A wooden signpost with 'WINTHROP' written on it, surrounded by greenery and trees.

Winthrop Holiday Rentals

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Check prices for these dates

In two weeks
31 Jul - 2 Aug
In two months
11 Sept - 13 Sept
In three months
9 Oct - 11 Oct
In four months
6 Nov - 8 Nov

Our top choices for Winthrop holiday rentals

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
10.0 out of 10, Exceptional, (1 review)
"This is an adorable newly constructed unit. Lots of day light, cute decor and lake views. The one confusing part was the use of the docks which was uncomfortable at the beginning but worked out in the end. We used the dock and swam every day. The location is also convenient and has plenty of parking. Jill is a great host. We would stay here again."
United States
Katie D.
The price is HK$1,568
HK$2,657 total
includes taxes & fees
16 Jul - 17 Jul
Jill's Place, new construction, lake access Cobbosee, 1 mile from Cabin Masters
Terrace/patio

Get in touch with nature.

Get in touch with nature.
Richmond
10.0 out of 10, Exceptional, (43 reviews)
"Wonderful place very peaceful very friendly Aaron was spectacular couldn't ask for a more wonderful enjoyable spot"
United States
Keith R
The price is HK$784
HK$1,282 total
includes taxes & fees
3 Aug - 4 Aug
Get in touch with nature.
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$2,013 total
includes taxes & fees
16 Jul - 17 Jul
Sister A-Frame in Woods B
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
The price is HK$948
HK$2,601 total
includes taxes & fees
29 Jul - 30 Jul
Private Dock on Messalonskee Lake: Cozy Cottage!
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, (67 reviews)
"My tenants said the accommodations were lovely "
United States
Nathan
The price is HK$973
HK$1,599 total
includes taxes & fees
22 Jul - 23 Jul
An Authentic Clean & Cozy Maine Homestay
Exterior

Pet-Friendly Island A-Frame w/ Lake Access

Pet-Friendly Island A-Frame w/ Lake Access
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$674
HK$1,845 total
includes taxes & fees
26 Jul - 27 Jul
Pet-Friendly Island A-Frame w/ Lake Access
Exterior

Discover Oakland charm near Colby College 10 min

Discover Oakland charm near Colby College 10 min
Oakland
9.8 out of 10, Exceptional, (14 reviews)
"Place was very clean. Host was wonderful and easy to communicate with. "
United States
Tammy W.
The price is HK$792
HK$1,657 total
includes taxes & fees
11 Aug - 12 Aug
Discover Oakland charm near Colby College 10 min
Fridge, microwave, oven, stovetop

Steps from Bates College, Quiet Cottage Retreat

Steps from Bates College, Quiet Cottage Retreat
Lewiston
10.0 out of 10, Exceptional, (2 reviews)
"Great little spot with easy access to the college. Host was great and included some very thoughtful touches, which were much appreciated."
United States
Joseph D.
The price is HK$1,037
HK$1,301 total
includes taxes & fees
28 Jul - 29 Jul
Steps from Bates College, Quiet Cottage Retreat
Spa

Floating Island Dome - Pet-Friendly Lake Retreat

Floating Island Dome - Pet-Friendly Lake Retreat
Monmouth
The price is HK$696
HK$1,827 total
includes taxes & fees
22 Jul - 23 Jul
Floating Island Dome - Pet-Friendly Lake Retreat
Terrace/patio

Hammock Haven Island Dome

Hammock Haven Island Dome
Monmouth
9.2 out of 10, Wonderful, (5 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$486
HK$1,470 total
includes taxes & fees
20 Jul - 21 Jul
Hammock Haven Island Dome
2 bedrooms, WiFi, bed sheets

The heart of the Belgrade Lakes

The heart of the Belgrade Lakes
Oakland
9.0 out of 10, Wonderful, (9 reviews)
"Host was very accommodating "
United States
Maureen
The price is HK$901
HK$1,828 total
includes taxes & fees
7 Aug - 8 Aug
The heart of the Belgrade Lakes
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, (23 reviews)
"Location is amazing "
United States
Laura Q.
The price is HK$1,411
HK$2,982 total
includes taxes & fees
11 Aug - 12 Aug
Cozy Cottage on water's edge of Lake Cobbosseecontee
Property grounds

