Clean Waterfront Classic Cottage with Private Beach

Gloucester, Massachusetts
$464 avg/night Minimum Stay 4 Nights
Bed 4

Bed

Bath 1

Bath

Home Private Vacation Home

Property Type

Sleep 7

Max Sleeps

Night 4 nights

Min Stay

Location x3! This classic, cozy, waterfront cottage that sits on a private beach overlooking the Annisquam River in Gloucester, MA (45 min drive north of Boston). Nine foot tides provide for a dynamic scenery and activities with a back drop of marshes, Wingaersheek beach, and the quaint seaside village of Annisquam. At low tide, the beach is immediately accessible via a staircase and walkway. At high tide, water rises all the way under the house. All this can be experienced on a full wrap-around deck with a screened in porch and ample seating for dining, sunbathing, and lounging.

The home itself is a former duck hunting cottage sitting waterside atop stilts. The interior has a vintage feel with wood, bright colors, and ample natural light throughout. Provided are all the necessities for your perfect New England vacation - beach chairs, beach towels, and more. High tide water reaches under the deck with a parade of boats, beaches, and crystal clear blue water in full view. Beach, fish, swim, float, unwind, and have fun!

Our family has rented our home to countless families, couples, and travelers for many summer seasons. Here is what past guests have had to say:

This seaside cottage is pure magic. It is everything it appears to be in the photos, is super comfortable, and with an amazing location right on the water where boats pass and birds fish and the air is fresh. We had a memorable happy time here with our young boys and their grandparents. Totally hope to come back, and definitely recommend to people seeking quiet comfort by the seashore. - Stephanie

“Jean’s place is awesome! The location/view is incredible. Sitting on the porch, sipping coffee in the mornings and wine in the evening was so relaxing. Was able to go kayaking in the Harbor out front. The house is adorable and perfectly furnished. You won't be disappointed! Thanks Jean.” - Mike

Our family loved our stay at Jean’s place. The home is unique, charming and everything you’d expect from the photos. The views from the porch are tranquil and will consume your whole day! Jean was a fabulous host and very much made us feel at home. Gloucester is a great little town... make sure you also get to Rockport! 5 out of 5 and would recommend it for couples and families! - Bill

Seasonally, the peak summer months are July and August when the sun is out and the weather trends around 80. June and September often are equally as beautiful but have a higher chance of colder/rainy weather. May and October can be on the cooler side, but are when the house is most cozy with the heat and fire place on.

Children are welcome, but must be vigilantly watched at all times due to the house’s waterfront location. Pets are family too and are welcome for an additional $100 fee (for cleaning service), provided they are well trained and are good with other dogs as there are many in the neighborhood. Coming by boat We can accommodate vessels up to 15 feet on our half tide mooring or otherwise refer you to a mooring with the local yacht club.

For activities, Cape Ann is a top summer destination with a variety of dining, outdoors, and sightseeing options. The closest major beaches are Wingaersheek and Good Harbor. We are also happy to recommend to you our favorite spots around town.

THIS HOUSE IS NOT FOR EVERYONE. Please note the following if you are going to book:

- This is an old house without creature comforts (no AC, dishwasher, laundry, only one bathroom).
- It is - As with being near a beach/marsh in any New England town, there are greenhead flies and midges/gnats outdoors
- It can get hot in the summer. With an ocean breeze it tends to be ~10 degrees cooler than the mainland. There are tons of windows and fans for circulation. The ocean is steps away for a nice dip. But if you can't sleep with all the windows open or without AC, please do not book with us.

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  • Feature Features
  • Map Map
  • School District Rates & Availability
  • Review Review

Feature Features

  • PETS

    Pet Friendly
  • BEACH

    Beach Sun Loungers Beach Towels On The Beach
  • DINING

    Dining Table
  • SAFETY

    Carbon Monoxide Detector Installed (host Has Indicated There Is A Carbon Monoxide Detector On The Property) Fire Extinguisher First Aid Kit Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    4 Bedrooms Bed Sheets Provided
  • GENERAL

    Property Does Not Allow Children
  • KITCHEN

    Cookware/dishes/utensils Dishwasher Electric Kettle Microwave Oven Paper Towels Refrigerator Spices Stovetop
  • LAUNDRY

    Laundry Facilities Near Coin Laundry
  • PARKING

    Onsite Parking
  • INTERNET

    Free WiFi
  • OUTDOORS

    Barbecue Grill Garden Outdoor Furniture Patio
  • BATHROOMS

    1 Bathroom Hair Dryer Shampoo Shower Soap Toilet Paper Towels Provided
  • WORKSPACES

    Computer Monitor Desk Desk Chair Office
  • THINGS TO DO

    Power Boating Nearby Whale Watching Nearby Wildlife And Game Walks Nearby
  • ENTERTAINMENT

    Books Games Stereo Smart TV
  • LIVING SPACES

    Fireplace Living Room
  • CLIMATE CONTROL

    Air Conditioning Heating
  • LOCATION HIGHLIGHTS

    Near A Health Or Beauty Spa Near Outlet Shopping Near The Ocean Near The Sea On The Waterfront
  • SERVICES AND CONVENIENCES

    Safe
  • SUITABILITY/ACCESSIBILITY

    Smoke-free Property

CheckIn Check-in : 04:00 PM CheckOut Check-out : 10:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 7

Map Map

School District Rates & Availability

Review Review

  • W Bradford C.

