A coastal lighthouse with red-roofed houses, rocky shoreline, and the ocean.

Cottages in Cumberland County

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Check prices for these dates

In two weeks
24 Jul - 26 Jul
In two months
4 Sep - 6 Sep
In three months
2 Oct - 4 Oct
In four months
30 Oct - 1 Nov

Top Cities in Cumberland County

A brick building with green shutters, a tree with red leaves, and a street with people walking.
CottagesCottages

Freeport

Freeport

Our top choices for Cumberland County cottages

Property grounds

Escape to Serenity: Your Private Maine Lakefront Awaits at Little Sebago Lookout

Escape to Serenity: Your Private Maine Lakefront Awaits at Little Sebago Lookout
Gray
9.4 out of 10, Exceptional, (96 reviews)
"Wonderful place to getaway "
United States
David A.
Escape to Serenity: Your Private Maine Lakefront Awaits at Little Sebago Lookout
Exterior

Private Contemporary Artist's Tree House on two acres with perennial gardens.

Private Contemporary Artist's Tree House on two acres with perennial gardens.
Unknown
10.0 out of 10, Exceptional, (60 reviews)
"Property was gorgeous and was perfect for us visiting Maine / Portland. Hosts are very attentive and knowledgeable on some great food / spots to visit during your stay!"
United States
Anthony P.
Private Contemporary Artist's Tree House on two acres with perennial gardens.
Exterior

Lakefront Traditional 4-bedroom cottage in Frye Island

Lakefront Traditional 4-bedroom cottage in Frye Island
Frye Island
9.8 out of 10, Exceptional, (7 reviews)
"To begin the host was on top of our stay and responded quickly. The house has everything one needs. It is a very comfortable house with an amazing view. I wanted a “unique Maine experience” for a long weekend and this did not disappoint. "
United States
V W.
Lakefront Traditional 4-bedroom cottage in Frye Island
Property grounds

WATERFRONT ON HIGHLAND LAKE. LESS THAN 30 MINUTES TO PORTLAND

WATERFRONT ON HIGHLAND LAKE. LESS THAN 30 MINUTES TO PORTLAND
WINDHAM
9.6 out of 10, Exceptional, (11 reviews)
"Good time. Great spot"
United States
Jim F.
WATERFRONT ON HIGHLAND LAKE. LESS THAN 30 MINUTES TO PORTLAND
Property grounds

Leave it All Behind! 4-Season Sebago Lake Area, Kayak, Canoe & Fish, Pets Free!

Leave it All Behind! 4-Season Sebago Lake Area, Kayak, Canoe & Fish, Pets Free!
Naples
10.0 out of 10, Exceptional, (159 reviews)
"Cute cottage on the water. Would be great in the summer. My dog had fun. Quiet and peaceful at night. Fun area. "
United States
Marnie D.
Leave it All Behind! 4-Season Sebago Lake Area, Kayak, Canoe & Fish, Pets Free!
Exterior

THIS IS THE PLACE - Intimate cottage with oceanfront views and AC!

THIS IS THE PLACE - Intimate cottage with oceanfront views and AC!
Harpswell
10.0 out of 10, Exceptional, (58 reviews)
"Beautiful views from a charming cottage with kind neighbors. Eclectic styled home which we enjoyed. Would stay again!!"
United States
Michelle H.
THIS IS THE PLACE - Intimate cottage with oceanfront views and AC!
Beach

Glamorous cottage-glamping at Sebago Lake

Glamorous cottage-glamping at Sebago Lake
North Sebago
9.8 out of 10, Exceptional, (83 reviews)
"The cabin was perfect for our family of five! "
United States
Justine C.
Glamorous cottage-glamping at Sebago Lake
Exterior

Relax & Recharge! Tranquil Family-Owned, Sebago Lake Area, Pets free

Relax & Recharge! Tranquil Family-Owned, Sebago Lake Area, Pets free
Naples
9.8 out of 10, Exceptional, (126 reviews)
"Quaint, quiet, stunning. "
United States
Meghan D.
Relax & Recharge! Tranquil Family-Owned, Sebago Lake Area, Pets free
Exterior

Waterview Cottage-Private Beach-Pets Welcome - Round Table Lodge, Sebago, Maine

Waterview Cottage-Private Beach-Pets Welcome - Round Table Lodge, Sebago, Maine
North Sebago
9.8 out of 10, Exceptional, (6 reviews)
"Loved this place! very clean, beautiful beach and great location. Would definitely book again. "
United States
Susan F.
Waterview Cottage-Private Beach-Pets Welcome - Round Table Lodge, Sebago, Maine
Property grounds

COZY,Newly renovated,West Shores ,short walk to Nasons Beach 🏖🏠

COZY,Newly renovated,West Shores ,short walk to Nasons Beach 🏖🏠
North Sebago
9.6 out of 10, Exceptional, (88 reviews)
"Hosts were fantastic!"
United States
Collin P.
COZY,Newly renovated,West Shores ,short walk to Nasons Beach 🏖🏠
Exterior

A coastal cottage steps from Pine Point Beach!

