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Winthrop Vacation Rentals

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Check prices for these dates

In two weeks
Jul 3 - Jul 5
In two months
Aug 14 - Aug 16
In three months
Sep 11 - Sep 13
In four months
Oct 9 - Oct 11

Our top choices for Winthrop vacation rentals

Terrace/patio

Cozy cottage in the Winthrop Lakes Area

Cozy cottage in the Winthrop Lakes Area
Winthrop
9.8 out of 10, Exceptional, (6 reviews)
"Lovely cottage! Everything we needed. The hosts were gracious and communicated well."
United States
Joshua
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
$268 nightly
The price is $292
Jun 22 - Jun 23
Total with taxes and fees
Jill's Place, new construction, lake access Cobbosee, 1 mile from Cabin Masters
Exterior

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.
$784 nightly
The price is $854
Jun 24 - Jun 25
Total with taxes and fees
July 7 to 14 Available: Big Porches w/ Scenic Views, Kayaks & Room to Gather
Terrace/patio

Get in touch with nature.

Get in touch with nature.
Richmond
10.0 out of 10, Exceptional, (38 reviews)
"Great place to stay and pet friendly. "
United States
Kevin M.
$140 nightly
The price is $153
Jun 22 - Jun 23
Total with taxes and fees
Get in touch with nature.
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
$174 nightly
The price is $190
Jun 23 - Jun 24
Total with taxes and fees
Hammock Haven Island Dome
Property grounds

Floating Island Cabin

Floating Island Cabin
Monmouth
10.0 out of 10, Exceptional, (8 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.
$274 nightly
The price is $299
Jun 21 - Jun 22
Total with taxes and fees
Floating Island Cabin
Exterior

Discover Oakland charm near Colby College 10 min

Discover Oakland charm near Colby College 10 min
Oakland
10.0 out of 10, Exceptional, (11 reviews)
"Very clean and comfy. A pleasure to stay there. "
United States
Vicki W.
$180 nightly
The price is $196
Jul 5 - Jul 6
Total with taxes and fees
Discover Oakland charm near Colby College 10 min
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.
$296 nightly
The price is $323
Jun 22 - Jun 23
Total with taxes and fees
Island Tree House Glamping
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, (67 reviews)
"My tenants said the accommodations were lovely "
United States
Nathan
$188 nightly
The price is $205
Jun 22 - Jun 23
Total with taxes and fees
An Authentic Clean & Cozy Maine Homestay
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, (47 reviews)
"Great hiking - nice views."
United States
Norbert A.
$235 nightly
The price is $256
Jun 22 - Jun 23
Total with taxes and fees
Central Maine Apartment offering 4 Seasons of Fun.
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
$269 nightly
The price is $293
Jul 8 - Jul 9
Total with taxes and fees
Island Aframe Adventure in Maine
Outdoor dining

Peaceful retreat on farm minutes to lake. Bring kayak or canoe!

Peaceful retreat on farm minutes to lake. Bring kayak or canoe!
Oakland
10.0 out of 10, Exceptional, (12 reviews)
"It was a great stay. The house is very comfortable"
United States
Benjamin C.
$413 nightly
The price is $441
Jun 21 - Jun 22
Total with taxes and fees
Peaceful retreat on farm minutes to lake. Bring kayak or canoe!
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
$216 nightly
The price is $235
Jul 2 - Jul 3
Total with taxes and fees
The heart of the Belgrade Lakes
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.
$256 nightly
The price is $279
Jun 22 - Jun 23
Total with taxes and fees
Cabin Style Studio Apt with Private Hot tub on 100 Acres Kayaks, Canoes & SUP
Outdoor dining

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, (19 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.
$410 nightly
The price is $447
Jun 28 - Jun 29
Total with taxes and fees
Maine river escape: free kayaks, paddle boards, tennis, cute rabbits and fun!
Living area

Beautifully remodeled first floor of a duplex home, surrounded by privacy fence

Beautifully remodeled first floor of a duplex home, surrounded by privacy fence
Sabattus
$246 nightly
The price is $268
Jun 21 - Jun 22
Total with taxes and fees
Beautifully remodeled first floor of a duplex home, surrounded by privacy fence
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.
$259 nightly
The price is $282
Jun 29 - Jun 30
Total with taxes and fees
Island Tent Overlook in Maine
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, (22 reviews)
"Location is amazing "
United States
Laura Q.
$332 nightly
The price is $362
Jun 25 - Jun 26
Total with taxes and fees
Cozy Cottage on water's edge of Lake Cobbosseecontee
Fridge, microwave, oven, stovetop

Whitsendsport unit 4 1 bedroom & queen pull out couch on 50 acres Smithfield

Whitsendsport unit 4 1 bedroom & queen pull out couch on 50 acres Smithfield
Smithfield
$150 nightly
The price is $164
Jun 21 - Jun 22
Total with taxes and fees
Whitsendsport unit 4 1 bedroom & queen pull out couch on 50 acres Smithfield
Paper towels

Cozy newly built 1-bedroom unit 2 Kentucky Bay in charming Smithfield Maine

Cozy newly built 1-bedroom unit 2 Kentucky Bay in charming Smithfield Maine
Smithfield
10.0 out of 10, Exceptional, (1 review)
"We had a great weekend stay at this newly built place in Smithfield while attending a swim event with my son at Colby College, which was just a short, easy drive away. Everything was clean and cozy, and the place had everything we needed for a comfortable stay. The host was helpful and highly responsive and recommended a local fishing spot on one of the three lakes right around the property which was very close and a nice way to spend down time. Overall, a solid choice!"
United States
Gustavo C.
$150 nightly
The price is $164
Jun 22 - Jun 23
Total with taxes and fees
Cozy newly built 1-bedroom unit 2 Kentucky Bay in charming Smithfield 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

Fairfield Inn & Suites by Marriott Augusta

Fairfield Inn & Suites by Marriott Augusta

8/10 Good
"Clean room and lobby. Pool"
Meagan Or Aaron 2-night trip
Posted 13 hours ago
Fairfield Inn & Suites by Marriott Augusta

Find out more about Winthrop

Everything you need to know about Winthrop vacation rentals

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

Winthrop vacation 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 low season months. For more hustle and bustle, you may prefer to visit Winthrop in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $153 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winthrop rentals

At Expedia, we put the best Winthrop vacation 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 vacation.

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.

Explore a world of travel with Expedia

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 Cottage on water's edge of Lake Cobbosseecontee: You might want to consider this vacation home rental near Winthrop, which is located on a lake and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave.

How many vacation rentals are there in Winthrop?

Expedia has 14 vacation rentals for your stay in Winthrop.

What can I see and do in Winthrop?

Cobbosseecontee Lake and Maranacook 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.