Cottages in Cumberland County

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Check prices for these dates

In two weeks
29 May - 31 May
In two months
10 Jul - 12 Jul
In three months
7 Aug - 9 Aug
In four months
4 Sep - 6 Sep

Top Cities in Cumberland County

CottagesCottages

Freeport

Freeport
Rocky shores of the Maine Coast, Fort Williams Park, Cape Elizabeth, Maine, New England, USA
CottagesCottages

Cape Elizabeth

Cape Elizabeth

Our top choices for Cumberland County cottages

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, (154 reviews)
"The property was beautiful, pet friendly and the host was fabntsstic and was able to be contacted so easily when we had a question! Great place, the ni est i have been in!! "
United States
Anonymous traveler
Leave it All Behind! 4-Season Sebago Lake Area, Kayak, Canoe & Fish, Pets Free!
Exterior

Updated Cottage - Steps to Pine Point Beach!

Updated Cottage - Steps to Pine Point Beach!
Pine Point
10.0 out of 10, Exceptional, (18 reviews)
"We have stayed here several times and really enjoy the cleanliness, and location to the beach."
United States
James C.
Updated Cottage - Steps to Pine Point Beach!
Exterior

Quaint cottage intimately set on the rocky coast overlooking Casco Bay

Quaint cottage intimately set on the rocky coast overlooking Casco Bay
Harpswell
9.8 out of 10, Exceptional, (27 reviews)
"Great little place with an amazing view. We enjoyed our time here. "
United States
Bill S.
Quaint cottage intimately set on the rocky coast overlooking Casco Bay
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, (53 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

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, (120 reviews)
"Quaint, quiet, stunning. "
United States
Meghan D.
Relax & Recharge! Tranquil Family-Owned, Sebago Lake Area, Pets free
Property grounds

Peaceful Waterfront Cottage in Midcoast Maine Near Bowdoin College, Harpswell and other coastal t...

Peaceful Waterfront Cottage in Midcoast Maine Near Bowdoin College, Harpswell and other coastal t...
Brunswick
10.0 out of 10, Exceptional, (17 reviews)
"We loved the cottage & the quiet location. It was so peaceful. We felt welcomed the minute we walked inside. The place was clean & very nice. "
United States
Shelly S.
Peaceful Waterfront Cottage in Midcoast Maine Near Bowdoin College, Harpswell and other coastal t...
Terrace/patio

Thorburn - Experience a classic ME vacation at this beautiful summer cottage

Thorburn - Experience a classic ME vacation at this beautiful summer cottage
Harpswell
9.8 out of 10, Exceptional, (25 reviews)
"Lovely ocean view cottage with access to a dock for kayaking - dog heaven with wide open share field. House is a great Harpswell location, easy to Brunswick, Freeport & Bath - up on a hill so cool and breezy to sleep. "
United States
Jodi A.
Thorburn - Experience a classic ME vacation at this beautiful summer cottage
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, (8 reviews)
"Good time. Great spot"
United States
Jim F.
WATERFRONT ON HIGHLAND LAKE. LESS THAN 30 MINUTES TO PORTLAND
Exterior

The Great Escape - Picturesque Sebago Lake

The Great Escape - Picturesque Sebago Lake
Raymond
9.8 out of 10, Exceptional, (57 reviews)
"Greta place to stay with family"
United States
Jenn T.
The Great Escape - Picturesque Sebago Lake
Outdoor dining

Classic Orr’s Island, Maine Cottage, sleeps 4, 1 Bath, Stunning ocean views!

Classic Orr’s Island, Maine Cottage, sleeps 4, 1 Bath, Stunning ocean views!
Orr's Island
9.8 out of 10, Exceptional, (37 reviews)
"Well-equipped, wonderful location, very comfortable"
United States
Dan C.
Classic Orr’s Island, Maine Cottage, sleeps 4, 1 Bath, Stunning ocean views!
Property grounds

WATERFRONT ON SAND POND WITH A PRIVATE SANDY BEACH

WATERFRONT ON SAND POND WITH A PRIVATE SANDY BEACH
East Baldwin
WATERFRONT ON SAND POND WITH A PRIVATE SANDY 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!
Exterior detail

4br2ba House parking A Peaceful Oasis on Munjoy Hill

4br2ba House parking A Peaceful Oasis on Munjoy Hill
Munjoy Hill
10.0 out of 10, Exceptional, (9 reviews)
"Ani was very friendly and communicative and the place was comfortable and inviting. We had a great stay!"
United States
Cristina Q.
The price is AED 1,488
AED 2,495 total
includes taxes & fees
17 May - 18 May
4br2ba House parking A Peaceful Oasis on Munjoy Hill
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, (7 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

Sea Bisquit Cottage by the Ocean

Sea Bisquit Cottage by the Ocean
Grand Beach
9.4 out of 10, Exceptional, (19 reviews)
"Lovely and clean cottage! Perfect for our stay."
United States
Viki C.
Sea Bisquit Cottage by the Ocean
Exterior

The Outlet House, Comfortable Cottage

The Outlet House, Comfortable Cottage
Freeport
9.8 out of 10, Exceptional, (57 reviews)
"Awesome place. Thank you for the hospitality!"
United States
Nick F.
The Outlet House, Comfortable Cottage
Terrace/patio

Charming Cottage Steps Away From Pine Point Beach

Charming Cottage Steps Away From Pine Point Beach
Pine Point
9.6 out of 10, Exceptional, (5 reviews)
"The house accommodated our growing family and is a quick walk to Pine Point Beach!! We really enjoyed our stay! The owner was very responsive to all of needs and questions!!"
United States
Robin H.
Charming Cottage Steps Away From Pine Point Beach
Terrace/patio

Charming 3BR, 1.5BA beachfront cottage with multi-level decks

Charming 3BR, 1.5BA beachfront cottage with multi-level decks
Harpswell
9.2 out of 10, Wonderful, (39 reviews)
"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Had everything we needed. Great customer service from rental managers"
United States
Barbara R.
Charming 3BR, 1.5BA beachfront cottage with multi-level decks
Exterior

Sea Salt Cottage: 4 BR, 1 BA Cottage in Harpswell, Sleeps 7

Sea Salt Cottage: 4 BR, 1 BA Cottage in Harpswell, Sleeps 7
Harpswell
Sea Salt Cottage: 4 BR, 1 BA Cottage in Harpswell, Sleeps 7
Exterior

THIS IS THE PLACE - Intimate luxury cottage w massive oceanfront steam room

THIS IS THE PLACE - Intimate luxury cottage w massive oceanfront steam room
Harpswell
10.0 out of 10, Exceptional, (55 reviews)
"No complaints. As advertised. Rustic, immaculate, beautiful home, with a view to die for. Locals are friendly and wildlife is abundant. Will be returning! "
United States
Elizabeth M.
THIS IS THE PLACE - Intimate luxury cottage w massive oceanfront steam room
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

Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

8/10 Good
"Food was great at the Armory. Staff was helpful & we enjoyed morning coffee in the lounge by the fire. Hotel is conveniently located near shops, restaurants, waterfront & attractions!"
Barry 2-night trip
Posted 1 hour ago
Portland Regency Hotel & Spa