Entire home

Annisquam Singing Pines: Riverfront Splendor

Photo gallery for Annisquam Singing Pines: Riverfront Splendor

A covered porch with white wicker furniture, a view of a lake, and a distant white house.
A kitchen with white cabinets, a marble countertop, and a wooden ceiling.
A staircase with wooden railings leading to an upper floor, white paneled walls, and a large landscape painting.
Host gracious dinners in the formal dining room.
A room with a large window overlooking a body of water, a blue cushioned bench, and a white birdhouse on the window sill.

Reviews

9.2 out of 10
Wonderful

Popular amenities

  • Barbecue grill
  • Air-conditioning
  • Pet-friendly
  • Refrigerator
  • Onsite parking available
  • Washing machine

Explore the area

View in a map
Gloucester, MA
  • Place, Good Harbor Beach
    ‪9 min drive‬
  • Place, Wingaersheek Beach
    ‪12 min drive‬
  • Place, TD Garden
    ‪60 min drive‬
  • Airport, Boston, MA (BNH-Boston Harbor Seaplane Base)
    ‪62 min drive‬

Rooms & beds

5 bedrooms (sleeps 10)

Bedroom 2

1 Queen Bed

Bedroom 3

1 Double Bed

Bedroom 4

1 Queen Bed

Bedroom 5

1 Double Bed

Primary Bedroom

1 King Bed

2 bathrooms

Bathroom 1

Bathroom 2

Spaces

Kitchen
Garden

Add dates for prices

Have a question?

AI iconBeta

Get instant answers with AI powered search of property information and reviews.

Similar properties

Front Porch overlooking Front Beach
Beach & King - Stunning Ocean Views!
Rockport
  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi
10.0 out of 10, Exceptional, (61 reviews)
Beach & King - Stunning Ocean Views!

About the area

Gloucester

Located in Gloucester, this holiday home is on the waterfront. Dogtown and Fishermen's Memorial Monument are local landmarks, and some of the area's attractions include Maritime Gloucester and Rocky Neck Art Colony. Essex Shipbuilding Museum and Cogswell's Grant are also worth visiting.
View more Holiday homes in GloucesterOpens in a new window
Map
Gloucester, MA

What's nearby

  • Stage Fort Park - 5 min drive - 3.9 km
  • Maritime Gloucester - 7 min drive - 4.6 km
  • Good Harbor Beach - 9 min drive - 7.5 km
  • Wingaersheek Beach - 12 min drive - 10.0 km
  • TD Garden - 60 min drive - 64.7 km

Getting around

  • Gloucester Station - 11 min drive
  • Beverly, MA (BVY-Beverly Municipal) - 27 min drive

Restaurants

  • ‪McDonald's - ‬5 min drive
  • ‪Dunkin' - ‬4 min drive
  • ‪Chipotle Mexican Grill - ‬6 min drive
  • ‪The Open Door Food Pantry - ‬5 min drive
  • ‪Mile Marker One Restaurant - ‬7 min drive

Frequently asked questions

Is Annisquam Singing Pines: Riverfront Splendor pet-friendly?

Yes, pets are allowed at this property.

How much is parking at Annisquam Singing Pines: Riverfront Splendor?

On-site parking is available at the property.

What time is check-in at Annisquam Singing Pines: Riverfront Splendor?

Check-in begins at 4:00 PM.

What time is check-out at Annisquam Singing Pines: Riverfront Splendor?

Checkout is at 10:00 AM.

Where is Annisquam Singing Pines: Riverfront Splendor located?

Situated on the waterfront, this holiday home is 1.2 mi (1.9 km) from Northeast Hospital Corporation - Addison Gilbert Campus and within 3 miles (5 km) of Dogtown and Gloucester Unitarian Universalist Church. Cape Ann Museum and Fishermen's Memorial Monument are also within 3 miles (5 km).

Reviews

9.2

Wonderful

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 9 out of 15 reviews
Rating 8 - Good. 5 out of 15 reviews
Rating 6 - Okay. 1 out of 15 reviews
Rating 4 - Poor. 0 out of 15 reviews
Rating 2 - Terrible. 0 out of 15 reviews

9.6/10

Cleanliness

8.4/10

Check-in

8.4/10

Communication

10/10

Location

8.4/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Excellent house. Very clean, big enough to accommodate our extended family. Would definitely recommend to others.
Stayed 4 nights in Oct 2026
Response from Annisquam Singing Pines: Riverfront Splendor on 19 Oct 2026
Thank you for your kind review Brian. We’re glad Annisquam Singing Pines was clean, comfortable, and spacious enough for your family. We appreciate the recommendation!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Whispering Pines was perfect for our extended Family of (8). Grandparents to Grandchildren, we would stay again in a heartbeat. This quintessential "Summer Cottage" is sooo peaceful & picturesque. The house layout provides wonderful conditions for gathering or privacy. Loved the pantry area! Caught some crabs off the Pier with the Grandkids & the water access was easy way to cool off during the hot summer days. We will def bring paddle boards or kayaks next time.Highly recommend & wish we could have stayed longer! The Sonder Family
Stayed 3 nights in Aug 2026
Response from VrboOwner on 31 Aug 2026
Thank you so much for your kind review Tobiah, we're so glad you loved the property and we look forward to welcoming you and the Sonder family back again!
Verified review

6/10 Okay

Liked: Cleanliness, location
Disliked: Check-in, communication
Very old house … 1902Great location on RiverFamily and pet friendly As clean as old house could be… bathrooms in particular were in poor condition…Check-in was horrible!!!
Stayed 14 nights in Sep 2025
From a partner site

