A wooden signpost with 'WINTHROP' written on it, surrounded by greenery and trees.

Winthrop Vacation Rentals

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Check prices for these dates

In two weeks
Jul 24 - Jul 26
In two months
Sep 4 - Sep 6
In three months
Oct 2 - Oct 4
In four months
Oct 30 - Nov 1

Our top choices for Winthrop vacation rentals

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
10.0 out of 10, Exceptional, (1 review)
"This is an adorable newly constructed unit. Lots of day light, cute decor and lake views. The one confusing part was the use of the docks which was uncomfortable at the beginning but worked out in the end. We used the dock and swam every day. The location is also convenient and has plenty of parking. Jill is a great host. We would stay here again."
United States
Katie D.
$291 nightly
The price is $317
Jul 14 - Jul 15
Total with taxes and fees
Jill's Place, new construction, lake access Cobbosee, 1 mile from Cabin Masters
Terrace/patio

Get in touch with nature.

Get in touch with nature.
Richmond
10.0 out of 10, Exceptional, (43 reviews)
"Great place to stay and pet friendly. "
United States
Kevin M.
$140 nightly
The price is $153
Jul 20 - Jul 21
Total with taxes and fees
Get in touch with nature.
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.
$237 nightly
The price is $258
Jul 15 - Jul 16
Total with taxes and fees
Sister A-Frame in Woods B
Exterior

Discover Oakland charm near Colby College 10 min

Discover Oakland charm near Colby College 10 min
Oakland
9.8 out of 10, Exceptional, (13 reviews)
"Place was very clean. Host was wonderful and easy to communicate with. "
United States
Tammy W.
$182 nightly
The price is $198
Jul 14 - Jul 15
Total with taxes and fees
Discover Oakland charm near Colby College 10 min
Cottage (2 Bedrooms) | Front of property

Private Dock on Messalonskee Lake: Cozy Cottage!

Private Dock on Messalonskee Lake: Cozy Cottage!
3.0 star property
Augusta
10.0 out of 10, Exceptional, (1 review)
"Great little lake cabin. Had everything we needed. Clean, comfortable, quite. Beautiful area and views. We had a wonderful stay and would stay again."
United States
John
$311 nightly
The price is $338
Jul 29 - Jul 30
Total with taxes and fees
Private Dock on Messalonskee Lake: Cozy Cottage!
Spa

Floating Island Dome - Pet-Friendly Lake Retreat

Floating Island Dome - Pet-Friendly Lake Retreat
Monmouth
$214 nightly
The price is $233
Jul 20 - Jul 21
Total with taxes and fees
Floating Island Dome - Pet-Friendly Lake Retreat
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
$215 nightly
The price is $234
Jul 24 - Jul 25
Total with taxes and fees
The heart of the Belgrade Lakes
Fridge, microwave, oven, stovetop

Steps from Bates College, Quiet Cottage Retreat

Steps from Bates College, Quiet Cottage Retreat
Lewiston
10.0 out of 10, Exceptional, (2 reviews)
"Great little spot with easy access to the college. Host was great and included some very thoughtful touches, which were much appreciated."
United States
Joseph D.
$147 nightly
The price is $160
Jul 22 - Jul 23
Total with taxes and fees
Steps from Bates College, Quiet Cottage Retreat
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.
$310 nightly
The price is $338
Jul 13 - Jul 14
Total with taxes and fees
Island Tree House Glamping
Property grounds

Floating Island Cabin

Floating Island Cabin
Monmouth
10.0 out of 10, Exceptional, (9 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.
$273 nightly
The price is $298
Jul 26 - Jul 27
Total with taxes and fees
Floating Island Cabin
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
Jul 20 - Jul 21
Total with taxes and fees
An Authentic Clean & Cozy Maine Homestay
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, (23 reviews)
"Location is amazing "
United States
Laura Q.
$349 nightly
The price is $380
Jul 16 - Jul 17
Total with taxes and fees
Cozy Cottage on water's edge of Lake Cobbosseecontee
Exterior

Perfectly Located 1 Bedroom, newly remodeled

Perfectly Located 1 Bedroom, newly remodeled
Augusta
10.0 out of 10, Exceptional, (3 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.
$246 nightly
The price is $268
Jul 13 - Jul 14
Total with taxes and fees
Perfectly Located 1 Bedroom, newly remodeled
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.
$172 nightly
The price is $187
Jul 14 - Jul 15
Total with taxes and fees
Cozy newly built 1-bedroom unit 2 Kentucky Bay in charming Smithfield Maine
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, (7 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.
$279 nightly
The price is $304
Aug 3 - Aug 4
Total with taxes and fees
Cabin Style Studio Apt with Private Hot tub on 100 Acres Kayaks, Canoes & SUP
1 bedroom, WiFi, bed sheets

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

Charming 1-bedroom apartment in Monmouth with AC, WiFi. Several lakes nearby.
Monmouth
9.0 out of 10, Wonderful, (2 reviews)
"For our 2 night stay we just needed a place to end the long day with, very quiet."
United States
Tricia R.
$220 nightly
The price is $240
Jul 13 - Jul 14
Total with taxes and fees
Charming 1-bedroom apartment in Monmouth with AC, WiFi. Several lakes nearby.
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)
$464 nightly
The price is $506
Jul 29 - Jul 30
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
$263 nightly
The price is $287
Jul 13 - Jul 14
Total with taxes and fees
Beautifully remodeled first floor of a duplex home, surrounded by privacy fence
TV

Readfield Retreat w/ Lake Maranacook Views!

Readfield Retreat w/ Lake Maranacook Views!
Readfield
9.4 out of 10, Exceptional, (14 reviews)
"very clean and quiet place "
United States
Ryan C.
Readfield Retreat w/ Lake Maranacook Views!
Interior

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

River View Retreat, Hot Tub, Balcony, Kayaks & Bikes
Hallowell
10.0 out of 10, Exceptional, (1 review)
"Great place and great host. Right in the water and close to New York and Canada"
United States
Anthony R.
$160 nightly
The price is $175
Jul 13 - Jul 14
Total with taxes and fees
River View Retreat, Hot Tub, Balcony, Kayaks & Bikes
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
"Great place! Friendly staff, good amenities and pub food was quite good."
Sandra 1-night trip
Posted 2 hours ago
Maine Evergreen Hotel, an Ascend Collection Hotel

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?

Enjoy Sunset views on tranquil Dexter Pond: Visitors like this Winthrop vacation home rental. It is located on the waterfront and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. 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 15 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, Annabessacook Lake and Wilson Pond 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.