Winthrop Vacation Rentals

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Check prices for these dates

In two weeks
May 8 - May 10
In two months
Jun 19 - Jun 21
In three months
Jul 17 - Jul 19
In four months
Aug 14 - Aug 16

Our top choices for Winthrop vacation rentals

Terrace/patio

Cozy cottage in the Winthrop Lakes Area

Cozy cottage in the Winthrop Lakes Area
Winthrop
9.6 out of 10, Exceptional, (4 reviews)
"Lovely cottage! Everything we needed. The hosts were gracious and communicated well."
United States
Joshua
The price is ￥16,576
￥29,360 total
includes taxes & fees
May 3 - May 4
Cozy cottage in the Winthrop Lakes Area
Interior

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
The price is ￥23,907
￥44,126 total
includes taxes & fees
Apr 27 - Apr 28
Jill's Place, new construction, lake access Cobbosee, 1 mile from Cabin Masters
Exterior

Charming Lakefront Home: Big Porches, Kayaks & Room to Gather

Charming Lakefront Home: Big Porches, Kayaks & Room to Gather
Winthrop
9.6 out of 10, Exceptional, (5 reviews)
"Nice place to stay"
United States
Michael Y.
The price is ￥46,619
￥107,797 total
includes taxes & fees
May 3 - May 4
Charming Lakefront Home: Big Porches, Kayaks & Room to Gather
Terrace/patio

Get in touch with nature.

Get in touch with nature.
Richmond
10.0 out of 10, Exceptional, (35 reviews)
"It was a great stay! My partner and i loved it. The whole vibe was great and i would definitely recommend it to others."
United States
Micheal B.
The price is ￥15,938
￥26,059 total
includes taxes & fees
May 11 - May 12
Get in touch with nature.
TV

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, (83 reviews)
"We like this property so much—-it was our second time staying! This apartment is spacious and comfortable. It is located in town and walking distance from small shops and quality restaurants. "
United States
jessica b.
The price is ￥20,719
￥38,219 total
includes taxes & fees
Apr 27 - Apr 28
Two bedroom Mid Century Modern apartment in Downtown Hallowell
Exterior

Sister A-Frame in Woods B

Sister A-Frame in Woods B
Oakland
10.0 out of 10, Exceptional, (9 reviews)
"Great stay. Would stay here again if in the area."
United States
Amanda M.
The price is ￥19,221
￥41,623 total
includes taxes & fees
Apr 27 - Apr 28
Sister A-Frame in Woods B
Exterior

Island Aframe Adventure in Maine

Island Aframe Adventure in Maine
Monmouth
10.0 out of 10, Exceptional, (6 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 ￥11,475
￥39,435 total
includes taxes & fees
May 1 - May 2
Island Aframe Adventure in Maine
Fridge, microwave, oven, stovetop

Waterfront 2br/2ba cottage

Waterfront 2br/2ba cottage
West Gardiner
9.8 out of 10, Exceptional, (17 reviews)
"Very nice and clean place. We used this rental as a hub to go around and see lots that Maine had to offer. Hosts were very nice and kept a very clean place."
United States
Bruce J.
The price is ￥17,213
￥52,291 total
includes taxes & fees
Apr 27 - Apr 28
Waterfront 2br/2ba cottage
Exterior

Discover Oakland charm near Colby College 10 min

Discover Oakland charm near Colby College 10 min
Oakland
10.0 out of 10, Exceptional, (9 reviews)
"Very clean and comfy. A pleasure to stay there. "
United States
Vicki W.
The price is ￥18,647
￥36,655 total
includes taxes & fees
Apr 27 - Apr 28
Discover Oakland charm near Colby College 10 min
2 bedrooms, WiFi, bed sheets

The heart of the Belgrade Lakes

The heart of the Belgrade Lakes
Oakland
9.0 out of 10, Wonderful, (9 reviews)
"Host was very accommodating "
United States
Maureen
The price is ￥18,329
￥37,177 total
includes taxes & fees
May 1 - May 2
The heart of the Belgrade Lakes
Property grounds

Central Maine Apartment offering 4 Seasons of Fun.

