Winthrop Vacation Rentals

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Nov 22 - Nov 23
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Nov 28 - Nov 30
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Dec 5 - Dec 7

Vacation Rentals in Winthrop

Exterior
Charming Guest House on Farm - Pets Welcome

Charming Guest House on Farm - Pets Welcome

Oakland
10.0 out of 10, Exceptional, (7)
"Enjoyed a 2 night stay at this quiet country retreat. Our host was friendly and took time to visit. The kitchen was well stocked and it's a charming historic structure, equipped with modern conveniences. What more could you want! "
United States
Alvin W.
$257 nightly
The price is $276
Nov 23 - Nov 24
Total with taxes and fees
Charming Guest House on Farm - Pets Welcome
Fridge, microwave, oven, stovetop
Waterfront 2br/2ba cottage

Waterfront 2br/2ba cottage

West Gardiner
9.8 out of 10, Exceptional, (15)
"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.
$263 nightly
The price is $286
Nov 23 - Nov 24
Total with taxes and fees
Waterfront 2br/2ba cottage
Living area
The heart of the Belgrade Lakes

The heart of the Belgrade Lakes

Oakland
9.0 out of 10, Wonderful, (9)
"Host was very accommodating "
United States
Maureen
$176 nightly
The price is $191
Nov 23 - Nov 24
Total with taxes and fees
The heart of the Belgrade Lakes
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, (80)
"Easy check in super clean comfy beds organizdd"
United States
Josee Y.
$217 nightly
The price is $237
Nov 29 - Nov 30
Total with taxes and fees
Two bedroom Mid Century Modern apartment in Downtown Hallowell
Fridge, microwave, oven, stovetop
Discover Oakland charm near Colby College 10 min

Discover Oakland charm near Colby College 10 min

2.0 star property
Oakland
10.0 out of 10, Exceptional, (6)
"New, clean and had everything we needed. "
United States
Lara B.
$238 nightly
The price is $260
Dec 1 - Dec 2
Total with taxes and fees
Discover Oakland charm near Colby College 10 min
Exterior
Sister A-Frame in Woods B

Sister A-Frame in Woods B

Oakland
10.0 out of 10, Exceptional, (8)
"Great stay. Would stay here again if in the area."
United States
Amanda M.
$210 nightly
The price is $228
Nov 24 - Nov 25
Total with taxes and fees
Sister A-Frame in Woods B
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, (43)
"The place was clean, very spacious and comfortable. Having the laundry was helpful, so I didn’t have to worry about doing laundry when I got home late (also, I spilled coffee on the way there, so I’m glad the stain was gone)."
United States
Keeko
$226 nightly
The price is $246
Nov 23 - Nov 24
Total with taxes and fees
Central Maine Apartment offering 4 Seasons of Fun.
Interior
Rustic Charm Meets Modern Luxury: Stylish 2BR, 1BA Apartment

Rustic Charm Meets Modern Luxury: Stylish 2BR, 1BA Apartment

Auburn
9.6 out of 10, Exceptional, (8)
"My daughter and I loved our stay at this property. Access instructions were communicated clearly and the location was safe and comfy. Definitely would recommend for visitors to Auburn/Lewiston area."
United States
Judith P.
$296 nightly
The price is $323
Nov 24 - Nov 25
Total with taxes and fees
Rustic Charm Meets Modern Luxury: Stylish 2BR, 1BA Apartment
Outdoor dining
Ice Fishing, Dog Friendly, Lake Great Pond

Ice Fishing, Dog Friendly, Lake Great Pond

Belgrade
10.0 out of 10, Exceptional, (48)
"The house was great, and the owners were very communicative and responsive. Would definitely recommend and stay again!"
United States
Jonathon R.
$254 nightly
The price is $276
Nov 23 - Nov 24
Total with taxes and fees
Ice Fishing, Dog Friendly, Lake Great Pond
Front of property
My Valhalla Farm

My Valhalla Farm

3.5 star property
Oakland
$249 nightly
The price is $272
Nov 23 - Nov 24
Total with taxes and fees
My Valhalla Farm
Property grounds
Cozy Cottage on water's edge of Lake Cobbosseecontee

