Search Gloucester pet friendly vacation rentals
Our top choices for a great stay

Private riverfront home with tidal dock, Annisquam Singing Pines
Stay at this vacation home in Gloucester. Enjoy a garden, laundry facilities, and cable/satellite TV service. Popular attractions Wingaersheek Beach and Good ...
10/10 Exceptional! (1 review)

Steps to Wingaersheek's Private 1.5 Mile White Dune Beach
Stay at this vacation home in Gloucester. Enjoy free WiFi, laundry facilities, and cable/satellite TV service. Popular attractions Wingaersheek Beach and Good ...
9.8/10 Exceptional! (36 reviews)

LABOR DAY SPECIAL: Save 10%! Come enjoy last weekend of summah on PRIVATE beach!
Stay at this vacation home in Gloucester. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Good Harbor Beach and Wingaersheek Beach are ...
9.8/10 Exceptional! (13 reviews)

Cape Ann, Annisquam panoramic ocean views from every room.
Stay at this vacation home in Gloucester. Enjoy a garden, laundry facilities, and patios. Popular attractions Wingaersheek Beach and Good Harbor Beach are located ...
9.6/10 Exceptional! (31 reviews)

Beach Life Bliss - steps to the beach
$428 nightly
The price is $478 total per night from Oct 19 to Oct 20
$478 total
Oct 19 - Oct 20
Total with taxes and fees
Stay at this vacation home in Gloucester. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Wingaersheek Beach and Cape Ann are located ...
9.6/10 Exceptional! (39 reviews)

Peaceful centrally located home: w/ yard & walking distance to town
Stay at this vacation home in Gloucester. Enjoy a garden, laundry facilities, and patios. Popular attractions Wingaersheek Beach and Good Harbor Beach are located ...
9.2/10 Wonderful! (5 reviews)

Cozy Beach cottage walkable to Good Harbor and Long Beach
Stay at this vacation home in Gloucester. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Good Harbor Beach and Cape Ann are located ...

Perrywinkle: Waterfront on Gloucester’s Rocky Neck.
Stay at this vacation home in Gloucester. Enjoy a garden, laundry facilities, and patios. Popular attractions Good Harbor Beach and Wingaersheek Beach are located ...

Antique Cottage RARE PRIVATE SAUNA Lighthouse Beach Nearby Trails Firepit
Stay at this vacation home in Gloucester. Enjoy free WiFi, a sauna, and a garden. Popular attractions Wingaersheek Beach and Good Harbor Beach are located ...

Wingaerchic: Woodsy retreat in West Gloucester
Stay at this vacation home in Gloucester. Enjoy laundry facilities, tennis courts, and patios. Popular attractions Wingaersheek Beach and Good Harbor Beach are ...
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.