Holiday Rentals in Winthrop

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Holiday Rentals in Winthrop

Fantastic Lakefront Cabin W/ Free WiFi, Three Kayaks, Private Dock, & Firepit

Winthrop
9.8 out of 10, Exceptional, (29)
"Amazing place to stay. Everything we needed was there."
United States
Ike T.
Fantastic Lakefront Cabin W/ Free WiFi, Three Kayaks, Private Dock, & Firepit

Cozy Keyes Cottage- Rare Lakefront Getaway

Winthrop
10.0 out of 10, Exceptional, (13)
"The lake was great - had a good time cruising the lake and the camp was perfect."
United States
Linda A.
Cozy Keyes Cottage- Rare Lakefront Getaway

Located directly in central downtown and beach area, fish or kayak from backyard

Winthrop
8.4 out of 10, Very good, (7)
"Great location"
Canada
Julia C.
Located directly in central downtown and beach area, fish or kayak from backyard

Classy AF Home Steps from Colby and Trails

Oakland
10.0 out of 10, Exceptional, (48)
"Clean, comfortable and incredibly close to campus for a college visit."
United States
Patricia R.
Classy AF Home Steps from Colby and Trails

Maine Cabin Masters Camp completely redone waiting for a Lake loving family !

2.0 star property
Readfield
10.0 out of 10, Exceptional, (7)
"It was a wonderful week. The cabin is very well appointed. We lacked for nothing! Thank you "
United States
Gigi A.
Maine Cabin Masters Camp completely redone waiting for a Lake loving family !

Spacious Country Home w/ Hot Tub, near Colby/Thomas

Sidney
9.8 out of 10, Exceptional, (35)
"Very nice hot tub, quite and beautiful area! Air quality amazing and AC works fantasticly!"
United States
Nathan
Spacious Country Home w/ Hot Tub, near Colby/Thomas

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.
The price is €282
includes taxes & fees
30 Nov - 1 Dec
Cozy Cottage on water's edge of Lake Cobbosseecontee

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.
The price is €262
includes taxes & fees
1 Dec - 2 Dec
Waterfront 2br/2ba cottage

Cozy lake house on Sabattus Pond 2 bed 1 Bath

Sabattus
9.2 out of 10, Wonderful, (22)
"We had a great time. Right by the water. Kids loved the upstairs/attic space. "
United States
Casey C.
Cozy lake house on Sabattus Pond 2 bed 1 Bath

Lakefront Cabin

China
10.0 out of 10, Exceptional, (27)
"My family and I attended a concert at the Bowl in the Pines and wanted to make a weekend out of it and found this perfect little cabin right on the lake! Kids absolutely loved swimming, fishing and canoeing! Great spot for family bonding! Thank you! "
United States
Laura L.
Lakefront Cabin

Private and Calming Waterfront to the Rescue!

Augusta
9.8 out of 10, Exceptional, (86)
"Absolutely amazing property, everything we were looking for and an amazing host too! Highly recommend! "
United States
samantha c.
Private and Calming Waterfront to the Rescue!

Sunfish Cove is the perfect year round getaway.

Monmouth
10.0 out of 10, Exceptional, (51)
"Awesome property for an extended family stay"
United States
shannon p.
Sunfish Cove is the perfect year round getaway.

Spectacular Cobbossee Lakefront with Hot Tub & Dog Friendly

Manchester
10.0 out of 10, Exceptional, (254)
"We had a fantastic time! The lake is beautiful and the house has everything you need to enjoy it. "
United States
Dave S.
Spectacular Cobbossee Lakefront with Hot Tub & Dog Friendly

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

Whitefield
9.8 out of 10, Exceptional, (30)
"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.
The price is €199
includes taxes & fees
9 Dec - 10 Dec
Tiny Cabin with Private Hot Tub on 100 Acres Kayaks, Canoes & Paddleboards

Charming 2-bedroom house in marvelous Auburn with AC, WiFi, and fenced yard.

Auburn
9.8 out of 10, Exceptional, (12)
"Perfect location for ours needs. Gracious host, clean house and quiet neighborhood."
United States
allison k.
Charming 2-bedroom house in marvelous Auburn with AC, WiFi, and fenced yard.

NEW! Long Pond Lake View Getaway w/HOT TUB, ME

Mount Vernon
10.0 out of 10, Exceptional, (2)
"This house was absolutely stunning! Had absolutely everything that you needed the house offered everything that one would need and plenty of space for everybody! The game room was so fun! The hot tub was a great bonus! Everyone had an amazing time while staying."
United States
Rachael L.
NEW! Long Pond Lake View Getaway w/HOT TUB, ME

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.
The price is €424
includes taxes & fees
1 Dec - 2 Dec
Lighthouse Lane

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.
The price is €253
includes taxes & fees
1 Dec - 2 Dec
Ice Fishing, Dog Friendly, Lake Great Pond

Cozy Long Pond Cottage: private mooring & shared dock

Rome
9.8 out of 10, Exceptional, (20)
"We had a great time kayaking on the lake and enjoying the beach. The house had plenty of room to get together with family for dinners. The house is well equipped and very comfortable."
United States
Jim U.
Cozy Long Pond Cottage: private mooring & shared dock

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.
The price is €202
includes taxes & fees
1 Dec - 2 Dec
Sister A-Frame in Woods B
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

Find out more about Winthrop

Everything you need to know about Winthrop holiday rentals

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

Winthrop holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winthrop holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winthrop holiday rentals we have selected for you start as low as €199 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Winthrop rentals

At Expedia, we put the best Winthrop holiday 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 holiday.

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. 

Frequently asked questions

Can I find a holiday rental in Winthrop?

Yes, there are holiday rentals close to the most popular sights in Winthrop, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Winthrop has to offer?

Little Landing Cottage | Lakefront · Dock · Kayaks: This highly rated holiday home rental in Winthrop is located on a lake, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

How many holiday rentals are there in Winthrop?

Expedia has 15 holiday 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 holiday rentals like in Winthrop?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winthrop. Holiday rentals provide amenities such as patios, hot tubs and fire pits so you'll have all the comforts of home. If you're concerned about cleanliness, holiday rentals can offer a sense of privacy away from public hotel lifts and lobbies bustling with people while still allowing you to travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive choice for small groups.