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Cape Ann, Annisquam panoramic ocean views from every room.

Holiday home in Gloucester with kitchen and balcony

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

Enjoy breathtaking views of the sea and distant shoreline from this room's window.
Relax in this serene room with a large bed, wooden headboard, and ocean views.
Cozy bedroom with a bed, table, and chair, featuring a window with curtains.
Relax on the covered porch with a view of the ocean, featuring a bench and Adirondack chairs.
Cozy living room with a fireplace, comfortable seating, and a view of the outdoors.

Entire home

4 bedrooms2 bathroomsSleeps 111700 sq ft

Popular amenities

  • Parking available
  • Hot tub
  • Dryer
  • Pet-friendly
  • Washer
  • Fireplace

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.

Holiday home in Gloucester with kitchen and balcony
This smoke-free holiday home features Access to hot tub, laundry facilities and a garden. Other amenities include barbecues. The holiday home has 4 bedrooms and offers a sofa bed and a DVD player. A kitchen comes with a fridge and an oven, and guests will also find upscale touches, such as a fireplace and a jetted bath.
Air-conditioned accommodation at this holiday home offers fireplaces and DVD players. Rooms open to balconies or patios. This accommodation is furnished with sofa beds, dining tables and kitchen islands. Kitchens offer fridges, stovetops, microwaves and separate dining areas.

Bathrooms include baths or showers with in-room jetted baths and hairdryers. Business-friendly amenities include printers and telephones. Additionally, rooms include coffee/tea makers and an iron/ironing board.

Recreational amenities at the holiday home include Access to hot tub.

The recreational activities listed below are available either on-site or nearby; fees may apply.

Property manager

John T. Gurley

Languages

English

Add dates for prices

Property amenities

Beach

  • Beach nearby
  • Beach towels

Pool/Spa

  • Hot tub

Internet

  • Available in the house: WiFi

Parking and transport

  • Car recommended
  • Limited on-site parking (max 5 spaces)

Kitchen

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

  • Smoke-free property
  • 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 centre
  • 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
  • Snorkelling 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

Similar properties

Beach nearby

Steps to Wingaersheek's Private 1.5 Mile White Dune Beach

  • Sea view
  • Kitchen
  • Washer
  • Dryer
9.8 out of 10, Exceptional, 36 reviews
Steps to Wingaersheek's Private 1.5 Mile White Dune Beach

Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in and check-out are 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 to 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 rubbish

Pets

Pets are allowed
Service animals are welcome, and are exempt from fees
Restrictions apply; for more information contact the property on the number on the booking confirmation
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.

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
On-site 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
Property Registration Number C1927699302

We should mention

A car is recommended for transport to and from this property

Property is also known as

Cape Ann Annisquam Panoramic Ocean Views From Every Room
Cape Ann Annisquam panoramic ocean views from every room.

About the area

Map
Gloucester, MA

What's nearby

  • Plum Cove Beach - 2 min drive - 1.5 km
  • Halibut Point State Park - 6 min drive - 4.7 km
  • Good Harbor Beach - 12 min drive - 11.0 km
  • Cape Ann - 14 min drive - 12.1 km
  • Wingaersheek Beach - 15 min drive - 12.4 km

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

Frequently asked questions

Is Cape Ann, Annisquam panoramic ocean views from every room. pet-friendly?

Yes, pets are allowed at this property.

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

Check-in begins at 4:00 PM.

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

Checkout is at 9:00 AM.

Where is Cape Ann, Annisquam panoramic ocean views from every room. located?

Situated by the sea, this holiday home is within 3 miles (5 km) of Plum Cove Beach, Dogtown and Halibut Point Reservation. Paper House is 3 mi (4.8 km) away.

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

Reviews

9.6

Exceptional

Rating 10 - Excellent. 35 out of 42 reviews
Rating 8 - Good. 6 out of 42 reviews
Rating 6 - Okay. 0 out of 42 reviews
Rating 4 - Poor. 1 out of 42 reviews
Rating 2 - Terrible. 0 out of 42 reviews

9.0/10

Cleanliness

Reviews

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

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
This review was submitted before 2018 and has not been verified.

10/10 Excellent

Emily Q., Boston, Massachusetts

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!

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
This review was submitted before 2018 and has not been verified.

8/10 Good

Anthony Simon M., Ottawa, Ontario

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.

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

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

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

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

10/10 Excellent

Reeah D., new york, usa

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

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

10/10 Excellent

Donald B., Milton, MA USA

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

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

10/10 Excellent

Sarah D., Boston, US

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

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

10/10 Excellent

Katherine b., Fairfax

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

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

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

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

10/10 Excellent

Tom G., Slingerlands NY

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

10/10 Excellent

Sarah D., Boston, US

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

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

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

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

8/10 Good

Sandy p.

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

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