Cape Ann, Annisquam panoramic ocean views from every room.

Gloucester, Massachusetts
$638 avg/night Minimum Stay 7 Nights
Bed 4

Bed

Bath 2

Bath

Home Private Vacation Home

Property Type

Sleep 11

Max Sleeps

Night 7 nights

Min Stay

This charming shingled house, built in 1917 and respectfully renovated in recent years, sits atop a rocky hill overlooking picturesque Diamond Cove, in Annisquam. The house has postcard seascape views of Ipswich Bay from both porches and from every room in the house. Guests enjoy beach privileges and swimming in Diamond Cove (short walk from the porch) and at nearby Squam Rock Beach, a 10 minute walk down quiet residential streets. Annisquam Village center is within walking and biking distance.

Please note: this house may not be appropriate for folks with mobility issues or difficulty with stairs, as a walk from the parking area up a gentle, rustic hill and porch stairs is required; both bathrooms and bedrooms are on the second floor. The breathtaking scenery makes it worthwhile.

Outdoor parking for 5 vehicles is provided.
The rental week is Saturday-to-Saturday only - no exceptions!
Rental is for private residential, noncommercial use only.
Rental is for private residential, noncommercial use only.
We never entertain offers for less than our posted rates.

Our cancellation terms are provided below:
In the event that the Renter cancels the reservation for any reason, a $100.00 cancellation fee will be charged. If the cancellation occurs at least sixty (60) days prior to the Check-In Date and the Owner is unable to re-rent the Rental Property by the Renter's Check-In Date, the Renter will be liable for fifty (50%) percent of the Rent. If the cancellation occurs less than sixty (60) days of the Check-In Date, all monies paid by Renter will be forfeited if the Rental Property is not re-rented by the Check-In Date.
Owner will make all reasonable efforts to re-rent the Rental Property by the Check-In Date. If the property is re-rented at a rate less than the Rent, any refund amounts will be reduced by the Rent, less the amount for which the Rental Property is re-rented. In all cases, the $100 cancellation fee will be charged.

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

Feature Features

  • PETS

    Pet Friendly
  • BEACH

    Beach Towels Near The Beach
  • DINING

    Dining Table
  • SAFETY

    Carbon Monoxide Detector Not Reported (host Has Not Indicated Whether There Is A Carbon Monoxide Detector On The Property; Consider Bringing A Portable Detector) Smoke Detector Not Reported (host Has Not Indicated Whether There Is A Smoke Detector On The Property)
  • BEDROOM

    4 Bedrooms Bed Sheets Provided Sofa Bed
  • GENERAL

    Unit Size: 1700 Sq Ft (158 Sq M)
  • KITCHEN

    Dishwasher Electric Kettle Kitchen Island Microwave Oven Paper Towels Refrigerator Stovetop Toaster
  • LAUNDRY

    Laundry Facilities Washing Machine And Dryer
  • PARKING

    Car Recommended Limited Onsite Parking (max 5 Spaces) Onsite Parking
  • INTERNET

    WiFi Available
  • OUTDOORS

    Barbecue Grill Garden Patio
  • POOL/SPA

    Hot Tub
  • BATHROOMS

    2 Bathrooms Bathtub Or Shower Hair Dryer Jetted Bathtub Soap Toilet Paper Towels Provided
  • WORKSPACES

    Printer
  • LANGS SPOKEN

    English
  • THINGS TO DO

    Birdwatching Nearby Fishing Nearby Horse Riding Nearby Marina Nearby Mountain Biking Nearby Sailing Nearby Snorkeling Nearby Swimming Nearby Whale Watching Nearby
  • ENTERTAINMENT

    Books DVD Player TV With Cable/satellite Service
  • LIVING SPACES

    Dining Room Fireplace Living Room
  • CLIMATE CONTROL

    Air Conditioning Heating
  • LOCATION HIGHLIGHTS

    In A Village Near A Hospital Near Outlet Shopping Near The Bay Near The Sea
  • SERVICES AND CONVENIENCES

    Iron/ironing Board Phone
  • SUITABILITY/ACCESSIBILITY

    Note From Host: No Smoking In The House Or On The Property. Smoke-free Property

CheckIn Check-in : 04:00 PM CheckOut Check-out : 09:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 11

Map Map

School District Rates & Availability

Review Review

  • Pamela E.

