Winthrop Holiday Rentals from €161: Search Short-Term Rentals

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Our top choices for Winthrop holiday rentals

A covered porch with wicker furniture, a white door, and a welcome mat.

1. Cozy cottage in the Winthrop Lakes Area

Winthrop

Treseanne A.

includes taxes & fees

7 Oct - 8 Oct

A spacious room with a wooden floor, a striped rug, a black chair, and a dining table.

2. Jill's Place, new construction, lake access Cobbosee, 1 mile from Cabin Masters

Winthrop

Laura M.

includes taxes & fees

20 Oct - 21 Oct

A two-story house with a red roof, located by a lake surrounded by dense green trees.

3. July 7 to 14 Available: Big Porches w/ Scenic Views, Kayaks & Room to Gather

Winthrop

Michael Y.

includes taxes & fees

28 Sept - 29 Sept

A wooden interior with a radial wooden ceiling design and a central skylight.

4. Island Tree House Glamping

Monmouth

Desiree L.

includes taxes & fees

29 Sept - 30 Sept

A cabin interior with a wooden interior, a kitchen area with a sink and cabinets, a television mounted above the counter, and a large window providing a view of the outdoors.

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

Monmouth

bill w.

includes taxes & fees

28 Sept - 29 Sept

A modern living room with a flat-screen TV, a yellow armchair, a beige sofa, and a coffee table.

6. Two bedroom Mid Century Modern apartment in Downtown Hallowell

Hallowell

Mike W.

A wooden cabin with a porch, a rocking chair, and a table with a lantern.

7. Naughty Dog Private Island Log Cabin

Monmouth

"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....

Peter O.

includes taxes & fees

30 Sept - 1 Oct

A room with a hexagonal glass ceiling, a bed with a plaid blanket, and a view of greenery outside.

8. Floating Island Dome - Pet-Friendly Lake Retreat

Monmouth

includes taxes & fees

27 Sept - 28 Sept

A cozy cabin interior with a brown leather sofa, a matching ottoman, a wooden cabinet, and a star decoration on the ceiling.

9. Glamping in the Lake - Ovah to Camp!

Manchester

includes taxes & fees

25 Sept - 26 Sept

A tent with a bed, two chairs, and a table.

10. Get in touch with nature.

Richmond

Keith R

includes taxes & fees

28 Sept - 29 Sept

A bathroom with a white sink, wooden paneling, a mirror with a bead trim, and a view of a house through a window.

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

Hallowell

Anthony R.

includes taxes & fees

30 Sept - 1 Oct

A covered outdoor seating area with wicker furniture, a ceiling fan, and a view of a lake.

12. Pocasset Lake Cottage, Screened Porch, Canoes and Kayaks

Wayne

"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...

Julie D.

includes taxes & fees

21 Oct - 22 Oct

A two-story house with a front porch, a small tree, and a brick pathway.

13. Perfectly Located 1 Bedroom, newly remodeled

Augusta

Lisa G.

includes taxes & fees

28 Sept - 29 Sept

A wooden cabin with a porch, a door, and a green chair.

14. Sister A-Frame in Woods B

Oakland

Amanda M.

includes taxes & fees

28 Sept - 29 Sept

15. Central Maine Apartment offering 4 Seasons of Fun.

Oakland

kathy e.

includes taxes & fees

28 Sept - 29 Sept

A covered deck with large windows overlooking a lake, a boat on the water, and a forested shoreline.

16. Camp Lintonia on Tacoma Lakes

Litchfield

Meghan C.

includes taxes & fees

28 Sept - 29 Sept

A bedroom with a bed, wooden ceiling, a window with blinds, a nightstand, and a framed picture on the wall.

17. An Authentic Clean & Cozy Maine Homestay

Buckfield

Meagan D.

includes taxes & fees

28 Sept - 29 Sept

A wooden deck with picnic tables overlooking a calm lake, surrounded by dense greenery.

18. Maine river escape: free kayaks, paddle boards, tennis, cute rabbits and fun!

West Gardiner

Robert M.

includes taxes & fees

20 Oct - 21 Oct

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Top Winthrop Hotel Reviews

Hampton Inn Augusta

10/10 Excellent

"We were a late check-in and the staff was fantastic."

Senator Inn & Spa

10/10 Excellent

"The staff were amazing and friendly they answered all our questions and treated us kindly, the spa was to die for it was clean and well maintained we didn’t eat breakfast there but we are booking again so we’ll give that a try next time and the cleanliness of the entire property was impressive there wasn’t an inch of that building that wasn’t clean. Also best coffee I’ve had in a WHILE 😃"

Escape to our cozy Winthrop cabin on Dexter Pond

10/10 Excellent

"It was the most serene place that I have been to in a long time. The cabin was cozy, and everything that could have been thought of to make our stay more comfortable was there. We loved the little statues hidden throughout the cabin, and we even left a memento of our own. I loved being able to wake up to the call of loons, and go to sleep to the hoot of owls. All in all, I will absolutely be booking this for another visit, hopefully longer the next time. Thank you so much Lou-Anne and Rick!"

Find out more about Winthrop

Everything you need to know about Winthrop holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winthrop holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winthrop holiday 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winthrop holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winthrop holiday rentals we have selected for you start as low as €161 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Winthrop rentals

At Expedia, we put the best Winthrop holiday 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 holiday.

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.

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 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.

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Check prices for these dates

Our top choices for Winthrop holiday rentals

1. Cozy cottage in the Winthrop Lakes Area

2. Jill's Place, new construction, lake access Cobbosee, 1 mile from Cabin Masters