Cape Ann, Annisquam panoramic ocean views from every room.
House in Gloucester, MA
11 guests · 4 bedrooms · 2 baths
Reasons to book
Guests love it hereGuests give this property a top rating
Great for petsBring all your friends and family, even the furry ones
Includes essentialsGarden, Pets allowed, Kitchen or Kitchenette and more
About this house rental
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.
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.
Amenities
Air conditioner
Pets allowed
Kitchen or Kitchenette
Internet / Wifi
Fireplace
Parking
Laundry
Balcony or Patio
Dishwasher
Hot tub or spa
TV
Garden
Map of Gloucester, MA
RRRR
Ratings and reviews
Summary of reviews
Beautiful views, comfortable rooms, well-stocked kitchen, and friendly neighborhood. Perfect for family gatherings!
10.0 / 10.0
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!
10.0 / 10.0
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!
10.0 / 10.0
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.
10.0 / 10.0
Five Diamond lived up to its billing. Great cottage on an incredible site. Will be back next year.
8.0 / 10.0
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!
10.0 / 10.0
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.
10.0 / 10.0
Amazing panoramic views!
Wonderful place for our family to gather! Beautiful views and walking distance to the ocean!!
10.0 / 10.0
Beautiful location and home
The home and the location are beautiful. We enjoyed our stay immensely.
10.0 / 10.0
xxx
Great views once you are able to climb the mountain from your car
10.0 / 10.0
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.
10.0 / 10.0
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.
10.0 / 10.0
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!
10.0 / 10.0
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.
10.0 / 10.0
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!
10.0 / 10.0
Respite from lockdown
We aggressively avoided infection all summer just so that we'd have another opportunity to stay here and spend a whole week taking in the panoramic views of Ipswich Bay. Plenty of room to spread out for generations wanting different activities, two great porches to soak in the sun, and a quiet neighborhood to walk around in for your vigorous constitutionals. COVID cleaning protocols put any concerns to rest regarding our stay.
10.0 / 10.0
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.
10.0 / 10.0
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.
10.0 / 10.0
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.
10.0 / 10.0
Excellent visit
Classic New England charm with modern amenities. The sunsets each day from the huge porch was great.
10.0 / 10.0
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.
10.0 / 10.0
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.
10.0 / 10.0
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.
10.0 / 10.0
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!
8.0 / 10.0
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.
10.0 / 10.0
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!
8.0 / 10.0
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.
8.0 / 10.0
Amazing views and accompanying beach
We had a wonderful week of the Fourth of July. Thank goodness the house has air conditioning because our week was in the upper 80s. Pictures of the view do not do it justice. We enjoyed walking to Squam Rock beach and had plenty of space for my parents and in-laws. We had some initial trouble with wasps outside but the owners dealt with it professionally. We wish we were back there now.
4.0 / 10.0
Time-weathered home on Steep Mountain
The first impression a visitor receives is staring up a steep slope of granite steps to access the property - both front and back entrances. It is difficult to appreciate the beauty of the seascape when your first daunting challenge is to haul your luggage and groceries up these steep slopes. Upon entry, you next learn that the bathrooms are up yet another steep slope of creaking stairs. Had the house measured up in every other way, you could almost forgive the challenge of reaching the summit. However, the house is rather drab and some of the kitchen items have accumulated years of grime. Despite this two-star review, the views from both porches do offer the beauty that is promised. You will want to spend each waking moment outside, even if the clean, white, sparkling photo of the front porch and chairs leaves something to be desired in real life, as nothing is exactly clean, white and sparkling anymore. Still, it's a great place to watch the sunset. I just wish the advertisement were a little more truthful about the stairs. The five of us are no longer spring chickens, but by no means feeble. The stairs were a challenge for even the spry-est among us. Between rusty knees and aching backs, some of us did not fare very well. Instead of leaving on Saturday morning, we cut our visit short and left on Wednesday. A telephone call to the owner to advise him that we were leaving early and to inquire about trash removal, as we would not be there for pick-up day, went unanswered. That was disconcerting. We did the best we could and placed the trash in the cans, but couldn't leave them out for pick-up. The place has many things to recommend itself, but unfortunately, it did not meet our expectations for the price. We have rented vacations homes in the past and paid less for much, much more.
10.0 / 10.0
Beautiful scenery, convient location and well kept home
This is a great place for a family vacation. Annisquam has been a spot for a many years where this group goes. Everyone agreed this was one of the best homes that has been rented. It is clean, well kept has ample space to relax in and amazing views of the water. A short walking distance to the beach and very convenient to everything around the area. It is everything the pictures present. So beautiful. A week to remember for sure.
10.0 / 10.0
A Perfectly Lovely Place
We loved so much about this place my description will no doubt miss things. The views, the sun rising and setting over the water, the beautiful porches, the precious old toy airplane and toy ice cream stand, the beaches, and for sure the old house, trees and gardens. You can feel the past, the generations of great times had, and yet everything modern you could ever need is provided. The hosts are helpful, available and gracious. We all left dreaming of and hoping for another visit next year.
10.0 / 10.0
We never wanted to leave!
This house was more than we could have ever imagined. The views from every room were spectacular. We had fantastic weather which did not hurt matters. It was a wonderful vacation and we made some beautiful memories.
Sincerely,
Paula Leger
7/1/17 to 7/8/17
10.0 / 10.0
Great House, Great Location
It's a great older house with lots of charm. The views are simply amazing off the front and back decks. It was about a 10 min walk to lighthouse beach, but it was never crowded. The house is well appointed, pots for lobsters, grill, beach towels, etc. It even has central air which we didn't need, but is nice to have. The front porch was perfect for relaxing at the end of the day and watching the sunset, it makes this house really special.
10.0 / 10.0
Great place to stay
This is a really great place to stay. The location is right on the ocean. There is a rock beach practically at the doorstep and a wonderful sandy beach a short walk away - especially perfect for young children at low tide. The house itself is in excellent shape with an especially well equipped kitchen, plenty of good quality towels, enough hot water for everyone and fantastic views out of virtually every window. Good restaurants and shopping are only a few minutes away by car.
FAQs
How much does this house cost compared to others in Gloucester?
The average price for a rental in Gloucester is R 6,157 per night. This rental is R 4,423 above the average.
Is parking included with this house?
Yes, parking is listed as an amenity at Cape Ann, Annisquam panoramic ocean views from every room.. For more information, we encourage you to contact the property about where to park.
Is there a pool at this house?
We didn’t find pool listed as an amenity for this house. It may be worth double checking if a pool is important for your stay.
Is Cape Ann, Annisquam panoramic ocean views from every room. pet friendly?
Yes! This house is pet-friendly. For more information, we recommend contacting the booking provider about animal policies.
What amenities are available at Cape Ann, Annisquam panoramic ocean views from every room.?
We found 12 amenities for this rental. This includes air conditioner, pets allowed, kitchen or kitchenette, internet / wifi, and fireplace.
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