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Sep 12 - Sep 14
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Sep 26 - Sep 28
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Nov 21 - Nov 23

Browse Select Cumberland Cottages

WATERFRONT ON PETTENGILL POND
Property grounds

WATERFRONT ON PETTENGILL POND

9.6 out of 10, Exceptional, (4)
"My kids and I loved our stay at the pond. We enjoyed kayaking and floating in the peaceful setting. "
WATERFRONT ON PETTENGILL POND
The Great Escape - Picturesque Sebago Lake
Interior

The Great Escape - Picturesque Sebago Lake

9.8 out of 10, Exceptional, (53)
"Property was perfect for our stay."
The Great Escape - Picturesque Sebago Lake
Lakefront Cottage - private dock, large decks, large fire pit
Property grounds

Lakefront Cottage - private dock, large decks, large fire pit

9.4 out of 10, Exceptional, (24)
"Good location "
Lakefront Cottage - private dock, large decks, large fire pit
Private Contemporary Artist's Tree House on two acres with perennial gardens.
Outdoor spa tub

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

10.0 out of 10, Exceptional, (45)
"Beautiful, fun space. Very comfortable, and accommodating. Great location and hosts!"
Private Contemporary Artist's Tree House on two acres with perennial gardens.
Charming 4-bedroom cottage with AC, WiFi on Little Sebago Lake waterfront
Microwave, oven, stovetop, dishwasher

Charming 4-bedroom cottage with AC, WiFi on Little Sebago Lake waterfront

10.0 out of 10, Exceptional, (1)
Charming 4-bedroom cottage with AC, WiFi on Little Sebago Lake waterfront
THIS IS THE PLACE - Intimate luxury cottage w massive oceanfront steam room
Terrace/patio

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

10.0 out of 10, Exceptional, (53)
"Beautiful views from a charming cottage with kind neighbors. Eclectic styled home which we enjoyed. Would stay again!!"
THIS IS THE PLACE - Intimate luxury cottage w massive oceanfront steam room
Cozy Cottage with stunning views of Stover's Cove.
Interior

Cozy Cottage with stunning views of Stover's Cove.

9.8 out of 10, Exceptional, (8)
"We loved our time at the Cozy Cottage. They have the space well stocked with laundry detergent, dish soap, and even toiletries! All the communication was smooth and fast replies. I would recommend staying here if you are visiting Harpswell! "
Cozy Cottage with stunning views of Stover's Cove.
Escape to Serenity: Your Private Maine Lakefront Awaits at Little Sebago Lookout
Property grounds

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

9.4 out of 10, Exceptional, (86)
"The setting was absolutely beautiful. Shawn was extremely responsive and went out of his away to be accommodating. Would highly recommend!"
Escape to Serenity: Your Private Maine Lakefront Awaits at Little Sebago Lookout
Laurel Shore Cottage with Seasonal Private Tidal Dock, Pet friendly.
Exterior

Laurel Shore Cottage with Seasonal Private Tidal Dock, Pet friendly.

9.6 out of 10, Exceptional, (39)
"Peaceful, beautiful property. Perfect for our honeymoon. Highly recommend this place and Gurnet Trading Post for seafood!"
Laurel Shore Cottage with Seasonal Private Tidal Dock, Pet friendly.
Relax & Recharge! Tranquil Family-Owned, Sebago Lake Area, Pets free
Marina

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

9.8 out of 10, Exceptional, (119)
"I stayed at the end of April, so it was very quiet. The location is great right on the river. The cabin is cozy. Host was very responsive and friendly."
Relax & Recharge! Tranquil Family-Owned, Sebago Lake Area, Pets free
Classic Orr’s Island, Maine Cottage, sleeps 4, 1 Bath, Stunning ocean views. New Listing !!
Fridge, microwave, oven, stovetop

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

9.8 out of 10, Exceptional, (33)
"Have stayed here two times over the years and it’s a great place for small families. We thoroughly enjoyed our recent visit."
Classic Orr’s Island, Maine Cottage, sleeps 4, 1 Bath, Stunning ocean views. New Listing !!
Cozy countryside cottage located on Crooked river in Naples Maine.
Property grounds

Cozy countryside cottage located on Crooked river in Naples Maine.

10.0 out of 10, Exceptional, (16)
"Cute place with lots of thoughtful amenities that made the stay wonderful. "
Cozy countryside cottage located on Crooked river in Naples Maine.
Ocean Watch - Relax and let the ocean sweep you away at this charming retreat
Terrace/patio

Ocean Watch - Relax and let the ocean sweep you away at this charming retreat

8.6 out of 10, Excellent, (19)
"Very relaxing."
Ocean Watch - Relax and let the ocean sweep you away at this charming retreat
3 BR Lake house in Sebago Maine steps from beach!
Beach

3 BR Lake house in Sebago Maine steps from beach!

10.0 out of 10, Exceptional, (2)
"Great house to stay at. We had the perfect week! Huge thanks Nelson family."
3 BR Lake house in Sebago Maine steps from beach!
Perfect Family Vacation Getaway
Terrace/patio

Perfect Family Vacation Getaway

10.0 out of 10, Exceptional, (3)
"Great place to stay "
Perfect Family Vacation Getaway
Point Sebago Resort, 30 Purple Road, Walking distance to beach!
Terrace/patio

Point Sebago Resort, 30 Purple Road, Walking distance to beach!

9.6 out of 10, Exceptional, (14)
"Great location, looks just like it does in the pictures. Jenna was great and super responsive. Overall we had a great time!"
Point Sebago Resort, 30 Purple Road, Walking distance to beach!
Leave it All Behind! 4-Season Sebago Lake Area, Kayak, Canoe & Fish, Pets Free!
Children's area

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

10.0 out of 10, Exceptional, (142)
"This place is amazing. Lots of relaxation and fun was spent here. "
Leave it All Behind! 4-Season Sebago Lake Area, Kayak, Canoe & Fish, Pets Free!
Cute 2+ Bedroom Cottage
Fridge, microwave, oven, stovetop

Cute 2+ Bedroom Cottage

9.6 out of 10, Exceptional, (18)
"Returned this year for our 2nd stay. Clean, comfortable and quiet. Will book again!"
Cute 2+ Bedroom Cottage
Sea Bisquit Cottage by the Ocean
Sun loungers, beach towels

Sea Bisquit Cottage by the Ocean

9.4 out of 10, Exceptional, (17)
"Cute cozy cottage a few minutes walk from quiet Old Orchard/Pine Point beach. "
Sea Bisquit Cottage by the Ocean
Sea Ledge S - Enjoy beautiful sunsets from this charming Bailey Isl cottage
Property grounds

Sea Ledge S - Enjoy beautiful sunsets from this charming Bailey Isl cottage

9.6 out of 10, Exceptional, (18)
"Loved the location."
Sea Ledge S - Enjoy beautiful sunsets from this charming Bailey Isl cottage
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 Hotel Reviews

Find out more about Cumberland

Find out more about Cumberland

Cumberland Cottages information

Number of reviews
Accommodation
257 Cottages
Lowest Price
Highest Price

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