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

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Property grounds
Interior
Beach
Interior
Fridge, microwave, oven, stovetop

Reviews

9.8 out of 10
Exceptional

Entire home

3 bedrooms2 bathroomsSleeps 6159 sq m

Popular amenities

  • Dryer
  • Washer
  • Barbecue grill
  • Kitchen
  • Parking available
  • Outdoor space

Explore the area

View in a map
Harpswell, Maine
  • Place, Bailey Island Bridge
    ‪19 min drive‬
  • Place, Bowdoin College
    ‪20 min drive‬
  • Place, LL Bean Flagship Store
    ‪33 min drive‬
  • Airport, Portland, ME (PWM-Portland Intl. Jetport)
    ‪57 min drive‬

Room options

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About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

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
During your stay at this vacation home, you're just a quick walk from Casco Bay. Features include laundry facilities. Enjoy your stay with amenities like free WiFi and a kitchen in the vacation home.
  • The vacation home offers a kitchen, a washing machine, and 2 bathrooms
  • Free WiFi
  • Amenities include laundry facilities
  • Steps from Casco Bay and 10 minutes by car from Mitchell Field
As a guest of this vacation home, you'll find barbecue grills, a garden, and laundry facilities. The front desk is open around the clock.

Property amenities

Internet

  • Available in the house: Free WiFi

Parking and transport

  • Onsite parking options include a garage

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Hob
  • Kitchen island
  • Microwave
  • Oven
  • Refrigerator
  • Toaster

Dining

  • Dining table

Bedrooms

  • 3 bedrooms
  • Bedsheets provided

Bathroom

  • 2 bathrooms
  • Bathtub or shower
  • Hair dryer
  • Shower
  • Towels provided

Living spaces

  • Dining table
  • Living room

Entertainment

  • TV with cable/satellite channels

Outdoor areas

  • Balcony
  • Barbecue grill
  • Garden

Laundry

  • Laundry facilities
  • Washing machine

Work spaces

  • Desk

Comfort

  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoke-free property

Services and conveniences

  • Iron/ironing board

Location highlights

  • Near a hospital
  • Near an outlet shopping centre
  • Near the ocean
  • On the waterfront

Things to do

  • Golf
  • Birdwatching nearby
  • Fishing nearby
  • Golfing nearby

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • Fire extinguisher

General

  • Garden
  • Unit size: 1,712 square feet

Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in available
Minimum check-in age: 25

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions

Pets

  • No pets allowed

Children and extra beds

  • Children are welcome.

Events

No events allowed

Smoking

Smoking is not permitted

Important information

You need to know

This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession.
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
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
You will receive an email from the host with check-in and check-out instructions. You will also receive an email from Vrbo with a link to a Vrbo account which will enable you to manage your booking.
If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with EU regulations about consumer rights, property booking services are not subject to the right of withdrawal.

Property is also known as

2769-214543

Reviews

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

9.8

Exceptional

9.8/10

Cleanliness
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

Reviews

10/10 Excellent

Vicki R.

Liked: Cleanliness
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

10/10 Excellent

Jenna L., New York

Liked: Cleanliness
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

10/10 Excellent

Chris B.

Liked: Cleanliness
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

6/10 Okay

Craig C.

Liked: Cleanliness

Winward

Older home. Not necessarily well appointed
Stayed 5 nights in Sep 2024

8/10 Good

Monica G.

Liked: Cleanliness

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

10/10 Excellent

Nina E.

Liked: Cleanliness

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

10/10 Excellent

Eric R.

Liked: Cleanliness

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

10/10 Excellent

Lia T., Dallas, TX

Liked: Cleanliness

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

8/10 Good

Stacey V., Woodbury, CT

Liked: Cleanliness

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

10/10 Excellent

Karin B.

Liked: Cleanliness

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

10/10 Excellent

Hector M.

Liked: Cleanliness

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

10/10 Excellent

Kit B.

Liked: Cleanliness

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

10/10 Excellent

Riley M.

Liked: Cleanliness

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

10/10 Excellent

Nini T.

Liked: Cleanliness

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