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Check prices for these dates

Next weekend
28 Rab. I - 30 Rab. I
In two weeks
4 Rab. II - 6 Rab. II
In one month
18 Rab. II - 20 Rab. II
In two months
16 Jum. I - 18 Jum. I

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

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
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
Whispering Waters Farmhouse/Barn
Interior

Whispering Waters Farmhouse/Barn

Whispering Waters Farmhouse/Barn
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)
Veedon Fleece on the Lake
Miscellaneous

Veedon Fleece on the Lake

10.0 out of 10, Exceptional, (15)
"We enjoyed the house tremendously "
Veedon Fleece on the Lake
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)
"This was our third year in a row spending most of August at the wonderful Loons nest! Brent and Sarah are great and responsive hosts. The views and water are incomparable and the cabin itself has all of the modern conveniences while maintaining a rustic charm. It is one of our favorite places in the world and hope to be back next year!"
Great Pond Waterfront: Dog-friendly Home Near Colby College
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
Private and Calming Waterfront to the Rescue!
Property grounds

Private and Calming Waterfront to the Rescue!

9.6 out of 10, Exceptional, (77)
"We stayed at the property for a trade show with our team and enjoyed a comfortable clean and amazing overall stay. The house was clean kept and the owner was easy to deal with would highly recommend "
Private and Calming Waterfront to the Rescue!
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
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
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
Sunfish Cove is the perfect year round getaway.
Exterior

Sunfish Cove is the perfect year round getaway.

10.0 out of 10, Exceptional, (44)
"We spent a long weekend here as a group of 13 adults and found the location to be amenable to everyone’s interests, including skiing and snowboarding, tubing, ice fishing, and day trips to Augusta and Portland. Everything was clean and as advertised on VRBO and furniture covers/blankets were available in nearly every room so our dog was just as welcome. Sleeping quarters were rather tight but the kitchen and living areas were very open and spacious, more than making up for it; in addition the...
Sunfish Cove is the perfect year round getaway.
Find Your Bliss at this Private and Captivating Lakeside Retreat
Smart TV, video games, foosball, table tennis

Find Your Bliss at this Private and Captivating Lakeside Retreat

10.0 out of 10, Exceptional, (20)
"We decided to book this beautiful property to bring our family together for a long weekend to celebrate Thanksgiving together for our first holiday since the passing of our father. This was the perfect spot! The house accommodated all 12 of us easily with plenty of space for more! The hope décor is perfection and the views are priceless! The days we spent there with filled with tears and laughter and reliving fond memories while making new memories. Dan was absolutely wonderful to deal with...
Find Your Bliss at this Private and Captivating Lakeside Retreat
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

Cottage on Cobbosseecontee Lake. Dates available.
Fridge, microwave, oven, stovetop

Cottage on Cobbosseecontee Lake. Dates available.

10.0 out of 10, Exceptional, (162)
"Second time at this location, this time to ice fish. Amazing location... cant get any closer to the lake!! All amenities are great, furniture super comfy. To incude the bed and pillows!! Will be back again this summer!! "
Cottage on Cobbosseecontee Lake. Dates available.
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.