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Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sept - 14 Sept
In two months
10 Oct - 12 Oct

Featured Cottages in Harpswell

Modern woodland privacy with ocean, trails, and lobster all in walking distance.
Outdoor dining

Modern woodland privacy with ocean, trails, and lobster all in walking distance.

10.0 out of 10, Exceptional, (48)
"My friend and I felt very relaxed at this house. The beds were comfortable and the kitchen was stocked with most every cooking equipment needed. The host answered any question I had very quickly and supplied information about the surrounding area. It was a great place to unwind!"
Modern woodland privacy with ocean, trails, and lobster all in walking distance.
The Outlet House, Comfortable Cottage
Interior

The Outlet House, Comfortable Cottage

9.8 out of 10, Exceptional, (43)
"We loved our stay here! The cottage was super clean and in a quiet area within walking distance to town and all the shops and restaurants. Check-in was simple and the hosts were very friendly and responded quickly. Would definitely stay again!"
The Outlet House, Comfortable Cottage
Waterfront Cottage in South Bristol w/ private dock and lobster boat views
Exterior

Waterfront Cottage in South Bristol w/ private dock and lobster boat views

10.0 out of 10, Exceptional, (105)
"We stayed at the property for two nights for a family getaway after the holidays. The house was in a great location, beautiful views, spotlessly clean, and very well equipped. We loved waking up to the light hitting the water and being able to explore the beautiful peninsula. Great hikes a short drive away. We would gladly stay again! "
Waterfront Cottage in South Bristol w/ private dock and lobster boat views
Boothbay Harbor Cottage Overlooking Mill Cove
Marina

Boothbay Harbor Cottage Overlooking Mill Cove

9.8 out of 10, Exceptional, (22)
"Clean, close to downtown."
Boothbay Harbor Cottage Overlooking Mill Cove
Beautiful 13 acre Property on Sheepscot River w/ 2 Bedroom Cottage & Air Stream
Exterior

Beautiful 13 acre Property on Sheepscot River w/ 2 Bedroom Cottage & Air Stream

10.0 out of 10, Exceptional, (68)
"The cottage was perfect for a post Christmas relaxing week of downtime."
Beautiful 13 acre Property on Sheepscot River w/ 2 Bedroom Cottage & Air Stream
Sunrise Cottage. Relaxing waterfront deck on the rocky shore of Bailey Island.
Property grounds

Sunrise Cottage. Relaxing waterfront deck on the rocky shore of Bailey Island.

9.8 out of 10, Exceptional, (29)
"Nice little hidden gem of a place."
Sunrise Cottage. Relaxing waterfront deck on the rocky shore of Bailey Island.
Cheerful Cottage Close to Everything 12
Marina

Cheerful Cottage Close to Everything 12

9.4 out of 10, Exceptional, (12)
"Well appointed and comfortable cabin. Loved the retro fridge and microwave and sitting on the deck with a morning coffee. We awoke to a woodsy view every morning. The location was perfect for us; convenient to Wiscasset, Damariscotta and Pemaquid Point. Our host was fabulous with his timely communication and down east hospitality. If we pass through this way again, we will be sure to stay here again."
Cheerful Cottage Close to Everything 12
Quiet 3-bedroom cottage w/ 2 specious deck with water views in Brunswick w/ WiFi
Microwave, oven, stovetop, dishwasher

Quiet 3-bedroom cottage w/ 2 specious deck with water views in Brunswick w/ WiFi

8.0 out of 10, Very good, (1)
"House was very clean with the exception of some dust/sand on floors, even though you could not see it walking on the floors in bare feet always felt that that maybe a good washing was needed. We just swept with the broom/vacuum and it was better. But one thing that really stood out when arriving is the cement stairs dug into the hill that you needed to go down to get to the house. So glad that there was a railing to hold onto because the stairs were not level at all. This posed a real threat to...
Quiet 3-bedroom cottage w/ 2 specious deck with water views in Brunswick w/ WiFi
Enjoyable 1-bedroom rustic cottage in Southport.
Terrace/patio

Enjoyable 1-bedroom rustic cottage in Southport.

