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Check prices for these dates

Next weekend
6 Jum. II - 8 Jum. II
In two weeks
13 Jum. II - 15 Jum. II
In one month
27 Jum. II - 29 Jum. II
In two months
25 Raj. - 27 Raj.

Compare 149 Vacation Homes in Winthrop with updated reviews, rates, and availability.

Year-Round Lakeside Retreat
Property grounds

Year-Round Lakeside Retreat

9.2 out of 10, Wonderful, (22)
"Plenty of room, great access. Super shower. Very quick response from owners. Very comfortable beds. Great view of pond."
Year-Round Lakeside Retreat
Waterfront retreat with stunning views, dock access and washer/dryer
Dining

Waterfront retreat with stunning views, dock access and washer/dryer

Waterfront retreat with stunning views, dock access and washer/dryer
Every window has a spectacular lake view Low fees
Miscellaneous

Every window has a spectacular lake view Low fees

10.0 out of 10, Exceptional, (34)
"location was great, the lake and the wildlife were amazing. enjoyed sitting in the glassed in room each night listening to all of the sounds. the kids were a bit shocked by the 'don't drink the water' warnings, which caused a bit of drama, but otherwise, it was a much needed week away."
Every window has a spectacular lake view Low fees
Lakefront home on Long Pond with private dock, firepit & woodstove- dog-friendly
Miscellaneous

Lakefront home on Long Pond with private dock, firepit & woodstove- dog-friendly

9.2 out of 10, Wonderful, (19)
"Location is beautiful and private"
Lakefront home on Long Pond with private dock, firepit & woodstove- dog-friendly
Warm & Inviting Lakeside Retreat, Private, Tranquil Picture Perfect Setting
Fridge, microwave, oven, dishwasher

Warm & Inviting Lakeside Retreat, Private, Tranquil Picture Perfect Setting

10.0 out of 10, Exceptional, (1)
"Nice time"
Warm & Inviting Lakeside Retreat, Private, Tranquil Picture Perfect Setting
Spacious Country Home w/ Hot Tub, near Colby/Thomas
Outdoor spa tub

Spacious Country Home w/ Hot Tub, near Colby/Thomas

9.8 out of 10, Exceptional, (19)
"This house has everything for a weekend family vacay; you can spend the whole weekend enjoying the house & amenities such as the hot tub!"
The price is SAR 840
SAR 1,924 total
includes taxes & fees
3 Jun - 4 Jun
Spacious Country Home w/ Hot Tub, near Colby/Thomas
Spacious 5-bedroom lakefront home on pristine Lower Narrows Pond in Winthrop
Fridge, microwave, oven, stovetop

Spacious 5-bedroom lakefront home on pristine Lower Narrows Pond in Winthrop

Spacious 5-bedroom lakefront home on pristine Lower Narrows Pond in Winthrop
Private and Calming Waterfront to the Rescue!
Property grounds

Private and Calming Waterfront to the Rescue!

9.6 out of 10, Exceptional, (78)
"This is a very nice home and was clean upon arrival. Very responsive owner as well."
Private and Calming Waterfront to the Rescue!
Riverfront Sanctuary
Interior

Riverfront Sanctuary

10.0 out of 10, Exceptional, (3)
"Home was perfect for cooking and relaxing out doors. Property owners are very responsive and helpful. No issues and we really enjoyed our stay!"
Riverfront Sanctuary
Great Pond Waterfront: Dog-friendly Home Near Colby College
Beach towels

Great Pond Waterfront: Dog-friendly Home Near Colby College

9.6 out of 10, Exceptional, (30)
"Thanks again for sharing your cottage with us! Everything was as described and the location was perfect. We’re looking forward to returning in the future."
Great Pond Waterfront: Dog-friendly Home Near Colby College
Loon Lake House- Private Home in Wayne- Lake view/ access
Interior

