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Winthrop Vacation Rentals

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Check prices for these dates

In two weeks
Aug 21 - Aug 23
In two months
Oct 2 - Oct 4
In three months
Oct 30 - Nov 1
In four months
Nov 27 - Nov 29

Our top choices for Winthrop vacation rentals

Terrace/patio

1. Cozy cottage in the Winthrop Lakes Area

Cozy cottage in the Winthrop Lakes Area
Winthrop
9.8 out of 10, Exceptional, (7 reviews)
"My only regret is that we were only there for one night & didn’t have time to enjoy the surroundings."
United States
Nicole B.
$169 nightly
The price is $184
Aug 31 - Sep 1
Total with taxes and fees
Cozy cottage in the Winthrop Lakes Area
Interior

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
10.0 out of 10, Exceptional, (2 reviews)
"The home was adorable, and beds were very comfortable. We checked out the dock (very convenient) though didn't spend any time in the lake, but she had lifejackets, pool noodles, and other lake amenities! Host was very responsive and helpful. We'd be delighted to stay here again!"
United States
Hannah
$290 nightly
The price is $316
Aug 14 - Aug 15
Total with taxes and fees
Jill's Place, new construction, lake access Cobbosee, 1 mile from Cabin Masters
Exterior

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
Sep 1 - Sep 2
Total with taxes and fees
July 7 to 14 Available: Big Porches w/ Scenic Views, Kayaks & Room to Gather
Property grounds

4. Cozy off grid cabin in the wood

Cozy off grid cabin in the wood
Hartford
Cozy off grid cabin in the wood
Terrace/patio

5. Naughty Dog Private Island Log Cabin

Naughty Dog Private Island Log Cabin
Monmouth
10.0 out of 10, Exceptional, (12 reviews)
"Our stay was amazing! The location was beyond what I expected. It was so peaceful and relaxing Kent the property owner was fabulous, anything we needed or wanted he brought to us. I highly recommend this property and we can’t wait to go back!"
United States
Anonymous traveler
$458 nightly
The price is $499
Sep 3 - Sep 4
Total with taxes and fees
Naughty Dog Private Island Log Cabin
Property grounds

6. Cozy Cottage on water's edge of Lake Cobbosseecontee

Cozy Cottage on water's edge of Lake Cobbosseecontee
Manchester
8.8 out of 10, Excellent, (25 reviews)
"Location is amazing "
United States
Laura Q.
$349 nightly
The price is $380
Aug 8 - Aug 9
Total with taxes and fees
Cozy Cottage on water's edge of Lake Cobbosseecontee
1 bedroom, WiFi, bed sheets

7. Charming 1-bedroom apartment in Monmouth with AC, WiFi. Several lakes nearby.

Charming 1-bedroom apartment in Monmouth with AC, WiFi. Several lakes nearby.
Monmouth
9.6 out of 10, Exceptional, (4 reviews)
"Really enjoyed my stay at this apartment. Quiet with all the comforts of home. Will definitely stay again next time I'm in town."
United States
bill w.
$220 nightly
The price is $240
Aug 5 - Aug 6
Total with taxes and fees
Charming 1-bedroom apartment in Monmouth with AC, WiFi. Several lakes nearby.
Interior

8. Island Tree House Glamping

Island Tree House Glamping
Monmouth
9.8 out of 10, Exceptional, (10 reviews)
"Sunset/rise were so perfect, and we got a special appearance of a double rainbow during our stay!"
United States
Desiree L.
$286 nightly
The price is $312
Sep 3 - Sep 4
Total with taxes and fees
Island Tree House Glamping
TV, books, offices

9. 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
10.0 out of 10, Exceptional, (1 review)
"The property was very nice!"
United States
James D.
$1,053 nightly
The price is $1,148
Sep 2 - Sep 3
Total with taxes and fees
Spacious Waterfront Log Home on Huge Lake in Private Cove: Host Weddings
Spa

10. Floating Island Dome - Pet-Friendly Lake Retreat

Floating Island Dome - Pet-Friendly Lake Retreat
Monmouth
$237 nightly
The price is $258
Aug 16 - Aug 17
Total with taxes and fees
Floating Island Dome - Pet-Friendly Lake Retreat
Outdoor dining

