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Windward - Enjoy privacy, comfortable living spaces, and easy water access
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Reviews
9.8 out of 10
Exceptional
3 bedrooms2 bathroomsSleeps 61712 sq ft
Popular amenities
Explore the area

Harpswell, ME
- Place, Paddleworks16 min drive
- Place, Bowdoin College18 min drive
- Place, Maine Street18 min drive
- Airport, Portland, ME (PWM-Portland Intl. Jetport)57 min drive
Rooms & beds
3 bedrooms (sleeps 6)
Bedroom 1
1 Queen Bed
Bedroom 2
1 Queen Bed
Bedroom 3
2 Single Beds
2 bathrooms
Bathroom 1
Bathtub or shower · Toilet
Bathroom 2
Toilet · Shower only
Spaces
Deck or patio
Kitchen
Balcony
Garden
Dining area
About this property
Windward - Enjoy privacy, comfortable living spaces, and easy water access
Resting on the gentle shores of Harpswell Sound, Windward offers three bedrooms, two bathrooms, wonderful natural light, open living spaces, stunning ocean views from almost every room, plentiful outdoor space, great water access, and a private pocket beach for the whole family to enjoy.
Inside you'll find an open concept kitchen, living, and dining, bringing the ocean in with sliding glass doors that open to a deck, patio, and spacious lawn overlooking the water. On the first floor, there is a spacious ocean view bedroom with a queen size bed and a sliding glass door that opens to a deck, the perfect place to enjoy your morning coffee or tea. There is also a full bathroom with a shower/tub just outside the door. Upstairs, you'll find a bedroom with two twins, a full bathroom with a large walk-in shower, and the master bedroom with a queen bed, stunning ocean views, and a balcony. Guests will enjoy all new furniture, mattresses, and bedding throughout the house.
Windward is located in the private neighborhood of High Head, offering a wonderful paved road, great for walking and biking. You'll love being just a few minutes from the hiking trails, stores, and restaurants Harpswell has to offer, while being just 10 minutes from Brunswick's lively Maine Street, offering a great variety of restaurants, shops, and pubs, as well as access to RT 1 and I-295 for day trips to Freeport, Portland, Bath, Boothbay Harbor and more.
Come enjoy the beauty of Harpswell at this lovely seaside home and make memories to last a lifetime!
Sorry, Windward does not allow pets.
Bed types/descriptions:
First Floor:
Bedroom with a Queen Bed, Ocean Views, and Private Access to the First Level Deck
Second Floor:
Bedroom with Two Twins
Master Bedroom with a Queen Bed, Ocean Views, and a Private Balcony
Bathroom setup/description:
First Floor- Full Bathroom with Shower/Tub Combo
Second Floor- Full Bath with Large Glass Walk-In Shower
Air Conditioning: No, fans are available
Beach/Water Access: Direct, on property via private stairs, sandy/pebbly shoreline
Beach Towels: Not included
Departure Cleaning: Included
Cable TV: Yes in Living Room
Closest Shopping Village: Brunswick, 15min away
Coffee Maker: Yes, regular drip coffeemaker
Dishwasher: Yes
Grill: Gas Grill available, Propane provided
Heat Source: Hot Water Baseboard Furnace
Internet Access: Yes, Xfinity Cable Internet and WiFi
Linens & Bath Towels: Included, beds are made prior to guest arrival and towels remain in their sanitized packaging, placed on each bed
Lobster Pot: Yes
Outdoor Firepit: No
Parking: 2 cars
Stairs to Water: Yes
Trash Removal: Included, picked up weekly (for multi-week stays) or upon departure
TV: Smart TV in Living Room
Usable Fireplaces: No
Washer & Dryer: Yes
Water Frontage: Direct water frontage
Water Source: Well water with filtration/softener system, bottled drinking water recommended
Inside you'll find an open concept kitchen, living, and dining, bringing the ocean in with sliding glass doors that open to a deck, patio, and spacious lawn overlooking the water. On the first floor, there is a spacious ocean view bedroom with a queen size bed and a sliding glass door that opens to a deck, the perfect place to enjoy your morning coffee or tea. There is also a full bathroom with a shower/tub just outside the door. Upstairs, you'll find a bedroom with two twins, a full bathroom with a large walk-in shower, and the master bedroom with a queen bed, stunning ocean views, and a balcony. Guests will enjoy all new furniture, mattresses, and bedding throughout the house.
Windward is located in the private neighborhood of High Head, offering a wonderful paved road, great for walking and biking. You'll love being just a few minutes from the hiking trails, stores, and restaurants Harpswell has to offer, while being just 10 minutes from Brunswick's lively Maine Street, offering a great variety of restaurants, shops, and pubs, as well as access to RT 1 and I-295 for day trips to Freeport, Portland, Bath, Boothbay Harbor and more.
Come enjoy the beauty of Harpswell at this lovely seaside home and make memories to last a lifetime!
Sorry, Windward does not allow pets.
Bed types/descriptions:
First Floor:
Bedroom with a Queen Bed, Ocean Views, and Private Access to the First Level Deck
Second Floor:
Bedroom with Two Twins
Master Bedroom with a Queen Bed, Ocean Views, and a Private Balcony
Bathroom setup/description:
First Floor- Full Bathroom with Shower/Tub Combo
Second Floor- Full Bath with Large Glass Walk-In Shower
Air Conditioning: No, fans are available
Beach/Water Access: Direct, on property via private stairs, sandy/pebbly shoreline
Beach Towels: Not included
Departure Cleaning: Included
Cable TV: Yes in Living Room
Closest Shopping Village: Brunswick, 15min away
Coffee Maker: Yes, regular drip coffeemaker
Dishwasher: Yes
Grill: Gas Grill available, Propane provided
Heat Source: Hot Water Baseboard Furnace
Internet Access: Yes, Xfinity Cable Internet and WiFi
Linens & Bath Towels: Included, beds are made prior to guest arrival and towels remain in their sanitized packaging, placed on each bed
Lobster Pot: Yes
Outdoor Firepit: No
Parking: 2 cars
Stairs to Water: Yes
Trash Removal: Included, picked up weekly (for multi-week stays) or upon departure
TV: Smart TV in Living Room
Usable Fireplaces: No
Washer & Dryer: Yes
Water Frontage: Direct water frontage
Water Source: Well water with filtration/softener system, bottled drinking water recommended
Add dates for prices
Amenities
Kitchen
Washing machine
Dryer
Free WiFi
Outdoor space
Sea view
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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
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
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
About the area
Harpswell
Located in Harpswell, this holiday home is on the waterfront. Ash Cove Pottery and Paddleworks are local attractions and those in the mood for shopping can visit Maine Street and LL Bean Flagship Store. Orion Performing Arts Center and Land's End Gift Shop are also worth visiting. Spend some time exploring the area's activities, including golfing, birdwatching and fishing.

