Row Wrapper 2

Windward

4.4545
(33 Reviews)

Capacity

3 Bedrooms
2 Bath
Sleeps 6

Search Availability

About

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

Sleeping Arrangements

Primary Bedroom (2nd Floor, Water View, Balcony)
1 queen bed
Second Bedroom (2nd Floor)
1 single bed, 1 single bed
Third Bedroom (1st Floor, Water View, Porch)
1 queen bed

Features

Amenities

  • Heating
  • Enhanced cleaning practices
  • Clean with disinfectant
  • No-contact check-in and check-out
  • High touch surfaces cleaned with disinfectant
  • Full Kitchen
  • Refrigerator
  • Microwave
  • Toaster
  • Cookware
  • Washer & Dryer
  • Ironing Board
  • High Speed Internet
  • Balcony
  • Gas Grill
  • Stairs to Water
  • Cable TV

Location

  • Harpswell

Pets

  • Pets Prohibited

View

  • Deck
  • Waterfront

Availability

Key
#Night Available#Night Unavailable#Arrive Only#Depart Only
December 2024
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Map

Reviews

Leave a Review

Last week in August

August 2024
, mill valley, CA US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

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.

Wonderful August Week at Windward

August 2024
, JAMAICA PLAIN, MA US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

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!

Lovely quiet location with a beautiful water view from each room

July 2024
, Pelham, MA United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

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!!

Great getaway near Casco Bay

July 2024
, Newburyport, MA United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

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.

Seclusion

October 2023
, Keller, TX US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Secluded and quiet like we wanted. Being from out of state we didn’t know we’d have no shoreline to walk on but were treated every day to an incredible tidal swing. The sunrises and sunsets were all photo worthy and the home’s relative location to Brunswick made for shopping plans. Unfortunately we arrived a day or two after the shooter incident and spent most of our time dining either by food truck or on the things we brought with us. Portland was up and running so we did make our way there to enjoy some great food as everything up towards Brunswick shut down. Management did reach out to us and offered to cancel at no penalty and I thought their communication was exceptional. We made the perfect weather and our own extensive food supplies work for a memorable getaway

Windward: A great rental.

August 2023
, Atlanta, GA United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Windward met our highest expectations

Good Choice

July 2023
, Irving, TX US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

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.

A relax right on the water.

July 2023
, South burlington, VT US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Lovely week on the ocean!”

Wonderful!

July 2023
, Newburyport , MA United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

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!

Kayaking, exploring tidal pools, swimming , fishing and more

July 2023
, United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

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.

Kayaking, exploring tidal pools, swimming , fishing and more

July 2023
, Williamstown , MA United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

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.

Great stay

June 2023
, Woodbury, CT US

Overall
5
Services from rental manager
5
Cleanliness
4
Location
5
Property condition
4

We had a wonderful time at this property. The views are even better than expected and the small beach was fun to explore. The house is simple but clean and had everything we needed. The MaineStay management team had were easy to communicate with and check in was simple. We stay in Harpswell every year and this neighborhood was a great place to relax. Bonus: the sunrises from the porches in the morning were amazing!

Peaceful Maine getaway

August 2022
, de pere, WI United States

Overall
5
Services from rental manager
4
Cleanliness
5
Location
5
Property condition
5

This is a VERY clean house in Harpswell. Despite rare heat in Maine 95 degrees in August, there were fans in the rooms and lots of windows to cool the house off. The house was as described. A few of the trees/scrubs lined the driveway could be trimmed back for easier driving and not hitting your vehicle when coming & going from the property. The location is very peaceful and relaxing. It is at least a 10-15 minutes drive to any food, gas or stores you might need. There are quite a few nice restaurants with in 20 minutes of the house. We would recommend this property to others.

Great location, needs supplies

June 2022
, Falls Church, VA United States

Overall
4
Services from rental manager
5
Cleanliness
4
Location
4
Property condition
3

Had a super 2-week stay at this home. It's roomy and airy with great light and a super yard for games and fun. The road is quiet and lovely for bike rides. Mainestay, as always, is a responsive and wonderful agency to work with!

All rentals have different supplies and small issues, and I wanted to make a few notes here for future guests (which hopefully will include us).

Some outside wear issues that we noted to Mainestay upon leaving in hopes the owner will make changes/repairs for the future (warped boards, outside furniture wear, dishwasher issues (that are noted in other reviews).

