Search Vacation Homes in Winthrop

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
2 May - 4 May
In two weeks
9 May - 11 May
In one month
23 May - 25 May
In two months
20 Jun - 22 Jun

Compare 149 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)
"This is a very nice home and was clean upon arrival. Very responsive owner as well."
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)
"Everything that was promised was fulfilled. Host & caretaker were available and great to deal with. House was welcoming and comfortable in this cold-weather visit. We’d love to return in summer, the lake access clearly is wonderful."
Spectacular Cobbossee Lakefront with Hot Tub&Dog Friendly
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
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)
"Wife, dog, and I had a great week away from home. House had everything we needed, quiet, and comfortable. Lot of great kayaking and fishing."
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.

9.4 out of 10, Exceptional, (3)
"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, (10)
"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)
"Peaceful and scenic location"
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 place to stay for a few days to collect the beautiful Togus Pond Beautiful view."
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
Property grounds

Cozy Long Pond Cottage: private mooring & shared dock

9.8 out of 10, Exceptional, (13)
"Very good stay."
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)
"Overall we had a good time "
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)
"Property was exactly as described and just as beautiful as the pictures. Amazing location right on the lake. My friends and I really enjoyed our stay and would definitely stay here again."
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, (18)
"This house has everything for a weekend family vacay; you can spend the whole weekend enjoying the house & amenities such as the hot tub!"
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)
"Very quiet with a nice view of the stream. House was very nice with everything you need."
Big Pines Cabin: A Waterfront Retreat Open 4 Seasons, with Private Dock
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
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.
Don't see what you're looking for?
See all available properties in Winthrop
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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.