10.0 out of 10, Exceptional, (10)
Enjoyable 1-bedroom rustic cottage in Southport.
Spacious 1 Bedroom Close to Everything 4
Marina

Spacious 1 Bedroom Close to Everything 4

10.0 out of 10, Exceptional, (18)
"This was a lovely little cabin. Everything was as described and my husband and I really enjoyed our stay."
Spacious 1 Bedroom Close to Everything 4
Peaceful, Oceanfront Retreat, Sleeps 8, Semi-Private Sandy Swim Area
Property grounds

Peaceful, Oceanfront Retreat, Sleeps 8, Semi-Private Sandy Swim Area

10.0 out of 10, Exceptional, (45)
"Beautiful property & so clean & well appointed, great location! Had everything we wanted for a wonderful vacation week!"
Peaceful, Oceanfront Retreat, Sleeps 8, Semi-Private Sandy Swim Area
Charming Cottage on the Great Pond in Boothbay Harbor, Maine
Terrace/patio

Charming Cottage on the Great Pond in Boothbay Harbor, Maine

10.0 out of 10, Exceptional, (7)
Charming Cottage on the Great Pond in Boothbay Harbor, Maine
Charming 3BR, 1.5BA beachfront cottage with multi-level decks
Interior

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

9.2 out of 10, Wonderful, (36)
"Wonderful "
Charming 3BR, 1.5BA beachfront cottage with multi-level decks
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, (6)
"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.
Happy Cottage Near Everything 11
Outdoor dining

Happy Cottage Near Everything 11

8.0 out of 10, Very good, (1)
"Very comfortable, clean small cottage. We slept great in the bed that was provided and it had a futon in the living area . We recommend that only 2 people stay there. They had a toaster oven , a full refrigerator and a coffee maker. It is very close to Route 1, Boothbay Harbor and Damariscotta. "
Happy Cottage Near Everything 11
Lilac Cottage - Near Georgetown Island - Midcoast Maine
Interior

Lilac Cottage - Near Georgetown Island - Midcoast Maine

10.0 out of 10, Exceptional, (23)
"We had a wonderful stay at this property. Our dogs loved being able to chase eachother around the yard"
Lilac Cottage - Near Georgetown Island - Midcoast Maine
Spacious 1 Bedroom Cottage Close to Everything 2
Marina

Spacious 1 Bedroom Cottage Close to Everything 2

9.2 out of 10, Wonderful, (15)
"Nice small older cottage that has been updated nicely. The location was perfect for exploring local State Parks and the marine area."
The price is NZ$469
includes taxes & fees
14 Aug - 15 Aug
Spacious 1 Bedroom Cottage Close to Everything 2
Charming Cottage: Deepwater Dock, Panoramic Linekin Bay Views, Near Village
Property grounds

Charming Cottage: Deepwater Dock, Panoramic Linekin Bay Views, Near Village

9.2 out of 10, Wonderful, (11)
"Incredible views!"
Charming Cottage: Deepwater Dock, Panoramic Linekin Bay Views, Near Village
Your own private island! Rustic and close to Nature.
Dining

Your own private island! Rustic and close to Nature.

9.4 out of 10, Exceptional, (32)
"wonderful place, glamping, wildlife all around, you can't but enjoy the beauty of Mid Coast Maine. Thanks for sharing your island with all of us !"
Your own private island! Rustic and close to Nature.
Unique oceanfront home with a deck, tons of natural light, & amazing views
Interior

Unique oceanfront home with a deck, tons of natural light, & amazing views

8.6 out of 10, Excellent, (57)
"Beautiful lcation, private & quiet"
Unique oceanfront home with a deck, tons of natural light, & amazing views
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 Harpswell Hotel Reviews

Inn at St John Portland In-Town

Inn at St John Portland In-Town

10/10 Excellent
"The property is not modern It is like a step back in time. Reminds me of my grandmother‘s house. However, the staff are brilliant, and the place is very clean and has all the amenities that you need."
ELSIE C 1-night trip
Posted 8 hours ago
Inn at St John Portland In-Town