Cape Ann, Annisquam panoramic ocean views from every room. | House in Gloucester

9.6 (42 Reviews) |   Pet Friendly   4 Bedrooms  2 Bathrooms  11 Guests
Gloucester House | Cape Ann, Annisquam panoramic ocean views from every room.

4 Bedroom House in Gloucester

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.

Cape Ann, Annisquam panoramic ocean views from every room is located in Gloucester. Cape Ann, Annisquam panoramic ocean views from every room provides accommodation, featuring Bedding/Linens, Entertainment, Internet, among other amenities. This House features Bedding/Linens, Entertainment, Internet, to make your stay a comfortable one.

Cape Ann, Annisquam panoramic ocean views from every room has 4 Bedrooms , 2 Bathrooms, and max occupancy of 11 people. The minimum rental for this property is 1 nights, but this can change depending on the season you plan on staying. Previous guests have given good rated it, and VRBO labeled it a top-rated House because of the excellent services rendered by the owner or manager of this House, and has consistently provided great experiences for their guests. Most families or guests that use it recommend it to their friends and some of them are repeat guests. House has a friendly neighborhood, and the Gloucester has interesting places to visit. If you want to learn more about the House in Gloucester, such as places to visit and things to do nearby, you can check below to learn more.

Show more
OneKey Logos

This Property is OneKey Eligible

Earn OneKeyCash for every dollar spent on eligible vacation rentals, villas, cottages, cabins, and more when you book on Vrbo.

JOIN TODAY

Amenities

Air Conditioner
Parking
Pet Friendly
TV
View
Ocean View
Balcony/Terrace
Oceanfront
Security/Safety
Bedding/Linens
Wellness Facilities
Fireplace/Heating
Entertainment
Barbecue/Outdoor Cooking
Child Friendly
Hot Tub
Internet
Kitchen
Laundry

Policies

Check-in
Check-in time starts at 4:00 pm contactless check-in available
Check-out
Check-out before 9:00 am
Child Policy
Children are welcome. note from host: we do not provide infant equipment or high chairs.
Pet Policy
Note from host: pre-approval required. pets allowed restrictions apply; for more information contact the property at the number on the booking confirmation service animals are welcome, and are exempt from fees

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 host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip host has not indicated whether there is a smoke detector on the property note from host: no parties with more than 25 guests. onsite parties or group events are strictly prohibited property registration number c1927699302 special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed 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

License number: C1927699302

Reviews

Pamela E.
Aug 3, 2025 08:05:16 AM
Review Score:   6
Summary: 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.
See All Reviews
Check House Availability
Nightly rates from:
USD638
You will be redirected to  
Hot Deal - It has been viewed 202 times today
Not the right fit? Check out our other properties in Gloucester
The Chill-a-Vista From US $535
         

New
Apartment
  • Air Conditioner
  • Parking
  • Child Friendly
Harborview Inn From US $211
         

|
9.6 (316 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • TV
Luxury Accommodations in Quiet Seaside Village From US $240
         

10.0 (130 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
The Buoys From US $396
         

|
10.0 (7 Reviews)
House
  • Air Conditioner
  • Parking
  • View
Stay at Rocky Neck From US $1,094
         

|
10.0 (3 Reviews)
House
  • Air Conditioner
  • Parking
  • Security/Safety
Thurston Point: Deepwater River Dock From US $591
         

9.4 (22 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Helena House: Close to Plum Cove Beach From US $494
         

8.2 (12 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Steps to Wingaersheek's Private 1.5 Mile White Dune Beach From US $560
         

5-star home with quick walk to 2 beaches! From US $578
         

10.0 (56 Reviews)
House
  • Air Conditioner
  • Parking
  • TV