House in Gloucester, MA
10 guests · 5 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
Top-tier experienceA high end property in this area
About this house rental
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.
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.
Amenities at Annisquam Singing Pines: Riverfront Splendor
Non-smoking
Pets allowed
Family friendly
Map of Gloucester, MA
Ratings and reviews
Summary of reviewsGuests thoroughly enjoyed their stay at Singing Pines, highlighting the ever-changing riverside view, comfortable living spaces, ample serving pieces for meals, and helpful property manager. They can't wait to return.
10 / 10Outstanding·Oct 2021
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!
8 / 10Excellent·Sep 2021
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.
8 / 10Excellent·Aug 2021
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.
6 / 10Average·Sep 2025
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!!!
$$$$
Top rated by guests
9.2Outstanding
(14 Ratings)
Guests thoroughly enjoyed their stay at Singing Pines, highlighting the ever-changing riverside view, comfortable living spaces, ample serving pieces for meals, and helpful property manager. They can't wait to return.
From real guest reviews summarized by AIDon't miss out! Price and availability may change
