Entire home

Cape Ann, Annisquam panoramic ocean views from every room.

Choose dates to view prices

Where to?

Dates

July 2025

August 2025

4 bedrooms, iron/ironing board, WiFi, bed sheets

Overview
Amenities
Policies
Location
Host

Exceptional

Entire home

4 bedrooms2 bathroomsSleeps 111700 sq ft

Popular amenities

Hot Tub
Parking available
Dryer
Pet friendly
Washer
Fireplace

Explore the area

Gloucester, MA

Good Harbor Beach
‪12 min drive‬
Cape Ann
‪14 min drive‬
Wingaersheek Beach
‪15 min drive‬
Boston, MA (BOS-Logan Intl.)
‪54 min drive‬

Room options

About the neighborhood

Gloucester

Located within 2 miles (3 km) of Plum Cove Beach, this vacation home is within 3 miles (5 km) of Dogtown. The vacation home includes a kitchen, a fireplace, and a balcony.

View more Vacation Homes in Gloucester

What's nearby

Plum Cove Beach - 2 min drive - 0.9 miles
Halibut Point State Park - 6 min drive - 2.9 miles
Good Harbor Beach - 12 min drive - 6.9 miles
Cape Ann - 14 min drive - 7.6 miles
Wingaersheek Beach - 15 min drive - 7.7 miles

Getting around

Gloucester Station - 8 min drive
Beverly, MA (BVY-Beverly Municipal) - 25 min drive

Restaurants

‪Starbucks - ‬9 min drive
‪McDonald's - ‬8 min drive
‪Holy Cow Ice Cream Cafe - ‬8 min drive
‪George's Coffee Shop - ‬7 min drive
‪Fish Shack Restaurant - ‬11 min drive

About this property

Entire place

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

Cape Ann, Annisquam panoramic ocean views from every room.

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.

The vacation home is air-conditioned and features a kitchen, 2 bathrooms, and a balcony or patio. There's space to spread out with 4 bedrooms and a dining area. Guests can expect to find a TV with a DVD player. The bathroom offers a jetted tub and hair dryers. Other standard amenities include a washing machine, a fireplace, and a sofa bed.

Property manager

John T. Gurley

Languages

English

Similar properties

Ocean view
Kitchen
Washer
Dryer

Property amenities

Beach

Beach nearby
Beach towels

Pool/Spa

Hot tub

Internet

Available in the house: WiFi

Parking and transportation

Car recommended
Limited onsite parking (max 5 spaces)

Kitchen

Blender
Coffee grinder
Coffee/tea maker
Cookware, dishware, and utensils
Dishwasher
Electric kettle
Kitchen island
Lobster/crab pot
Microwave
Oven
Paper towels
Refrigerator
Spices
Stovetop
Toaster

Dining

Dining table

Bedrooms

4 bedrooms
Bedsheets provided
Sofa bed

Bathroom

2 bathrooms
Bathtub or shower
Hair dryer
Jetted bathtub
Shower
Soap
Toilet paper
Towels provided

Living spaces

Dining table
Fireplace
Living room
Separate dining area

Entertainment

Books
DVD player
TV with cable/satellite channels

Outdoor areas

Barbecue grill
Garden
Patio

Laundry

Laundry facilities
Washing machine

Work spaces

Printer

Comfort

Air conditioning
Heating

Pets

Pet friendly

Suitability/Accessibility

Smoking not allowed
Note from host: No smoking in the house or on the property.

Services and conveniences

Iron/ironing board
Phone

Location highlights

In a village
Near a hospital
Near an outlet shopping mall
Near the bay
Near the marina
Near the sea

Things to do

Birdwatching nearby
Fishing nearby
Golfing nearby
Hiking/biking trails nearby
Horseback riding nearby
Jet skiing nearby
Mountain biking nearby
Sailing nearby
Scuba diving nearby
Snorkeling nearby
Surfing/bodyboarding nearby
Swimming nearby
Water skiing nearby
Whale watching nearby
Windsurfing nearby

Safety features

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)

General

Garden
Unit size: 1,700 square feet

Policies

Check-in

Check-in time starts at 4:00 PM

Contactless check-in available

Check-out

Check-out before 9:00 AM

Special check-in instructions

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

Check-out instructions

The host requires you complete the following before checking out:

Load and start the dishwasher

Gather used towels

Remove personal items, remove leftover food and drinks, and take out the trash

Pets

This property welcomes pets
Restrictions apply
For more information, guests can reach out to the property at the number on the booking confirmation
Service animals exempt from fees
Note from host: Pre-approval required.

