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Cape Ann, Annisquam panoramic ocean views from every room.

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

A covered porch with a view of the ocean, wooden chairs, and a bench.
A room with a bed, a desk, and a chair. There are large windows with curtains, a red chair, and a patterned rug.
A cozy living room with a fireplace, a sofa, a chair, and a table.
A two-story house with a covered porch and a large rock in front.
A coastal landscape with a sandy beach, rocky outcrops, and a calm sea under a cloudy sky.

Reviews

9.6 out of 10
Exceptional

Entire home

4 bedrooms2 bathroomsSleeps 11158 sq m

Popular amenities

  • Ocean view
  • Spa pool
  • Kitchen
  • Washing machine
  • Dryer
  • Pet-friendly

Explore the area

View map
Gloucester, MA
  • Place, Plum Cove Beach
    ‪4 min drive‬
  • Place, Halibut Point State Park
    ‪8 min drive‬
  • Place, Stage Fort Park
    ‪10 min drive‬
  • Airport, Boston, MA (BOS-Logan Intl.)
    ‪66 min drive‬

Room options

About the area

Gloucester

At this holiday home you'll be 2 km (1.3 mi) from Plum Cove Beach and 4.8 km (3 mi) from Dogtown. Highlights at this holiday home include a kitchen, a washing machine and a fireplace. .You can enjoy a TV with a DVD player, and home features 2 bathrooms, a balcony or patio and a sofa bed. In-room dining is easy with a kitchen that comes equipped with a fridge, a microwave and a stovetop. In-room jetted baths, a dining area and a coffee/tea maker are also available. .This pet-friendly holiday home offers a garden and barbecues. Other amenities include a hot tub and laundry facilities. .With a stay at this Gloucester holiday home, you'll be 4.8 km (3 mi) from Halibut Point Reservation and 4.8 km (3 mi) from Paper House.
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What's nearby

  • Plum Cove Beach - 4 min drive - 2.5 km
  • Halibut Point State Park - 8 min drive - 5.8 km
  • Stage Fort Park - 10 min drive - 8.1 km
  • Fishermen's Memorial Monument - 10 min drive - 8.1 km
  • Cape Ann Museum - 10 min drive - 8.2 km

Getting around

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

Restaurants

  • ‪McDonald's - ‬8 min drive
  • ‪Chipotle Mexican Grill - ‬9 min drive
  • ‪Common Crow Natural Market - ‬10 min drive
  • ‪Talise - ‬4 min drive
  • ‪Brothers Brew - ‬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 centre 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 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
  • 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

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

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
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
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 has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that 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 and terraces, which may not be suitable for children. If you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room. On-site 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

Are there any beaches close to Cape Ann, Annisquam panoramic ocean views from every room.?

The closest beach to Cape Ann, Annisquam panoramic ocean views from every room. is Plum Cove Beach (1.3 km).

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

No, this holiday home doesn't have a pool.

What luxury perks are available at Cape Ann, Annisquam panoramic ocean views from every room.?

This property features 1 hot tub, as well as a jetted bath and a fireplace.

What makes Cape Ann, Annisquam panoramic ocean views from every room. a romantic place to stay?

1 hot tub, Jetted bath, and fireplaces all help set the scene for a sizzling getaway at Cape Ann, Annisquam panoramic ocean views from every room..

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

Yep, there is a hot tub.

Is there a free airport shuttle available at Cape Ann, Annisquam panoramic ocean views from every room.?

No, Cape Ann, Annisquam panoramic ocean views from every room. does not offer an airport shuttle service.

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

Check-in begins at 4:00 PM. Check-out time is 9:00 AM.

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

Reviews

9.6

Exceptional

Rating 10 - Excellent. 39 out of 47 reviews
Rating 8 - Good. 6 out of 47 reviews
Rating 6 - Okay. 1 out of 47 reviews
Rating 4 - Poor. 1 out of 47 reviews
Rating 2 - Terrible. 0 out of 47 reviews

9.0/10

Cleanliness

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful house with everything we needed! Highly recommend, we would stay again in a blink. Loved the view from the porch, the kitchen was fantastic, the beds so comfortable. It was the perfect place for our family.
Stayed 7 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Always a joy to stay here. Barely need to leave the porch to feel the full Annisquam relaxation vibe, but easy to walk to the beach or into the town, and of course a short drive to downtown Gloucester or Rockport.
Stayed 7 nights in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This home was delightful- a huge wraparound covered porch from which to view the sunset, another deck on which to eat dinner outside, views from everywhere, and in a great neighborhood for walking. It was outfitted with most everything you'd need. we were able to watch fireworks from both sides of the house without ever leaving home!
Stayed 7 nights in Jul 2026
Verified review

10/10 Excellent

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
Archival

10/10 Excellent

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 review

10/10 Excellent

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
Verified review

8/10 Good

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 review

10/10 Excellent

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

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 review

6/10 Okay

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 review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This is a nice property in a quiet neighborhood with plenty of room. We traveled with 11 people and never felt crowded. Property is on top of a hill so you’ll get some exercise coming and going, but the views alone are worth the effort. Every sunset was an event!The nearby sandy beach is worth the 10 minute walk. The rocky beach which is very close by was not so useful to us but the park bench above it was a nice place to sit and enjoy the views while walking the dogs. Pet friendly. House was clean, beds comfortable, 2 bathrooms one with a shower, one with a hot tub/shower. Kitchen is well stocked with pots pans utensils etc. tv on first and second floor. WiFi access. Large gas grill on porch as well as lots of porch furniture and a hammock. Air conditioning kept the place comfortable. There is a gas fireplace which we did not use but would be nice for a fall visit. Laundry facilities on the second floor. 10-15 min drive to stores, Good Harbor, Long Beach Gloucester. Communication with host was excellent. Would recommend this property.
Stayed 7 nights in Jul 2026
Verified review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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