Entire home
Headwinds.
Photo gallery for Headwinds.
2 bedrooms2+ bathroomsSleeps 4
Popular amenities
Explore the area
Bristol, ME
- Pemaquid Point Lighthouse Park12 min walk
- La Verna Preserve11 min drive
- Carousel Music Theater51 min drive
- Wiscasset, ME (ISS)43 min drive
Rooms & beds
2 bedrooms (sleeps 4)
Bedroom 1
1 Queen Bed
Bedroom 2
1 Queen Bed
2 bathrooms, 1 half bathroom
Bathroom 1
Soap · Towels provided · Bathtub or shower · Toilet · Shampoo · Hair dryer
Bathroom 2
Soap · Towels provided · Toilet · Shower only · Shampoo · Hair dryer
Bathroom 3
Soap · Towels provided · Toilet · Shampoo · Hair dryer
Spaces
Deck or patio
Porch or lanai
Kitchen
Kitchenette
Separate dining area
Garden
Dining Area
About this property
Headwinds.
Enjoy premium views of Pemaquid Point at Headwinds in New Harbor, Maine, featuring spectacular sunsets over deep water views across John’s Bay! Soak in the hot tub & enjoy the custom steam shower for 2. Start up the grill or chef up the fully equipped kitchen, enjoy the fireplace while you dine, & wake up to the salt of the sea. Lobsters in fridge available on request.
20 minutes from Damariscotta, Headwinds is accessible to restaurants, a hometown grocer, an ice cream stand, art galleries, Pemaquid Beach & Lighthouse, plus many hiking trails and land preserves.
20 minutes from Damariscotta, Headwinds is accessible to restaurants, a hometown grocer, an ice cream stand, art galleries, Pemaquid Beach & Lighthouse, plus many hiking trails and land preserves.
Property manager
Lauren Jackson
Amenities
Hot tub
Kitchen
Washer
Dryer
Air conditioning
Outdoor space
Similar properties
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Kitchen
Washer
Dryer
9.4 out of 10, (13 reviews)
House Rules
Check in after 4:00 PM
Minimum age to rent: 18
Check out before 10:00 AM
Children
Adults only
Events
No events allowed
Pets
No pets allowed
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
This property uses eco-friendly cleaning products
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has not indicated whether there is a smoke detector on the property
We should mention
This property does not have any lifts
About the area
New Harbor
Pemaquid Point, a neighbourhood in New Harbor, is home to this holiday home. Pemaquid Point Lighthouse Park and Colonial Pemaquid State Historic Site are local landmarks, and the area's natural beauty can be seen at La Verna Preserve and Rachel Carson Salt Pond Preserve. Pemaquid Craft Co-op and Penobscot Marine Museum are also worth visiting.
Bristol, ME
What's nearby
- Pemaquid Point Lighthouse Park - 12 min walk
- Opera House at Boothbay Harbor - 52 min drive
- Coastal Maine Botanical Gardens - 52 min drive
- Boothbay Harbor Marina - 52 min drive
- Burnt Island Living Lighthouse - 53 min drive
Getting around
Restaurants
- East Boothbay General Store - 55 min drive
- Boothbay Lobster Wharf - 53 min drive
- McSeagull’s Restaurant - 52 min drive
- Osier's Wharf Store - 25 min drive
- Spruce Point Inn Resort & Spa - 57 min drive
Frequently asked questions
Reviews
Reviews
No reviews yet
Be the first to leave a review for this property after your stay.
About the host
Hosted by Lauren Jackson
My name is Lauren & I am grateful to serve your hospitality needs as Headwinds’ property manager. I have been cleaning this property since 2020 as both a residence & VRBO destination as it was rented as a partial unit in the past Headwinds sold in December 2023 & is now available to rent in full or by unit separated with a deadbolt lock. I am from NY & NJ but have been enjoying living & working in midcoast Maine since 2011 & know all the sweet spots for hiking, dining, & shopping. Please feel welcome to reach out with questions or requests; I am happy to be as hands-on or off with your planning & stay as needed.
Why they chose this property
Pemaquid Point is a historic & charming nook of the rocky Maine coastline beloved by locals & tourists alike for its gorgeous views, peaceful quiet, & incredible seafood. It is also along the corridor of unique bird migrations. From this private sanctuary almost all the way down the peninsula, Headwinds is close to a hometown grocer, restaurants, art galleries, ice cream, land preservations, beaches, & more! 20 minutes south of Damariscotta, guests can easily visit nearby destinations such as Rockland, Boothbay, Wiscasset, & Bath.
What makes this property unique
Headwinds is the ultimate luxury destination for relaxation, unwinding with close ones, or a couples’ getaway. The Lodge offers a king sized bed, fully equipped kitchen, warm dining space, fireplace, screened-in porch, fire pit, grill, office with wifi printer, Roku TV, & full bathroom. The Master Suite features a California king sized bed with en suite bathtub and full vanity, gas stove, kitchenette, patio with hot tub, walk-in closet with designated work space & desk, 1.5 bathrooms featuring a custom steam shower for 2, as well as a designated Ladies Room water closet with heated toilet seat.
Headwinds can provide the most breathtaking sunsets New England has to offer from the hot tub, fire pit, lawn chairs, or screened-in porch. There’s nothing quite like the salty Maine air and ocean views for the perfect escape. We are also happy to stock snacks as well as the fridge with lobsters, your choice wine, &/or favorite Maine beer on request.
Headwinds can provide the most breathtaking sunsets New England has to offer from the hot tub, fire pit, lawn chairs, or screened-in porch. There’s nothing quite like the salty Maine air and ocean views for the perfect escape. We are also happy to stock snacks as well as the fridge with lobsters, your choice wine, &/or favorite Maine beer on request.
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