Winthrop Holiday Rentals

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Check prices for these dates

In two weeks
13 Mar - 15 Mar
In two months
24 Apr - 26 Apr
In three months
22 May - 24 May
In four months
19 Jun - 21 Jun

Our top choices for Winthrop holiday rentals

TV

Apartment in Hallowell

Two bedroom Mid Century Modern apartment in Downtown Hallowell
10.0 out of 10, Exceptional, (83 reviews)
"Great apartment, close to town, very clean, comfortable beds. Loved the little extras too.. coffee, creamer, etc! Will definitely stay again. "
United States
Rebekah B.
The price is HK$993
HK$1,867 total
includes taxes & fees
1 Mar - 2 Mar
Two bedroom Mid Century Modern apartment in Downtown Hallowell
Exterior

Cabin in Oakland

Sister A-Frame in Woods B
10.0 out of 10, Exceptional, (9 reviews)
"Great stay. Would stay here again if in the area."
United States
Amanda M.
The price is HK$943
HK$1,787 total
includes taxes & fees
4 Mar - 5 Mar
Sister A-Frame in Woods B
2 bedrooms, WiFi, bed sheets

Apartment in Oakland

The heart of the Belgrade Lakes
9.0 out of 10, Wonderful, (9 reviews)
"Host was very accommodating "
United States
Maureen
The price is HK$630
HK$1,496 total
includes taxes & fees
27 Feb - 28 Feb
The heart of the Belgrade Lakes
Fridge, microwave, oven, stovetop

Cottage in West Gardiner

Waterfront 2br/2ba cottage
9.8 out of 10, Exceptional, (16 reviews)
"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$1,337
HK$2,838 total
includes taxes & fees
2 Mar - 3 Mar
Waterfront 2br/2ba cottage
Property grounds

Apartment in Oakland

Central Maine Apartment offering 4 Seasons of Fun.
10.0 out of 10, Exceptional, (43 reviews)
"Great hiking - nice views."
United States
Norbert A.
The price is HK$821
HK$1,926 total
includes taxes & fees
1 Mar - 2 Mar
Central Maine Apartment offering 4 Seasons of Fun.
Exterior

Holiday Home in Oakland

Discover Oakland charm near Colby College 10 min
10.0 out of 10, Exceptional, (6 reviews)
"Very clean and comfy. A pleasure to stay there. "
United States
Vicki W.
The price is HK$697
HK$1,961 total
includes taxes & fees
9 Mar - 10 Mar
Discover Oakland charm near Colby College 10 min
Property grounds

Holiday Home in Wayne

Every window has a spectacular lake view Low fees
9.8 out of 10, Exceptional, (45 reviews)
"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$1,232
HK$2,502 total
includes taxes & fees
1 Mar - 2 Mar
Every window has a spectacular lake view Low fees
Terrace/patio

Holiday Home in Belgrade

Family's Paradise: 3BR/2BA,Game Room & Lake Access
9.8 out of 10, Exceptional, (9 reviews)
"We enjoyed our stay."
United States
Tyson W.
The price is HK$1,478
HK$6,369 total
includes taxes & fees
1 Mar - 2 Mar
Family's Paradise: 3BR/2BA,Game Room & Lake Access
Property grounds

Holiday Home in Manchester

Cozy Cottage on water's edge of Lake Cobbosseecontee
8.8 out of 10, Excellent, (19 reviews)
"Very quiet spot right on the lake, relatively easy to get to, close to town. Cabin is small, which was perfect for the two of us. "
United States
Stephanie P.
The price is HK$1,134
HK$2,634 total
includes taxes & fees
1 Mar - 2 Mar
Cozy Cottage on water's edge of Lake Cobbosseecontee
Outdoor dining

Cottage in Manchester

Lighthouse Lane
10.0 out of 10, Exceptional, (71 reviews)
"Very nice stay Beautiful lake views "
United States
Karen G.
The price is HK$1,759
HK$2,438 total
includes taxes & fees
2 Mar - 3 Mar
Lighthouse Lane
3 bedrooms, desk, iron/ironing board, free WiFi

Holiday Home in Buckfield

An Authentic Clean & Cozy Maine Homestay
9.8 out of 10, Exceptional, (65 reviews)
"Very nice and comfortable house, clean and quiet. The hosts were very responsive. We had a great stay."
United States
Jessica Stebbins B.
The price is HK$971
HK$1,596 total
includes taxes & fees
27 Feb - 28 Feb
An Authentic Clean & Cozy Maine Homestay
Outdoor spa tub

