Winthrop Vacation Rentals

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Vacation Rentals in Winthrop

Escape to our cozy Winthrop cabin on Dexter Pond

10.0 out of 10, Exceptional, (11)
"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

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

Spacious 5-bedroom lakefront home on pristine Lower Narrows Pond in Winthrop

Spacious 5-bedroom lakefront home on pristine Lower Narrows Pond in Winthrop

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

Sister A-Frame in Woods B

10.0 out of 10, Exceptional, (2)
"Great stay. Would stay here again if in the area."
The price is ¥17,487
¥33,601 total
includes taxes & fees
Jul 1 - Jul 2
Sister A-Frame in Woods B

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

10.0 out of 10, Exceptional, (36)
"We came to Ice Fish.We had a great time.Nice spot, had everything we wanted, and super easy….Thanks!"
The price is ¥28,566
¥53,814 total
includes taxes & fees
Jun 22 - Jun 23
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, (4)
"Nice time"
Warm & Inviting Lakeside Retreat, Private, Tranquil Picture Perfect Setting

Belgrade Lakes Cottage w/ Long Pond beach access close to Augusta, Colby College

9.6 out of 10, Exceptional, (11)
"Great location and wonderful hosts!"
Belgrade Lakes Cottage w/ Long Pond beach access close to Augusta, Colby College

Get in touch with nature.

10.0 out of 10, Exceptional, (21)
"Nice location, beautiful tent, quiet place among the forest. Great for a retreat"
The price is ¥13,094
¥22,202 total
includes taxes & fees
Jun 23 - Jun 24
Get in touch with nature.

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

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!

The heart of the Belgrade Lakes

10.0 out of 10, Exceptional, (2)
"We were visiting town for a friend's wedding. Very comfortable, had a great time. Easy access to Belgrade Lakes/Augusta/Waterville area."
The price is ¥16,675
¥29,871 total
includes taxes & fees
Jul 1 - Jul 2
The heart of the Belgrade Lakes

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

ENJOY TWIN PONDS WHILE EXPLORING MIDCOAST MAINE

10.0 out of 10, Exceptional, (64)
"It was fantastic both Brian and Luana were amazing hosts"
ENJOY TWIN PONDS WHILE EXPLORING MIDCOAST MAINE

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

9.4 out of 10, Exceptional, (11)
"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

6.0 out of 10, (1)
"Location"
Serene Cabin with Lakefront Access, Cozy Fire Pit, and Bunk House

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

9.8 out of 10, Exceptional, (22)
"This house has everything for a weekend family vacay; you can spend the whole weekend enjoying the house & amenities such as the hot tub!"
Spacious Country Home w/ Hot Tub, near Colby/Thomas

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

Cozy Cottage on Togus Pond

9.8 out of 10, Exceptional, (36)
"Beautiful little cottage on the lake. Clean, easy check-in, and quiet. Loved our stay and will come back again!"
Cozy Cottage on Togus Pond

Lakeside retreat in Central Maine

9.8 out of 10, Exceptional, (82)
"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
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 vacation rental in Winthrop?

Yes, we offer vacation rentals close to popular sights in Winthrop, or you can choose a secluded option if you want a relaxing place to stay.

What are some of the best vacation rentals in Winthrop?

Located directly in central downtown and beach area, fish or kayak from backyard: Visitors like this Winthrop vacation home rental. It is located on a lake and has a balcony, a garden, and a barbecue grill 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 you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

How many vacation rentals are there in Winthrop?

Expedia has 15 vacation 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 vacation rentals like in Winthrop?

Vacation rentals are private accommodations you can book for a few days or a quick weekend in Winthrop. Vacation rentals provide amenities such as patios, hot tubs, and fire pits so you'll have all the conveniences of home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of privacy away from public hotel elevators and busy reception areas while still allowing you to travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive choice for families.