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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

A spacious room with a large sliding glass door leading to a deck overlooking a lake and forest.
A spacious living room with a large TV, comfortable seating, and a view of the outdoors.
A spacious dining area with a large wooden table, black chairs, and a decorative bowl in the center. A large wooden clock and a modern pendant light are visible on the walls.
A living room with a sofa, coffee table, and TV. There are large windows with a view of trees and a body of water.
A wooden deck with a staircase leading to a viewing platform overlooking a lake.

Reviews

9.8 out of 10
Exceptional

Highlights

  • Garage parking available
    Enjoy the convenience of garage parking - a rare offering in the area.
  • Discover nearby landmarks
    Near Casco Bay

Popular amenities

  • Balcony
  • Barbecue grill
  • Refrigerator
  • Garage parking available
  • Internet
  • Washer

Explore the area

View in a map
Harpswell, ME
  • Place, Casco Bay
    ‪1 min walk‬
  • Place, LL Bean Flagship Store
    ‪33 min drive‬
  • Place, Maine Mall
    ‪54 min drive‬
  • Airport, Portland, ME (PWM-Portland Intl. Jetport)
    ‪55 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

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About the neighborhood

Harpswell

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

What's nearby

  • Casco Bay - 1 min walk - 0.0 km
  • Bowdoin College - 17 min drive - 17.6 km
  • LL Bean Flagship Store - 33 min drive - 39.8 km
  • State Theatre - 51 min drive - 72.3 km
  • Maine Mall - 54 min drive - 80.3 km

Getting around

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

Restaurants

  • ‪Wild Oats - ‬17 min drive
  • ‪Ledges Pub at Sebasco - ‬46 min drive
  • ‪Sam's Italian Sandwich Shoppes - ‬17 min drive
  • ‪Anna's Water's Edge Restaurant - ‬48 min drive
  • ‪Cook's Lobster & Ale House - ‬18 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 Oct 23, 2026, prices found for a 1-night stay for 2 adults at Windward - Enjoy privacy, comfortable living spaces, and easy water access on Oct 25, 2026 start from $548, 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. 25 out of 28 reviews
Rating 8 - Good. 2 out of 28 reviews
Rating 6 - Okay. 1 out of 28 reviews
Rating 4 - Poor. 0 out of 28 reviews
Rating 2 - Terrible. 0 out of 28 reviews

9.8/10

Cleanliness

10/10

Check-in

10/10

Communication

9.8/10

Location

9.8/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Very pleasant inside and out with quiet and privacy. Staff at Maine Stay were very prompt and helpful.
Stayed 10 nights in Sep 2026
From a partner site

10/10 Excellent

Beautiful spot

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was more than satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We enjoyed our week at Windward. Our only complaint was that the time went too fast.
From a partner site

10/10 Excellent

Windward - a secluded gem in Harpswell

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: Four adult members of our family gathered for a perfect reunion - nestled in the privacy of a wooded, water's edge site on the Harpswell inlet near Brunswick Maine. The contemporary 2 story house has large windows with water or woods views in 3 directions. A large deck on the ground level is supplemented by private decks off the main bedrooms. The kitchen is generously equipped for every need; plenty of dining seating; comfortable lounging areas. Bedrooms and bathrooms on both levels are generously sized, with roomy closets, fresh linens and bagged bath towels. The house was immaculately clean upon arrival. The location is within a short drive of eating out and grocery options; and nearby Brunswick offers most anything else one would want. The hosts were very cordial and helpful all along, and we can't wait to come back next year!
Verified review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

8/10 Good

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 review

8/10 Good

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 review

6/10 Okay

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

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 review

10/10 Excellent

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
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
A very nice private space with beautiful views of the water, large deck & patio with multiple seating options, open living / dining area, good kitchen. We would happily stay again.
Stayed 3 nights in Jun 2026
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

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

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

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

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

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

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

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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
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