Loon Lake House- Private Home in Wayne- Lake view/ access

9.2 out of 10, Wonderful, (7)
"Great location, lots of attractions space, beautiful view"
Loon Lake House- Private Home in Wayne- Lake view/ access
Spectacular Location Reasonably Priced
Exterior

Spectacular Location Reasonably Priced

9.6 out of 10, Exceptional, (29)
"Peaceful and scenic location"
Spectacular Location Reasonably Priced
Whispering Waters Farmhouse/Barn
Interior

Whispering Waters Farmhouse/Barn

Whispering Waters Farmhouse/Barn
Cozy Long Pond Cottage: private mooring & shared dock
Property grounds

Cozy Long Pond Cottage: private mooring & shared dock

9.8 out of 10, Exceptional, (14)
"Very good stay."
Cozy Long Pond Cottage: private mooring & shared dock
Lakefront Maine House ~ 4 Mi to Colby College
Microwave, stovetop, dishwasher, coffee/tea maker

Lakefront Maine House ~ 4 Mi to Colby College

8.0 out of 10, Very Good, (2)
"Convenient very clean but we were hardly there except to sleep. Thank you"
Lakefront Maine House ~ 4 Mi to Colby College
The Modern Maine Retreat
Outdoor dining

The Modern Maine Retreat

9.0 out of 10, Wonderful, (4)
"Worked out perfectly for our needs. Owner responded immediately to assist us with minor issue. We would, and most likely will, rent this home again. Location was great for our purpose. Plenty of room."
The Modern Maine Retreat
Spectacular Cobbossee Lakefront with Hot Tub&Dog Friendly
Outdoor spa tub

Spectacular Cobbossee Lakefront with Hot Tub&Dog Friendly

10.0 out of 10, Exceptional, (242)
"Had another great fishing trip with this as our home base! Always clean and comfortable! "
Spectacular Cobbossee Lakefront with Hot Tub&Dog Friendly
Spring Couples Retreat in Sumner – Dog Friendly!
Exterior

Spring Couples Retreat in Sumner – Dog Friendly!

10.0 out of 10, Exceptional, (23)
"This was a return trip for us. We love the house and the area so much, perfect winter weekend getaway from Boston. Hope to come back a third time."
Spring Couples Retreat in Sumner – Dog Friendly!
Light-Filled Log Home, 4 Wooded Acres, & Lake Access. The water is 0.4 mi away.
Exterior

Light-Filled Log Home, 4 Wooded Acres, & Lake Access. The water is 0.4 mi away.

10.0 out of 10, Exceptional, (56)
"Super cozy place. Use a silver popper on the pond"
Light-Filled Log Home, 4 Wooded Acres, & Lake Access. The water is 0.4 mi away.
Lakefront All Season Home
Fridge, microwave, oven, stovetop

Lakefront All Season Home

8.8 out of 10, Excellent, (18)
"Stunning lake views. Sitting on the dock was extremely relaxing. Very close to Bates college which was great. "
Lakefront All Season Home
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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Other property types in Winthrop

Waterfront retreat with stunning views, dock access and washer/dryer
Dining

Waterfront retreat with stunning views, dock access and washer/dryer

Waterfront retreat with stunning views, dock access and washer/dryer
Escape to our cozy Winthrop cabin on Dexter Pond
Terrace/patio

Escape to our cozy Winthrop cabin on Dexter Pond

10.0 out of 10, Exceptional, (11)
"Cute little cabin overlooking a beautiful view of the lake. The owners were extremely kind and easy to work with. Overall amazing experience and would stay again in a heartbeat."
Escape to our cozy Winthrop cabin on Dexter Pond
Spacious 5-bedroom lakefront home on pristine Lower Narrows Pond in Winthrop
Fridge, microwave, oven, stovetop

Spacious 5-bedroom lakefront home on pristine Lower Narrows Pond in Winthrop

Spacious 5-bedroom lakefront home on pristine Lower Narrows Pond in Winthrop
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.