A coastal cottage steps from Pine Point Beach!
Pine Point
10.0 out of 10, Exceptional, (12 reviews)
"Great location for walking to the beach and restaurants. Quiet neighborhood, perfect for taking evening walks to see the sunset. Great little cottage."
United States
Dorian N.
A coastal cottage steps from Pine Point Beach!
Exterior

3 BR Lake house in Sebago Maine steps from beach!

3 BR Lake house in Sebago Maine steps from beach!
Sebago
10.0 out of 10, Exceptional, (2 reviews)
"Great house to stay at. We had the perfect week! Huge thanks Nelson family."
United States
Jonathan M.
3 BR Lake house in Sebago Maine steps from beach!
Property grounds

Moon Tide Cottage on a tranquil cove in Harpswell is where your vacation begins!

Moon Tide Cottage on a tranquil cove in Harpswell is where your vacation begins!
Harpswell
10.0 out of 10, Exceptional, (1 review)
"Moon Tide Cottage, located in a gorgeous tidal cove, is a special and peaceful sanctuary. We had a wonderful stay at this adorable house beside the sea in Harpswell. The deck above the water is incredible, the views fantastic, and the breeze and sun/shade on the deck were perfect. There were no mosquitos, flies or bugs when sitting on the deck. The number of birds that we saw in the cove as the tide went in and out were amazing! Eagles across the water, and egrets, herons, cormorants, ducks...
United States
Cynthia C.
Moon Tide Cottage on a tranquil cove in Harpswell is where your vacation begins!
Outdoor dining

Waterfront Cottage on Barker Pond

Waterfront Cottage on Barker Pond
SEBAGO
8.8 out of 10, Excellent, (8 reviews)
"Great stay, great location, and a neat cottage where we had everything we needed. Would definitely go back!"
United States
Olga M.
Waterfront Cottage on Barker Pond
Property grounds

Stunning Ocean Views, newly renovated cottage-close to preserves, trails, and Harpswell Beaches

Stunning Ocean Views, newly renovated cottage-close to preserves, trails, and Harpswell Beaches
Harpswell
10.0 out of 10, Exceptional, (8 reviews)
"Beautiful location!! Very comfortable and clean home "
United States
Beth L.
Stunning Ocean Views, newly renovated cottage-close to preserves, trails, and Harpswell Beaches
Beach

GREAT Newly Renovated Sebago Lake- short walk to Nason`s beach🏠🏖🚗

GREAT Newly Renovated Sebago Lake- short walk to Nason`s beach🏠🏖🚗
North Sebago
9.8 out of 10, Exceptional, (86 reviews)
"Property was clean and as described. The location was great and check-in was very easy. Would recommend! "
United States
Andrew K.
GREAT Newly Renovated Sebago Lake- short walk to Nason`s beach🏠🏖🚗
Exterior

The Outlet House, Comfortable Cottage

The Outlet House, Comfortable Cottage
Freeport
9.8 out of 10, Exceptional, (58 reviews)
"Miranda is excellent hostess and I would recommend tourists check this out…"
United States
Lynn-Ann M.
The Outlet House, Comfortable Cottage
Property grounds

Quiet & Remote Cottage on Panther Pond!

Quiet & Remote Cottage on Panther Pond!
Raymond
9.4 out of 10, Exceptional, (28 reviews)
"Lovely location "
United States
Audrey H.
Quiet & Remote Cottage on Panther Pond!
Exterior

Dog-Friendly Lakefront Cottage w/Lake Access, Deck, Gas Grill, A/C

Dog-Friendly Lakefront Cottage w/Lake Access, Deck, Gas Grill, A/C
Standish
Dog-Friendly Lakefront Cottage w/Lake Access, Deck, Gas Grill, A/C
Terrace/patio

Waterfront, Updated Oceanfront Gem for 2, near Bowdoin College, Harpswell, and much more!

Waterfront, Updated Oceanfront Gem for 2, near Bowdoin College, Harpswell, and much more!
Brunswick
9.8 out of 10, Exceptional, (55 reviews)
"Lovely little cottage on Casco Bay. Thoroughly enjoyed our stay."
United States
charles k.
Waterfront, Updated Oceanfront Gem for 2, near Bowdoin College, Harpswell, and much more!
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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Top Cumberland County Hotel Reviews

Canopy by Hilton Portland Waterfront

Canopy by Hilton Portland Waterfront

10/10 Excellent
"The hotel had a great restaurant on the main level - was perfect for breakfast and lunch. The valet was super useful as well."
Heidi 1-night trip
Posted less than an hour ago
Canopy by Hilton Portland Waterfront