Floating Island Cabin

Floating Island Cabin
Monmouth
10.0 out of 10, Exceptional, (9 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$980
HK$2,230 total
includes taxes & fees
26 Jul - 27 Jul
Floating Island Cabin
Exterior

Perfectly Located 1 Bedroom, newly remodeled

Perfectly Located 1 Bedroom, newly remodeled
Augusta
10.0 out of 10, Exceptional, (3 reviews)
"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$1,176
HK$2,085 total
includes taxes & fees
21 Jul - 22 Jul
Perfectly Located 1 Bedroom, newly remodeled
Living area

Beautifully remodeled first floor of a duplex home, surrounded by privacy fence

Beautifully remodeled first floor of a duplex home, surrounded by privacy fence
Sabattus
The price is HK$1,215
HK$2,247 total
includes taxes & fees
29 Jul - 30 Jul
Beautifully remodeled first floor of a duplex home, surrounded by privacy fence
1 bedroom, WiFi, bed sheets

Charming 1-bedroom apartment in Monmouth with AC, WiFi. Several lakes nearby.

Charming 1-bedroom apartment in Monmouth with AC, WiFi. Several lakes nearby.
Monmouth
9.0 out of 10, Wonderful, (2 reviews)
"For our 2 night stay we just needed a place to end the long day with, very quiet."
United States
Tricia R.
The price is HK$1,113
HK$1,871 total
includes taxes & fees
23 Jul - 24 Jul
Charming 1-bedroom apartment in Monmouth with AC, WiFi. Several lakes nearby.
Paper towels

Cozy newly built 1-bedroom unit 2 Kentucky Bay in charming Smithfield Maine

Cozy newly built 1-bedroom unit 2 Kentucky Bay in charming Smithfield Maine
Smithfield
10.0 out of 10, Exceptional, (1 review)
"We had a great weekend stay at this newly built place in Smithfield while attending a swim event with my son at Colby College, which was just a short, easy drive away. Everything was clean and cozy, and the place had everything we needed for a comfortable stay. The host was helpful and highly responsive and recommended a local fishing spot on one of the three lakes right around the property which was very close and a nice way to spend down time. Overall, a solid choice!"
United States
Gustavo C.
The price is HK$1,176
HK$1,461 total
includes taxes & fees
12 Aug - 13 Aug
Cozy newly built 1-bedroom unit 2 Kentucky Bay in charming Smithfield Maine
Property grounds

Glamping Lakefront Island Retreat w/ Kayak & Pet-Friendly

Glamping Lakefront Island Retreat w/ Kayak & Pet-Friendly
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$674
HK$1,837 total
includes taxes & fees
21 Jul - 22 Jul
Glamping Lakefront Island Retreat w/ Kayak & Pet-Friendly
Interior

Pool, Dream Home Gym, TV+Desk in Each Room, 85" TV, Games, 2 BKB Hoops, Fire Pit

Pool, Dream Home Gym, TV+Desk in Each Room, 85" TV, Games, 2 BKB Hoops, Fire Pit
Lewiston
The price is HK$2,039
HK$5,460 total
includes taxes & fees
19 Jul - 20 Jul
Pool, Dream Home Gym, TV+Desk in Each Room, 85" TV, Games, 2 BKB Hoops, Fire Pit
Outdoor dining

Maine river escape: free kayaks, paddle boards, tennis, cute rabbits and fun!

Maine river escape: free kayaks, paddle boards, tennis, cute rabbits and fun!
West Gardiner
9.8 out of 10, Exceptional, (19 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$1,959
HK$3,998 total
includes taxes & fees
10 Aug - 11 Aug
Maine river escape: free kayaks, paddle boards, tennis, cute rabbits and fun!
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

Hampton Inn Augusta

Hampton Inn Augusta

10/10 Excellent
"Our stay here was very nice. The room was clean and comfortable and the breakfast was good. The staff was very nice and helpful. We will recommend this place to our family and friends."
David 1-night trip
Posted 2 hours ago
Hampton Inn 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?

Enjoy Sunset views on tranquil Dexter Pond: This highly rated holiday home rental in Winthrop is located on the waterfront, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. 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, 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.