Winthrop Holiday Rentals

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Holiday Rentals in Winthrop

Escape to our cozy Winthrop cabin on Dexter Pond

10.0 out of 10, Exceptional, (20)
"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, (27)
"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 NZ$990
includes taxes & fees
2 Sept - 3 Sept
Lighthouse Lane

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

7.4 out of 10, Good, (10)
"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 NZ$532
includes taxes & fees
17 Aug - 18 Aug
Cozy Cottage on water's edge of Lake Cobbosseecontee

ENJOY TWIN PONDS WHILE EXPLORING MIDCOAST MAINE

10.0 out of 10, Exceptional, (67)
"Twin Ponds is a lovely location on a beautiful pond setting. Lovely landscaping and plantings with a walking path around the pond. We totally enjoyed our stay here. The suite is like a small cottage, wonderfully appointed and immaculate. Everything you could possibly need including freshly ground delicious coffee. A well- equipped and charming suite. This was a very special stay for us and hope to return one day. Brian and Luana are such gracious and friendly hosts. Thank you so much Brian and...
ENJOY TWIN PONDS WHILE EXPLORING MIDCOAST MAINE

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!

10.0 out of 10, Exceptional, (1)
"This property was so peaceful and quiet. It sits on a large lot with lots of privacy. The walk down to the dock is fun for kids, lots of rocks and it’s a little trail. We spent most of our time down at the dock. The views were spectacular, beautiful reflections in the water each morning, calm quiet lake and the sunset right in front of us each night. It wasn’t buggy and we used the kayak, but wear water shorts bc it does take in some water. We also brought our own paddle board and would highly...
Belgrade Lake house with Dock!

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

9.2 out of 10, Wonderful, (23)
"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 NZ$384
includes taxes & fees
25 Aug - 26 Aug
Sister A-Frame in Woods B

Every window has a spectacular lake view Low fees

9.8 out of 10, Exceptional, (39)
"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, (22)
"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

9.6 out of 10, Exceptional, (11)
"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, (25)
"Very nice quiet location. Loved the game room. Relaxing stay."
The price is NZ$1,269
includes taxes & fees
31 Aug - 1 Sept
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!

Find Your Bliss at this Private and Captivating Lakeside Retreat

10.0 out of 10, Exceptional, (25)
"Great stay, amazing house and property!"
Find Your Bliss at this Private and Captivating Lakeside Retreat

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 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.