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, (9 reviews)
"The property was lovely, and the host was wonderful!"
United States
Treseanne A.
The price is NZ$328
includes taxes & fees
1 Nov - 2 Nov
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$532
includes taxes & fees
19 Oct - 20 Oct
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$1,565
includes taxes & fees
26 Oct - 27 Oct
July 7 to 14 Available: Big Porches w/ Scenic Views, Kayaks & Room to Gather

4. Pet-Friendly Island A-Frame w/ Lake Access

Pet-Friendly Island A-Frame w/ Lake Access
Monmouth
10.0 out of 10, Exceptional, (7 reviews)
"A very pleasant, peaceful place to stay. The hosts were very proactive about making sure we had a great stay and did everything to could to make it as stress-free as possible."
United States
Robert
The price is NZ$262
includes taxes & fees
28 Oct - 29 Oct
Pet-Friendly Island A-Frame w/ Lake Access

5. 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.
The price is NZ$388
includes taxes & fees
28 Oct - 29 Oct
Island Tree House Glamping

6. Floating Island Dome - Pet-Friendly Lake Retreat

Floating Island Dome - Pet-Friendly Lake Retreat
Monmouth
The price is NZ$415
includes taxes & fees
12 Oct - 13 Oct
Floating Island Dome - Pet-Friendly Lake Retreat

7. 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.
The price is NZ$412
includes taxes & fees
12 Oct - 13 Oct
Floating Island Cabin

8. 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.
The price is NZ$718
includes taxes & fees
30 Oct - 31 Oct
Naughty Dog Private Island Log Cabin

9. 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
The price is NZ$377
includes taxes & fees
2 Nov - 3 Nov
High End Apartment in Downtown Hallowell

10. 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
The price is NZ$272
includes taxes & fees
13 Oct - 14 Oct
Get in touch with nature.

11. 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$313
includes taxes & fees
13 Oct - 14 Oct
River View Retreat, Hot Tub, Balcony, Kayaks & Bikes

12. The Ripple- Kut Away Campground- Travel trailer

The Ripple- Kut Away Campground- Travel trailer
Livermore Falls
The price is NZ$252
includes taxes & fees
19 Oct - 20 Oct
The Ripple- Kut Away Campground- Travel trailer

13. 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.
The price is NZ$414
includes taxes & fees
3 Nov - 4 Nov
Sister A-Frame in Woods B

14. 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.
The price is NZ$895
includes taxes & fees
1 Nov - 2 Nov
Pocasset Lake Cottage, Screened Porch, Canoes and Kayaks

15. Renovated Year-Round Lake Retreat on Annabessacook Lake

Renovated Year-Round Lake Retreat on Annabessacook Lake
Monmouth
The price is NZ$700
includes taxes & fees
19 Oct - 20 Oct
Renovated Year-Round Lake Retreat on Annabessacook Lake

16. 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.
The price is NZ$497
includes taxes & fees
12 Oct - 13 Oct
Perfectly Located 1 Bedroom, newly remodeled

17. Central Maine Apartment offering 4 Seasons of Fun.

Central Maine Apartment offering 4 Seasons of Fun.
Oakland
10.0 out of 10, Exceptional, (50 reviews)
"Apartment was comfortable and as described. I had a nice stay."
United States
kathy e.
The price is NZ$429
includes taxes & fees
1 Nov - 2 Nov
Central Maine Apartment offering 4 Seasons of Fun.

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
The price is NZ$415
includes taxes & fees
12 Oct - 13 Oct
The heart of the Belgrade Lakes
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?

Stunning Belgrade Lakes Waterfront Retreat – Dock, Kayaks & Breathtaking Views!: This holiday home rental outside of Winthrop offers a patio, a garden and air conditioning to help you feel perfectly comfortable in your new surroundings.

How many holiday rentals are there in Winthrop?

Expedia has 15 holiday 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 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.