Lake Annabessacook Rentals
From $383 per night (USD)VRBO
Peaceful Fisherman's Paradise w/ Deck + Fire Pit!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 100
Dust off your fishing pole and head to this Winthrop vacation rental for a relaxing getaway with your nature-loving frie ...
From $383 per night (USD)VRBO
From $204 per night (USD)VRBO
SUMMER OF '26 RESERVATIONS BEGIN AFTER 1/1/26....HAPPY NEW YEAR!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
THE LOON'S NEST IS RENTED ON A WEEKLY BASIS - SUNDAY TO SUNDAY JUNE & SEPTEMBER '26 - $2000 A WEEK ($285 - NIGHT) JUL ...
From $204 per night (USD)VRBO
From $376 per night (USD)VRBO
Life on the Lake with Private Dock & Fire Pit!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Steal a sweet summer escape to the lake with this Winthrop vacation rental! The family-friendly abode comes equipped wit ...
From $376 per night (USD)VRBO
From $305 per night (USD)Expedia
Located directly in central downtown and beach area, fish or kayak from backyard
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Enjoy the beautiful Lakes Region of central Maine! This charming 1900's home is on a quiet dead-end street, walking dist ...
From $305 per night (USD)Expedia
From $397 per night (USD)VRBO
Naughty Dog Private Island Log Cabin
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 8
Summary: Be alone with your pup enjoying leash freedom on this remote island. Your 1400 acre backyard is Annabessacook ...
From $397 per night (USD)VRBO
From $265 per night (USD)Expedia
Island Tree House Glamping
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 8
Summary: Rest easy in the Oaktagon Tree House of 1 Big Sustainable Island. This off-the-grid unique home is perched on ...
From $265 per night (USD)Expedia
From $222 per night (USD)VRBO
Island Aframe Adventure in Maine
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 5
Summary: Relaxing island life made easy: Sleep comfortably. Cook your favorite meals. Chill out in a hammock. Bask in g ...
From $222 per night (USD)VRBO
From $258 per night (USD)Expedia
Floating Island Cabin
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Waves peacefully lapping at your cabin door... Watch the sunrise over the lake from your comfy bed. Cook your f ...
From $258 per night (USD)Expedia
From $237 per night (USD)VRBO
Island Tent Overlook in Maine
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
Summary: A majestic lake, an inspiring and remote site, and a breathtaking 270 degree view - Glamping at its finest. Be ...
From $237 per night (USD)VRBO
From $199 per night (USD)Expedia
Hammock Haven Island Dome
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Summary: The Hammock Haven Island Dome looks at sunsets on Annabessacook Lake. Sleep comfortably, cook your favorite me ...
From $199 per night (USD)Expedia
From $1935 per night (USD)VRBO
Eco-Island Events: Weddings, Families, Retreats
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 45
Summary: Host your own private island event on a 14 acre Maine island with 5 unique stays. 2026 bookings are open on a ...
From $1935 per night (USD)VRBO