Winthrop Vacation Rentals

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Check prices for these dates

In two weeks
Jun 12 - Jun 14
In two months
Jul 24 - Jul 26
In three months
Aug 21 - Aug 23
In four months
Sep 18 - Sep 20

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, (5 reviews)
"Lovely cottage! Everything we needed. The hosts were gracious and communicated well."
United States
Joshua
$181 nightly
The price is $197
Jun 16 - Jun 17
Total with taxes and fees
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
$266 nightly
The price is $290
Jun 1 - Jun 2
Total with taxes and fees
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.
$657 nightly
The price is $716
Jun 14 - Jun 15
Total with taxes and fees
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)
"Great place to stay and pet friendly. "
United States
Kevin M.
$140 nightly
The price is $153
Jun 1 - Jun 2
Total with taxes and fees
Get in touch with nature.
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
$297 nightly
The price is $324
Jun 8 - Jun 9
Total with taxes and fees
Private Dock on Messalonskee Lake: Cozy Cottage!
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.
$240 nightly
The price is $261
May 29 - May 30
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
10.0 out of 10, Exceptional, (11 reviews)
"Very clean and comfy. A pleasure to stay there. "
United States
Vicki W.
$181 nightly
The price is $197
Jun 1 - Jun 2
Total with taxes and fees
Discover Oakland charm near Colby College 10 min
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, (86 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.
$234 nightly
The price is $255
Jun 7 - Jun 8
Total with taxes and fees
Two bedroom Mid Century Modern apartment in Downtown Hallowell
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
$186 nightly
The price is $203
May 31 - Jun 1
Total with taxes and fees
Hammock Haven Island Dome
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.
$321 nightly
The price is $350
Jun 4 - Jun 5
Total with taxes and fees
Waterfront 2br/2ba cottage
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)
"Location is amazing "
United States
Laura Q.
$308 nightly
The price is $336
May 29 - May 30
Total with taxes and fees
Cozy Cottage on water's edge of Lake Cobbosseecontee
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
$234 nightly
The price is $255
Jun 3 - Jun 4
Total with taxes and fees
Island Aframe Adventure in Maine
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, (45 reviews)
"Great hiking - nice views."
United States
Norbert A.
$227 nightly
The price is $247
Jun 1 - Jun 2
Total with taxes and fees
Central Maine Apartment offering 4 Seasons of Fun.
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.
$304 nightly
The price is $331
May 31 - Jun 1
Total with taxes and fees
Island Tree House Glamping
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.
$218 nightly
The price is $238
May 31 - Jun 1
Total with taxes and fees
Island Tent Overlook in Maine
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, (54 reviews)
"Great location!"
United States
Gail D.
$319 nightly
The price is $347
Jun 1 - Jun 2
Total with taxes and fees
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.
$187 nightly
The price is $204
Jun 1 - Jun 2
Total with taxes and fees
An Authentic Clean & Cozy Maine Homestay
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 9 - Jun 10
Total with taxes and fees
Cabin Style Studio Apt with Private Hot tub on 100 Acres Kayaks, Canoes & SUP
Exterior

Perfectly Located 1 Bedroom, newly remodeled

Perfectly Located 1 Bedroom, newly remodeled
Augusta
10.0 out of 10, Exceptional, (1 review)
"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.
$243 nightly
The price is $265
Jun 1 - Jun 2
Total with taxes and fees
Perfectly Located 1 Bedroom, newly remodeled
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

Best Western Plus Augusta Civic Center Inn

Best Western Plus Augusta Civic Center Inn

4/10 Poor
"One of my rooms smelled like wet dog, there was a used bar of soap on the tub, the shower was terrible. Barely any hot water. The beds were not comfortable. I wouldn’t stay there again!"
Chrissy 1-night trip
Posted 4 hours ago
Best Western Plus Augusta Civic Center Inn

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 $197 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?

Spacious 5-bedroom lakefront home on pristine Lower Narrows Pond in Winthrop: Visitors like this Winthrop vacation home rental. It offers a fireplace, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

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?

Wilson Pond and Cobbosseecontee Lake are a couple of lovely local spots to get outside and enjoy nature. While here, Maranacook Lake 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.