    Submitted Aug 3, 2025

    Stayed Jul 26, 2025

    Great location, view and wonderful old beachhouse. the climb up was brutal - I definitely got my steps in!! It would have been nice if the house was less cluttered. So many trinkets and Knick knacks made it a bit claustrophobic. The kitchen woujd be so lovely if you cleaned it out and put back 1/4 of the stuff. Master bedroom was amazing! I gave our stay three stars because it was very dirty. The kitchen sink drains were slimy and disgusting and we arrived to a large bouquet of almost dead flowers. I’m highly allergic to flowers as is one of the other guests. It made for an uncomfortable couple of days until the pollen dissipated. I encourage you to perhaps pay closer attention to the job your cleaner is doing. It’s a lovely old home but does need some love and attention.

  • Toni C.

    Submitted Aug 2, 2024

    Stayed Jul 20, 2024

    What a beautiful setting for an enjoyable holiday with family. The house had everything and more than we ever needed for our stay. The views were breathtaking. The little private beach, only a 10-minute walk away was so enjoyable. I love Good Harbor, but why would I go there when this beach was so close and so private? We loved our stay!

  • Polly C.

    Submitted Apr 22, 2024

    Stayed Apr 13, 2024

    A rustic and charming cottage, high on the rocks with beautiful views. Cottage was clean. Beds were comfortable. Kitchen totally adequate. Location was perfect! Walkable neighborhood for grandkids and dog. Hodgkin's Cove Beach/Davis Neck & Lighthouse Beach were enjoyed. Breakfast deck for the sunrise and Porch for the sunset were amazing! The walk up the hill to the cottage was exercise indeed, but so worth the view when you got there. Be ready for some wind off of the ocean! Communication with the hosts was delightful. Thank you to John, Cally & Family for opening up your Diamond by the Sea. We hope to return!

  • Susan B.

    Submitted Jul 15, 2023

    Stayed Jul 8, 2023

    A comfortable, roomy house with a spectacular view of the bay! We are return renters and feel lucky to be in such a friendly, quiet community close to so many fine restaurants and such superb entertainment, like Rockport Music Shalin Liu Performance Center. This house is a true gem.

  • Peter L.

    Submitted Sep 14, 2022

    Stayed Aug 13, 2022

    Five Diamond lived up to its billing. Great cottage on an incredible site. Will be back next year.

  • Susan B.

    Submitted Jul 23, 2022

    Stayed Jul 16, 2022

    A wonderful, casual, sprawling beachfront house in Annisquam with extraordinary breezes and views. While the kitchen is sub-par and needs a through cleaning, the location and roominess more than compensate. We will return!

  • Damon P.

    Submitted Jun 5, 2022

    Stayed May 28, 2022

    Great place in a quiet, scenic neighborhood. Loved the decks - very relaxing! Its an old house for sure, but with tons of character, and has all the amenities you would want. We loved how it was decorated. Definitely recommend.

  • Tonya E.

    Submitted Oct 16, 2021

    Stayed Oct 9, 2021

    Wonderful place for our family to gather! Beautiful views and walking distance to the ocean!!

  • Reeah D.

    Submitted Sep 20, 2021

    Stayed Sep 4, 2021

    The home and the location are beautiful. We enjoyed our stay immensely.

  • James H.

    Submitted Sep 18, 2021

    Stayed Sep 11, 2021

    Great views once you are able to climb the mountain from your car

Your dates are Available!

Total

Includes taxes and fees
$638+
View details