Winthrop Holiday Rentals

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Check prices for these dates

In two weeks
12 Jun - 14 Jun
In two months
24 Jul - 26 Jul
In three months
21 Aug - 23 Aug
In four months
18 Sept - 20 Sept

Our top choices for Winthrop holiday rentals

Terrace/patio

Cozy cottage in the Winthrop Lakes Area

Cozy cottage in the Winthrop Lakes Area
Winthrop
9.6 out of 10, Exceptional, (5 reviews)
"Lovely cottage! Everything we needed. The hosts were gracious and communicated well."
United States
Joshua
The price is HK$940
HK$1,589 total
includes taxes & fees
22 Jun - 23 Jun
Cozy cottage in the Winthrop Lakes Area
Interior

Jill's Place, new construction, lake access Cobbosee, 1 mile from Cabin Masters

Jill's Place, new construction, lake access Cobbosee, 1 mile from Cabin Masters
Winthrop
The price is HK$1,394
HK$2,451 total
includes taxes & fees
10 Jun - 11 Jun
Jill's Place, new construction, lake access Cobbosee, 1 mile from Cabin Masters
Exterior

Charming Lakefront Home: Big Porches, Kayaks & Room to Gather

Charming Lakefront Home: Big Porches, Kayaks & Room to Gather
Winthrop
9.6 out of 10, Exceptional, (5 reviews)
"Nice place to stay"
United States
Michael Y.
The price is HK$2,547
HK$5,612 total
includes taxes & fees
14 Jun - 15 Jun
Charming Lakefront Home: Big Porches, Kayaks & Room to Gather
Terrace/patio

Get in touch with nature.

Get in touch with nature.
Richmond
10.0 out of 10, Exceptional, (35 reviews)
"Great place to stay and pet friendly. "
United States
Kevin M.
The price is HK$705
HK$1,195 total
includes taxes & fees
3 Jun - 4 Jun
Get in touch with nature.
Front of property

Private Dock on Messalonskee Lake: Cozy Cottage!

Private Dock on Messalonskee Lake: Cozy Cottage!
3.0 star property
Augusta
10.0 out of 10, Exceptional, (1 review)
"Great little lake cabin. Had everything we needed. Clean, comfortable, quite. Beautiful area and views. We had a wonderful stay and would stay again."
United States
John
Private Dock on Messalonskee Lake: Cozy Cottage!
Exterior

Sister A-Frame in Woods B

Sister A-Frame in Woods B
Oakland
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$945
HK$2,003 total
includes taxes & fees
10 Jun - 11 Jun
Sister A-Frame in Woods B
Exterior

Discover Oakland charm near Colby College 10 min

Discover Oakland charm near Colby College 10 min
Oakland
10.0 out of 10, Exceptional, (11 reviews)
"Very clean and comfy. A pleasure to stay there. "
United States
Vicki W.
The price is HK$776
HK$1,649 total
includes taxes & fees
1 Jun - 2 Jun
Discover Oakland charm near Colby College 10 min
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, (86 reviews)
"Spacious and clean"
United States
Dwayne Lee
The price is HK$1,097
HK$1,998 total
includes taxes & fees
7 Jun - 8 Jun
Two bedroom Mid Century Modern apartment in Downtown Hallowell
Terrace/patio

Hammock Haven Island Dome

Hammock Haven Island Dome
Monmouth
10.0 out of 10, Exceptional, (3 reviews)
"Could not have asked for a better way to end our vacation than a visit to this island. For being a sustainable space it does not lack in amenities conducive to comfort, and the setting is pristine. I had particular fondness for the rope swing!!"
United States
BlairR
The price is HK$400
HK$1,589 total
includes taxes & fees
31 May - 1 Jun
Hammock Haven Island Dome
Fridge, microwave, oven, stovetop

Waterfront 2br/2ba cottage

Waterfront 2br/2ba cottage
West Gardiner
9.8 out of 10, Exceptional, (17 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$987
HK$2,742 total
includes taxes & fees
4 Jun - 5 Jun
Waterfront 2br/2ba cottage
Property grounds

Cozy Cottage on water's edge of Lake Cobbosseecontee

Cozy Cottage on water's edge of Lake Cobbosseecontee
Manchester
8.8 out of 10, Excellent, (21 reviews)
"Location is amazing "
United States
Laura Q.
The price is HK$1,293
HK$2,836 total
includes taxes & fees
4 Jun - 5 Jun
Cozy Cottage on water's edge of Lake Cobbosseecontee
Exterior

