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Winthrop Vacation Rentals

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Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

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.
$171 nightly
The price is $186
Sep 7 - Sep 8
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
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.
$288 nightly
The price is $314
Aug 31 - Sep 1
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.
$827 nightly
The price is $901
Sep 1 - Sep 2
Total with taxes and fees
July 7 to 14 Available: Big Porches w/ Scenic Views, Kayaks & Room to Gather
Room

4. 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 31 - Sep 1
Total with taxes and fees
Charming 1-bedroom apartment in Monmouth with AC, WiFi. Several lakes nearby.
Living area

5. 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.
$1,006 nightly
The price is $1,097
Sep 14 - Sep 15
Total with taxes and fees
Spacious Waterfront Log Home on Huge Lake in Private Cove: Host Weddings
Interior

6. High End Apartment in Downtown Hallowell

High End Apartment in Downtown Hallowell
Hallowell
10.0 out of 10, Exceptional, (107 reviews)
"Lovely stay in Hallowell."
United States
Lori D.
$192 nightly
The price is $209
Sep 15 - Sep 16
Total with taxes and fees
High End Apartment in Downtown Hallowell
Property grounds

7. Glamping Lakefront Island Retreat w/ Kayak & Pet-Friendly

Glamping Lakefront Island Retreat w/ Kayak & Pet-Friendly
Monmouth
10.0 out of 10, Exceptional, (4 reviews)
"The island is great from the walking trails, amenities and great fishing. "
United States
Jeremy F.
$166 nightly
The price is $181
Sep 3 - Sep 4
Total with taxes and fees
Glamping Lakefront Island Retreat w/ Kayak & Pet-Friendly
Property grounds

8. Floating Island Cabin

Floating Island Cabin
Monmouth
10.0 out of 10, Exceptional, (9 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.
$203 nightly
The price is $221
Sep 16 - Sep 17
Total with taxes and fees
Floating Island Cabin
Interior

9. 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.
$400 nightly
The price is $436
Sep 1 - Sep 2
Total with taxes and fees
Camp Lintonia on Tacoma Lakes
Living area

10. 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.
$193 nightly
The price is $210
Sep 1 - Sep 2
Total with taxes and fees
Two bedroom Mid Century Modern apartment in Downtown Hallowell
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)
"The place was spacious and plenty of room for our family to stay in. Pet friendly was very important to us. The beds were extremely comfortable!The coffee maker with the freshly gound beans every morning was a delight! The place is on a nice country road with beautiful views. Area restaurants and a bike/walking path only a couple miles away."
United States
heather w.
$500 nightly
The price is $545
Sep 5 - Sep 6
Total with taxes and fees
Maine river escape: free kayaks, paddle boards, tennis, cute rabbits and fun!
Interior

12. 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.
$173 nightly
The price is $189
Sep 1 - Sep 2
Total with taxes and fees
River View Retreat, Hot Tub, Balcony, Kayaks & Bikes
Spa

13. Floating Island Dome - Pet-Friendly Lake Retreat

Floating Island Dome - Pet-Friendly Lake Retreat
Monmouth
Floating Island Dome - Pet-Friendly Lake Retreat
Exterior

14. 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.
$257 nightly
The price is $280
Aug 31 - Sep 1
Total with taxes and fees
Perfectly Located 1 Bedroom, newly remodeled
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.
$450 nightly
The price is $491
Sep 20 - Sep 21
Total with taxes and fees
Boat launch and Trailer parking, Dog Friendly, Lake Great Pond
Terrace/patio

16. 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 31 - Sep 1
Total with taxes and fees
Get in touch with nature.
Terrace/patio

17. Family's Paradise: 3BR/2BA,Game Room & Lake Access

Family's Paradise: 3BR/2BA,Game Room & Lake Access
Belgrade
10.0 out of 10, Exceptional, (11 reviews)
"We enjoyed our stay."
United States
Tyson W.
$942 nightly
The price is $1,027
Sep 4 - Sep 5
Total with taxes and fees
Family's Paradise: 3BR/2BA,Game Room & Lake Access
Cottage (2 Bedrooms) | Front of property

18. 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
$298 nightly
The price is $324
Sep 16 - Sep 17
Total with taxes and fees
Private Dock on Messalonskee Lake: Cozy Cottage!
Terrace/patio

19. Lakefront Log Cabin Getaway on Sabattus Pond - Dog Friendly!

Lakefront Log Cabin Getaway on Sabattus Pond - Dog Friendly!
Wales
9.0 out of 10, Wonderful, (7 reviews)
"Excellent log cabin right on the water. Property owners were great to deal with. Will stay again."
United States
Jared F.
$646 nightly
The price is $704
Aug 30 - Aug 31
Total with taxes and fees
Lakefront Log Cabin Getaway on Sabattus Pond - Dog Friendly!
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

Maine Evergreen Hotel, an Ascend Collection Hotel

Maine Evergreen Hotel, an Ascend Collection Hotel

10/10 Excellent
"Inviting, beautifully decorated, clean, comfortable. Plentiful and tasty breakfast. Right off 95."
MONICA 1-night trip
Posted 10 hours ago
Maine Evergreen Hotel, an Ascend Collection Hotel

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?

Warm & Inviting Lakeside Retreat, Private, Tranquil Picture Perfect Setting: You might want to consider this vacation home rental near Winthrop, which 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.

How many vacation rentals are there in Winthrop?

Expedia has 14 vacation rentals for your stay in Winthrop.

What can I see and do in Winthrop?

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