Note: There is no vacuum, and when you're staying in a spot with a beach + kids, the house can get dirty fast and a broom/dustpan doesn't really cut it. Again, it's a GREAT location, but the beach is more muddy than sandy. We used the outside hose a lot!

The kitchen is very lightly equipped; we bought and left several items for future guests like Tupperware and grill lighters; a serving platter or large dishes would have been great to have (and if you're going to host a large dinner, make a note it may be good to request your guests to bring).

Great location, needs supplies

June 2022
, Falls Church, VA United States

Overall
4
Services from rental manager
5
Cleanliness
4
Location
4
Property condition
3

Had a super 2-week stay at this home. It's roomy and airy with great light and a super yard for games and fun. The road is quiet and lovely for bike rides. Mainestay, as always, is a responsive and wonderful agency to work with!

All rentals have different supplies and small issues, and I wanted to make a few notes here for future guests (which hopefully will include us).

Some outside wear issues that we noted to Mainestay upon leaving in hopes the owner will make changes/repairs for the future (warped boards, outside furniture wear, dishwasher issues (that are noted in other reviews).

Note: There is no vacuum, and when you're staying in a spot with a beach + kids, the house can get dirty fast and a broom/dustpan doesn't really cut it. Again, it's a GREAT location, but the beach is more muddy than sandy. We used the outside hose a lot!

The kitchen is very lightly equipped; we bought and left several items for future guests like Tupperware and grill lighters; a serving platter or large dishes would have been great to have (and if you're going to host a large dinner, make a note it may be good to request your guests to bring).

Lovely House in Harpswell

May 2022

Overall
5

This property is exactly as advertised. We couldn't have been happier with everything and would recommend this property to anyone. Just beautiful!!

Lovely Girls Weekend

May 2022
, Cambridge, MA United States

Overall
4
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Loved the property. Plenty of room for 4 adult ladies. Location was perfect to watch the tide, birds, boats. Kitchen stocked. Only con was the dishwasher was not bolted down which made it difficult to load or unload. Otherwise great place.

Do not hesitate to book this lovely property!

April 2022

Overall
5

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!

The Windward home th

June 2018

Overall
5

The Windward home that we rented through MaineStay turned out to be the perfect place for our family vacation along the shores of the Gulf of Maine. We would definitely recommend this home to anyone looking for a place to watch beautiful sunrises and lobster catching or walking out on the rock shore at low tide. The home was well equipped with all of the essentials we needed and we enjoyed the cool Maine ocean breeze through the many screened windows and sliding doors. Great hiking trails are close by this home and sailing, kayaking, great seafood restaurants, shopping and country stores are also just a short drive away. We're so glad we decided to stay here instead of Portland due to the privacy of the home and availability of activities we were interested in doing on our vacation.

Windward is a lovely

July 2019

Overall
-1

Windward is a lovely cottage in a perfect setting. We kayaked, fished and searched for sea treasures everyday.

Windward is a beauti

September 2019

Overall
5

Windward is a beautiful, modern open plan home with incredible views of the water. The kitchen is really well designed and the outdoor decks were wonderful. Windward is great for families as there is a master bedroom on the first floor and two bedrooms and a full bath on the second floor. Very nice place to stay while visiting with our son, who is a student at Bowdoin!

Wonderful cottage an

May 2020

Overall
5

Wonderful cottage and setting for a family vacation.

Our family had a won

April 2021

Overall
5

Our family had a wonderful stay here. The location is spectacular and the house has plenty of space and a great layout. It's also convenient to many Harpswell highlights and trails to explore. We look forward to returning some day!

March 2018

Overall
4

March 2019

Overall
4

A lovely home that f

May 2019

Overall
4

A lovely home that feels comfortable and inviting. Great views. A nice area to walk--the road is quiet and pretty scenery along the way. Mainstay makes renting easy and has a nice website that offers lots of pictures and details.

July 2020

Overall
4

August 2020

Overall
4

While we found sever

May 2021

Overall
4

While we found several faults: -The dishwasher is not anchored. -There is no cheese grater. -Most interior doors do not close easily if at all. -Some of the exterior sliding doors are nearly impossible to move. We would definitely stay there again even if none of those were ever fixed. It's in a beautiful, quiet location and the amenities were adequate if not plentiful.

March 2021

Overall
4

March 2021

Overall
3

This house has a nic

March 2021

Overall
3

This house has a nice layout for a family and provides privacy and a peaceful ocean view. The road it is on is quiet, and there are many things to do in the area.

June 2020

Overall
1

February 2019

Overall
5