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

Winthrop Vacation Rentals

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Our top choices for Winthrop vacation rentals

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.
The price is CA $151
CA $263 total
includes taxes & fees
Sep 7 - Sep 8
Cozy cottage in the Winthrop Lakes Area

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 CA $263
CA $450 total
includes taxes & fees
Sep 7 - Sep 8
Jill's Place, new construction, lake access Cobbosee, 1 mile from Cabin Masters

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 CA $450
CA $1,230 total
includes taxes & fees
Sep 2 - Sep 3
July 7 to 14 Available: Big Porches w/ Scenic Views, Kayaks & Room to Gather

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.
The price is CA $197
CA $326 total
includes taxes & fees
Aug 31 - Sep 1
Charming 1-bedroom apartment in Monmouth with AC, WiFi. Several lakes nearby.

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.
The price is CA $633
CA $1,498 total
includes taxes & fees
Sep 2 - Sep 3
Spacious Waterfront Log Home on Huge Lake in Private Cove: Host Weddings

6. High End Apartment in Downtown Hallowell

High End Apartment in Downtown Hallowell
Hallowell
10.0 out of 10, Exceptional, (108 reviews)
"Lovely stay in Hallowell."
United States
Lori D.
The price is CA $165
CA $297 total
includes taxes & fees
Sep 13 - Sep 14
High End Apartment in Downtown Hallowell

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.
The price is CA $50
CA $240 total
includes taxes & fees
Sep 3 - Sep 4
Glamping Lakefront Island Retreat w/ Kayak & Pet-Friendly

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.
The price is CA $102
CA $302 total
includes taxes & fees
Sep 16 - Sep 17
Floating Island Cabin

9. 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.
The price is CA $65
CA $370 total
includes taxes & fees
Sep 3 - Sep 4
Island Tree House Glamping

10. 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.
The price is CA $485
CA $598 total
includes taxes & fees
Sep 3 - Sep 4
Camp Lintonia on Tacoma Lakes

11. 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.
The price is CA $141
CA $294 total
includes taxes & fees
Sep 1 - Sep 2
Two bedroom Mid Century Modern apartment in Downtown Hallowell

12. 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, (21 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.
The price is CA $389
CA $755 total
includes taxes & fees
Sep 5 - Sep 6
Maine river escape: free kayaks, paddle boards, tennis, cute rabbits and fun!

13. 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 CA $201
CA $249 total
includes taxes & fees
Sep 2 - Sep 3
River View Retreat, Hot Tub, Balcony, Kayaks & Bikes

14. Floating Island Dome - Pet-Friendly Lake Retreat

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

15. 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.
The price is CA $222
CA $385 total
includes taxes & fees
Sep 3 - Sep 4
Perfectly Located 1 Bedroom, newly remodeled

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, (56 reviews)
"Great place, quiet neighborhood off the lake, very comfortable. Would definitely stay again!"
United States
Steve C.
The price is CA $339
CA $673 total
includes taxes & fees
Sep 20 - Sep 21
Boat launch and Trailer parking, Dog Friendly, Lake Great Pond

17. 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
The price is CA $125
CA $211 total
includes taxes & fees
Sep 9 - Sep 10
Get in touch with nature.

18. 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.
The price is CA $497
CA $1,421 total
includes taxes & fees
Sep 4 - Sep 5
Family's Paradise: 3BR/2BA,Game Room & Lake Access

19. 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
The price is CA $159
CA $451 total
includes taxes & fees
Sep 16 - Sep 17
Private Dock on Messalonskee Lake: Cozy Cottage!

20. 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.
The price is CA $436
CA $975 total
includes taxes & fees
Sep 2 - Sep 3
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

Find out more about Winthrop

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Winthrop. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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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?

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.