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Tailwinds - Upscale Oceanfront! Stunning Views!

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Living area
Exterior
Room
Terrace/patio
Private kitchen

Reviews

10 out of 10
Exceptional
4 bedrooms5 bathroomsSleeps 8

Popular amenities

  • Onsite parking available
  • Kitchen
  • Washer
  • Air conditioning
  • Barbecue grill
  • Balcony

Explore the area

View in a map
Boothbay, ME
  • Place, Linekin Bay
    ‪2 min walk‬
  • Place, Opera House at Boothbay Harbor
    ‪9 min drive‬
  • Place, Boothbay Harbor Marina
    ‪9 min drive‬
  • Airport, Wiscasset, ME (ISS)
    ‪33 min drive‬

Rooms & beds

4 bedrooms (sleeps 8)

Mudroom

1 Twin Bed

Queen 3

1 Queen Bed

Twin

2 Twin Beds

Waterfront Queen 1

1 Queen Bed

Waterfront Queen 2

1 Queen Bed

5 bathrooms

Downstairs Bathroom

Toilet · Shower only

Queen 1 en-suite

Toilet · Shower only

Queen 2 en-suite

Toilet · Shower only

Queen 3 en-suite

Toilet · Shower only

Upstairs Hallway Bathroom

Bathtub or shower · Toilet

Spaces

Deck or patio
Kitchen
Balcony
Garden
Dining area

About this property

Tailwinds - Upscale Oceanfront! Stunning Views!

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!
Our prices include all fees. No hidden fees.

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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
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Children

Children allowed: ages 0-17
Please note that the house sits directly on the sh
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Events

No events allowed
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Pets

No pets allowed, service animals permitted
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Smoking

Smoking is not permitted
Due to the prevailing wind, smoking is not allowed
Your rental agreement must be signed within 48 hours of booking or your reservation will be cancelled, & you will not be given access to the property
3rd party bookings are not allowed. The name on the credit card must match the name on the booking, and of the rental agreement signee.
We partner with VRBO and act as the payment processor. A security deposit hold is required and will be made using the card used for final payment

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a first aid kit
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room

About the neighborhood

East Boothbay

Located in East Boothbay, this vacation home is on the waterfront. Ovens Mouth Preserve and Linekin Bay reflect the area's natural beauty and area attractions include Opera House at Boothbay Harbor and Coastal Maine Botanical Gardens. Maine State Aquarium and Boothbay Railway Village are also worth visiting. Discover the area's water adventures with kayaking and snorkeling nearby, or enjoy the great outdoors with ecotours and hiking/biking trails.
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Map
Boothbay, ME

What's nearby

  • Linekin Bay - 2 min walk - 0.2 km
  • Opera House at Boothbay Harbor - 9 min drive - 7.9 km
  • Boothbay Harbor Marina - 9 min drive - 8.3 km
  • Coastal Maine Botanical Gardens - 12 min drive - 12.2 km
  • Bowdoin College - 51 min drive - 66.3 km

Getting around

  • Wiscasset, ME (ISS) - 32 min drive

Restaurants

  • ‪Circle K - ‬7 min drive
  • ‪South Bristol Fisherman's Coop - ‬62 min drive
  • ‪Carriage House Restaurant - ‬7 min walk
  • ‪Footbridge Brewery - ‬7 min drive
  • ‪Tugboat Inn - ‬9 min drive

Frequently asked questions

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

No, only service animals are welcome at the property.

How much does it cost to stay at Tailwinds - Upscale Oceanfront! Stunning Views!?

As of May 6, 2026, prices found for a 1-night stay for 2 adults at Tailwinds - Upscale Oceanfront! Stunning Views! on Aug 7, 2026 start from $899, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking?

Onsite parking is available at the property.

What time is check-in at Tailwinds - Upscale Oceanfront! Stunning Views!?

Check-in begins at 4:00 PM.

What time is check-out at Tailwinds - Upscale Oceanfront! Stunning Views!?

Check-out is at 10:00 AM.

Where is Tailwinds - Upscale Oceanfront! Stunning Views! located?

Situated on the waterfront, this vacation home is steps from Linekin Bay and 2.4 mi (3.8 km) from Grimes Cove Beach. Carousel Music Theater and Boothbay Region Land Trust are also within 6 mi (10 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window
Rating 10 - Excellent. 2 out of 2 reviews
Rating 8 - Good. 0 out of 2 reviews
Rating 6 - Okay. 0 out of 2 reviews
Rating 4 - Poor. 0 out of 2 reviews
Rating 2 - Terrible. 0 out of 2 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

From a partner site

10/10 Excellent

Jody H.

Tailwinds Home

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.
Verified

10/10 Excellent

JOANNE R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Friends reunion

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.
Stayed 3 nights in Jun 2025

About the host

Hosted by Pamela P Cunningham

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Languages:

English

Premier Host

They consistently provide great experiences for their guests
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