Winthrop Holiday Rentals

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Holiday Rentals in Winthrop

Fridge, microwave, stovetop, dishwasher
Peaceful Fisherman's Paradise w/ Deck + Fire Pit!
10.0 out of 10, Exceptional, (23)
"Lovely little house right on Annabessacook Lake in Maine, with everything you might need. Great kayaking right from the property. Thoroughly enjoyed our stay."
Peaceful Fisherman's Paradise w/ Deck + Fire Pit!
Interior
Dog Friendly Cabin Right On The Water!!!
2.0 out of 10, (1)
"The renter is not worth coming about the fact that her home is on a very steep hill. I told her I was a senior and had foot and ankle and knee surgeries and had a hard time walking. I saved up to rent a place all year. When I got there I had to call her to find out how to get to the lake. It is so steep I couldn't find an entrance to the lake, I finally found a foot wide muddy, slippery path which was 90 degrees straight up and down. I only took a few steps and realized I would break my neck if...
Dog Friendly Cabin Right On The Water!!!
Fridge, microwave, oven, stovetop
Fantastic Lakefront Cabin W/ Free WiFi, Three Kayaks, Private Dock, & Firepit
9.6 out of 10, Exceptional, (20)
"I just wrote an extensive review to VACASA. Please see that!!"
Fantastic Lakefront Cabin W/ Free WiFi, Three Kayaks, Private Dock, & Firepit
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Fridge, microwave, oven, stovetop
Cottage on Cobbosseecontee Lake. Dates available.
10.0 out of 10, Exceptional, (146)
"Sweet house and view"
Cottage on Cobbosseecontee Lake. Dates available.
Property grounds
Lakefront Cottage - sleeps 6 - 2 baths
10.0 out of 10, Exceptional, (2)
"Great size, very clean. The posted pictures do not do this camp justice! Lots of upgrades and Beth is very responsive. Beautiful cove with little traffic. Sounds of loons day and night. Great bass fishing too! There is a wonderful dock but be sure to bring your own water toys. Great place for children with neighbors that encourage lots of kid play, exploring/adventuring, and boisterous fun."
Lakefront Cottage - sleeps 6 - 2 baths
Fridge, microwave, oven, stovetop
Waterfront 2br/2ba cottage
10.0 out of 10, Exceptional, (3)
"Great location. Clean. Very well stocked. Great communication."
The price is NZ$789
per night
11 Jun - 12 Jun
Waterfront 2br/2ba cottage
Fridge, microwave, oven, stovetop
Dog-friendly lakefront home with dock, fireplace, firepit, lake views, & 1 kayak
8.4 out of 10, Very good, (6)
"Myself and 4 friends booked this home on the water for an annual super bowl ice fishing trip. The house was just as described, spacious and comfortable. The pond is beautiful and the fishing was outstanding, we caught fish all day long. Location is good as well, with plenty of restaurants and downtown Augusta within 10 to 15 minutes. Great home for the price."
Dog-friendly lakefront home with dock, fireplace, firepit, lake views, & 1 kayak
Fridge, microwave, oven, stovetop
An Authentic Clean & Cozy Maine Homestay
10.0 out of 10, Exceptional, (47)
"Our stay at this property was excellent, start to finish. Priced right for the location and the amenities, the place was everything as described. Comfortable bedding, flexible sleeping arrangements (3 bedrooms) and well equipped. Communication with the manager/owner was easy and quick. Highly recommend this property for a no frills experience. About an hour drive to Sunday River resort where we skied."
The price is NZ$304
per night
22 May - 23 May
An Authentic Clean & Cozy Maine Homestay
Fridge, microwave, oven, stovetop
*Lakefront Maine* @Sabattus Sunset Cottage 🌅
10.0 out of 10, Exceptional, (12)
"What a great house! The house was everything it was advertised to be, complete with a beautiful sunset over the lake. Super comfortable, clean with nice decor/touches throughout the house. It was a wonderful home away from home!"
*Lakefront Maine* @Sabattus Sunset Cottage 🌅
Exterior
Tiny House on 100 Acres Kayaks/Canoes/Paddleboards
9.8 out of 10, Exceptional, (20)
"I was offered Stella which is a beautiful little apartment due to a mistake I made when applying to stay in Roxie. I didn't realize Roxie was solar and I really needed electricity for this stay. It was a more a business trip not a camping trip.Sherri very graciously let me stay in Stella which was wonderful . Very clean, bright , everything you could need . I would definitely stay there again.."
The price is NZ$258
per night
1 Jun - 2 Jun
Tiny House on 100 Acres Kayaks/Canoes/Paddleboards
Fridge, microwave, stovetop, coffee/tea maker
Sunset Chalet- Stylish Waterfront Gem
10.0 out of 10, Exceptional, (20)
"This is by far one of the best places we’ve stayed. From the beautiful decor, exposed wood and cozy fireplace. It was the attention to detail and small little extras that made this an extra special visit. The serene music playing as you enter the home to the specialized note and picnic basket! They are very accommodating to any situation that may arise and communicate on a five star level. An amazing stay and will be visiting again!"
The price is NZ$1,465
per night
23 May - 24 May
Sunset Chalet- Stylish Waterfront Gem
Smart TV, books
ENJOY TWIN PONDS WHILE EXPLORING MIDCOAST MAINE
10.0 out of 10, Exceptional, (47)
"Had a really nice stay at twin ponds. Luana and Brian are great host and the place was ideal for me visit. Can’t wait to visit again."
ENJOY TWIN PONDS WHILE EXPLORING MIDCOAST MAINE
Interior
MoonLight Treehouse- Luxury Waterfront Escape
10.0 out of 10, Exceptional, (10)
"My husband and I have 4 kids together and 7 pets, to say we needed this little trip is an understatement. It was peaceful, beautiful and so relaxing."
The price is NZ$1,370
per night
22 May - 23 May
MoonLight Treehouse- Luxury Waterfront Escape
TV, fireplace, books
Waterfront Dresden Cabin with Deck + Fire Pit!
8.0 out of 10, Very good, (4)
"Relaxed, peaceful, pleasantly cool, embedded in nature. Day trip into Boothbay for kayaking. Wiscasset for notorious Red's Eats line and lobster rolls. Evening and rainy afternoon family time in and around the cabin were among the highlights of our stay in Maine."
Waterfront Dresden Cabin with Deck + Fire Pit!
View from property
Cozy lake house on Sabattus Pond 2 bed 1 Bath
10.0 out of 10, Exceptional, (3)
"Very nice stay. Nice safe area with access to the pond. Very clean. Great place to stay for a little getaway to do some fishing."
The price is NZ$352
per night
15 Jun - 16 Jun
Cozy lake house on Sabattus Pond 2 bed 1 Bath
Exterior
Light-Filled Log Home, 4 Wooded Acres, & Lake Access. The water is 0.4 mi away.
10.0 out of 10, Exceptional, (51)
"The property was just as described and we enjoyed the peace and quiet. The cabin is beautiful and very well appointed. I would definitely recommend it to friends."
Light-Filled Log Home, 4 Wooded Acres, & Lake Access. The water is 0.4 mi away.
Nature lovers Paradise your own island
9.8 out of 10, Exceptional, (59)
"This is our third summer staying here for a week and it was perfect as usual! Thanks Deb!"
Nature lovers Paradise your own island
Property grounds
Screen Porch with see thru roof, BQ, 30' from sandy beach, canoe and 3 kayaks
7.6 out of 10, Good, (22)
"The location of King’s Kastle on Salmon Lake is excellent. The lake is wide at that point and offers great views of the sunrise, particularly from the upstairs master bedroom suite. The lake has less development than others where we have stayed in Maine. We enjoyed seeing loons, eagles, and osprey which are abundant. We went in the latter part of August when the kids’ summer camps had closed, which reduced boat traffic. The cottage is roomy and has a long list of amenities. All appliances were...
Screen Porch with see thru roof, BQ, 30' from sandy beach, canoe and 3 kayaks
Terrace/patio
Chalet in Western Maine, Fireplace, Fire pit, sleeps 6
10.0 out of 10, Exceptional, (15)
"Great rental house for 6. Property was clean and well maintained, amnesties were what we needed. Self check-in/out process was too easy. Looking forward to revisiting in the future."
Chalet in Western Maine, Fireplace, Fire pit, sleeps 6
TV, DVD player
Rustic lakefront cabin w/gas grill, firepit, kayaks, one canoe, A/C - 2 dogs OK
9.0 out of 10, Wonderful, (4)
"Beautiful stay and awesome host! Bill was just as amazing as the fishing. Will be venturing back for sure! -Derek"
Rustic lakefront cabin w/gas grill, firepit, kayaks, one canoe, A/C - 2 dogs OK
Don't see what you're looking for?
See all available properties in Winthrop
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.

