Winthrop Holiday Rentals

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Check prices for these dates

In two weeks
5 Dec - 7 Dec
In two months
16 Jan - 18 Jan
In three months
13 Feb - 15 Feb
In four months
13 Mar - 15 Mar

Holiday Rentals in Winthrop

Exterior
Charming Guest House on Farm - Pets Welcome

Charming Guest House on Farm - Pets Welcome

Oakland
10.0 out of 10, Exceptional, (7)
"It was that was said to be The host was very nice and helpful . I enjoyed my stay "
United States
Andrea C.
The price is HK$1,426
HK$2,150 total
includes taxes & fees
24 Nov - 25 Nov
Charming Guest House on Farm - Pets Welcome
Fridge, microwave, oven, stovetop
Waterfront 2br/2ba cottage

Waterfront 2br/2ba cottage

West Gardiner
9.8 out of 10, Exceptional, (15)
"Very nice and clean place. We used this rental as a hub to go around and see lots that Maine had to offer. Hosts were very nice and kept a very clean place."
United States
Bruce J.
The price is HK$876
HK$2,227 total
includes taxes & fees
24 Nov - 25 Nov
Waterfront 2br/2ba cottage
Living area
The heart of the Belgrade Lakes

The heart of the Belgrade Lakes

Oakland
9.0 out of 10, Wonderful, (9)
"Host was very accommodating "
United States
Maureen
The price is HK$627
HK$1,489 total
includes taxes & fees
24 Nov - 25 Nov
The heart of the Belgrade Lakes
TV
Two bedroom Mid Century Modern apartment in Downtown Hallowell

Two bedroom Mid Century Modern apartment in Downtown Hallowell

Hallowell
10.0 out of 10, Exceptional, (80)
"Easy check in super clean comfy beds organizdd"
United States
Josee Y.
The price is HK$973
HK$1,841 total
includes taxes & fees
29 Nov - 30 Nov
Two bedroom Mid Century Modern apartment in Downtown Hallowell
Fridge, microwave, oven, stovetop
Discover Oakland charm near Colby College 10 min

Discover Oakland charm near Colby College 10 min

2.0 star property
Oakland
10.0 out of 10, Exceptional, (6)
"New, clean and had everything we needed. "
United States
Lara B.
The price is HK$732
HK$2,054 total
includes taxes & fees
1 Dec - 2 Dec
Discover Oakland charm near Colby College 10 min
Exterior
Sister A-Frame in Woods B

Sister A-Frame in Woods B

Oakland
10.0 out of 10, Exceptional, (8)
"Great stay. Would stay here again if in the area."
United States
Amanda M.
The price is HK$939
HK$1,778 total
includes taxes & fees
24 Nov - 25 Nov
Sister A-Frame in Woods B
Property grounds
Central Maine Apartment offering 4 Seasons of Fun.

Central Maine Apartment offering 4 Seasons of Fun.

Oakland
10.0 out of 10, Exceptional, (43)
"The place was clean, very spacious and comfortable. Having the laundry was helpful, so I didn’t have to worry about doing laundry when I got home late (also, I spilled coffee on the way there, so I’m glad the stain was gone)."
United States
Keeko
The price is HK$817
HK$1,917 total
includes taxes & fees
24 Nov - 25 Nov
Central Maine Apartment offering 4 Seasons of Fun.
Interior
Rustic Charm Meets Modern Luxury: Stylish 2BR, 1BA Apartment

Rustic Charm Meets Modern Luxury: Stylish 2BR, 1BA Apartment

Auburn
9.6 out of 10, Exceptional, (8)
"My daughter and I loved our stay at this property. Access instructions were communicated clearly and the location was safe and comfy. Definitely would recommend for visitors to Auburn/Lewiston area."
United States
Judith P.
The price is HK$681
HK$2,515 total
includes taxes & fees
24 Nov - 25 Nov
Rustic Charm Meets Modern Luxury: Stylish 2BR, 1BA Apartment
Outdoor dining
Ice Fishing, Dog Friendly, Lake Great Pond

Ice Fishing, Dog Friendly, Lake Great Pond

Belgrade
10.0 out of 10, Exceptional, (48)
"The house was great, and the owners were very communicative and responsive. Would definitely recommend and stay again!"
United States
Jonathon R.
The price is HK$1,033
HK$2,229 total
includes taxes & fees
24 Nov - 25 Nov
Ice Fishing, Dog Friendly, Lake Great Pond
Front of property
My Valhalla Farm

My Valhalla Farm

3.5 star property
Oakland
The price is HK$1,226
HK$2,115 total
includes taxes & fees
24 Nov - 25 Nov
My Valhalla Farm
Property grounds
Cozy Cottage on water's edge of Lake Cobbosseecontee

Cozy Cottage on water's edge of Lake Cobbosseecontee

Manchester
8.6 out of 10, Excellent, (18)
"Check in was a breeze. Right on the lake. House was just the right size for me and my 3 adult sons. Was lovely to paddle, canoe or swim just walking down the porch stairs"
United States
Heather A.
The price is HK$1,016
HK$2,482 total
includes taxes & fees
24 Nov - 25 Nov
Cozy Cottage on water's edge of Lake Cobbosseecontee
Property grounds
Tiny Cabin with Private Hot Tub on 100 Acres Kayaks, Canoes & Paddleboards

