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

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.
$169 nightly
The price is $184
Nov 1 - Nov 2
Total with taxes and fees
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.
$284 nightly
The price is $310
Oct 19 - Oct 20
Total with taxes and fees
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.
$828 nightly
The price is $903
Oct 26 - Oct 27
Total with taxes and fees
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.
$200 nightly
The price is $218
Oct 28 - Oct 29
Total with taxes and fees
Island Tree House Glamping
A room with a hexagonal glass ceiling, a bed with a plaid blanket, and a view of greenery outside.

5. Floating Island Dome - Pet-Friendly Lake Retreat

Floating Island Dome - Pet-Friendly Lake Retreat
Monmouth
Floating Island Dome - Pet-Friendly Lake Retreat
A floating house with a glass door, a deck, and a table and chairs.

6. Floating Island Cabin

Floating Island Cabin
Monmouth
10.0 out of 10, Exceptional, (13 reviews)
"What an absolute pleasure it was staying in the floating home on the island. It was everything we wanted it to be. We will make this an annual trip. "
United States
Carissa P.
Floating Island Cabin
A wooden cabin with a porch, a rocking chair, and a table with a lantern.

7. 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.
$371 nightly
The price is $404
Oct 30 - Oct 31
Total with taxes and fees
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.

8. 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
$197 nightly
The price is $215
Nov 2 - Nov 3
Total with taxes and fees
High End Apartment in Downtown Hallowell
A tent with a bed, two chairs, and a table.

9. Get in touch with nature.

Get in touch with nature.
Richmond
10.0 out of 10, Exceptional, (50 reviews)
"Wonderful place very peaceful very friendly Aaron was spectacular couldn't ask for a more wonderful enjoyable spot"
United States
Keith R
$140 nightly
The price is $153
Oct 13 - Oct 14
Total with taxes and fees
Get in touch with nature.
A bathroom with a white sink, wooden paneling, a mirror with a bead trim, and a view of a house through a window.

10. 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.
$160 nightly
The price is $174
Oct 19 - Oct 20
Total with taxes and fees
River View Retreat, Hot Tub, Balcony, Kayaks & Bikes
A compact RV interior with a bed, seating area, and a small kitchenette.

11. Lemon Balm - Kut Away Campground

Lemon Balm - Kut Away Campground
Livermore Falls
$99 nightly
The price is $108
Oct 13 - Oct 14
Total with taxes and fees
Lemon Balm - Kut Away Campground
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
$362 nightly
The price is $394
Oct 19 - Oct 20
Total with taxes and fees
Renovated Year-Round Lake Retreat on Annabessacook Lake
A covered outdoor seating area with wicker furniture, a ceiling fan, and a view of a lake.

13. 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.
$485 nightly
The price is $528
Nov 1 - Nov 2
Total with taxes and fees
Pocasset Lake Cottage, Screened Porch, Canoes and Kayaks
A wooden cabin with a porch, a door, and a green chair.

14. 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.
$216 nightly
The price is $235
Nov 3 - Nov 4
Total with taxes and fees
Sister A-Frame in Woods B
A two-story house with a front porch, a small tree, and a brick pathway.

15. 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.
$257 nightly
The price is $280
Oct 13 - Oct 14
Total with taxes and fees
Perfectly Located 1 Bedroom, newly remodeled
A wooden deck with picnic tables overlooking a calm lake, surrounded by dense greenery.

16. 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.
$400 nightly
The price is $436
Oct 20 - Oct 21
Total with taxes and fees
Maine river escape: free kayaks, paddle boards, tennis, cute rabbits and fun!
A single-story house with a gray siding exterior, a white front door, and two flower planters on either side of the entrance.

17. Discover Oakland charm near Colby College 10 min

Discover Oakland charm near Colby College 10 min
Oakland
9.8 out of 10, Exceptional, (20 reviews)
"Great communication. The location was excellent for a few day trips. Very clean and well maintained. Would definitely stay here again if in the area."
United States
Patricia
$214 nightly
The price is $233
Oct 13 - Oct 14
Total with taxes and fees
Discover Oakland charm near Colby College 10 min
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
$215 nightly
The price is $234
Oct 13 - Oct 14
Total with taxes and fees
The heart of the Belgrade Lakes
A spacious log cabin interior with a large living area, a stone fireplace, and a staircase leading to an upper level.

19. 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.
$968 nightly
The price is $1,055
Nov 2 - Nov 3
Total with taxes and fees
Spacious Waterfront Log Home on Huge Lake in Private Cove: Host Weddings
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
"Room was clean. Perfect for a short stay."
Theresa 2-night trip
Posted 3 hours ago
The Elmwood

Find out more about Winthrop

Everything you need to know about Winthrop vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winthrop vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winthrop vacation 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 low season months. For more hustle and bustle, you may prefer to visit Winthrop in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $184 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winthrop rentals

At Expedia, we put the best Winthrop vacation 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 vacation.

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.

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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.