Apartment in Whitefield

Cabin Style Studio Apt with Private Hot tub on 100 Acres Kayaks, Canoes & SUP
10.0 out of 10, Exceptional, (6 reviews)
"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$1,447
HK$2,216 total
includes taxes & fees
1 Mar - 2 Mar
Cabin Style Studio Apt with Private Hot tub on 100 Acres Kayaks, Canoes & SUP
WiFi, bed sheets

Apartment in Lewiston

Quaint 1-bedroom apartment with AC in charming Lewiston
The price is HK$782
HK$1,926 total
includes taxes & fees
27 Feb - 28 Feb
Quaint 1-bedroom apartment with AC in charming Lewiston
Exterior detail

Holiday Home in Sidney

Peaceful Home in Central Maine
8.4 out of 10, Very good, (5 reviews)
"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$2,297
HK$3,347 total
includes taxes & fees
2 Mar - 3 Mar
Peaceful Home in Central Maine
Exterior

Holiday Home in Oakland

Cozy getaway: farmhouse with wood stove & jacuzzi tub
10.0 out of 10, Exceptional, (10 reviews)
"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$1,525
HK$2,802 total
includes taxes & fees
28 Feb - 1 Mar
Cozy getaway: farmhouse with wood stove & jacuzzi tub
Interior

Apartment in Auburn

Rustic Charm Meets Modern Luxury: Stylish 2BR, 1BA Apartment
9.6 out of 10, Exceptional, (8 reviews)
"Nice condo"
United States
lara g.
The price is HK$997
HK$2,910 total
includes taxes & fees
6 Mar - 7 Mar
Rustic Charm Meets Modern Luxury: Stylish 2BR, 1BA Apartment
Interior

Apartment in Lewiston

Fully Furnished 1st Floor Retreat, Comfort Awaits
10.0 out of 10, Exceptional, (3 reviews)
"Everything was excellent "
United States
Rafael M.
The price is HK$1,564
HK$3,261 total
includes taxes & fees
2 Mar - 3 Mar
Fully Furnished 1st Floor Retreat, Comfort Awaits
Interior

Holiday Home in Litchfield

Camp Lintonia on Tacoma Lakes
10.0 out of 10, Exceptional, (12 reviews)
"Booked this property for a girls trip and this property was stunning! Wish we would’ve booked for more days! Ample space for everyone, views were amazing, and the house was gorgeous! Already considering booking again next year! "
United States
Emma B.
The price is HK$1,759
HK$2,165 total
includes taxes & fees
3 Mar - 4 Mar
Camp Lintonia on Tacoma Lakes
Living area

Apartment in Smithfield

Cozy newly built 1-bedroom apartment in charming Smithfield
The price is HK$1,290
HK$1,935 total
includes taxes & fees
12 Mar - 13 Mar
Cozy newly built 1-bedroom apartment in charming Smithfield
Interior

Holiday Home in New Sharon

A soul soothing escape. Artistically built and lovingly maintained.
10.0 out of 10, Exceptional, (30 reviews)
"Loved the cabin and the view!! Had a great stay, thank you to our host!! Would love to stay again "
United States
Matt W.
The price is HK$2,007
HK$3,296 total
includes taxes & fees
1 Mar - 2 Mar
A soul soothing escape. Artistically built and lovingly maintained.
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

Discover your retreat - 3-bedroom cottage in Winthrop

Discover your retreat - 3-bedroom cottage in Winthrop

10/10 Excellent
"Great host - we got a pretty big snow storm the host was making sure everything was ok. 2nd time staying here and won’t be our last. House is very clean and the host is great "
Dan G. 4-night trip
Posted 2 days ago
Discover your retreat - 3-bedroom cottage in Winthrop

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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  • Enter your travel dates to view the best deals on holiday rentals in Winthrop while they last

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?

Spacious 5-bedroom lakefront home on pristine Lower Narrows Pond in Winthrop: This highly rated holiday home rental in Winthrop offers a fireplace, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 5 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 14 holiday rentals for your stay in Winthrop.

What can I see and do in Winthrop?

Cobbosseecontee Lake and Maranacook 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.