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Tailwinds - Upscale Oceanfront! Stunning Views!

Top rated by guests
Living area
Private kitchen
Private kitchen
Private kitchen
Exterior
review stars
10Outstanding
(2 Ratings)
"Pam 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 famil..."
Jody H.
Don't miss out! Price and availability may change
10 / 10
Outstanding(2 Ratings)

House in East Boothbay, ME

8 guests · 4 bedrooms · 5 baths

Reasons to book

Guests love it hereGuests give this property a top rating
Top-tier experienceA high end property in this area
Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental

About this house rental

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 Boothbay Harbor and Ocean Point, this is a gorgeous spot for your next family vacation!

Amenities at Tailwinds - Upscale Oceanfront! Stunning Views!

Non-smoking

Map of East Boothbay, ME

city location on map

Nearby attractions

Coastal Maine Botanical Gardens
3.9 mi
Rockland Breakwater Lighthouse
30.9 mi
Rockland Breakwater Light parking
31.1 mi
Owls Head Transportation Museum
28.4 mi

Ratings and reviews

10 / 10
Outstanding(2 Ratings)
10 / 10Outstanding·Aug 2025
Pam 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.
10 / 10Outstanding·Jul 2025
We 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.
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FAQs

Is parking included with this house?

Parking is not specified as an available amenity at Tailwinds - Upscale Oceanfront! Stunning Views!. For more information, we encourage you to contact the property about where to park.

Is there a pool at this house?

We didn’t find pool listed as an amenity for this house. It may be worth double checking if a pool is important for your stay.

Is Tailwinds - Upscale Oceanfront! Stunning Views! pet friendly?

Unfortunately, this house is not pet-friendly. Try searching again and filter for "Pets Allowed"

What amenities are available at Tailwinds - Upscale Oceanfront! Stunning Views!?

We found 1 amenities for this rental. This includes , and non-smoking.