Entire home

Tailwinds - Upscale Oceanfront! Stunning Views!

Photo gallery for Tailwinds - Upscale Oceanfront! Stunning Views!

Living area
Living area
Exterior
Miscellaneous
Interior

Reviews

9.8 out of 10
Exceptional
4 bedrooms5 bathroomsSleeps 8223.0 sq m

Popular amenities

  • Dryer
  • Washer
  • Fireplace
  • Parking available
  • Kitchen
  • Barbecue grill

Explore the area

Map
Boothbay, ME
  • Opera House at Boothbay Harbor
    ‪7 min drive‬
  • Boothbay Harbor Marina
    ‪7 min drive‬
  • Cabbage Island
    ‪11 min drive‬
  • Wiscasset, ME (ISS)
    ‪32 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!

Property manager

Pamela P Cunningham
Premier Host

Languages

English

Add dates for prices

Amenities

Kitchen
Washer
Dryer
Air conditioning
Outdoor space
Parking available

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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 may be cancelled, and 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.
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

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.
Map
Boothbay, ME

What's nearby

  • Opera House at Boothbay Harbor - 7 min drive - 6.6 km
  • Boothbay Harbor Marina - 7 min drive - 6.9 km
  • Burnt Island Living Lighthouse - 7 min drive - 7.0 km
  • Cabbage Island - 11 min drive - 7.9 km
  • Coastal Maine Botanical Gardens - 12 min drive - 9.8 km

Getting around

  • Wiscasset, ME (ISS) - 32 min drive

Restaurants

  • ‪Boothbay Lobster Wharf - ‬9 min drive
  • ‪East Boothbay General Store - ‬20 min walk
  • ‪Coveside Bar & Grill - ‬53 min drive
  • ‪Dunton's Doghouse - ‬8 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.

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).

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About the host

Hosted by Pamela P Cunningham

Host profile image

Languages:

English

Premier Host

They consistently provide great experiences for their guests