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, (21)
"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

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
29 Aug - 30 Aug
Cozy Cottage on water's edge of Lake Cobbosseecontee

Nature lovers Paradise your own island

9.8 out of 10, Exceptional, (67)
"Amazing property! "
Nature lovers Paradise your own island

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 €472
includes taxes & fees
3 Sept - 4 Sept
Lighthouse Lane

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

2.0 star property
10.0 out of 10, Exceptional, (6)
"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 !

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

8.8 out of 10, Excellent, (3)
"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

Cozy lake house on Sabattus Pond 2 bed 1 Bath

9.0 out of 10, Wonderful, (12)
"Perfect place to stay for a weekend "
Cozy lake house on Sabattus Pond 2 bed 1 Bath

Private Dock on Messalonskee Lake: Cozy Cottage!

2.0 star property
9.0 out of 10, Wonderful, (6)
"We had a peaceful and relaxing stay. Nice and quiet!"
Private Dock on Messalonskee Lake: Cozy Cottage!

Central Maine Apartment offering 4 Seasons of Fun.

10.0 out of 10, Exceptional, (39)
"Cozy, quiet, clean, close to family and affordable"
The price is €218
includes taxes & fees
31 Aug - 1 Sept
Central Maine Apartment offering 4 Seasons of Fun.

Cabin China Lake

9.6 out of 10, Exceptional, (13)
"Second time there and is always nice. "
Cabin China Lake

Downtown studio/ open concept with king bed. Pets welcome

10.0 out of 10, Exceptional, (1)
"The studio was charming and spotless! Plus the location was perfect for our visit to Auburn."
Downtown studio/ open concept with king bed. Pets welcome

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 €204
includes taxes & fees
4 Sept - 5 Sept
Sister A-Frame in Woods B

New Waterfront Lake House - completed 2021

10.0 out of 10, Exceptional, (25)
"We love this place, it's the perfect Lake House and we intend on staying every year!"
New Waterfront Lake House - completed 2021

Blue Loon Camp on Pleasant Pond in Litchfield

8.8 out of 10, Excellent, (3)
"This comfy cabin can sleep 6 people no problem! With a close quarters experience made staying more the fun! EasyAccess to kayaks and canoes was awesome. Had a couple Beavers going back n forth in front of the cabin as well! Bailey the Neighbor dog stopped by to say hi in the yard along with Chancellor and Lous minutes prior. Thanks again for your accommodations. We would love to visit again in the future! "
Blue Loon Camp on Pleasant Pond in Litchfield

Driftwood Cottage with Cottages of Maine, Lake Great Pond, Dog Friendly, Kayaks

10.0 out of 10, Exceptional, (43)
"Very clean and comfortable."
The price is €339
includes taxes & fees
28 Aug - 29 Aug
Driftwood Cottage with Cottages of Maine, Lake Great Pond, Dog Friendly, Kayaks

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

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

Lakeview Central Hub

10.0 out of 10, Exceptional, (1)
"Beautiful place. Super quick communication. Quiet neighborhood. Loved it!"
The price is €309
includes taxes & fees
24 Aug - 25 Aug
Lakeview Central Hub

Sunset Chalet Lakefront Hot Tub Game Room

10.0 out of 10, Exceptional, (25)
"Very nice quiet location. Loved the game room. Relaxing stay."
The price is €677
includes taxes & fees
26 Aug - 27 Aug
Sunset Chalet Lakefront Hot Tub Game Room

Charming 2-bedroom 1930's apartment waterfront.

8.0 out of 10, Very good, (4)
"My daughter and I came to the area to visit some colleges. We were so glad to have such a warm and comfortable spot to rest at the end of the day. The view was also beautiful."
The price is €220
includes taxes & fees
1 Sept - 2 Sept
Charming 2-bedroom 1930's apartment waterfront.

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
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 Cottage on water's edge of Lake Cobbosseecontee: This holiday home rental outside of Winthrop is located on a lake, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

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.