Tiny Cabin with Private Hot Tub on 100 Acres Kayaks, Canoes & Paddleboards

Whitefield
9.8 out of 10, Exceptional, (29)
"We stayed in this cabin for two nights with our dog and it was very peaceful and fun! The cabin has a campfire, lots of batteries for charging, lights, battery fans, etc. There were many long walking trails with fun activities; like kayaking, axe throwing, a pizza oven… Exactly what we were looking for! Would stay again! "
United States
Ben R.
The price is HK$1,168
HK$1,748 total
includes taxes & fees
24 Nov - 25 Nov
Tiny Cabin with Private Hot Tub on 100 Acres Kayaks, Canoes & Paddleboards
3 bedrooms, desk, iron/ironing board, free WiFi
An Authentic Clean & Cozy Maine Homestay

An Authentic Clean & Cozy Maine Homestay

Buckfield
10.0 out of 10, Exceptional, (63)
"The host provided excellent information and was very easy to communicate with. The property was very comfortable and clean. "
United States
Meg
The price is HK$967
HK$1,588 total
includes taxes & fees
24 Nov - 25 Nov
An Authentic Clean & Cozy Maine Homestay
Outdoor spa tub
Cabin Style Studio Apt with Private Hot tub on 100 Acres Kayaks, Canoes & SUP

Cabin Style Studio Apt with Private Hot tub on 100 Acres Kayaks, Canoes & SUP

Whitefield
10.0 out of 10, Exceptional, (6)
"Great getaway! We loved all of the discoveries to be made both in the cabin and on the property. We stayed in Stella. It was adorable, functional, and very welcoming. We also enjoyed an outing to Kennebec Maine Cabin Masters only 20 min away! "
United States
Sandra L.
The price is HK$1,440
HK$2,299 total
includes taxes & fees
25 Nov - 26 Nov
Cabin Style Studio Apt with Private Hot tub on 100 Acres Kayaks, Canoes & SUP
Exterior
Fall fun in Oxford Hills

Fall fun in Oxford Hills

Sumner
10.0 out of 10, Exceptional, (27)
"Very nice. Plenty of room for family. "
United States
Sylvia Y.
The price is HK$1,152
HK$2,392 total
includes taxes & fees
24 Nov - 25 Nov
Fall fun in Oxford Hills
Fridge, microwave, stovetop, coffee/tea maker
NEW Cozy Cabin located in Oakland tucked away in a peaceful wooded scene.

NEW Cozy Cabin located in Oakland tucked away in a peaceful wooded scene.

Oakland
The price is HK$1,212
HK$2,432 total
includes taxes & fees
24 Nov - 25 Nov
NEW Cozy Cabin located in Oakland tucked away in a peaceful wooded scene.
Property grounds
3350 Middle Road

3350 Middle Road

Sidney
8.0 out of 10, Very good, (3)
"A great spot for all 7 of us. Nice house with zones for everyone. Lovely backyard. Big kitchen and dining table"
United States
Pat D.
The price is HK$2,095
HK$2,614 total
includes taxes & fees
1 Dec - 2 Dec
3350 Middle Road
Outdoor dining
Lighthouse Lane

Lighthouse Lane

Manchester
10.0 out of 10, Exceptional, (70)
"The house location on the lake is perfect! So beautiful and quiet:) The house was overall very nice to live in."
United States
Nathalie N.
The price is HK$2,802
HK$3,733 total
includes taxes & fees
24 Nov - 25 Nov
Lighthouse Lane
Property grounds
Every window has a spectacular lake view Low fees

Every window has a spectacular lake view Low fees

Wayne
9.8 out of 10, Exceptional, (45)
"Tina was great and very informative with places to visit and place to eat. Will definitely be checking in again "
United States
Nancy
The price is HK$1,576
HK$2,923 total
includes taxes & fees
24 Nov - 25 Nov
Every window has a spectacular lake view Low fees
Property grounds
Fully Furnished 1st Floor Retreat, Comfort Awaits

Fully Furnished 1st Floor Retreat, Comfort Awaits

Lewiston
10.0 out of 10, Exceptional, (2)
"Everything was excellent "
United States
Rafael M.
The price is HK$1,557
HK$3,272 total
includes taxes & fees
30 Nov - 1 Dec
Fully Furnished 1st Floor Retreat, Comfort Awaits
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

Homewood Suites by Hilton Augusta

Homewood Suites by Hilton Augusta

10/10 Excellent
"Great stay very comfortable and clean "
Thomas 2-night trip
Posted 3 days ago
Homewood Suites by Hilton Augusta

Find out more about Winthrop

Search for holiday rentals in Winthrop on Expedia! You can easily find your home rentals, villas, holiday apartments in Winthrop using one of the methods below:

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Look no further and take a look at our great range of rental properties in Winthrop!

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?

Classy AF Home Steps from Colby and Trails: This holiday home rental outside of Winthrop offers a private garden, a selection of games and a BBQ to help you feel perfectly comfortable 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.

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, 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.