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Windward - Enjoy privacy, comfortable living spaces, and easy water access

Photo gallery for Windward - Enjoy privacy, comfortable living spaces, and easy water access

Outdoor dining
Outdoor dining
Property grounds
Beach
Living area

Reviews

9.8 out of 10
Exceptional
3 bedrooms2 bathroomsSleeps 61712 sq ft

Popular amenities

  • Ocean view
  • Kitchen
  • Washer
  • Dryer
  • Free WiFi
  • Outdoor Space

Explore the area

View in a map
Harpswell, ME
  • Place, Paddleworks
    ‪16 min drive‬
  • Place, Bowdoin College
    ‪18 min drive‬
  • Place, Maine Street
    ‪18 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 Twin 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
Our prices include all fees. No hidden fees.

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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
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Children

Children allowed: ages 0-17
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Events

No events allowed
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Pets

No pets allowed
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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
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher

About the neighborhood

Harpswell

Located in Harpswell, this vacation home is on the waterfront. Ash Cove Pottery and Paddleworks are local attractions and those in the mood for shopping can visit LL Bean Flagship Store and Maine Street. Orion Performing Arts Center and Land's End Gift Shop are also worth visiting. Spend some time exploring the area's activities, including fishing, birdwatching, and golfing.
View more Vacation Homes in HarpswellOpens in a new window
Map
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

  • Brunswick Station - 17 min drive
  • Wiscasset, ME (ISS) - 34 min drive

Restaurants

  • ‪Wild Oats - ‬17 min drive
  • ‪Cook's Lobster & Ale House - ‬18 min drive
  • ‪Sam's Italian Sandwich Shoppes - ‬17 min drive
  • ‪Iris Eats Maine - ‬13 min drive
  • ‪Anna's Water's Edge Restaurant - ‬48 min drive

Frequently asked questions

Is Windward - Enjoy privacy, comfortable living spaces, and easy water access pet-friendly?

No, pets are not allowed at this property.

How much does it cost to stay at Windward - Enjoy privacy, comfortable living spaces, and easy water access?

As of Apr 21, 2026, prices found for a 1-night stay for 2 adults at Windward - Enjoy privacy, comfortable living spaces, and easy water access on Jun 6, 2026 start from $660, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking?

Onsite parking is available at the property.

What time is check-in at Windward - Enjoy privacy, comfortable living spaces, and easy water access?

Check-in begins at 4:00 PM.

What time is check-out at Windward - Enjoy privacy, comfortable living spaces, and easy water access?

Check-out is at 10:00 AM.

Where is Windward - Enjoy privacy, comfortable living spaces, and easy water access located?

Situated on the waterfront, this vacation home is steps from Casco Bay, and within 6 mi (10 km) of Mitchell Field and Brunswick Town Commons. Ash Cove Pottery and Maine Street are also within 9 mi (15 km).

Reviews

9.8

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window
Rating 10 - Excellent. 20 out of 23 reviews
Rating 8 - Good. 2 out of 23 reviews
Rating 6 - Okay. 1 out of 23 reviews
Rating 4 - Poor. 0 out of 23 reviews
Rating 2 - Terrible. 0 out of 23 reviews

9.8/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

9.8/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Vicki R.

Liked: Cleanliness, check-in, communication, location, listing accuracy
A great place to spend time with family! Coincidentally, two family members stayed in this house a few years ago. They noticed some updates and were impressed.
Stayed 3 nights in Oct 2025
Verified

10/10 Excellent

Chris B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Truly lovely house in a fabulous location. We have been coming to Harpswell 2-4 times a year for a decade and this is by far the best place we have stayed. Roomy, beautifully decorated, private, and great views. Kitchen had everything needed to cook at home. Will be back!
Stayed 7 nights in Sep 2025
Verified

10/10 Excellent

Jenna L.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful quiet Maine getaway! Everything we could have wanted in the kitchen and throughout the house. The location is incredible, gorgeous views for the morning sunrise. My husband and I stayed with our parents and our 9 month old. Plenty of space, we were able to run some laundry, give my son a bath, and we all slept well. Close to restaurants, hiking, and we took a ride to Freeport and Brunswick. Highly recommend and would stay again!
Stayed 4 nights in Sep 2025
Verified

10/10 Excellent

Nina E.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Loved watching the birds on the water.

