Lake Annabessacook Rentals
From $210 per night (USD)VRBO
Island Aframe Adventure
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Summary: Discover how easy and relaxing secluded island life can be. Sleep comfortably. Cook your favorite meals. Chill ...
From $210 per night (USD)VRBO
Click For PricingExpedia
Nautilus: Floating Island Waterhouse
- 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 ...
Click For PricingExpedia
From $153 per night (USD)VRBO
Island Glamping in a Luxury Tent in Maine
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: The Hemlock Haven tent overlooks Annabessacook Lake. Sleep comfortably, cook your favorite meals, nap in the h ...
From $153 per night (USD)VRBO
From $1021 per night (USD)Expedia
Eco-Island Resort:14 Private Acres, 5 Unique Stays
- Bedrooms:
- 4
- Bathrooms:
- 7
- Sleeps:
- 45
Summary: Weddings, Retreats, & Family Reunions - Prepare for Adventure! 1BSI is a 14 acre playground for the naturally c ...
From $1021 per night (USD)Expedia
From $281 per night (USD)VRBO
Escape to Tree House Island Life
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 8
Summary: Rest easy in the Oaktagon Tree Yurt of 1 Big Sustainable Island. This off the grid unique home is perched on a ...
From $281 per night (USD)VRBO
From $357 per night (USD)Expedia
Peaceful Fisherman's Paradise w\/ Deck + Fire Pit!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 4
Dust off your fishing pole and head to this Winthrop vacation rental for a relaxing getaway with your nature-loving frie ...
From $357 per night (USD)Expedia
From $383 per night (USD)VRBO
Life on the Lake with Private Dock & Fire Pit!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Steal a sweet summer escape to the lake with this Winthrop vacation rental! The family-friendly abode comes equipped wit ...
From $383 per night (USD)VRBO
From $265 per night (USD)Expedia
Walk to TownBeach or kayak from backyard to Lake Annabessacook. Walk downtown
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Enjoy the beautiful Lakes Region of central Maine! This charming 1900's home is on a quiet street, walking distance to L ...
From $265 per night (USD)Expedia
From $225 per night (USD)VRBO
Quaint Cottage with Dock on Annabessacook Lake!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 7
Boasting waterfront views of Annabessacook Lake, this 2-bedroom, 1-bath vacation rental is a perfect home base for fishe ...
From $225 per night (USD)VRBO
Click For PricingExpedia
Cozy Cabin with Sandy Beach
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Cozy 1 bedroom (queen bed), 1 full bath cabin sitting on nearly 2 acres. Located on Annabessacook Lake with 200 feet of ...
Click For PricingExpedia
From $272 per night (USD)VRBO
SUMMER OF 2025 NOW OPEN FOR RESERVATIONS
- Bedrooms:
- 1
- Bathrooms:
- 5
- Sleeps:
- 8
THE LOON'S NEST IS RENTED ON A WEEKLY BASIS - SUNDAY TO SUNDAY JUNE & SEPTEMBER '25- $1900 A WEEK ($271- NIGHT) JULY ...
From $272 per night (USD)VRBO
From $213 per night (USD)Expedia
Family friendly, 2-Bedroom cottage with lakeview
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Enjoy your stay at The Coop, a brand new family-friendly, 2-bedroom cozy, modern cottage packed with amenities, nestled ...
From $213 per night (USD)Expedia
From $303 per night (USD)VRBO
Annabessacook Lake, Monmouth, Maine
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
3 bedroom, 2 bath house on beautiful Annabessacook Lake, Monmouth, Maine with 100' of shallow sandy frontage. First fl ...
From $303 per night (USD)VRBO
From $310 per night (USD)Expedia
Log Cabin at Naughty Dog Private Island
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 8
Summary: Be all alone on this remote island with 1400 acres of Annabessacook Lake as your backyard. It's the Micro Islan ...
From $310 per night (USD)Expedia
From $249 per night (USD)VRBO
Island Tent Overlook in Maine
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
Summary: Enjoy the majesty of a Maine lake at this breathtaking tent site - Glamping at its finest. An inspiring 270 de ...
From $249 per night (USD)VRBO
From $436 per night (USD)Expedia
ANNABESSACOOK WATERFRONT WITH DOCK
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
OCCUPANCY- LIMIT 8 - Waterfront on Annabessacook Lake in Winthrop. This 3-bedroom 1.5 bath is located just steps away f ...
From $436 per night (USD)Expedia
From $72 per night (USD)VRBO
Spacious Apartment in Downtown Winthrop
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Enjoy the Winthrop Lakes Region from this spacious 1 bedroom loft apartment on Metcalf Rd. Just a short walk from downto ...
From $72 per night (USD)VRBO