Harpswell, ME
What's nearby
- Paddleworks - 16 min drive - 12.2 km
- Ash Cove Pottery - 16 min drive - 13.3 km
- Bowdoin College - 18 min drive - 15.7 km
- Maine Street - 18 min drive - 15.4 km
- Bailey Island Bridge - 19 min drive - 14.3 km
Getting around
Restaurants
- Wild Oats - 17 min drive
- Iris Eats Maine - 13 min drive
- Cook's Lobster & Ale House - 18 min drive
- Anna's Water's Edge Restaurant - 48 min drive
- Gurnet Trading Company - 16 min drive
Frequently asked questions
Reviews
9.8
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window9.8/10
Cleanliness
10/10
Check-in
10/10
Communication
10/10
Location
9.8/10
Listing accuracy
Reviews
20 Oct, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 3 nights in Oct 2025
10/10 Excellent
Chris B.
13 Sept, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Chris B.
Stayed 7 nights in Sep 2025
10/10 Excellent
Jenna L.
9 Oct, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy

Jenna L.
Stayed 4 nights in Sep 2025
10/10 Excellent
Nina E.
20 Jun, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Loved watching the birds on the water.
Nina E.
Stayed 3 nights in Jun 2024
10/10 Excellent
Lia T.
20 Jun, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful Maine home
Lia T.
Stayed 3 nights in Jun 2023
8/10 Good
Stacey V.
17 Jun, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Lovely short trip to Harpswell
Stacey V.
Stayed 5 nights in Jun 2023
8/10 Good
Monica G.
21 Sept, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
So Beautiful!
Monica G.
Stayed 6 nights in Sep 2024
6/10 Okay
Craig C.
6 Oct, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Winward
Craig C.
Stayed 5 nights in Sep 2024
This review is from a guest who booked and stayed through a partner site and can't be verified.
10/10 Excellent
pam b.
18 Jul, 2023
Wonderful!
pam b.
10/10 Excellent
Eric R.
30 Oct, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Quiet seclusion
Eric R.
Stayed 3 nights in Oct 2023
This review is from a guest who booked and stayed through a partner site and can't be verified.
10/10 Excellent
29 Sept, 2024
Wonderful August Week at Windward
Stayed 7 nights in Aug 2024
This review is from a guest who booked and stayed through a partner site and can't be verified.
10/10 Excellent
Ward F.
8 Sept, 2024
Last week in August
Ward F.
Stayed 5 nights in Aug 2024
This review is from a guest who booked and stayed through a partner site and can't be verified.
10/10 Excellent
Susan M.
31 Jul, 2024
Lovely quiet location with a beautiful water view from each room
Susan M.
This review is from a guest who booked and stayed through a partner site and can't be verified.
10/10 Excellent
A guest from Newburyport, MA
22 Jul, 2024
Great getaway near Casco Bay
A guest from Newburyport, MA
This review is from a guest who booked and stayed through a partner site and can't be verified.
10/10 Excellent
A guest from Atlanta, GA
15 Aug, 2023
Windward: A great rental.
A guest from Atlanta, GA
This review is from a guest who booked and stayed through a partner site and can't be verified.
10/10 Excellent
Nancy C.
8 Aug, 2023
A relax right on the water.
Nancy C.
Stayed 7 nights in Jul 2023
This review is from a guest who booked and stayed through a partner site and can't be verified.
10/10 Excellent
Jerome G.
8 Aug, 2023
Good Choice
Jerome G.
Stayed 7 nights in Jul 2023
This review is from a guest who booked and stayed through a partner site and can't be verified.
10/10 Excellent
Ruth H.
25 Jul, 2023
Kayaking, exploring tidal pools, swimming , fishing and more
Ruth H.
10/10 Excellent
Karin B.
17 Oct, 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Private with wonderful views
Karin B.
Stayed 7 nights in Oct 2022
10/10 Excellent
Hector M.
21 Sept, 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Very nice place with a lovely view of Maine nature.
Hector M.
Stayed 3 nights in Sep 2022
10/10 Excellent
Kit B.
2 Aug, 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Amazing spot!
Kit B.
Stayed 7 nights in Jul 2022
10/10 Excellent
Riley M.
1 Jun, 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Lovely House in Harpswell
Riley M.
Stayed 3 nights in May 2022
10/10 Excellent
Nini T.
5 Apr, 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Do not hesitate to book this lovely property!
Nini T.
Stayed 3 nights in Apr 2022
About the host
Hosted by MaineStay Vacations
Languages:
English
Premier Host
They consistently provide great experiences for their guests
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