Island Aframe Adventure in Maine

Island Aframe Adventure in Maine
Monmouth
10.0 out of 10, Exceptional, (6 reviews)
"A very pleasant, peaceful place to stay. The hosts were very proactive about making sure we had a great stay and did everything to could to make it as stress-free as possible."
United States
Robert
The price is HK$509
HK$1,888 total
includes taxes & fees
3 Jun - 4 Jun
Island Aframe Adventure in Maine
Interior

Island Tree House Glamping

Island Tree House Glamping
Monmouth
10.0 out of 10, Exceptional, (9 reviews)
"Sunset/rise were so perfect, and we got a special appearance of a double rainbow during our stay!"
United States
Desiree L.
The price is HK$572
HK$2,596 total
includes taxes & fees
4 Jun - 5 Jun
Island Tree House Glamping
Property grounds

Floating Island Cabin

Floating Island Cabin
Monmouth
10.0 out of 10, Exceptional, (8 reviews)
"What an absolute pleasure it was staying in the floating home on the island. It was everything we wanted it to be. We will make this an annual trip. "
United States
Carissa P.
The price is HK$650
HK$2,042 total
includes taxes & fees
31 May - 1 Jun
Floating Island Cabin
Property grounds

Island Tent Overlook in Maine

Island Tent Overlook in Maine
Monmouth
10.0 out of 10, Exceptional, (4 reviews)
"The island is great from the walking trails, amenities and great fishing. "
United States
Jeremy F.
The price is HK$509
HK$1,862 total
includes taxes & fees
31 May - 1 Jun
Island Tent Overlook in Maine
Interior

Boat launch and Trailer parking, Dog Friendly, Lake Great Pond

Boat launch and Trailer parking, Dog Friendly, Lake Great Pond
Belgrade
10.0 out of 10, Exceptional, (54 reviews)
"House was very comfortable and neat! Great location!"
United States
Brian D.
The price is HK$1,203
HK$2,704 total
includes taxes & fees
31 May - 1 Jun
Boat launch and Trailer parking, Dog Friendly, Lake Great Pond
3 bedrooms, desk, iron/ironing board, free WiFi

An Authentic Clean & Cozy Maine Homestay

An Authentic Clean & Cozy Maine Homestay
Buckfield
9.8 out of 10, Exceptional, (66 reviews)
"My tenants said the accommodations were lovely "
United States
Nathan
The price is HK$973
HK$1,599 total
includes taxes & fees
1 Jun - 2 Jun
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 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$1,411
HK$2,187 total
includes taxes & fees
10 Jun - 11 Jun
Cabin Style Studio Apt with Private Hot tub on 100 Acres Kayaks, Canoes & SUP
Exterior

Perfectly Located 1 Bedroom, newly remodeled

Perfectly Located 1 Bedroom, newly remodeled
Augusta
10.0 out of 10, Exceptional, (1 review)
"The area is so convenient for any business you have in the Augusta area- right off the main thoroughfare yet far enough away to be private. Check in was as simple as getting the lock code from vrbo check in emails. The apartment is even more lovely than the pictures- almost too clean and comfortable to be real! Bedtime was silent so I got a great night sleep. I only wish we would have had more time to enjoy :) Highly recommend!! "
United States
w c.
The price is HK$1,175
HK$2,076 total
includes taxes & fees
1 Jun - 2 Jun
Perfectly Located 1 Bedroom, newly remodeled
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

Best Western Plus Augusta Civic Center Inn

Best Western Plus Augusta Civic Center Inn

4/10 Poor
"Rooms are fine. This is a budget hotel in an area void of other options. Issue with check in. They had trouble locating the pre-paid hotels.com booking. Employee and manager made us pay for a room and only after it was processed and paid, that they located the other room. They refused to cancel the room that they made us pay citing there were other active reservations and that they have a 24 cancelation policy. Well, I had checked in one day earlier than the rest of the group with the other 3 rooms. I had asked the front desk employee to make sure there are no other reservations other than the 3 pre-paid rooms. He said we are all set. Then found out next day during check in that we were not. Wasted more than an hour at the front desk to try to sort this out, and the manager and the clerk couldn't and wouldn't help. They were more interested in talking over me than to listen and to help."
Eric 2-night trip
Posted 22 hours ago
Best Western Plus Augusta Civic Center Inn

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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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?

Wilson Pond and Cobbosseecontee Lake are a couple of lovely local spots to get outside and enjoy nature. While here, Maranacook Lake 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.