Tailwinds - Upscale Oceanfront! Stunning Views! | House in Boothbay

10.0 (2 Reviews) |   4 Bedrooms  5 Bathrooms  8 Guests
East Boothbay House | Tailwinds - Upscale Oceanfront! Stunning Views!

4 Bedroom House in East Boothbay, Boothbay

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!

Tailwinds - Upscale Oceanfront! Stunning Views! is located in East Boothbay. Tailwinds - Upscale Oceanfront! Stunning Views! provides accommodation, featuring View, Bedding/Linens, Internet, among other amenities. This House features View, Bedding/Linens, Internet, to make your stay a comfortable one.

Tailwinds - Upscale Oceanfront! Stunning Views! has 4 Bedrooms , 5 Bathrooms, and max occupancy of 8 people. The minimum rental for this property is 1 nights, but this can change depending on the season you plan on staying. Previous guests have given good rated it, and VRBO labeled it a top-rated House because of the excellent services rendered by the owner or manager of this House, and has consistently provided great experiences for their guests. Most families or guests that use it recommend it to their friends and some of them are repeat guests. House has a friendly neighborhood, and the East Boothbay has interesting places to visit. If you want to learn more about the House in East Boothbay, such as places to visit and things to do nearby, you can check below to learn more.

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Amenities

Air Conditioner
Parking
TV
View
Ocean View
Balcony/Terrace
Oceanfront
Security/Safety
Bedding/Linens
Wellness Facilities
Fireplace/Heating
Guest Services
Barbecue/Outdoor Cooking
Child Friendly
Internet
Kitchen
Laundry

Facility Overview

Air Conditioner
  • Air conditioning
  • Heating
Bathrooms
  • Bathtub or shower
  • Hair dryer
  • 5 bathrooms
  • Towels provided
Bedroom
  • Bed sheets provided
  • 4 bedrooms
  • Dining table
  • Living room
  • Fireplace
Kitchen
  • Microwave
  • Coffee/tea maker
  • Dishwasher
  • Toaster
  • Oven
  • Cookware/dishes/utensils
  • Refrigerator
  • Spices
  • Stovetop
Laundry
  • Near laundromat
  • Laundry facilities
  • Washing machine and dryer
Parking
  • Car recommended
  • Onsite parking
Pet Friendly
  • Service animals only (pets not allowed)
Accessibility
  • Note from host: Due to the prevailing wind, smoking is not allowed
  • Smoke-free property
Activities
  • Wildlife and game walks nearby
  • Swimming nearby
  • Sailing nearby
  • Whale watching nearby
  • Kayaking nearby
  • Fitness facilities nearby
  • Birdwatching nearby
  • Fishing nearby
  • Marina nearby
  • Hiking/biking trails nearby
Entertainment
  • TV
General
  • Unit size: 2400 sq ft (223 sq m)
  • English
  • Near the ocean
  • Near outlet shopping
  • Near the sea
  • Near a health or beauty spa
  • Near the bay
  • On the waterfront
  • Desk
  • Desk chair
Guest Services
  • Iron/ironing board
Internet
  • Free WiFi
Outdoors
  • Garden
  • Barbecue grill
  • Balcony
Security/Safety
  • Carbon monoxide detector installed (host has indicated there is a carbon monoxide detector on the property)
  • First aid kit
  • Fire extinguisher
  • Smoke detector installed (host has indicated there is a smoke detector on the property)

Policies

Check-in
Check-in time starts at 4:00 pm contactless check-in available minimum check-in age: 25
Check-out
Check-out before 10:00 am
Child Policy
Children are welcome. note from host: please note that the house sits directly on the sh
Event Policy
No events allowed
Pet Policy
Pets not allowed (service animals are welcome, and are exempt from fees)
Smoking Policy
Smoking is not permitted;due to the prevailing wind, smoking is not allowed

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 host has indicated there is a carbon monoxide detector on the property host has indicated there is a smoke detector on the property onsite parties or group events are strictly prohibited safety features at this property include a fire extinguisher and a first aid kit special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed this property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room this property is managed through our partner, vrbo. you will receive an email from vrbo with a link to a vrbo account, where you can change or cancel your reservation

Reviews

Jody H.
Aug 19, 2025 10:29:44 PM
Review Score:   10
Summary: 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.
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