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Annisquam Singing Pines: Riverfront Splendor

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Welcome to Annisquam Singing Pines!
Aptly named, this home is nestled in the pines.
Aerial view of Annisquam Singing Pines (starred) and the river.
Relax in the screened porch, perfect for quiet mornings or evenings.
Unwind while enjoying the fresh air and water views.

Reviews

9.0 out of 10
Wonderful
5 bedrooms2 bathroomsSleeps 10

Popular amenities

  • Kitchen
  • Washing machine
  • Pet-friendly
  • Air-conditioning
  • Outdoor space
  • Parking available

Explore the area

View map
Gloucester, MA
  • Place, Good Harbor Beach
    ‪9 min drive‬
  • Place, Wingaersheek Beach
    ‪12 min drive‬
  • Place, Boston Common
    ‪61 min drive‬
  • Airport, Boston, MA (BOS-Logan Intl.)
    ‪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

About this property

Annisquam Singing Pines: Riverfront Splendor

Experience a Classic Cape Ann Summer at Annisquam Singing Pines

Imagine spending your days swimming from the private dock at high tide or exploring the sandy shoreline at low tide. Launch a kayak or paddleboard from the beach and glide across the water to nearby islands or Wingaersheek Beach for a day of sun, surf, and adventure. Nestled on over an acre of waterfront land, Annisquam Singing Pines is a historic retreat that offers stunning river views, ample outdoor space, and charming indoor comforts—all designed to create unforgettable vacation memories.

Originally built as the summer home of Governor Bates, Massachusetts’ governor at the turn of the 20th century, this beautifully updated home seamlessly blends historic character with modern amenities. With five bedrooms and space for up to 10 guests, this is the perfect destination for family gatherings, friend getaways, or a relaxing waterfront escape.

Property Highlights:
Expansive Waterfront Property – Private dock, beach access, and panoramic views
Multiple Porches & Outdoor Living Spaces – Screened-in and open-air options
Renovated Kitchen (2023) – Fully equipped with modern appliances
Historic Charm Meets Modern Comforts – Updated interiors with original character
Prime Location – Easy access to Gloucester, Rockport, Salem, and Boston
Parking – There is off-street parking for up to 6 cars.

2,418 SF. No Smoking. No events or parties. No fire pits allowed.

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  • Washing machine
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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

Pets allowed
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Smoking

Smoking is not permitted

Important information

You need to know

Property Registration Number C0164051070
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
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher

About the area

Gloucester

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

What's nearby

  • Good Harbor Beach - 9 min drive - 7.5 km
  • Wingaersheek Beach - 12 min drive - 10.0 km
  • Boston Harbor - 58 min drive - 63.9 km
  • TD Garden - 59 min drive - 65.7 km
  • Boston Common - 61 min drive - 66.4 km

Getting around

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

Restaurants

  • ‪Dunkin' - ‬4 min drive
  • ‪McDonald's - ‬5 min drive
  • ‪Starbucks - ‬6 min drive
  • ‪The Open Door Food Pantry - ‬5 min drive
  • ‪George's Coffee Shop - ‬4 min drive

Frequently asked questions

Is Annisquam Singing Pines: Riverfront Splendor pet-friendly?

Yes, pets are allowed at this property.

How much does it cost to stay at Annisquam Singing Pines: Riverfront Splendor?

As of 5 May 2026, prices found for a 1-night stay for 2 adults at Annisquam Singing Pines: Riverfront Splendor on 22 May 2026 start from NZ$1,297, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

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 Cape Ann Museum. Sargent House Museum and Cape Ann Historical Museum are also within 3 miles (5 km).

Reviews

9.0

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. 7 out of 13 reviews
Rating 8 - Good. 5 out of 13 reviews
Rating 6 - Okay. 1 out of 13 reviews
Rating 4 - Poor. 0 out of 13 reviews
Rating 2 - Terrible. 0 out of 13 reviews

9.4/10

Cleanliness

7.4/10

Check-in

7.4/10

Communication

10/10

Location

7.4/10

Listing accuracy

Reviews

Verified

6/10 Okay

Robert Q.

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

8/10 Good

Cheryl A.

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!
From a partner site

10/10 Excellent

heather w.

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.
Verified

10/10 Excellent

Sheri G.

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

heather w.

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

Nancy B.

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

10/10 Excellent

Karen N.

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!
From a partner site

8/10 Good

Elizabeth E.

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

Karen P.

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

A guest from ,

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.
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

Todd A.

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

10/10 Excellent

Amy D.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 2 nights in Sep 2025

About the host

Hosted by Atlantic Vacation Homes

Host profile image
Atlantic Vacation Homes is the premier vacation home rental & real estate company on Boston's North Shore, with over 30 years of creating dream vacations for our guests. Situated a little more than a half-hour’s drive from downtown Boston, the North Shore is the ideal spot for an east coast vacation. We specialize in coastal vacation rentals for families, large groups, and anyone else who wants a beach vacation in Massachusetts.

Premier Host

They consistently provide great experiences for their guests
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