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

Winthrop Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Winthrop holiday 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 NZ$308
includes taxes & fees
7 Sept - 8 Sept
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 NZ$505
includes taxes & fees
1 Sept - 2 Sept
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 NZ$1,466
includes taxes & fees
1 Sept - 2 Sept
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 NZ$392
includes taxes & fees
27 Aug - 28 Aug
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 NZ$1,854
includes taxes & fees
15 Sept - 16 Sept
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, (107 reviews)
"Lovely stay in Hallowell."
United States
Lori D.
The price is NZ$354
includes taxes & fees
13 Sept - 14 Sept
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 NZ$303
includes taxes & fees
3 Sept - 4 Sept
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 NZ$379
includes taxes & fees
21 Sept - 22 Sept
Floating Island Cabin

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.
The price is NZ$722
includes taxes & fees
1 Sept - 2 Sept
Camp Lintonia on Tacoma Lakes

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.
The price is NZ$346
includes taxes & fees
1 Sept - 2 Sept
Two bedroom Mid Century Modern apartment in Downtown Hallowell

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.
The price is NZ$897
includes taxes & fees
5 Sept - 6 Sept
Maine river escape: free kayaks, paddle boards, tennis, cute rabbits and fun!

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.
The price is NZ$291
includes taxes & fees
31 Aug - 1 Sept
River View Retreat, Hot Tub, Balcony, Kayaks & Bikes

13. Floating Island Dome - Pet-Friendly Lake Retreat

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

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.
The price is NZ$465
includes taxes & fees
27 Aug - 28 Aug
Perfectly Located 1 Bedroom, newly remodeled

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.
The price is NZ$801
includes taxes & fees
20 Sept - 21 Sept
Boat launch and Trailer parking, Dog Friendly, Lake Great Pond

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
The price is NZ$255
includes taxes & fees
31 Aug - 1 Sept
Get in touch with nature.

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.
The price is NZ$1,573
includes taxes & fees
9 Sept - 10 Sept
Family's Paradise: 3BR/2BA,Game Room & Lake Access

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
The price is NZ$542
includes taxes & fees
16 Sept - 17 Sept
Private Dock on Messalonskee Lake: Cozy Cottage!

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.
The price is NZ$1,152
includes taxes & fees
27 Aug - 28 Aug
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Winthrop Hotel Reviews

Find out more about Winthrop

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Winthrop holiday 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. 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 holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Winthrop. 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 Winthrop. 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 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 holiday 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 Winthrop short-term rentals, that won’t be hard to do.

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?

Warm & Inviting Lakeside Retreat, Private, Tranquil Picture Perfect Setting: This holiday home rental outside of Winthrop is located on a lake, and has a fireplace, a patio and a BBQ 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 that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals are there in Winthrop?

Expedia has 14 holiday 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 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.