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Cape Ann, Annisquam panoramic ocean views from every room.

Vacation home near Wingaersheek Beach in Gloucester

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Photo gallery for Cape Ann, Annisquam panoramic ocean views from every room.

Terrace/patio
Exterior
4 bedrooms, iron/ironing board, WiFi, bed sheets
Beach nearby, beach towels
TV, fireplace, DVD player, books

Reviews

9.6 out of 10
Exceptional

Entire home

4 bedrooms2 bathroomsSleeps 111700 sq ft

Popular amenities

  • Ocean view
  • Hot tub
  • Kitchen
  • Washer
  • Dryer
  • Pet friendly

Explore the area

View in a map
Gloucester, MA
  • Place, Plum Cove Beach
    ‪4 min drive‬
  • Place, Good Harbor Beach
    ‪13 min drive‬
  • Place, Wingaersheek Beach
    ‪17 min drive‬
  • Airport, Boston, MA (BOS-Logan Intl.)
    ‪66 min drive‬

Room options

About the neighborhood

Gloucester

Seaside stay .You'll find Plum Cove Beach and Dogtown within 3 miles (5 km) of this vacation home. Halibut Point Reservation and Paper House are also within 3 miles (5 km).
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What's nearby

  • Plum Cove Beach - 4 min drive - 1.6 miles
  • Half Moon Beach - 11 min drive - 5.7 miles
  • Good Harbor Beach - 13 min drive - 7.3 miles
  • Wingaersheek Beach - 17 min drive - 8.9 miles
  • Cape Ann - 17 min drive - 8.7 miles

Getting around

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

Restaurants

  • ‪Starbucks - ‬10 min drive
  • ‪Chipotle Mexican Grill - ‬9 min drive
  • ‪Common Crow Natural Market - ‬10 min drive
  • ‪Salt Water Grille - ‬7 min drive
  • ‪Talise - ‬4 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.

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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
Information provided by the property may be translated using automated translation tools

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
Failure to complete these may result in a negative review from the host.

Rules

Quiet Time Our homeowner association asks that our renters refrain from making loud noises after 9:00pm and before 8:00am

Pets

  • Pets are welcome
  • Restrictions apply
  • For more information, you can reach out to the property at the number on the booking confirmation
  • Service animals are exempt from fees
  • Note from host: Pre-approval required.

Children and extra beds

  • Children are welcome.
  • Note from host: We do not provide infant equipment or high chairs.

Events

No events allowed
No parties with more than 25 guests.

Smoking

Smoking is not permitted
No smoking in the house or on the property.

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 has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
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
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a private host, not a professional engaged in trade or business. This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children. If you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room. Onsite parties or group events are strictly prohibited. Note from host: No parties with more than 25 guests.

Property Registration Number C1927699302

We should mention

  • To make arrangements for your pet, contact the property directly using the information on your booking confirmation.

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

How close is Cape Ann, Annisquam panoramic ocean views from every room. to the airport?

This vacation home is 17.8 mi (25-min drive) away from the Beverly, MA (BVY-Beverly Municipal) airport, the closest popular airport to the property.

Does Cape Ann, Annisquam panoramic ocean views from every room. have an airport shuttle?

Airport shuttle services are not available at this vacation home.

How close is Cape Ann, Annisquam panoramic ocean views from every room. to the beach?

This vacation home is 6 mi (16-min drive) from Good Harbor Beach and 7.7 mi (21-min drive) from Wingaersheek Beach. Don't forget your sunscreen!

Does Cape Ann, Annisquam panoramic ocean views from every room. offer free breakfast?

This vacation home does not offer free breakfast.

Is there a casino at Cape Ann, Annisquam panoramic ocean views from every room.?

No, there is no casino at this vacation home.

What time is check-in at Cape Ann, Annisquam panoramic ocean views from every room.?

Check-in begins at 4:00 PM.

Is there free parking at Cape Ann, Annisquam panoramic ocean views from every room.?

Free parking is not available at this vacation home.

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

This vacation home does not have a pool.

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

There are no spa services available at this vacation home.

How close is Cape Ann, Annisquam panoramic ocean views from every room. to downtown Gloucester?

This vacation home is 3.7 mi away from Gloucester.

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

Reviews

9.6

Exceptional

Rating 10 - Excellent. 35 out of 43 reviews
Rating 8 - Good. 6 out of 43 reviews
Rating 6 - Okay. 1 out of 43 reviews
Rating 4 - Poor. 1 out of 43 reviews
Rating 2 - Terrible. 0 out of 43 reviews

8.8/10

Cleanliness

Reviews

Verified

10/10 Excellent

Toni C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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
Verified

10/10 Excellent

Susan B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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
Archival

10/10 Excellent

Emily Q.

The Perfect Getaway

This rental was everything we could have asked for and more. The owners were friendly and responsive, the house was warm and inviting, the views were spectacular and the beach was just a short walk away! What a wonderful week we had enjoying the scenery and some delicious dinners on the deck. A must for anyone looking to get away from it all and relax!
Verified

8/10 Good

Susan B.

Liked: Check-in, communication, location, listing accuracy

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
Verified

10/10 Excellent

Polly C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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
Archival

8/10 Good

Anthony Simon M.

Worth the climb to the top of the hill.

5 adults and 5 kids (3 thru 9) shared a picture perfect week at this beautiful location. Two full baths with showers meant no waiting. Laundry facilities very handy for large group. All bedrooms on the 2nd fl made it easy to keep noise down for those going to bed early. Small rocky beach right in front is perfect at low tide, but cramped at high tide. Sandy beach visible in photos was not accessible to us, according to neighbor. Cottage owner had great info packet, but I was unable to locate anything re: sandy beach access. That said, there are more fabulous sandy beaches within a short drive than one could visit in a week. Also recommend Family Night at Annisquam Yacht Club for anyone with guest privileges.
Verified

6/10 Okay

Pamela E.

Liked: Check-in, communication, location, listing accuracy
Disliked: Cleanliness

Underwhelmed

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.
Stayed 7 nights in Jul 2025
Verified

10/10 Excellent

Peter L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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
Verified

10/10 Excellent

Damon P.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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
Verified

10/10 Excellent

Tonya E.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing panoramic views!

Wonderful place for our family to gather! Beautiful views and walking distance to the ocean!!
Stayed 7 nights in Oct 2021
Verified

10/10 Excellent

Reeah D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful location and home

The home and the location are beautiful. We enjoyed our stay immensely.
Stayed 7 nights in Sep 2021
Verified

10/10 Excellent

James H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

xxx

Great views once you are able to climb the mountain from your car
Stayed 7 nights in Sep 2021
Verified

10/10 Excellent

Donald B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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
Verified

10/10 Excellent

Sandra A.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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
Verified

10/10 Excellent

Sarah D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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
Verified

10/10 Excellent

Susan Anderson W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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
Verified

10/10 Excellent

Katherine b.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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
Verified

10/10 Excellent

Katherine H.

Disliked: Cleanliness, check-in, communication, location, listing accuracy

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
Verified

10/10 Excellent

Peter L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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
Verified

10/10 Excellent

Connie L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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
Verified

10/10 Excellent

Tom G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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
Verified

10/10 Excellent

Sarah D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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
Verified

10/10 Excellent

Jessic K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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
Verified

10/10 Excellent

Titi A.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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
Verified

10/10 Excellent

Melissa M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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