Cozy Cottage on water's edge of Lake Cobbosseecontee

Manchester
8.6 out of 10, Excellent, (18)
"Check in was a breeze. Right on the lake. House was just the right size for me and my 3 adult sons. Was lovely to paddle, canoe or swim just walking down the porch stairs"
United States
Heather A.
$293 nightly
The price is $319
Nov 23 - Nov 24
Total with taxes and fees
Cozy Cottage on water's edge of Lake Cobbosseecontee
Property grounds
Tiny Cabin with Private Hot Tub on 100 Acres Kayaks, Canoes & Paddleboards

Tiny Cabin with Private Hot Tub on 100 Acres Kayaks, Canoes & Paddleboards

Whitefield
9.8 out of 10, Exceptional, (29)
"We stayed in this cabin for two nights with our dog and it was very peaceful and fun! The cabin has a campfire, lots of batteries for charging, lights, battery fans, etc. There were many long walking trails with fun activities; like kayaking, axe throwing, a pizza oven… Exactly what we were looking for! Would stay again! "
United States
Ben R.
$206 nightly
The price is $225
Nov 23 - Nov 24
Total with taxes and fees
Tiny Cabin with Private Hot Tub on 100 Acres Kayaks, Canoes & Paddleboards
3 bedrooms, desk, iron/ironing board, free WiFi
An Authentic Clean & Cozy Maine Homestay

An Authentic Clean & Cozy Maine Homestay

Buckfield
10.0 out of 10, Exceptional, (63)
"The host provided excellent information and was very easy to communicate with. The property was very comfortable and clean. "
United States
Meg
$187 nightly
The price is $204
Nov 24 - Nov 25
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)
"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.
$271 nightly
The price is $295
Nov 24 - Nov 25
Total with taxes and fees
Cabin Style Studio Apt with Private Hot tub on 100 Acres Kayaks, Canoes & SUP
Exterior
Fall fun in Oxford Hills

Fall fun in Oxford Hills

Sumner
10.0 out of 10, Exceptional, (27)
"Very nice. Plenty of room for family. "
United States
Sylvia Y.
$284 nightly
The price is $310
Nov 23 - Nov 24
Total with taxes and fees
Fall fun in Oxford Hills
Fridge, microwave, stovetop, coffee/tea maker
NEW Cozy Cabin located in Oakland tucked away in a peaceful wooded scene.

NEW Cozy Cabin located in Oakland tucked away in a peaceful wooded scene.

Oakland
$287 nightly
The price is $313
Nov 23 - Nov 24
Total with taxes and fees
NEW Cozy Cabin located in Oakland tucked away in a peaceful wooded scene.
Property grounds
3350 Middle Road

3350 Middle Road

Sidney
8.0 out of 10, Very Good, (3)
"A great spot for all 7 of us. Nice house with zones for everyone. Lovely backyard. Big kitchen and dining table"
United States
Pat D.
$308 nightly
The price is $336
Dec 1 - Dec 2
Total with taxes and fees
3350 Middle Road
Outdoor dining
Lighthouse Lane

Lighthouse Lane

Manchester
10.0 out of 10, Exceptional, (70)
"The house location on the lake is perfect! So beautiful and quiet:) The house was overall very nice to live in."
United States
Nathalie N.
$438 nightly
The price is $477
Nov 23 - Nov 24
Total with taxes and fees
Lighthouse Lane
Property grounds
Every window has a spectacular lake view Low fees

Every window has a spectacular lake view Low fees

Wayne
9.8 out of 10, Exceptional, (45)
"Tina was great and very informative with places to visit and place to eat. Will definitely be checking in again "
United States
Nancy
$344 nightly
The price is $374
Nov 23 - Nov 24
Total with taxes and fees
Every window has a spectacular lake view Low fees
Property grounds
Fully Furnished 1st Floor Retreat, Comfort Awaits

Fully Furnished 1st Floor Retreat, Comfort Awaits

Lewiston
10.0 out of 10, Exceptional, (2)
"Everything was excellent "
United States
Rafael M.
$398 nightly
The price is $420
Nov 30 - Dec 1
Total with taxes and fees
Fully Furnished 1st Floor Retreat, Comfort Awaits
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

Homewood Suites by Hilton Augusta

Homewood Suites by Hilton Augusta

10/10 Excellent
"Great stay very comfortable and clean "
Thomas 2-night trip
Posted 3 days ago
Homewood Suites by Hilton 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 $286 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?

Classy AF Home Steps from Colby and Trails: Visitors like this Winthrop vacation home rental. It offers a private yard, a selection of games, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 3 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 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.