10/10 Excellent
JOANNE R.
4 July 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Friends reunion
JOANNE R.
Stayed 3 nights in Jun 2025
Entire home
Tailwinds - Upscale Oceanfront! Stunning Views!
Photo gallery for Tailwinds - Upscale Oceanfront! Stunning Views!
Reviews
10 out of 10
Exceptional
4 bedrooms5 bathroomsSleeps 8223.0 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!
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
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
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
- 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
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window10/10
Cleanliness
10/10
Check-in
10/10
Communication
10/10
Location
10/10
Listing accuracy
Reviews
About the host
Hosted by Pamela P Cunningham
Languages:
English
Premier Host
They consistently provide great experiences for their guests
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