Children and extra beds

Note from host: We do not provide infant equipment or high chairs.

Important information

You need to know

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

Note from host: No parties with more than 25 guests.

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

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

Check-in: 4:00 PM
Check-out: 9:00 AM

Property Registration Number C1927699302

We should mention

Details about charges, deposits, or other important information:

This property is managed by a private host, not a professional engaged in trade or business.
Charges for extra guests may apply and vary depending on the property's policy.
A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
Onsite parties or group events are strictly prohibited.
Note from host: No parties with more than 25 guests.

Property is also known as

Cape Ann Annisquam Panoramic Ocean Views From Every Room

Cape Ann Annisquam panoramic ocean views from every room.

Frequently asked questions

What is there to do close to this vacation home?

This vacation home is located in Gloucester, close to Wingaersheek Beach, Good Harbor Beach, and Cape Ann. You'll also find Plum Cove Beach and Halibut Point State Park within a short drive.

Will I be able to park at this vacation home?

Yes, though there is a max of 5 spaces.

Is this vacation home adjacent to a casino?

No, this vacation home is not connected to a casino.

Is there an indoor pool at this vacation home?

No, this vacation home doesn't have an indoor pool; however, there is a hot tub.

Is Cape Ann, Annisquam panoramic ocean views from every room. a good place to stay for couples?

Amenities that appeal to couples at this historic vacation home include a fireplace and a jetted bathtub in each accommodation with some featuring ocean views.

Does Cape Ann, Annisquam panoramic ocean views from every room. have a hot tub?

Yes, guests can enjoy a spa tub at this vacation home.

Does this vacation home include breakfast service?

No, this vacation home doesn't offer breakfast.

Does this vacation home allow pets to stay free of charge?

Although pets can't stay for free, they are welcome at this vacation home.

Does this vacation home have connecting rooms?

No, there aren't connecting rooms at this vacation home.

Where is the closest airport to this vacation home?

The closest major airport to this vacation home is Beverly, MA (BVY-Beverly Municipal), which is 17.8 mi away (25 minutes by car). Another top airport is Lawrence, MA (LWM-Lawrence Municipal), which is around 22.9 mi away.

Are there rooms with balconies at Cape Ann, Annisquam panoramic ocean views from every room.?

Yes, every accommodation at Cape Ann, Annisquam panoramic ocean views from every room. comes with a balcony with some featuring ocean views.

Cape Ann, Annisquam panoramic ocean views from every room. Reviews

9.6

Exceptional

9.0/10

Cleanliness

10/10 Excellent

Toni C.

Aug 2, 2024

Liked: Cleanliness

Awesome Vacation

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!

Stayed 7 nights in Jul 2024

10/10 Excellent

Polly C.

Apr 22, 2024

Liked: Cleanliness

Diamond by the Sea Annisquam

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!

Stayed 7 nights in Apr 2024

10/10 Excellent

Susan B.

Jul 15, 2023

Liked: Cleanliness

A Gem of a Place

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.

Stayed 7 nights in Jul 2023

10/10 Excellent

Peter L.

Sep 14, 2022

Liked: Cleanliness

Five Diamond

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

Stayed 21 nights in Aug 2022

8/10 Good

Susan B.

Jul 23, 2022

Divine location and views

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!

Stayed 7 nights in Jul 2022

10/10 Excellent

Damon P.

Jun 5, 2022

Liked: Cleanliness

Great Place!

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.

Stayed 7 nights in May 2022

10/10 Excellent

Tonya E.

Oct 16, 2021

Liked: Cleanliness

Amazing panoramic views!

