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Check prices for these dates

Next weekend
4 Rab. II - 6 Rab. II
In two weeks
11 Rab. II - 13 Rab. II
In one month
25 Rab. II - 27 Rab. II
In two months
23 Jum. I - 25 Jum. I

Compare 147 Vacation Homes in Winthrop with updated reviews, rates, and availability.

Whispering Waters Farmhouse/Barn
Interior

Whispering Waters Farmhouse/Barn

Whispering Waters Farmhouse/Barn
Warm & Inviting Lakeside Retreat, Private, Tranquil Picture Perfect Setting
Fridge, microwave, oven, dishwasher

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

Warm & Inviting Lakeside Retreat, Private, Tranquil Picture Perfect Setting
Private and Calming Waterfront to the Rescue!
Property grounds

Private and Calming Waterfront to the Rescue!

9.6 out of 10, Exceptional, (77)
"clean place listed accordingly "
Private and Calming Waterfront to the Rescue!
Beautiful lakeside 4 bedroom retreat with private dock and walkout basement
Property grounds

Beautiful lakeside 4 bedroom retreat with private dock and walkout basement

2.0 star property
Beautiful lakeside 4 bedroom retreat with private dock and walkout basement
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, (240)
"Had another great fishing trip with this as our home base! Always clean and comfortable! "
Spectacular Cobbossee Lakefront with Hot Tub&Dog Friendly
The Modern Maine Retreat
Outdoor dining

The Modern Maine Retreat

10.0 out of 10, Exceptional, (3)
"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
Brand New Waterfront Lake House (completed July 2021)
Miscellaneous

Brand New Waterfront Lake House (completed July 2021)

10.0 out of 10, Exceptional, (22)
"We had an amazing week at this property. House was spacious, clean and had everything that we needed. We plan to stay here again next summer! "
Brand New Waterfront Lake House (completed July 2021)
Peaceful Fisherman's Paradise w/ Deck + Fire Pit!
Fridge, microwave, stovetop, dishwasher

Peaceful Fisherman's Paradise w/ Deck + Fire Pit!

10.0 out of 10, Exceptional, (26)
"The property was as advertised! For a family with little kids, this was a great place to stay. David was helpful and very responsive!"
Peaceful Fisherman's Paradise w/ Deck + Fire Pit!
Charming 2-bedroom house in marvelous Auburn with AC, WiFi, and fenced yard.
Fridge, microwave, oven, stovetop

Charming 2-bedroom house in marvelous Auburn with AC, WiFi, and fenced yard.

10.0 out of 10, Exceptional, (2)
"I enjoyed my stay. The amenities were perfect "
Charming 2-bedroom house in marvelous Auburn with AC, WiFi, and fenced yard.
Taylor Pond Lake House with Private beach
Fridge, microwave, oven, stovetop

Taylor Pond Lake House with Private beach

9.8 out of 10, Exceptional, (9)
"A great home base to explore southern Maine, or to just enjoy some quiet time at the lake."
Taylor Pond Lake House with Private beach
Spectacular Location Reasonably Priced
Exterior

Spectacular Location Reasonably Priced

9.6 out of 10, Exceptional, (29)
"This is the quintessential cabin rental which provides good modern facilities with the vintage Maine camp feel we have always looked for. We will return to our 3rd rental at this property next year. Very satisfied with our experience."
Spectacular Location Reasonably Priced
Dog-friendly lakefront home with dock, fireplace, firepit, lake views, & 1 kayak
Fridge, microwave, oven, stovetop

Dog-friendly lakefront home with dock, fireplace, firepit, lake views, & 1 kayak

8.2 out of 10, Very Good, (16)
"Great location! Very nice place"
Dog-friendly lakefront home with dock, fireplace, firepit, lake views, & 1 kayak
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.
Cozy Long Pond Cottage: private mooring & shared dock
Miscellaneous

Cozy Long Pond Cottage: private mooring & shared dock

9.8 out of 10, Exceptional, (13)
" Cute place"
Cozy Long Pond Cottage: private mooring & shared dock
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
Modern 4 BR Waterfront Lake House, beautiful Belgrade Lakes Area, Mt. Vernon, ME
Property grounds

Modern 4 BR Waterfront Lake House, beautiful Belgrade Lakes Area, Mt. Vernon, ME

10.0 out of 10, Exceptional, (16)
"We were a group of 6 men on our annual fishing trip. The rental did not disappoint, Owners were very attentive to our needs leading up to our visit. Home was well appointed, clean and came as advertised. Great Lake for fishing, caught trout, bass, cusk and perch. The eagle that hung around while we fished was an added bonus. Overall a great trip!!!"
Modern 4 BR Waterfront Lake House, beautiful Belgrade Lakes Area, Mt. Vernon, ME
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)
"We had an awesome time playing in the snow in the backyard and enjoying the relaxing hot tub. The house accommodated our large family and the host was very responsive and came quickly when we needed help. Will definitely come back "
Spacious Country Home w/ Hot Tub, near Colby/Thomas
Big Pines Cabin: A Waterfront Retreat Open 4 Seasons, with Private Dock
Terrace/patio

Big Pines Cabin: A Waterfront Retreat Open 4 Seasons, with Private Dock

2.0 star property
10.0 out of 10, Exceptional, (5)
"Did not want to leave. So thankful work took me to this beautiful property. The views did not disappoint. Alyssa and Mike were such a pleasure to work with. Thank you for opening your home away from home for me. My family and I will definitely be back. "
Big Pines Cabin: A Waterfront Retreat Open 4 Seasons, with Private Dock
Riverfront Sanctuary
Interior

Riverfront Sanctuary

10.0 out of 10, Exceptional, (3)
"This was a perfect location and setting for our family stay to attend our nephews wedding. The home has so much character with antique furnishings and a beautiful country setting overlooking the river. The hosts were very accommodating, responsive and a pleasure to deal with. "
Riverfront Sanctuary
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

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
Dog Friendly Cabin Right On The Water!!!
Exterior detail

Dog Friendly Cabin Right On The Water!!!

2.0 out of 10, (1)
"The renter is not worth coming about the fact that her home is on a very steep hill. I told her I was a senior and had foot and ankle and knee surgeries and had a hard time walking. I saved up to rent a place all year. When I got there I had to call her to find out how to get to the lake. It is so steep I couldn't find an entrance to the lake, I finally found a foot wide muddy, slippery path which was 90 degrees straight up and down. I only took a few steps and realized I would break my neck if...
Dog Friendly Cabin Right On The Water!!!
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
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.