Central Maine Apartment offering 4 Seasons of Fun.
Oakland
10.0 out of 10, Exceptional, (44 reviews)
"Great hiking - nice views."
United States
Norbert A.
The price is ￥16,097
￥38,393 total
includes taxes & fees
May 7 - May 8
Central Maine Apartment offering 4 Seasons of Fun.
Property grounds

Cozy Cottage on water's edge of Lake Cobbosseecontee

Cozy Cottage on water's edge of Lake Cobbosseecontee
Manchester
8.8 out of 10, Excellent, (21 reviews)
"Very quiet spot right on the lake, relatively easy to get to, close to town. Cabin is small, which was perfect for the two of us. "
United States
Stephanie P.
The price is ￥23,110
￥53,681 total
includes taxes & fees
Apr 27 - Apr 28
Cozy Cottage on water's edge of Lake Cobbosseecontee
WiFi, bed sheets

Quaint 1-bedroom apartment with AC in charming Lewiston

Quaint 1-bedroom apartment with AC in charming Lewiston
Lewiston
The price is ￥15,938
￥39,262 total
includes taxes & fees
May 1 - May 2
Quaint 1-bedroom apartment with AC in charming Lewiston
Interior

Island Tree House Glamping

Island Tree House Glamping
Monmouth
10.0 out of 10, Exceptional, (9 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 ￥13,069
￥53,333 total
includes taxes & fees
May 1 - May 2
Island Tree House Glamping
Terrace/patio

Hammock Haven Island Dome

Hammock Haven Island Dome
Monmouth
10.0 out of 10, Exceptional, (3 reviews)
"Could not have asked for a better way to end our vacation than a visit to this island. For being a sustainable space it does not lack in amenities conducive to comfort, and the setting is pristine. I had particular fondness for the rope swing!!"
United States
BlairR
The price is ￥9,403
￥33,702 total
includes taxes & fees
May 3 - May 4
Hammock Haven Island Dome
Exterior

Pool, fire pit & dogs welcome, close to lakes and trails - Maine Farm Getaway

Pool, fire pit & dogs welcome, close to lakes and trails - Maine Farm Getaway
Oakland
10.0 out of 10, Exceptional, (11 reviews)
"Very accommodating host. Loved everything about it. Highly recommend "
United States
Mike M.
The price is ￥31,717
￥57,632 total
includes taxes & fees
Apr 27 - Apr 28
Pool, fire pit & dogs welcome, close to lakes and trails - Maine Farm Getaway
Outdoor spa tub

Cabin Style Studio Apt with Private Hot tub on 100 Acres Kayaks, Canoes & SUP

Cabin Style Studio Apt with Private Hot tub on 100 Acres Kayaks, Canoes & SUP
Whitefield
10.0 out of 10, Exceptional, (6 reviews)
"Great getaway! We loved all of the discoveries to be made both in the cabin and on the property. We stayed in Stella. It was adorable, functional, and very welcoming. We also enjoyed an outing to Kennebec Maine Cabin Masters only 20 min away! "
United States
Sandra L.
The price is ￥28,688
￥44,126 total
includes taxes & fees
May 4 - May 5
Cabin Style Studio Apt with Private Hot tub on 100 Acres Kayaks, Canoes & SUP
Interior

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, (53 reviews)
"Great location!"
United States
Gail D.
The price is ￥22,536
￥52,708 total
includes taxes & fees
May 3 - May 4
Boat launch and Trailer parking, Dog Friendly, Lake Great Pond
3 bedrooms, desk, iron/ironing board, free WiFi

An Authentic Clean & Cozy Maine Homestay

An Authentic Clean & Cozy Maine Homestay
Buckfield
9.8 out of 10, Exceptional, (66 reviews)
"Very nice and comfortable house, clean and quiet. The hosts were very responsive. We had a great stay."
United States
Jessica Stebbins B.
The price is ￥19,795
￥32,695 total
includes taxes & fees
Apr 28 - Apr 29
An Authentic Clean & Cozy Maine Homestay
Property grounds

Island Tent Overlook in Maine

Island Tent Overlook in Maine
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 ￥11,475
￥39,261 total
includes taxes & fees
May 1 - May 2
Island Tent Overlook in Maine
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

Maine Evergreen Hotel, an Ascend Collection Hotel

Maine Evergreen Hotel, an Ascend Collection Hotel

10/10 Excellent
"The breakfast"
alison 1-night trip
Posted 14 hours ago
Maine Evergreen Hotel, an Ascend Collection Hotel

Find out more about Winthrop

Search for holiday rentals in Winthrop on Expedia! You can easily find your home rentals, villas, holiday apartments in Winthrop using one of the methods below:

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Look no further and take a look at our great range of rental properties in Winthrop!

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?

Cozy Long Pond Cottage: community access, private mooring & shared dock.: Visitors like this Winthrop vacation home rental. It 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 12 vacation 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, Wilson Pond 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.