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

Stayed 7 nights in Oct 2021

10/10 Excellent

Reeah D., new york, usa

Sep 20, 2021

Liked: Cleanliness

Beautiful location and home

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

Stayed 7 nights in Sep 2021

10/10 Excellent

James H.

Sep 18, 2021

Liked: Cleanliness

xxx

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

Stayed 7 nights in Sep 2021

10/10 Excellent

Donald B., Milton, MA USA

Sep 5, 2021

Liked: Cleanliness

Good times in Annisquam

Beautiful views of Ipswich Bay, in a friendly and quiet Annisquam neighborhood. About a 12 minute walk to a Sandy beach, but an easy drive to Plum Cove, where you can drop off at a Town Beach. We had to adjust to not having a first floor bathroom, and stairs to the house are steep for the very young. We stayed the week prior to Labor Day, and never turned on the AC. The Kitchen is spacious and well stocked.

Stayed 7 nights in Aug 2021

10/10 Excellent

Sandra A.

Jul 11, 2021

Liked: Cleanliness

Wonderful post COVID family reunion.

I booked this special house during the trauma of COVID with the hopeful expectation that everyone would be vaccinated. And they were! When I was searching for a place large enough for 11 people, the house in Anisquam appeared and had one week available. The 4th of July was part of it. That night was magical - we had an expansive view of fireworks all along the coastline from 9pm until midnight. The house was a joy to be in from start to finish even though we arrived in the pouring rain. Each day proved different, a roller coaster ride of clouds one day, bright sun and a heat wave another day, and a hurricane on our last full day. We used the gas fireplace a few times and the AC at other times. The best was when we could just open all the windows and sit on the great porch and look at the sea and sky. For those who like to swim, Squam Rock Beach is a sandy expanse of clear water, perfect for families with children. The fun challenge is finding it. My greatest pleasure was being surrounded by all my family and to witness their pleasure with the house and the area. They loved the experience as did I. PS. There is enough space in the house and on the grounds to get away from everyone if you need some moments alone.

Stayed 7 nights in Jul 2021

10/10 Excellent

Sarah D., Boston, US

Jun 12, 2021

Liked: Cleanliness

We love this spot

This was our second year staying at John’s and Sarah’s beautiful Annisquam home. Fantastic hosts, a great house and a perfect, relaxing beach vacation. We hope to be back again!

Stayed 7 nights in Jun 2021

10/10 Excellent

Susan Anderson W.

Oct 6, 2020

Liked: Cleanliness

Great views of the Atlantic from every window and fabulous sunsets!

Wonderful unique spot from which to experience Cape Ann and enjoy family in comfortable surroundings.

Stayed 7 nights in Sep 2020

10/10 Excellent

Katherine b., Fairfax

Sep 17, 2020

Liked: Cleanliness

Best house on Cape Ann

This is a wonderfully old turn of the century summer home, but absolutely updated where needed (bathrooms, beds, appliances, gas fireplace, AC, new windows with screens) with loads of charm and color and everything you need provided except food and drink (plenty of linens, coffee grinder, hot water pot, etc etc). It is located in a charming, quiet and walkable neighborhood and has water access via a small pebbly beach surrounded by the granite boulders Cape Ann is famous for, perfect for a swim or launching a kayak. It is a marvelous covered front porch and open back deck so you can be outside all day. The views are just amazing and it is high enough up that there are few bugs. It is a short drive from Rockport and Gloucester and their shops, restaurants and harbors, where everyone inside and outside was wearing a mask for Covid safety. We all loved it and hope to return!

Stayed 7 nights in Sep 2020

10/10 Excellent

Katherine H.

Sep 2, 2020

Disliked: Cleanliness

Great views

The views from two porches and all rooms are lovely; neighborhood is quiet and welcoming. Pretty views from small neighborhood beach just steps away. Kitchen is perfect for foodies, but there are also lots of great restaurants nearby. Owners could not have been nicer.

Stayed 7 nights in Aug 2020

10/10 Excellent

Peter L.

Aug 23, 2020

Liked: Cleanliness

No AC for Two Weeks

An absolutely superior two weeks at Five Diamond. Already rebooked for 2021. Couldn’t possibly be in a better spot with the best views in Cape Anne. House is ridiculously charming and cozy. No pretense, just an ideal summer retreat.

