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Tailwinds - Upscale Oceanfront! Stunning Views!

Waterfront holiday home with kitchen and balcony

Photo gallery for Tailwinds - Upscale Oceanfront! Stunning Views!

Living area
Exterior
Room
Terrace/patio
Private kitchen

Reviews

10 out of 10
Exceptional
4 bedrooms5 bathroomsSleeps 8223.0 sq m

Popular amenities

  • Ocean view
  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi
  • Air-conditioning

Explore the area

View map
Boothbay, ME
  • Place, Linekin Bay
    ‪2 min walk‬
  • Place, Boothbay Harbor Marina
    ‪9 min drive‬
  • Place, Coastal Maine Botanical Gardens
    ‪13 min drive‬
  • Airport, Wiscasset, ME (ISS)
    ‪37 min drive‬

Rooms & beds

4 bedrooms (sleeps 8)

Mudroom

1 Single Bed

Queen 3

1 Queen Bed

Twin

2 Single 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!

Add dates for prices

Amenities

Kitchen
Washing machine
Dryer
Free WiFi
Air conditioning
Outdoor space

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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
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
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that 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 and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
Property # 3313490vb

We should mention

A car is recommended for transport to and from this property

About the area

East Boothbay

Located in East Boothbay, this holiday home is on the waterfront. Ovens Mouth Preserve and Linekin Bay reflect the area's natural beauty and area attractions include Coastal Maine Botanical Gardens and Maine State Aquarium. Boothbay Railway Village and Dolphin Mini Golf are also worth visiting. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
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Map
Boothbay, ME

What's nearby

  • Linekin Bay - 2 min walk - 0.2 km
  • Opera House at Boothbay Harbor - 8 min drive - 7.2 km
  • Boothbay Harbor Marina - 9 min drive - 7.6 km
  • Coastal Maine Botanical Gardens - 13 min drive - 10.8 km
  • Bowdoin College - 55 min drive - 65.2 km

Getting around

  • Wiscasset, ME (ISS) - 32 min drive

Restaurants

  • ‪Carriage House Restaurant - ‬7 min walk
  • ‪Boothbay Lobster Wharf - ‬9 min drive
  • ‪Harborside 1901 Bar & Grill - ‬8 min drive
  • ‪Red Cup Coffeehouse - ‬8 min drive
  • ‪McSeagull’s Restaurant - ‬8 min drive

Frequently asked questions

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

No, only service animals are welcome at the property.

How much is parking at Tailwinds - Upscale Oceanfront! Stunning Views!?

On-site 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!?

Checkout is at 10:00 AM.

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

Situated on the waterfront, this holiday 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 miles (10 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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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

This review comes from a trusted partner site and has not been verified.

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.

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

Host profile image

Languages:

English

Premier Host

They consistently provide great experiences for their guests
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