10/10 Excellent

fantastic waterfront views of the salt marsh and Annisquam river

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was somewhat dissatisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We adored the location, the wrap around porches, the lawn, the dock, the kayaking, the VIEWS which changed every hour of the day like a moving painting. We would definitely stay again. Just a bit disappointed by the beds, pillows, couches, lack of lighting for reading, and stove/oven (silly toaster too!) Furnishings either pretty tired or if new, pretty uncomfy. But in the long run, we would choose it again. Very restorative vacation for us. Hardly ever left the premises.
Response from VrboOwner on 23 Jul 2021
Thanks so much for taking the time to review your stay. We are so glad you enjoyed the beauty of the area. Since your visit, the owner has made several furnishing upgrades. We hope you will come again!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location

A beautiful location

We thoroughly enjoyed our stay at Singing Pines. The riverside view was ever changing and perfect. We loved sitting on the gently rocking dock for morning coffee or long talks. And we’d move from porch to dock to chairs on the hill to try out all the views. Beds were firmer than we like, but the rooms were easy to live in with a/c if needed. Plenty of serving pieces for family meals. Our gas was low for the grill, and was quickly remedied after a quick call. Can’t wait to go back!
Stayed 5 nights in Sep 2021
From a partner site

8/10 Good

beautiful location on the Annisquam

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was more than satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Our favorite things about this home is it's location and view of the Annisquam with a constant parade of boats going by, access to the water for kayaking and swimming, the change of tides presenting an ever changing view of the marsh, the wrap around porch with indoor, screened in and open air sections and the lawn and dock. Our family returned this year for the second time and enjoyed the house even more.
From a partner site

8/10 Good

Location

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: This property has the perfect location for our family. Screened porch and outdoor porch. Beautiful lawn, dock and parking. The views and sunset incredible. The overall house could use some updating, but that did not bother us. We could love to come back again.
From a partner site

8/10 Good

Relaxing on the Annisquam

Rating Details: The property manager was more than helpful. The vacation rental was very clean. I was more than happy with the location. I was more than satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Amazing sunsets. Beautiful water views. Watching the boats pass by was very relaxing.House was very comfortable and large enough to accommodate friends and family.Kitchen and Upstairs bathroom could use a little updating.Wish we could have stayed longer!!Hope to be back next summer!
Response from VrboOwner on 10 Dec 2020
Thank you for taking the time to share your feedback on your stay. Glad to hear that you, your family and friends had a relaxing time on vacation. We will share your recommendations for improvements with the homeowners. We hope to welcome you back next summer!
From a partner site

10/10 Excellent

Awesome Weekend

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Annisquam Singing Pines was perfect for our daughter’s wedding weekend! The lighting in various rooms was gorgeous for pictures! We had ample space for dressing, relaxing, and playing before the wedding. We all agreed that the lime green counter tops added to the charm of the house. Would definitely recommend or stay again!
Response from VrboOwner on 9 May 2022
Thank you for sharing your experience with us. We are glad that you and your family had an awesome weekend! We hope to see you and your family next year!
From a partner site

8/10 Good

Gloucester get-away

Rating Details: The property manager was more than helpful. The vacation rental was clean. I was more than happy with the location. I was somewhat dissatisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Great location
From a partner site

8/10 Good

Singing Pines

Rating Details: The property manager was more than helpful. The vacation rental was spotless. I was very happy with the location. I was satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Lovely location atop a steep bluff to watch the boaters glide by, a dock to moor our raft, and calm low tide for morning swims. The house has old world charm and, while not updated, had plenty of floor space inside and outside on the three porches. We did ask for and received an A/C unit for the bottom floor after being surprised that it is not standard with the property; fans only downstairs. Made the short trip to Rockport for steamed lobsters which we ate on the back porch. The grass was long and bugs were out so bug spray is recommended. Overall, a great first north shore experience.
Stayed 4 nights in Jul 2018
From a partner site

10/10 Excellent

Perfect Location with a wonderful view

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: The house is old but extremely well equipped. The view is the most amazing I ever had. There is a lot of space for a group of eight with places to sit and rest.
Response from VrboOwner on 11 Dec 2020
We are glad to hear that you enjoyed your time staying at Annisquam Singing Pines. We agree that the view is quite exquisite. We look forward to welcoming you back in the future!
Archival

10/10 Excellent

The Bates Cottage-Singing Pines

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: This historic home has been beautifully maintained. It is filled with all the charm and history of an old house but has all the modern conveniences. The sunsets over the dock were spectacular. Many places to just sit and wonder at the surroundings. The rental agency went well above expectation--a tote bag of necessities plus a bottle of wine with 2 Singing Pine Glasses. Very easy check in and out with great website. Would highly recommend for a large get together. Beds were very comfortable and the grill was perfect for a late day cookout. Not to be missed the next time in the Gloucester area. Great restaurants in Gloucester and Rockport--especially Rudders, the Gloucester House and My Place by the Sea in Bearskin Neck.
Archival

10/10 Excellent

Annjsquam Singing Pines stay

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Our stay was quite pleasant. The house was immaculate. Everything was in its proper place and ready for us to spend relaxing two week vacation. Since this was our second year at Annisquam Singing pines the improvements from the previous year were greatly appreciated.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 2 nights in Sep 2025
Tell us how we can improve our siteShare feedback