Located on over an acre of waterfront land, Annisquam Singing Pines offers a serene retreat with lovely gathering spaces. Enjoy the huge lawn for games, sit in the shade on one of the screened or open porches and watch the river flow by, or take in sunsets from several peaceful spots around the property.
Reviews
9.09.0 out of 10
Wonderful
Entire home
5 bedrooms2 bathrooms225 sq m
Popular amenities
Kitchen
Washing machine
Pet-friendly
Air-conditioning
Outdoor space
Parking available
Add dates for prices
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.
Property amenities
Internet
Available in the house: WiFi
Parking and transport
Parking on site
Kitchen
Coffee/tea maker
Cookware, dishware, and utensils
Dishwasher
Hob
Microwave
Refrigerator
Toaster
Bedrooms
5 bedrooms
Bedsheets provided
Bathroom
2 bathrooms
Entertainment
TV with cable/satellite channels
Outdoor areas
Barbecue grill
Garden
Laundry
Laundry facilities
Washing machine
Work spaces
Desk
Comfort
Air conditioning
Pets
Pet friendly
Suitability/Accessibility
Smoke-free property
Location highlights
On a river
On the waterfront
Safety features
Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
Smoke detector (host has indicated there is a smoke detector on the property)
Fire extinguisher
General
Garden
Unit size: 2,418 square feet
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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
Pets
Pets are allowed
Service animals are welcome, and are exempt from fees
Children and extra beds
Children are welcome
Events
No events 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
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
Property Registration Number C0164051070
About the area
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. Visit our Gloucester travel guide
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 Cape Ann Museum. Sargent House Museum and Cape Ann Historical Museum are also within 3 miles (5 km).
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All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
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!!!
Robert Q.
Stayed 14 nights in Sep 2025
From a partner site
8/10 Good
Cheryl A.
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!
Cheryl A.
From a partner site
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.
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!
Sheri G.
Stayed 5 nights in Sep 2021
From a partner site
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.
heather w.
From a partner site
8/10 Good
Nancy B.
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.
Nancy B.
From a partner site
10/10 Excellent
Karen N.
7 Aug 2019
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!
Karen N.
From a partner site
8/10 Good
Elizabeth E.
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
Elizabeth E.
From a partner site
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.
Karen P.
Stayed 4 nights in Jul 2018
From a partner site
10/10 Excellent
A guest from ,
20 June 2018
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.
A guest from ,
Archival
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.
Archival
10/10 Excellent
Todd A.
2 Aug 2017
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.