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

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

Best-rates for the East Boothbay house starts from $781 per night with includes Air Conditioner, TV, Balcony/Terrace, Bedding/Linens, Internet, Laundry, Ocean View, Security/Safety, Kitchen, Oceanfront, Wellness Facilities, Fireplace/Heating, Guest Services, Parking, View, Barbecue/Outdoor Cooking, Child Friendly with all other amenities. Perfect for Weddings is committed to ensuring every guest experiences a comfortable and extraordinary stay, whether planning a romantic getaway, a honeymoon, a pet-friendly stay, or celebrating with the entire wedding party.

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 Guest Services, Parking, View, among other amenities. This House features Guest Services, Parking, View, to make your stay a comfortable one.

Tailwinds - Upscale Oceanfront! Stunning Views! has 4 Bedrooms , 5 Bathrooms, and max occupancy of 8 persons. The minimum rental for this property is 1 night, 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.

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

Policies

Event Policy No events allowed

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)

Smoking Policy Smoking is not permitted;due to the prevailing wind, smoking is not allowed

Other Policy 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

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Reviews

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

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.

JOANNE R. Jul 4, 2025 10:45:39 PM

Summary: We had a fabulous time during our recent visit to Boothbay Harbor, our stay at Tailwinds was wonderful. The home is beautiful, well appointed, clean and comfortable with a stunning view of the inlet. East Boothbay is just a short drive to Boothbay Harbor, the location worked very well for us. We loved hanging out on the back decks and enjoying the peaceful view. Our group of 4, we are long-time friends, enjoyed the 4 bedrooms with our own bathroom to use during our stay, we all found the beds to be very comfortable. While we didn't need to contact Pam during our stay, she had provided clear instructions on how to contact her. We all agreed that we would definitely consider staying here again next year.

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 $781 per night with includes Air Conditioner, TV, Balcony/Terrace, Bedding/Linens, Internet, Laundry, Ocean View, Security/Safety, Kitchen, Oceanfront, Wellness Facilities, Fireplace/Heating, Guest Services, Parking, View, Barbecue/Outdoor Cooking, Child Friendly with all other amenities. Perfect for Weddings is committed to ensuring every guest experiences a comfortable and extraordinary stay, whether planning a romantic getaway, a honeymoon, a pet-friendly stay, or celebrating with the entire wedding party.

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?

Based on the information reported by the owner or manager, details for the cancellation policy for the East Boothbay house are as follows: Cancellation policy 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:

US $781