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

Winthrop Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
17 Jul - 19 Jul
In two months
28 Aug - 30 Aug
In three months
25 Sep - 27 Sep
In four months
23 Oct - 25 Oct

Our top choices for Winthrop vacation 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
The price is AED 654
AED 1,157 total
includes taxes & fees
15 Jul - 16 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, (39 reviews)
"Great place to stay and pet friendly. "
United States
Kevin M.
The price is AED 331
AED 561 total
includes taxes & fees
8 Jul - 9 Jul
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 AED 443
AED 951 total
includes taxes & fees
15 Jul - 16 Jul
Sister A-Frame in Woods B
Terrace/patio

Hammock Haven Island Dome

Hammock Haven Island Dome
Monmouth
9.6 out of 10, Exceptional, (4 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 AED 228
AED 797 total
includes taxes & fees
7 Jul - 8 Jul
Hammock Haven Island Dome
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 AED 290
AED 829 total
includes taxes & fees
8 Jul - 9 Jul
Island Aframe Adventure in Maine
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, (1 review)
"A hidden gem!"
United States
Nadra H.
The price is AED 434
AED 553 total
includes taxes & fees
7 Jul - 8 Jul
Steps from Bates College, Quiet Cottage Retreat
WiFi, bed sheets

The StarGazer Floating Dome

The StarGazer Floating Dome
Monmouth
The price is AED 300
AED 827 total
includes taxes & fees
8 Jul - 9 Jul
The StarGazer Floating Dome
Exterior

Discover Oakland charm near Colby College 10 min

Discover Oakland charm near Colby College 10 min
Oakland
9.8 out of 10, Exceptional, (13 reviews)
"Very clean and comfy. A pleasure to stay there. "
United States
Vicki W.
The price is AED 364
AED 773 total
includes taxes & fees
9 Jul - 10 Jul
Discover Oakland charm near Colby College 10 min
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 AED 456
AED 753 total
includes taxes & fees
9 Jul - 10 Jul
An Authentic Clean & Cozy Maine Homestay
TV, fireplace, books

Private Dock on Messalonskee Lake: Cozy Cottage!

Private Dock on Messalonskee Lake: Cozy Cottage!
Sidney
9.0 out of 10, Wonderful, (12 reviews)
"Great place to stay for our annual fishing weekend in the Belgrade Lakes region! "
United States
Shawn H.
The price is AED 393
AED 1,341 total
includes taxes & fees
29 Jul - 30 Jul
Private Dock on Messalonskee Lake: Cozy Cottage!
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 AED 422
AED 973 total
includes taxes & fees
7 Jul - 8 Jul
Floating Island Cabin
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 AED 422
AED 869 total
includes taxes & fees
11 Jul - 12 Jul
The heart of the Belgrade Lakes
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, (48 reviews)
"Fantastic quiet location and beautiful property.Everything you could possibly need has been supplied and the property is absolutely spotless.The hosts communicated perfectly, including facilitating an extremely late check-in.We would highly recommend this property - and we are hoping to return in the summer.Thank you for a wonderful stay!"
United States
Stephen R.
Central Maine Apartment offering 4 Seasons of Fun.
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, (7 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 AED 621
AED 969 total
includes taxes & fees
4 Jul - 5 Jul
Cabin Style Studio Apt with Private Hot tub on 100 Acres Kayaks, Canoes & SUP
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 AED 569
AED 1,053 total
includes taxes & fees
6 Jul - 7 Jul
Beautifully remodeled first floor of a duplex home, surrounded by privacy fence
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 AED 918
AED 1,846 total
includes taxes & fees
29 Jul - 30 Jul
Maine river escape: free kayaks, paddle boards, tennis, cute rabbits and fun!
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 AED 522
AED 881 total
includes taxes & fees
6 Jul - 7 Jul
Charming 1-bedroom apartment in Monmouth with AC, WiFi. Several lakes nearby.
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 AED 661
AED 1,397 total
includes taxes & fees
8 Jul - 9 Jul
Cozy Cottage on water's edge of Lake Cobbosseecontee
Exterior

Perfectly Located 1 Bedroom, newly remodeled

Perfectly Located 1 Bedroom, newly remodeled
Augusta
10.0 out of 10, Exceptional, (2 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 AED 551
AED 985 total
includes taxes & fees
6 Jul - 7 Jul
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winthrop Hotel Reviews

Maine Evergreen Hotel, an Ascend Collection Hotel

Maine Evergreen Hotel, an Ascend Collection Hotel

10/10 Excellent
"This hotel is a gem. Excellent staff, interesting artwork. Comfortable stay."
Cynthia 1-night trip
Posted 1 hour ago
Maine Evergreen Hotel, an Ascend Collection Hotel

Explore a world of travel with Expedia

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?

Cozy Cottage on water's edge of Lake Cobbosseecontee: You might want to consider this vacation rental near Winthrop, which is located on a lake and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave.

How many vacation rentals are there in Winthrop?

Expedia has 14 vacation rentals for your stay in Winthrop.

What can I see and do in Winthrop?

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