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, (12)
"Small but very funcional, cozy and pleasant. Good location for enjoying fishing and exploring the surrounding area."
Escape to our cozy Winthrop cabin on Dexter Pond

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

9.6 out of 10, Exceptional, (25)
"Well kept with all the right amenities. Beautiful views."
Fantastic Lakefront Cabin W/ Free WiFi, Three Kayaks, Private Dock, & Firepit

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

8.0 out of 10, Very good, (6)
"Enjoyed our stay. House was clean and well equipped. However, access to Lake Annabessacook is limited. Will consider staying there again in the future."
Located directly in central downtown and beach area, fish or kayak from backyard

Cottage on Cobbosseecontee Lake.

10.0 out of 10, Exceptional, (168)
"Brought my son fishing for the weekend ! Property was great- right on the lake and was perfect for a weekend away. Very clean and had everything we needed! We will be staying here again for sure "
Cottage on Cobbosseecontee Lake.

Get in touch with nature.

10.0 out of 10, Exceptional, (22)
"Nice location, beautiful tent, quiet place among the forest. Great for a retreat"
The price is AU$237
includes taxes & fees
7 July - 8 July
Get in touch with nature.

The Modern Maine Retreat

9.0 out of 10, Wonderful, (4)
"Multi generation family in town to visit other family. Kitchen adequate for meal prep, "
The Modern Maine Retreat

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

10.0 out of 10, Exceptional, (38)
"Very clean and comfortable."
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, (5)
Warm & Inviting Lakeside Retreat, Private, Tranquil Picture Perfect Setting

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

2.0 star property
10.0 out of 10, Exceptional, (3)
"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 !

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

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

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

8.0 out of 10, Very good, (6)
"Daughter lives in area it suited us just fine."
Cozy Home Away From Home! Right Outside of the City! Dog Friendly!

Every window has a spectacular lake view Low fees

10.0 out of 10, Exceptional, (35)
"location was great, the lake and the wildlife were amazing. enjoyed sitting in the glassed in room each night listening to all of the sounds. the kids were a bit shocked by the 'don't drink the water' warnings, which caused a bit of drama, but otherwise, it was a much needed week away."
Every window has a spectacular lake view Low fees

Year-Round Lakeside Retreat

9.2 out of 10, Wonderful, (24)
"We had a wonderful stay. Everyone enjoyed themselves. Perfect location. It was very peaceful and loved that it was on the water. We would definitely recommend and wished we had more time to stay. "
Year-Round Lakeside Retreat

Lakefront Escape w/ Dock, Fire Pit & Views

Lakefront Escape w/ Dock, Fire Pit & Views

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

8.0 out of 10, Very good, (18)
"Great location! Very nice place"
Dog-friendly lakefront home with dock, fireplace, firepit, lake views, & 1 kayak

Lakeside retreat in Central Maine

9.8 out of 10, Exceptional, (83)
"This was a great place to spend the weekend. Spent the day out on the ice and came in to a shower that was very hot and had great pressure. The place was very clean and the kitchen was well equipped. Would love to stay here again at some point."
Lakeside retreat in Central Maine

Private Dock & Deck: Tranquil Dam Pond Cottage!

10.0 out of 10, Exceptional, (3)
"Restful retreat with everything you need. From the sound of the loons, the comfortable accommodations, accessibility to so many great spots, and wonderful hosts you can't beat it. Can't wait to come back. "
Private Dock & Deck: Tranquil Dam Pond Cottage!

Lakefront, dog-friendly cottage with screened porch, firepit, WiFi & lake access

9.2 out of 10, Wonderful, (12)
"Such a nice little spot to relax on the lake."
Lakefront, dog-friendly cottage with screened porch, firepit, WiFi & lake access

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

Lakefront Maine House ~ 4 Mi to Colby College

8.0 out of 10, Very good, (2)
"Convenient very clean but we were hardly there except to sleep. Thank you"
Lakefront Maine House ~ 4 Mi to Colby College
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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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?

Located directly in central downtown and beach area, fish or kayak from backyard: 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. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

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, Wilson Pond and Annabessacook Lake 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.