Entire home
Tailwinds - Upscale Oceanfront! Stunning Views!
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Reviews
10 out of 10
Exceptional
4 bedrooms 5 bathrooms Sleeps 8 223.0 sq m
Popular amenities
Explore the area

Boothbay, ME
- Cabbage Island
- Carousel Music Theater8 min drive
- Boothbay Harbor Marina10 min drive
- Wiscasset, ME (ISS)39 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
Children
Children allowed: ages 0–17
Please note that the house sits directly on the sh
Events
No events allowed
Pets
No pets allowed, service animals permitted
Smoking
Smoking is not permitted
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
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.

Boothbay, ME
What's nearby
- Carousel Music Theater - 8 min drive - 6.5 km
- Opera House at Boothbay Harbor - 9 min drive - 7.2 km
- Burnt Island Living Lighthouse - 9 min drive - 7.6 km
- Boothbay Harbor Marina - 10 min drive - 7.6 km
- Coastal Maine Botanical Gardens - 13 min drive - 11.2 km
Getting around
Restaurants
- Boothbay Lobster Wharf - 9 min drive
- The Thistle Inn - 6 min drive
- McSeagull’s Restaurant - 8 min drive
- Boothbay Harbor House of Pizza
- Harborside 1901 Bar & Grill
Frequently asked questions
About the host
Hosted by Pamela P Cunningham

Languages:
English
Premier Host
They consistently provide great experiences for their guests
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