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Compare 125 Vacation Homes in Winthrop with updated reviews, rates, and availability.

Sunfish Cove is the perfect year round getaway.
Breathtaking sunrise!

Sunfish Cove is the perfect year round getaway.

10.0 out of 10, Exceptional, (39)
"We had a great time staying at sunfish cove! Very spacious home with great views of the water! Really enjoyed the fire pit and the outdoor amenities!"
Sunfish Cove is the perfect year round getaway.
Every window has a spectacular lake view Low fees
Property grounds

Every window has a spectacular lake view Low fees

10.0 out of 10, Exceptional, (31)
"We chose this property based on it's proximity to relatives we were visiting, the low fees (like you, I refuse to pay a $300 'host fee'), the reports of a easy-to-communicate with property manager and views from every window. We were NOT disappointed. I especially want to thank Tina for her fast responses to any questions, and her flexibility and generosity. Due to the time of year, we were unable to enjoy the swimming and boating so many others rave about. But we did enjoy sitting in the...
Every window has a spectacular lake view Low fees
Lakeside retreat in Central Maine
Beach

Lakeside retreat in Central Maine

9.8 out of 10, Exceptional, (79)
"I can't explain the ease and how helpful the host was. We were traveling from a long distance for this. The host was helpful with late check in. The house was well maintained and clean everywhere. You get everything you need. The wifi is also fast. I wish they did provide some body wash and some extra stuff. No complaints at all. It was a memorable stay"
Lakeside retreat in Central Maine
Spectacular Cobbossee Lakefront with Hot Tub&Dog Friendly
View of house from lake

Spectacular Cobbossee Lakefront with Hot Tub&Dog Friendly

10.0 out of 10, Exceptional, (236)
"Had a nice quiet getaway here in the off-season. Enjoyed the hot tub and peace and quiet looking out on the lake. Very spacious and as advertised. Dog friendly for our small dog. Easy to check-in/out. Would definitely consider again if we were coming up to this area."
Spectacular Cobbossee Lakefront with Hot Tub&Dog Friendly
3 Bedroom year round lakefront home on Three Mile Pond in South China, ME

3 Bedroom year round lakefront home on Three Mile Pond in South China, ME

9.8 out of 10, Exceptional, (81)
"Great property, third tine here, excellent stocked kitchen"
3 Bedroom year round lakefront home on Three Mile Pond in South China, ME
Dog-friendly lakefront home with dock, fireplace, firepit, lake views, & 1 kayak

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

8.0 out of 10, Very Good, (15)
"This house has a beautiful location. My husband and I stayed for a weekend getaway and enjoyed our stay. One issue that we had was the water pressure. It was hard to shower because the water kept going in and out. As others have stated, the inside of the house could use some TLC. Some of the decorations are falling apart on the wall. The paint on the walls in some rooms look incomplete. Overall it was a good stay. "
Dog-friendly lakefront home with dock, fireplace, firepit, lake views, & 1 kayak
Secluded escape with three beaches, lake access, grill & fast WiFi - dogs OK

Secluded escape with three beaches, lake access, grill & fast WiFi - dogs OK

9.0 out of 10, Wonderful, (18)
"Comfortable, quiet location. Appreciated the many nightlights. Both showers need grab bars. Basement shower drain not attached to shower floor."
Secluded escape with three beaches, lake access, grill & fast WiFi - dogs OK
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.
5BED HOUSE-HOT TUB, SAUNA, POOL TABLE, FIRE PIT, 3+ LG TV, PRIVATE LAKE FRONTAGE
Exterior

5BED HOUSE-HOT TUB, SAUNA, POOL TABLE, FIRE PIT, 3+ LG TV, PRIVATE LAKE FRONTAGE

10.0 out of 10, Exceptional, (4)
"The house had a lot of room. This would be a great family getaway place. The host was available and very attentive. I would recommend this house. "
5BED HOUSE-HOT TUB, SAUNA, POOL TABLE, FIRE PIT, 3+ LG TV, PRIVATE LAKE FRONTAGE
Year-Round Lakeside Retreat
View from property

Year-Round Lakeside Retreat

9.2 out of 10, Wonderful, (20)
"We only had a couple of hiccups with the heat upon arrival and a small electrical issue, but the host communicated quickly and all was resolved without further inconvenience to our family. Clean. Beds were very comfortable. Kitchen was well stocked. Overall we had a great stay, would stay again, and recommend to others! "
Year-Round Lakeside Retreat
Private and Calming Waterfront to the Rescue!
40 foot dock for boating, fishing and swimming

Private and Calming Waterfront to the Rescue!

