Lake Annabessacook Rentals
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 $208 per night (USD)VRBO
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 $208 per night (USD)VRBO
From $231 per night (USD)VRBO
HUGE PRICE DROP FOR THE WEEK OF AUGUST 24 -- 1200 FOR THE WEEK -45% DISCOUNT
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
THE LOON'S NEST IS RENTED ON A WEEKLY BASIS - SUNDAY TO SUNDAY A LATE AUGUST PRICE DROP -- WEEKS OF 8/24 & 8/31 $1500 ...
From $231 per night (USD)VRBO
From $287 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 $287 per night (USD)VRBO
From $293 per night (USD)VRBO
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 $293 per night (USD)VRBO
From $164 per night (USD)Expedia
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 $164 per night (USD)Expedia
From $501 per night (USD)VRBO
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 $501 per night (USD)VRBO
From $389 per night (USD)Expedia
Island Tree House: Lake Front, Kayaks, & Fire Pit
- 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 $389 per night (USD)Expedia
From $264 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 $264 per night (USD)VRBO
From $284 per night (USD)Expedia
Floating Island Cabin Private Pet-Friendly Retreat
- 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 $284 per night (USD)Expedia
From $263 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 $263 per night (USD)VRBO
From $221 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 $221 per night (USD)Expedia
From $1618 per night (USD)VRBO
Eco-Island Resort:14 Private Acres, 5 Unique Stays
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 45
Summary: Island Adventure - Weddings, Reunions, Events 1BSI is now taking 2026 bookings on its 14 acre natural island pl ...
From $1618 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 $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 $209 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 $209 per night (USD)Expedia
From $332 per night (USD)VRBO
Dock + Kayaks: Annabessacook Lake Retreat!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Bird-Watcher's Paradise | Family Lake Trip | 'Hubbard Point' There’s nothing like a Maine lake day, especially when the ...
From $332 per night (USD)VRBO
From $672 per night (USD)Expedia
Designer 5-bedroom farmhouse with private lake access in rural Monmouth Maine.
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 11
Consider this farmhouse your home away from home while you visit Monmouth. This lovely property boasts 4 bedrooms, plus ...
From $672 per night (USD)Expedia
From $413 per night (USD)VRBO
3 bedroom lake house in Winthrop me
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 11
Your peaceful lakefront getaway awaits! This cozy and comfortable lake house sits right on the shores of Annabessacook ...
From $413 per night (USD)VRBO