    Submitted Sep 16, 2025

    Stayed Sep 2, 2025

    We arrived at the cottage as the sun was setting and found the scene from the front porch to be beautiful and peaceful. The cottage is very well and accurately described in its VRBO listing. This is a comfortably furnished quaint but small space, not for everyone, but if your vacation objective includes decompressing and simply chilling-out for extended periods of time we would highly recommend it. Following our first full day of witnessing the dramatic tidal change, the point of our 10-day trip quickly became not to leave this little point of land on the Annisquam River. To that end deliveries from Whole Foods, Sebastian’s pizza, take out from Lobsta Land and steamed lobsters from Market Basket helped us achieve our objective. A day trip to Rockport, a great whale watching venture and long walks on nearby Wingaersheek Beach accounted for our departures from the cottage. Jean and Austen were excellent hosts who made us feel most welcome and were always available to answer any questions.

  • Jennifer M.

    Submitted Aug 24, 2025

    Stayed Aug 17, 2025

    It was fabulous waking up each morning to the gentle sounds of waves! Location was great with easy access to other day trip events.

  • Sarah W.

    Submitted Aug 17, 2025

    Stayed Aug 10, 2025

    Fourth times a charm! Perfect location, charming house and ideal week. So appreciate the quick communication and comfort of this place. Booked already for next year

  • Kate M.

    Submitted Jul 22, 2025

    Stayed Jul 12, 2025

    Picture perfect vacation spot! Plenty to see and do without ever leaving the property! The host was great about checking in to be sure that all was well and house was complete with everything we needed. We would definitely love to return to this beautiful location.

  • SHEY M.

    Submitted Jun 15, 2024

    Stayed Jun 7, 2024

    We loved it and will be back❣️ wonderful location, friendly people, an overall great vacation. .

  • Sarah W.

    Submitted Aug 23, 2023

    Stayed Aug 16, 2023

    Third visit and can’t get enough of this sweet house! The view is the best on Cape Ann. Cozy, charming location. Woke up everyday to paddling and gazing at the sea! Great hosts! Excellent communication! See you next year!

  • Matt D.

    Submitted Aug 16, 2023

    Stayed Aug 12, 2023

    We had a great short visit. The property is right on a private black sand beach, with ample opportunity to swim or use kayaks, paddle board, and more. My kids loved finding hermit crabs and playing with the incoming tide. The screened porch is a great spot to watch the boat traffic, especially at sunset with a beverage of choice. It is easy to get to shopping, restaurants, and attractions. Gloucester has it all. One note - and it is called out in the listing - is this is a tiny home with one toilet and shower, with some steep stairs to the property entrance as well as to the second floor. Those with mobility challenges will find this property inaccessible. Think more on the rustic side. That said, we were comfortable and enjoyed ourselves.

  • carol k.

    Submitted Jun 20, 2023

    Stayed Jun 3, 2023

    It happened to be cold and rainy to start for our second stay here but wonderful nonetheless. Warm and toasty with the wood stove going and enjoying the priceless view. Right on the water you can’t help but feel you’re on vacation. The home is charming with everything you might need to prepare meals. We preferred to stay in, bringing in take out a couple of nights. The water is so calming and magical.

  • Sarah W.

    Submitted Aug 24, 2022

    Stayed Aug 17, 2022

    Love this place! Super charming! Cozy! Best location! Already booked for our third year in 2023! Communication with owners timely and easy. Went out to dinner once and my hub and I decided that there’s really no need to ever leave that screened in porch. The view and comfort of the house is the best on Cape Ann! Paddling and kayaking is perfect- just a short paddle to my fav beach in New England. Thanks Jean and Austen!

  • Lynne P.

    Submitted Aug 22, 2022

    Stayed Aug 8, 2022

    You can’t get any closer to the water! At high tide, I could be sitting in the screened-in porch and carry on a conversation with my kids swimming in the water. Loved the vintage feel of the cottage! We enjoyed every moment of our time, the sunset views filled the sky, and can’t wait to return next year.

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Total

Includes taxes and fees
$464+
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