Other types of properties in Winthrop you may be interested in

Interior
Dog Friendly Cabin Right On The Water!!!
2.0 out of 10, (1)
"The renter is not worth coming about the fact that her home is on a very steep hill. I told her I was a senior and had foot and ankle and knee surgeries and had a hard time walking. I saved up to rent a place all year. When I got there I had to call her to find out how to get to the lake. It is so steep I couldn't find an entrance to the lake, I finally found a foot wide muddy, slippery path which was 90 degrees straight up and down. I only took a few steps and realized I would break my neck if...
Dog Friendly Cabin Right On The Water!!!
Fridge, microwave, oven, stovetop
Fantastic Lakefront Cabin W/ Free WiFi, Three Kayaks, Private Dock, & Firepit
9.6 out of 10, Exceptional, (20)
"I just wrote an extensive review to VACASA. Please see that!!"
Fantastic Lakefront Cabin W/ Free WiFi, Three Kayaks, Private Dock, & Firepit
Fridge, microwave, oven, stovetop
Cottage on Cobbosseecontee Lake. Dates available.
10.0 out of 10, Exceptional, (146)
"Sweet house and view"
Cottage on Cobbosseecontee Lake. Dates available.
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.

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?

Dog-friendly lakefront home with dock, fireplace, firepit, lake views, & 1 kayak: This holiday home rental outside of Winthrop is located on a lake, and has a fireplace, a patio and laundry facilities to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind.

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?

Cobbosseecontee Lake and Annabessacook Lake are a couple of lovely local spots to get outside and enjoy nature. While here, Maranacook Lake and Mt Pisgah Conservation Area Trailhead 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.

Recent reviews of Winthrop properties
Expedia verified reviews