop holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winthrop. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently Asked Questions

Can I find a holiday rental in Winthrop?

Yes, there are holiday rentals close to the most popular sights in Winthrop, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Winthrop has to offer?

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

How many holiday rentals are there in Winthrop?

Expedia has 15 holiday 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 holiday rentals like in Winthrop?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winthrop. Holiday rentals provide amenities such as patios, hot tubs and fire pits so you'll have all the comforts of home. If you're concerned about cleanliness, holiday rentals can offer a sense of privacy away from public hotel lifts and lobbies bustling with people while still allowing you to travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive choice for small groups.