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 Balcony/Terrace, Oceanfront, Security/Safety, among other amenities. This House features Air Conditioner, Parking and TV 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.

Show more
OneKey Logos

This Property is OneKey Eligible

Earn OneKeyCash for every dollar spent on eligible vacation rentals, villas, cottages, cabins, and more when you book on Vrbo.

JOIN TODAY

Amenities

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

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
Pet Policy
Pets not allowed (service animals are welcome, and are exempt from fees)

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.
See All Reviews

FAQ's

Is this East Boothbay house pet-friendly for guests?

No, pets are not allowed at this property. Check the guest reviews to learn what guests had to share.

Does the East Boothbay house have a swimming pool?

No, this East Boothbay house does not have a swimming pool. Check the Facility Overview section for details about the pool and other available facilities.

How much does it cost per night to stay in East Boothbay house?

Best-rates for the East Boothbay house starts from $892 per night with includes Barbecue/Outdoor Cooking, Internet, Laundry, Fireplace/Heating, Guest Services, Parking, Ocean View, Bedding/Linens, Child Friendly, Wellness Facilities, Air Conditioner, TV, Balcony/Terrace, Oceanfront, Security/Safety, Sports/Activities, Kitchen, View, Entertainment with all other facilities. matches every traveler with their perfect accommodation, whether you are traveling with a group, friends, family, or pets.

Is East Boothbay house a family-friendly place to stay?

Based on the information we have received from the owner or our partner, this is considered to be a family-friendly property. Families have rated this house Good or guests have recommended them suitable for families. As reported by the owner or manager, the house has specified that children are welcome. Please see details about suitability for your family or inquire with the property to learn more.

Is the East Boothbay house wheelchair accessible or offer services for disabled guests?

Based on the information received from our partner, the East Boothbay house has not specified they are wheelchair accessible. Likewise, there is not an elevator specified as being available at the property. Specific accessibility details may be addressed in the property details section of this page.

What is the minimum night stay policy for the East Boothbay house?

Based on the information reported by the owner or manager, the East Boothbay house indicates 1 day stay policy at this house. Guests are cautioned that the minimum stay policy may differ based on seasonality or availability and may be at the discretion of the owner or manager.

What cancellation policy is in place for East Boothbay house?

Guests are cautioned that the cancellation policy may differ based on seasonality, availability, or current travel restrictions. Guests should also be aware that this policy may be subject to change and should be confirmed prior to booking. More details may be available on this page in the property description. However, early check-in or late check-out can sometimes be negotiated between the guest and the owner or the manager of this property.

Check House Availability
Nightly rates from:
USD892
You will be redirected to  
Hot Deal - It has been viewed 180 times today
Not the right fit? Check out our other properties in East Boothbay
Smuggler's Cove Inn From US $313
         

9.0 (496 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Cozy Detached Guest Cottage on Mill Pond From US $209
         

Three Porches by Sea Maine From US $789
         

10.0 (14 Reviews)
House
  • Parking
  • TV
  • Balcony/Terrace
Deck w/Water Views: Quiet East Boothbay Retreat! From US $364
         

10.0 (8 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
All Aboard Cottage From US $651
         

10.0 (6 Reviews)
Cottage
  • Parking
  • TV
  • View
Owl`s Nest by Sea Maine From US $582
         

10.0 (4 Reviews)
House
  • Parking
  • TV
  • Balcony/Terrace