11. 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, (20 reviews)
"Very nice and clean place. We used this rental as a hub to go around and see lots that Maine had to offer. Hosts were very nice and kept a very clean place."
United States
Bruce J.
$450 nightly
The price is $490
Aug 5 - Aug 6
Total with taxes and fees
Maine river escape: free kayaks, paddle boards, tennis, cute rabbits and fun!
Exterior

12. 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.
$254 nightly
The price is $277
Aug 5 - Aug 6
Total with taxes and fees
Perfectly Located 1 Bedroom, newly remodeled
Interior

13. Camp Lintonia on Tacoma Lakes

Camp Lintonia on Tacoma Lakes
Litchfield
10.0 out of 10, Exceptional, (15 reviews)
"Amazing Host, beautiful place to stay with an awesome view, pleanty of room for everyone, all the amenities worked great and the showers had great pressure and were nice and hot! Definitely plan on renting this location in the summer! DEFINITELY a place to stay... solid 5 stars!!!"
United States
Meghan C.
$398 nightly
The price is $434
Sep 1 - Sep 2
Total with taxes and fees
Camp Lintonia on Tacoma Lakes
Terrace/patio

14. Get in touch with nature.

Get in touch with nature.
Richmond
10.0 out of 10, Exceptional, (45 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
Aug 10 - Aug 11
Total with taxes and fees
Get in touch with nature.
TV

15. 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, (90 reviews)
"House and community was amazing love the vibe of house experience was far and above expectations "
United States
Mike W.
$216 nightly
The price is $235
Sep 1 - Sep 2
Total with taxes and fees
Two bedroom Mid Century Modern apartment in Downtown Hallowell
Interior

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

River View Retreat, Hot Tub, Balcony, Kayaks & Bikes
Hallowell
10.0 out of 10, Exceptional, (1 review)
"Great place and great host. Right in the water and close to New York and Canada"
United States
Anthony R.
$166 nightly
The price is $181
Sep 1 - Sep 2
Total with taxes and fees
River View Retreat, Hot Tub, Balcony, Kayaks & Bikes
Interior

17. 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, (55 reviews)
"Great place, quiet neighborhood off the lake, very comfortable. Would definitely stay again!"
United States
Steve C.
$559 nightly
The price is $609
Aug 20 - Aug 21
Total with taxes and fees
Boat launch and Trailer parking, Dog Friendly, Lake Great Pond
3 bedrooms, desk, iron/ironing board, WiFi (free)

18. An Authentic Clean & Cozy Maine Homestay

An Authentic Clean & Cozy Maine Homestay
Buckfield
9.8 out of 10, Exceptional, (68 reviews)
"My tenants said the accommodations were lovely "
United States
Nathan
$188 nightly
The price is $205
Aug 7 - Aug 8
Total with taxes and fees
An Authentic Clean & Cozy Maine Homestay
Outdoor spa tub

19. Cabin Style Studio Apt with Private Hot tub on 100 Acres Kayaks, Canoes & SUP

Cabin Style Studio Apt with Private Hot tub on 100 Acres Kayaks, Canoes & SUP
Whitefield
10.0 out of 10, Exceptional, (8 reviews)
"Great getaway! We loved all of the discoveries to be made both in the cabin and on the property. We stayed in Stella. It was adorable, functional, and very welcoming. We also enjoyed an outing to Kennebec Maine Cabin Masters only 20 min away! "
United States
Sandra L.
$277 nightly
The price is $302
Aug 6 - Aug 7
Total with taxes and fees
Cabin Style Studio Apt with Private Hot tub on 100 Acres Kayaks, Canoes & SUP
Interior

20. High End Apartment in Downtown Hallowell

High End Apartment in Downtown Hallowell
Hallowell
10.0 out of 10, Exceptional, (106 reviews)
"Lovely stay in Hallowell."
United States
Lori D.
High End Apartment in Downtown Hallowell
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

Hampton Inn Lewiston-Auburn

Hampton Inn Lewiston-Auburn

8/10 Good
"The room was clean and it was quiet."
Leanne 1-night trip
Posted 8 hours ago
Hampton Inn Lewiston-Auburn

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 $153 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.

Explore a world of travel with Expedia

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?

Enjoy Sunset views on tranquil Dexter Pond: Visitors like this Winthrop vacation home rental. It is located on the waterfront and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You and your friends and family can relax into your vacation with amenities like a selection of games.

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.