Very nice place. Everyone had a good time. Enjoyed the Dolphin Restaurant and exploring the whole area.
Stayed 3 nights in Jun 2024
Verified

10/10 Excellent

Lia T.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful Maine home

A perfect little getaway! Great views of the bays - driving distance to Bath and beyond. Hosts were great about connecting with us.
Stayed 3 nights in Jun 2023
Verified

8/10 Good

Stacey V.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Lovely short trip to Harpswell

We had a really lovely stay at this property. The communication with the property managers was great and the view was even. Enter than expected. We really enjoyed the little beach and rocky shoreline and had a great time watching the sun come up each morning. The neighborhood was quiet but felt close to lots of our favorite spots in Harpswell and Brunswick.
Stayed 5 nights in Jun 2023
Verified

8/10 Good

Monica G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

So Beautiful!

It is a beautiful spot to stay. The house is right on the water and it is very pretty. The house was very clean, there were most things that we needed there. There could’ve been a few extra utensils for cooking such as spatulas etc. Coffee was plentiful, which was a plus:) The towels were nice and fluffy. We loved staying at Windward and would stay again!
Stayed 6 nights in Sep 2024
Verified

6/10 Okay

Craig C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Winward

Older home. Not necessarily well appointed
Stayed 5 nights in Sep 2024
From a partner site

10/10 Excellent

pam b.

Wonderful!

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: My husband and I were looking for a spot to spend some relaxing time hanging with our two adult children. Windward was just perfect! There was plenty of space, gorgeous views and a lot of quiet seclusion! The whole area was breathtaking. We found fabulous restaurants in Brunswick, Harpswell and Bailey’s Island, with outstanding food. The house was very clean and had everything we needed and more. Breakfast out on the deck with that view and listening to the birds was heavenly. MaineStay Vacation was a great company to work with. I’m sure we’ll be back!
Verified

10/10 Excellent

Eric R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Quiet seclusion

Loved the location. We happened to be there just after the shooter incident and found Brunswick ‘shut down’. We still made the most of our getaway having brought large amounts of our own food to enjoy. The property owners emailed and texted me offering us the opportunity to cancel given the situation and had great communication throughout. The ladies in our group did feel a bit uncomfortable in that the none of large glass sliding doors had curtains that could be closed making them feel a bit exposed at night like living in a fish bowl. We also came prepared to walk on the rocky ‘private’ beach. Nope. It’s a mud flat with deep mud and no access. Having said that, we really enjoyed watching the huge tidal movement each day and marveled at the change in the water view. Sunrises were spectacular and we blew up our cell phones with pics.
Stayed 3 nights in Oct 2023
From a partner site

10/10 Excellent

Wonderful August Week at Windward

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We had 4-5 days of beautiful warm days, then one impressive thunderstorm! We brought our own kayaks and spent most days paddling right from the bottom of the stairs. The house was well-equipped and the bountiful outside comfortable chairs are a great place to relax after paddling or sight-seeing down the rest of the peninsula. We caught "Beautiful" the Carole King musical at the Maine State theater. Very enjoyable spot. There were just two of us, the house could easily accommodate at least 6. We hope to return!
Stayed 7 nights in Aug 2024
From a partner site

10/10 Excellent

Ward F.

