Tailwinds - Upscale Oceanfront! Stunning Views!
Boothbay, Maine
4
Bed
5
Bath
Private Vacation Home
Property Type
8
Max Sleeps
3 nights
Min Stay
Welcome to Tailwinds in East Boothbay, where you will enjoy stunning sunsets over Linekin Bay from the comfort of this beautifully updated home. Formerly a B&B, Tailwinds has 3 queen bedrooms, all with en-suite baths, a bedroom with 2 twins and a bathroom down the hall, 2 living areas, a kitchen and a large porch. The home had a major renovation in 2023, and features all new beds and furniture, luxurious 100% cotton sheets and duvets, and a crisp, nautical feel. Located between downtown B
Features
Map
Rates & Availability
Review
Features
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PETS
Service Animals Only (pets Not Allowed) -
DINING
Dining Table -
SAFETY
Carbon Monoxide Detector Installed (host Has Indicated There Is A Carbon Monoxide Detector On The Property) Fire Extinguisher First Aid Kit Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property) -
BEDROOM
4 Bedrooms Bed Sheets Provided -
GENERAL
Unit Size: 2400 Sq Ft (223 Sq M) -
KITCHEN
Coffee/tea Maker Cookware/dishes/utensils Dishwasher Microwave Oven Refrigerator Spices Stovetop Toaster -
LAUNDRY
Laundry Facilities Near Laundromat Washing Machine And Dryer -
PARKING
Car Recommended Onsite Parking -
INTERNET
Free WiFi -
OUTDOORS
Balcony Barbecue Grill Garden -
BATHROOMS
5 Bathrooms Bathtub Or Shower Hair Dryer Towels Provided -
WORKSPACES
Desk Desk Chair -
LANGS SPOKEN
English -
THINGS TO DO
Fitness Facilities Nearby Golf Nearby Hiking Nearby Hiking/biking Trails Nearby Kayaking Nearby Marina Nearby Power Boating Nearby Sailing Nearby Whale Watching Nearby Winery Tours Nearby -
ENTERTAINMENT
TV -
LIVING SPACES
Fireplace Living Room -
CLIMATE CONTROL
Air Conditioning Heating -
LOCATION HIGHLIGHTS
Near A Health Or Beauty Spa Near Outlet Shopping Near The Bay Near The Ocean Near The Sea On The Waterfront -
SERVICES AND CONVENIENCES
Iron/ironing Board -
SUITABILITY/ACCESSIBILITY
Note From Host: Due To The Prevailing Wind, Smoking Is Not Allowed Smoke-free Property
Check-in : 04:00 PM
Check-out : 10:00 AM
No Wheelchair
No smoking
No pets
Children allowed
Max occupancy : 8
Map
Rates & Availability
Review
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Jody H.
Submitted Aug 19, 2025
Stayed Aug 1, 2025Pam and her team are professional and accessible! Beautiful 19th century home in East Boothbay! The 4 bedrooms, plus a single bed tucked into a downstairs nook was so accommodating for a large family. 5 full bathrooms, one being on first floor, a real luxury! Wrap around porch overlooking a huge yard and Linekin Bay is delightful.
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JOANNE R.
Submitted Jul 4, 2025
Stayed Jun 27, 2025We had a fabulous time during our recent visit to Boothbay Harbor, our stay at Tailwinds was wonderful. The home is beautiful, well appointed, clean and comfortable with a stunning view of the inlet. East Boothbay is just a short drive to Boothbay Harbor, the location worked very well for us. We loved hanging out on the back decks and enjoying the peaceful view. Our group of 4, we are long-time friends, enjoyed the 4 bedrooms with our own bathroom to use during our stay, we all found the beds to be very comfortable. While we didn't need to contact Pam during our stay, she had provided clear instructions on how to contact her. We all agreed that we would definitely consider staying here again next year.
