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East Boothbay, Maine

Upscale, Waterfront on Linekin Bay

Welcome to Tailwinds! Situated on the shore of Linekin Bay with gorgeous sunset views, you'll experience the very best of Boothbay in the perfect location. Tailwinds has recently undergone an extensive renovation and has all new furniture and beds. 

With two living areas, 3 queen bedrooms with en-suite bathrooms, a twin bedroom and two additional full bathrooms, there is plenty of space to relax and gather together. There are window AC units in the queen bedrooms. The location is perfect for exploring Maine and is only 4.5 miles to downtown Boothbay Harbor and within an hour of Camden, Rockland, Damariscotta, Bath, Brunswick and Pemaquid. 

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Property Type:   House

Size:   2,500 sq ft 

Bedrooms:   4

Baths:   5

Sleeps:   8


Main Bedroom:   Queen Bed

En-suite Bathroom:  Shower Only

2nd Bedroom:  Queen Bed

En-suite Bathroom:  Shower

3rd Bedroom: Queen Bed

En-suite Bathroom: Shower

4th Bedroom: 2 Twin Beds

4th Bathroom: Shower/Tub Combo

5th Bathroom: Shower

Region:   Mid-Coast

Town:   East Boothbay

Location Type:   Waterfront, Oceanfront

Exposure:   Western

Smoking Allowed:   No
Pets Allowed:   No

Wheelchair Accessible:   No

AC:  Window AC Units in 3 of 4 bedrooms


Tailwinds Coffee


The Location

Tailwinds is located on Ocean Point Road about halfway between downtown Boothbay Harbor and Ocean Point, in East Boothbay.

It's only about 4.5 miles to downtown Boothbay Harbor, 1/4 to Linekin Preserve and within 1 mile to the Carriage House Restaurant and the East Boothbay General Store.


The Boothbay Country Club, Maine Botanical Gardens, and numerous boat excursions are only a short drive away.

Included with all Chill Vacation Rentals

Great Amenities

Every rental has a gas grill, bluetooth speaker, fully-stocked kitchen, flat-screen TVs and WiFi.

Luxury Linens

You'll have high quality, crisp sheets, cozy duvets, a variety of pillows & fluffy towels bath towels.

Excellent Condition

Everything is in good working order. You will have comfy furniture and high quality mattresses.

Tailwinds View

Important Things to Know

  • The house sits close to the road and there is the potential for some road noise.

  • There are AC window units in all of the queen bedrooms and in the main living area downstairs. 

  • Due to the setting, high above the bay, there is no water access from the property. 

  • All bedrooms are on the 2nd floor.


  • There is parking for 3 cars in the driveway. There is no street parking.

  • The house has 8 stairs to enter. 


  • 30% Payment due at time of booking. Balance due 60 days prior to arrival.

  • We accept payment via American Express, Master Card, Visa and Discover.

  • $500 Security Deposit Hold


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