Name: Trade Winds on the Bay
Price range: $204 total
Rating: 8.6

Flagship Inn and Suites

200 Townsend Avenue Boothbay Harbor ME

$171 nightly

$186 total

Jun 28 - Jun 29

Total with taxes and fees

Stay at this hotel in Boothbay Harbor. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the breakfast and the pool in our reviews. Popular ...

8/10 Very Good! (1,003 reviews)

"Room was good, staff helpful, breakfast good"

Reviewed on Jun 22, 2026

Ocean Gate Inn

70 Ocean Gate Rd Southport ME

$227 nightly

$247 total

Jun 25 - Jun 26

Total with taxes and fees

Stay at this hotel in Southport. Enjoy free breakfast, an outdoor pool, and a garden. Our guests praise the breakfast and the pool in our reviews. Popular attractions ...

8.6/10 Excellent! (1,002 reviews)

"What a hidden gem in the area! We loved this beautiful property"

Reviewed on Jun 23, 2026

Trade Winds on the Bay

2 Park Dr Rockland ME

$187 nightly

$204 total

Jun 29 - Jun 30

Total with taxes and fees

Stay at this aparthotel in Rockland. Enjoy free WiFi, free parking, and a health club. Our guests praise the helpful staff and the clean rooms in our reviews. ...

8.6/10 Excellent! (417 reviews)

"The air conditioner in the room was so loud, didn't make for a peaceful night. Also the TV did not have cable access, we are not accustomed to having to log into any streaming service to be able to watch something."

Reviewed on Jun 22, 2026

See all 1,534 properties in Damariscotta

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.

Trade Winds on the Bay

2 Park Dr Rockland ME

Stay at this aparthotel in Rockland. Enjoy free WiFi, free parking, and a health club. Our guests praise the helpful staff and the clean rooms in our reviews. ...

8.6/10 Excellent! (417 reviews)

"The air conditioner in the room was so loud, didn't make for a peaceful night. Also the TV did not have cable access, we are not accustomed to having to log into any streaming service to be able to watch something."

Reviewed on Jun 22, 2026

Cozy Renovated Cabin in Central Boothbay– Peaceful, Private, Close to Everything

Boothbay ME

Stay at this cabin in Boothbay. Enjoy a garden, laundry facilities, and concierge services. Popular attractions Boothbay Railway Village and Dolphin Mini Golf ...

7.6/10 Good! (9 reviews)

"Not as advertised; teeny. The photos made it look spacious. The front yard was being raked and seeded for grass when we arrived so there were broken branches on our path. The deck, table and chairs had not been cleaned and we're dirty and covered with leaf litter. The room had no comfy chair, only ..."

Reviewed on Jun 6, 2026

Smuggler's Retreat ExploreTrails, Botanic Gardens, Kayak and MORE

East Boothbay ME

Stay at this vacation home in East Boothbay. Enjoy free WiFi, a water park, and a garden. Popular attractions Linekin Bay and Cabbage Island are located ...

9.8/10 Exceptional! (33 reviews)

"Nice cozy cabin with water views. Easy to get to shops, Botonical Gardens and boat tours."

Reviewed on Jun 12, 2026

See all properties in Damariscotta

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.

Popular places to visit

Damariscotta Farmer's Market

You can browse for the perfect souvenirs at Damariscotta Farmer's Market during your visit to Damariscotta. Stroll along this relaxing area's waterfront, or simply enjoy its coffeehouses.

Frances Perkins Center

You can spend an afternoon browsing the exhibits at Frances Perkins Center during your trip to Damariscotta. Stroll along this relaxing area's waterfront, or simply enjoy its coffeehouses.

Whaleback Shell Midden State Historic Site

Explore the great outdoors at Whaleback Shell Midden State Historic Site, a lovely green space in Damariscotta. Stroll along this relaxing area's waterfront, or simply enjoy its coffeehouses.