Holiday Rentals in Winthrop

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Holiday Rentals in Winthrop

Escape to our cozy Winthrop cabin on Dexter Pond

10.0 out of 10, Exceptional, (19)
"Awesome cabin on Dexter Pond! Rick and LouAnne were terrific hosts! We loved drinking coffee on porch overlooking the pond, watching sunset and kayaking. Saw family of loons and bald eagle on the large pond. Classic Maine cabin! Not big but comfortable. Hosts were very responsive if we had any questions. Make sure to try their farm fresh eggs and honey!! Hope to visit again!! "
Escape to our cozy Winthrop cabin on Dexter Pond

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

9.8 out of 10, Exceptional, (26)
"Well kept with all the right amenities. Beautiful views."
Fantastic Lakefront Cabin W/ Free WiFi, Three Kayaks, Private Dock, & Firepit

Lighthouse Lane

10.0 out of 10, Exceptional, (59)
"Check in and check out was super easy. Photos are super accurate and the property is beautiful. Thank you for sharing your beautiful with us!"
The price is €519
includes taxes & fees
3 Sept - 4 Sept
Lighthouse Lane

Cozy Home Away From Home! Right Outside of the City! Dog Friendly!

8.0 out of 10, Very good, (8)
"Daughter lives in area it suited us just fine."
Cozy Home Away From Home! Right Outside of the City! Dog Friendly!

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

2.0 star property
10.0 out of 10, Exceptional, (5)
"Wonderful hosts, they thought of everything we might need including many nice extra touches! Beautiful quiet spot with the opportunity to paddle boat, kayak, canoe, swim, fish, enjoy campfires, outdoor grilling, observe wildlife (Osprey, Bald Eagle, Deer)"
Maine Cabin Masters Camp completely redone waiting for a Lake loving family !

Cozy Cottage on water's edge of Lake Cobbosseecontee

8.8 out of 10, Excellent, (12)
"Great little getaway, sitting right by the water. We loved our time there. Alarice is a great hot and responded quickly to any needs or questions."
The price is €281
includes taxes & fees
17 Aug - 18 Aug
Cozy Cottage on water's edge of Lake Cobbosseecontee

Charming 3-bedroom waterfront cottage with AC, WiFi and spectacular sunset views

9.0 out of 10, Wonderful, (2)
"Cozy cottage by the lake. Great scenery and wildlife. Great communication with host. "
Charming 3-bedroom waterfront cottage with AC, WiFi and spectacular sunset views

Belgrade Lake house with Dock!

Belgrade Lake house with Dock!

Lakefront home on McGrath Pond - once featured on Maine Cabin Masters

9.0 out of 10, Wonderful, (21)
"Great view, clean, central a/c, even the ppl using powerboats (4th of July!) were respectful. Exactly the getaway I needed!"
Lakefront home on McGrath Pond - once featured on Maine Cabin Masters

Sister A-Frame in Woods B

10.0 out of 10, Exceptional, (3)
"Great stay. Would stay here again if in the area."
The price is €203
includes taxes & fees
11 Aug - 12 Aug
Sister A-Frame in Woods B

Every window has a spectacular lake view Low fees

9.8 out of 10, Exceptional, (38)
"We had an amazing time and will definitely book again."
Every window has a spectacular lake view Low fees

Serene Cabin with Lakefront Access, Cozy Fire Pit, and Bunk House

8.0 out of 10, Very good, (2)
"My husband and his good friend stayed there and absolutely loved everything about the house, location and the host. "
Serene Cabin with Lakefront Access, Cozy Fire Pit, and Bunk House

Warm & Inviting Lakeside Retreat, Private, Tranquil Picture Perfect Setting

10.0 out of 10, Exceptional, (11)
Warm & Inviting Lakeside Retreat, Private, Tranquil Picture Perfect Setting

Dog-friendly lakefront home with dock, fireplace, firepit, lake views, & 1 kayak

7.6 out of 10, Good, (21)
"We enjoyed this place and will definitely come back again."
Dog-friendly lakefront home with dock, fireplace, firepit, lake views, & 1 kayak

Rustic lakefront cabin w/gas grill, firepit, kayaks, one canoe, A/C - 2 dogs OK

9.4 out of 10, Exceptional, (9)
"Great place for a relaxing weekend on the lake."
Rustic lakefront cabin w/gas grill, firepit, kayaks, one canoe, A/C - 2 dogs OK

Sunset Chalet Lakefront Hot Tub Game Room

10.0 out of 10, Exceptional, (24)
"Very nice quiet location. Loved the game room. Relaxing stay."
The price is €678
includes taxes & fees
10 Aug - 11 Aug
Sunset Chalet Lakefront Hot Tub Game Room

Private Dock on Messalonskee Lake: Cozy Cottage!

2.0 star property
9.6 out of 10, Exceptional, (5)
"Great spot right on the lake, True to what was listed. The beds weren’t very comfortable but otherwise everything was great."
Private Dock on Messalonskee Lake: Cozy Cottage!

Lakefront Home on Togus Pond with 2 Decks, Great View & Shared Canoe/Firepit

6.4 out of 10, (7)
"The listing stated there were upstairs tenants. Long story short, on Thanksgiving when they arrived home to me enjoying an outdoor fire, the accused me of using their firewood, I had brought my own. Then another night I left to do an activity with my kids and returned to not being able to park, due to them taking up three spaces with their truck. They were noisy every night until midnight and up every morning by 7a. In have no living family besides my kids and I was looking for a relaxing...
Lakefront Home on Togus Pond with 2 Decks, Great View & Shared Canoe/Firepit

Cozy Open Concept Lake House with Large Deck & Waterfront, perfect for families!

9.0 out of 10, Wonderful, (22)
"We had an amazing week. This is the perfect lake cabin… swimming, boating, tubing, campfires at night… we even used a projector to do an outdoor movie night. The owners are very responsive and helpful. We would definitely stay here again."
Cozy Open Concept Lake House with Large Deck & Waterfront, perfect for families!

Spectacular Cobbossee Lakefront with Hot Tub&Dog Friendly

10.0 out of 10, Exceptional, (248)
"Had another great fishing trip with this as our home base! Always clean and comfortable! "
Spectacular Cobbossee Lakefront with Hot Tub&Dog Friendly
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

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?

Cozy Home Away From Home! Right Outside of the City! Dog Friendly! : This holiday home rental outside of Winthrop offers a fireplace, a patio and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals are there in Winthrop?

Expedia has 14 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.