Last week in August

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Lovely indoor and outdoor space, well maintained and comfortable. Kitchen well equipped, beds comfortable, linen service was well worth it. Location requires a car to get around the otherwise residential neighborhood, but lots of local hiking trails and lobster purveyors nearby. The water view is filtered. The single discrepancy with the listing is that the "private pocket beach" is only a few feet wide at high tide, and at low tide is a large mud flat. However the grandkids spent hours collecting things, so it served well. The management responded immediately when the hot water system failed, and fixed it the same evening, a complex repair that needed a professional.
Stayed 5 nights in Aug 2024
From a partner site

10/10 Excellent

Susan M.

Lovely quiet location with a beautiful water view from each room

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Perfect for our daughter and her family on top floor and us grandparents on the first floor. Clean and spacious. We went for an endless walk on the quiet road each morning, kayaked on the water and ate outdoors each night on the picnic table without being bothered by bugs in Maine. Will certainly come here again!!
From a partner site

10/10 Excellent

A guest from Newburyport, MA

Great getaway near Casco Bay

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Great open, airy home on the bank of Harpswell Sound, with great views. House was available earlier than expected and was very clean upon arrival. Household staples were available, beds comfortable, etc. The neighborhood was quiet and peaceful. Watching the waterscape and the wildlife was never boring. House was close to Brunswick, Freeport, Bath, Popham Beach and all Mid-Coast attractions.Harpswell is a beautiful town, with nature preserves and villages that remind one of a past era of seaside life.
From a partner site

10/10 Excellent

A guest from Atlanta, GA

Windward: A great rental.

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Windward met our highest expectations
From a partner site

10/10 Excellent

Nancy C.

A relax right on the water.

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Lovely week on the ocean!”
Stayed 7 nights in Jul 2023
From a partner site

10/10 Excellent

Jerome G.

Good Choice

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Great location on the water with views to watch the tide roll in and out everyday. Property was large with no views of neighbors or road. House was equipped sufficiently for us, we did not cooking. Coffee pot, refrigerator, and basic dished were all we needed. 6 comfortable chairs outside.The property was clean inside and out. Refrigerator leaked from the evaporator some, but a hand towel took care of it. Only other issue was the MBR closet door was off the rails. These two items did not affect our stay. Everything else in the house was well maintained, washer and dryer worked fine and plenty of hot water. I would recommend the property to anyone else.
Stayed 7 nights in Jul 2023
From a partner site

10/10 Excellent

Ruth H.

Kayaking, exploring tidal pools, swimming , fishing and more

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Great week. Lots of indoor and outdoor family fun. What could be better than playing a game of monopoly indoors than walking down the well maintained steps to wade and skip stones.
Verified

10/10 Excellent

Karin B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Private with wonderful views

Fabulous property...beautiful views, very private yet short drive to shopping and hiking. Home was well equiped with everything needed for a very easy, enjoyable stay.
Stayed 7 nights in Oct 2022
Verified

10/10 Excellent

Hector M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Very nice place with a lovely view of Maine nature.

We had a very pleasant and peaceful stay at the house. Clean, well organized, with a very spacious kitchen, dining, and living room. The outside porch and grill space were also really just wonderful.
Stayed 3 nights in Sep 2022
Verified

10/10 Excellent

Kit B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing spot!

Our family had the best week at Windward! The house had everything you needed and the view and waterfront access was a highlight! Would definitely come back!
Stayed 7 nights in Jul 2022
Verified

10/10 Excellent

Riley M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Lovely House in Harpswell

This property is exactly as advertised. We couldn't have been happier with everything and would recommend this property to anyone. Just beautiful!!
Stayed 3 nights in May 2022
Verified

10/10 Excellent

Nini T.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Do not hesitate to book this lovely property!

The house itself is beautiful, spacious, and clean. The floor to ceiling windows provide a stunning view of the water and the shore which are just steps away. The kitchen is thoughtfully stocked with many convenient essentials. My two kids, who are 4 and 6 years old, had a great time here!
Stayed 3 nights in Apr 2022

About the host

Hosted by MaineStay Vacations

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