Skip to main content

Tailwinds - Upscale Oceanfront! Stunning Views!

Photo gallery for Tailwinds - Upscale Oceanfront! Stunning Views!

A covered outdoor seating area with wicker furniture and a view of a lake.
A kitchen with a double sink, two windows, and a view of the outdoors.
A dining area with a round table and four chairs, large windows with a view of the sea, and a wooden floor.
A spacious living room with a large window, a ceiling fan, and a view of the outdoors.
A large, two-story house with a porch and a well-maintained lawn.

Reviews

10 out of 10
Exceptional

Highlights

  • Room to spread out
    Enjoy a spacious layout that gives everyone more room to relax.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
  • Discover nearby landmarks
    Close to Linekin Bay
Sleeps 8•4 bedrooms•6 beds

Popular amenities

  • Onsite parking available
  • Kitchen
  • Washing machine
  • Air-conditioning
  • Barbecue
  • Balcony

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
    ‪12 min drive‬
  • Airport, Wiscasset, ME (ISS)
    ‪33 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

Have a question?

AI iconBeta

Get instant answers with AI powered search of property information and reviews.

Similar properties

Terrace/patio
Gorgeous home with spectacular ocean views near Boothbay Harbor
Ocean Point
  • Ocean view
  • Kitchen
  • Washing machine
  • Dryer
10.0 out of 10, Exceptional, (31 reviews)
Gorgeous home with spectacular ocean views near Boothbay Harbor

House Rules

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

Children

Children allowed: ages 0–17
Please note that the house sits directly on the sh
default

Events

No events allowed
default

Pets

No pets allowed, service animals permitted
default

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

Property # 3313490vb
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

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 Opera House at Boothbay Harbor. Maine State Aquarium and Boothbay Railway Village are also worth visiting. Discover the area's water adventures with kayaking and snorkelling nearby, or enjoy the great outdoors with hiking and horse riding.
View more Holiday homes in East BoothbayOpens in a new window
Map
Boothbay, ME

What's nearby

  • Linekin Bay - 2 min walk - 0.2 km
  • Opera House at Boothbay Harbor - 9 min drive - 8.3 km
  • Boothbay Harbor Marina - 9 min drive - 8.7 km
  • Coastal Maine Botanical Gardens - 12 min drive - 12.2 km
  • Pemaquid Point Lighthouse Park - 56 min drive - 72.1 km

Getting around

  • Wiscasset, ME (ISS) - 32 min drive

Restaurants

  • ‪Circle K - ‬7 min drive
  • ‪South Bristol Fisherman's Coop - ‬62 min drive
  • ‪Robinson's Wharf - ‬12 min drive
  • ‪Tugboat Inn - ‬9 min drive
  • ‪Pinkham’s Gourmet Market - ‬7 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).

About the host

Hosted by Pamela P Cunningham

Host profile image

Languages:

English

Premier Host

They consistently provide great experiences for their guests
Tell us how we can improve our siteShare feedback