Lake Annabessacook Rentals
From $317 per night (USD)VRBO
Island Aframe Adventure in Maine
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 5
Summary: Discover how easy and relaxing secluded island life can be. Sleep comfortably. Cook your favorite meals. Chill ...
From $317 per night (USD)VRBO
From $359 per night (USD)Expedia
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 ...
From $359 per night (USD)Expedia
From $289 per night (USD)VRBO
Island Glamping in a Luxury Dome in Maine
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Summary: The Hemlock Haven Dome looks out at sunsets on Annabessacook Lake. Sleep comfortably, cook your favorite meals ...
From $289 per night (USD)VRBO
From $2108 per night (USD)Expedia
Eco-Island Resort:14 Private Acres, 5 Unique Stays
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 45
Summary: Weddings, Retreats, & Family Reunions - Prepare for Adventure! 1BSI is a 14 acre playground for the naturally c ...
From $2108 per night (USD)Expedia
From $451 per night (USD)VRBO
Escape to Tree House Island Life
- Bedrooms:
- 1
- Bathrooms:
- 1
- 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 $451 per night (USD)VRBO
From $236 per night (USD)Expedia
Peaceful Fisherman's Paradise w/ Deck + Fire Pit!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Dust off your fishing pole and head to this Winthrop vacation rental for a relaxing getaway with your nature-loving frie ...
From $236 per night (USD)Expedia
From $280 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 $280 per night (USD)VRBO
From $289 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 $289 per night (USD)Expedia
From $812 per night (USD)VRBO
Spacious 5-bedroom lakefront home on pristine Lower Narrows Pond in Winthrop
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 15
Experience luxurious lakefront living in this exquisite 5-bedroom, 4.5-bathroom contemporary that seamlessly blends eleg ...
From $812 per night (USD)VRBO
From $275 per night (USD)Expedia
Charming 1-bedroom apartment in Monmouth with AC, WiFi. Several lakes nearby.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Unwind in Monmouth at this lovely apartment. This cozy space is perfect for guests looking for a peaceful retreat. With ...
From $275 per night (USD)Expedia
From $218 per night (USD)VRBO
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 ...
From $218 per night (USD)VRBO
From $272 per night (USD)VRBO
WEEKS OF 8/24 & 8/31 OPEN AND SEPTEMBER RATES APPLY - 1900 A WEEK.
- Bedrooms:
- 1
- Bathrooms:
- 3
- 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 $315 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 $315 per night (USD)VRBO
From $373 per night (USD)Expedia
Naughty Dog Private Island Log Cabin
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 8
Summary: Be all alone on this remote island with 1400 acres of Annabessacook Lake as your backyard. Enjoy pristine surr ...
From $373 per night (USD)Expedia
From $371 per night (USD)VRBO
Dock + Kayaks: Annabessacook Lake Retreat!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Bird-Watcher's Paradise | Family Lake Trip | Multiple Living Areas There’s nothing like a Maine lake day, especially wh ...
From $371 per night (USD)VRBO
From $453 per night (USD)Expedia
ANNABESSACOOK WATERFRONT WITH DOCK
- Bedrooms:
- 1
- 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 $453 per night (USD)Expedia
From $317 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 $317 per night (USD)VRBO