Entire home

Annisquam Singing Pines: Riverfront Splendor

Riverside holiday home in Gloucester with kitchen

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.

Overview
Amenities
Policies
Location

Wonderful

5 bedrooms2 bathroomsSleeps 102418 sq ft

Popular amenities

Washer
Parking available
Kitchen
Pet-friendly
Barbecue grill
Air conditioning

Explore the area

Gloucester, MA

Place, Hammond Castle
Place, Good Harbor Beach
‪7 min drive‬
Place, Wingaersheek Beach
‪11 min drive‬
Airport, Boston, MA (BOS-Logan Intl.)
‪50 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.

Add dates for prices

Amenities

Kitchen

Washing machine

Pet-friendly

Air conditioning

Outdoor space

Water view

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Kitchen
Washer
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House Rules

Check in after 4:00 PM

Minimum age to rent: 25

Check out before 10:00 AM

Children

Children allowed: ages 0–17

Events

No events allowed

Pets

Pets allowed

Smoking

Smoking is not permitted

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

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

Property Registration Number C0164051070

About the area

Gloucester

Located in Gloucester, this holiday home is on the waterfront. The area's natural beauty can be seen at Good Harbor Beach and Wingaersheek Beach. Maritime Gloucester and Schooner Adventure are also worth visiting.

View more Holiday homes in Gloucester

Gloucester, MA

What's nearby

Maritime Gloucester - 6 min drive - 4.6 km
Half Moon Beach - 6 min drive - 4.6 km
Good Harbor Beach - 7 min drive - 6.8 km
Rocky Neck Art Colony - 8 min drive - 6.4 km
Wingaersheek Beach - 11 min drive - 8.2 km

Getting around

Gloucester Station - 4 min drive
Beverly, MA (BVY-Beverly Municipal) - 22 min drive

Restaurants

‪McDonald's - ‬5 min drive
‪Starbucks - ‬6 min drive
‪Dunkin' - ‬4 min drive
‪George's Coffee Shop - ‬4 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.

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

9.2

Wonderful

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.

Learn more

10/10

Cleanliness

10/10

Check-in

8.0/10

Communication

10/10

Location

6.0/10

Listing accuracy

6/10 Okay

Robert Q.

17 Sept, 2025

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

This review comes from a trusted partner site and has not been verified.

8/10 Good

Cheryl A., North Las Vegas

7 Sept, 2019

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!

This review comes from a trusted partner site and has not been verified.

10/10 Excellent

heather w.

3 Oct, 2020

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.

10/10 Excellent

Sheri G.

8 Oct, 2021

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

This review comes from a trusted partner site and has not been verified.

8/10 Good

heather w.

29 Sept, 2021

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.

This review comes from a trusted partner site and has not been verified.

8/10 Good

Nancy B., Odessa, TX

26 Aug, 2021

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.

This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Karen N.

7 Aug, 2019

Awesome Weekend

This review comes from a trusted partner site and has not been verified.

8/10 Good

Elizabeth E., Vermont

5 Aug, 2019

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

This review comes from a trusted partner site and has not been verified.

8/10 Good

Karen P.

4 Aug, 2018

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

This review comes from a trusted partner site and has not been verified.

10/10 Excellent

A guest from ,

20 Jun, 2018

Perfect Location with a wonderful view

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

10/10 Excellent

6 Oct, 2017

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.

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

10/10 Excellent

Todd A., Boston

2 Aug, 2017

Annjsquam Singing Pines stay

About the host

Hosted by Atlantic Vacation Homes

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.

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