9.6 out of 10, Exceptional, (75)
"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!
An Authentic Clean & Cozy Maine Homestay
The Village House in Spring.

An Authentic Clean & Cozy Maine Homestay

10.0 out of 10, Exceptional, (54)
"Third time staying at this location, works out great for my yearly 10 day visit to this area."
The price is AED 470
AED 749 total
includes taxes & fees
2 Dec - 3 Dec
An Authentic Clean & Cozy Maine Homestay
Lakefront All Season Home
Property grounds

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
Classy AF Home Steps from Colby and Trails
Exterior

Classy AF Home Steps from Colby and Trails

10.0 out of 10, Exceptional, (39)
"Lovely house. Only thing was just one bathroom bit otherwise recommend. "
Classy AF Home Steps from Colby and Trails
Pet-friendly, peaceful lakeside retreat on Cobboseecontee Lake peninsula
Exterior

Pet-friendly, peaceful lakeside retreat on Cobboseecontee Lake peninsula

9.2 out of 10, Wonderful, (16)
"Our family had a great time at the Chin's Lake House. The house inside was modern, the outside rustic which made it interesting. Inside the house it was fairly clean. We did need to go though 2 cabinets and bag food as it was left opened. This made us uncomfortable as there are a lot of ants in critters on the property. Otherwise the rest of the house was clean. The outside is rustic and in need of TLC but a typical Lake house with wear and tear. The Lake and dock were perfect as we are outdoor...
Pet-friendly, peaceful lakeside retreat on Cobboseecontee Lake peninsula
Lake Front with Amazing Sunsets on McGrath Pond
Enjoy beautiful sunsets every night.

Lake Front with Amazing Sunsets on McGrath Pond

10.0 out of 10, Exceptional, (17)
"Very clean, cute lake house. Owner responsive, everything you need for a rental home. Lake and lake toys were so great! We really enjoyed our stay. Thank you!!! "
Lake Front with Amazing Sunsets on McGrath Pond
4-bedroom Waterfront LAKEHOUSE in Maine. Hot tub, firepit, deck & private dock.
View of the lake from our dock.

4-bedroom Waterfront LAKEHOUSE in Maine. Hot tub, firepit, deck & private dock.

2.0 star property
9.0 out of 10, Wonderful, (4)
"We enjoyed this house with plenty of comfortable spaces for our family! It had all the essentials and a nice Hot Tub to enjoy the cooler weather in. The beds were comfortable, plenty of pillows and extra blankets. The space in the basement was lovely. We did have to be mindful of the water pressure so someone could shower 1 at a time. But overall, this was a beautiful home away from home"
4-bedroom Waterfront LAKEHOUSE in Maine. Hot tub, firepit, deck & private dock.
Dog-friendly house with water sports gear, firepit, grill, & enclosed yard

Dog-friendly house with water sports gear, firepit, grill, & enclosed yard

2.0 star property
2.0 out of 10, (1)
Dog-friendly house with water sports gear, firepit, grill, & enclosed yard
Home Theater & Hot Tub: Mtn-View Winthrop Home
Winthrop Vacation Rental | 2BR | 1BA | 1,600 Sq Ft | Stairs Required

Home Theater & Hot Tub: Mtn-View Winthrop Home

Home Theater & Hot Tub: Mtn-View Winthrop Home
PRIVATE WATERFRONT DOG FRIENDLY LAKE HOUSE
Miscellaneous

PRIVATE WATERFRONT DOG FRIENDLY LAKE HOUSE

8.0 out of 10, Very Good, (3)
"Beautiful deck with plenty of space for family barbecues, lots of wildlife in the backyard, and great place to stay with your furry family members!"
PRIVATE WATERFRONT DOG FRIENDLY LAKE HOUSE
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.
Loon Cottage on Cobbossecontee Lake

Cottage on Cobbosseecontee Lake. Dates available.

10.0 out of 10, Exceptional, (158)
"Incredible location, perfect choice for a small group to spend a little time on the lake shore."
Cottage on Cobbosseecontee Lake. Dates available.
Dog Friendly Cabin Right On The Water!!!
Beautiful fireplace table overlooking the water!

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!!!
Fantastic Lakefront Cabin W/ Free WiFi, Three Kayaks, Private Dock, & Firepit

Fantastic Lakefront Cabin W/ Free WiFi, Three Kayaks, Private Dock, & Firepit

9.6 out of 10, Exceptional, (25)
"Well kept with all the right amenities. Beautiful views."
Fantastic Lakefront Cabin W/ Free WiFi, Three Kayaks, Private Dock, & Firepit
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.