Stayed 14 nights in Aug 2020

10/10 Excellent

Connie L.

Aug 11, 2020

Liked: Cleanliness

Fabulous views

Truly loved our stay. The character of the house gave you such a comfortable feeling, the front porch provided a very relaxing setting as did the back porch. The neighborhood was quiet and the neighbors (long time residents) were very welcoming. Definitely need to be mindful of how easily noise travels as this house sit up higher than all of others. If you are looking for a quiet , relaxing vacation... then this is your spot. I would highly recommend this home to others.

Stayed 7 nights in Aug 2020

10/10 Excellent

Tom G., Slingerlands NY

Jul 22, 2020

Liked: Cleanliness

Excellent visit

Classic New England charm with modern amenities. The sunsets each day from the huge porch was great.

Stayed 7 nights in Jun 2020

10/10 Excellent

Sarah D., Boston, US

Jul 17, 2020

Liked: Cleanliness

Absolute perfection

My friends and I had a magical experience at this special Annisquam home. John and Sarah were helpful and welcoming, from inquiry and booking to arrival. And while the photos are accurate, they cannot possibly convey the knockout views from every room in the home, much less the beautiful millwork and lovely little details throughout. I can't imagine a more ideal location and we so enjoyed the two-cove option for swimming. The house is well supplied with bed/bath/beach linens, a fully stocked kitchen, ample parking, and perhaps most importantly, a comfy hammock in just the right spot of the best room in the house. We could not get enough of that front porch! Look no further on Cape Ann.

Stayed 7 nights in Jul 2020

10/10 Excellent

Jessic K.

Jul 12, 2020

Liked: Cleanliness

Fantastic location!

Perfect place for a summertime beach house. We truly enjoyed every minute of it. Very clean, No issues whatsoever. Will look into going back there again.

Stayed 7 nights in Jun 2020

10/10 Excellent

Titi A.

Sep 1, 2019

Liked: Cleanliness

An Annual Treat

Second year renting here and look forward to more. So many hours spent basking in the sun on either of the porches, both overlooking the bay.

Stayed 7 nights in Aug 2019

10/10 Excellent

Melissa M.

Aug 30, 2019

Liked: Cleanliness

Breathtaking Location

We spent a wonderful week at this amazing house. There truly are views of the water from every window. The kitchen was well equipped with everything we needed, the bath/bed amenities were impressive, and other than my own home, I have not slept on such a comfortable mattress. The owners were easily reachable for a few questions and the only thing we would have enjoyed having was some history about the house. It is such a fascinating location and layout, we kept wishing for the details. The ages of our family group ranged from 6 to 71, and there were things to do and sights to see for everyone, including a fantastic day whale watching out of Gloucester. The Squam Rock beach was beautiful and just perfect for the kids. Thank you so much for opening your beautiful home to us - we will all have the best memories of this vacation for years to come!

Stayed 7 nights in Aug 2019

8/10 Good

Sandy p.

Jul 17, 2019

Liked: Cleanliness

Great view, location, but needs a little tlc

Loved, the location and the river view from the deck. The house was clean, well equipped and satisfied all our basic needs. The only questionable items, from a safety issue, were the stairs up to the deck and the deck itself needed some boards replaced. Additionally, the kitchen oven door needed some adjustment.

Stayed 7 nights in Jun 2019

10/10 Excellent

Titi A.

Sep 28, 2018

Superb views

The house provides so many ways to look out over Ipswich Bay, especially the beautiful sunsets. The rocky beach just steps away is calm and great for swimming or sea-glass hunting. Lighthouse Beach is only a short walk away as well. Great response from the owners for questions both before arrival and during the week. Looking forward to returning next summer!

Stayed 7 nights in Aug 2018

8/10 Good

Doreen H.

Aug 15, 2018

Best view on Cape Ann

This lovely house was perfect for our family. The porch was our morning and evening gathering place and the views were beautiful. The house provided sufficient room for indoor gathering without our family being crowded. The owner was very gracious. We would definitely recommend this rental and look forward to staying there again.

Stayed 7 nights in Jul 2018