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

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 ...
10/10 Exceptional! (9 reviews)

Joseph's Way: Quiet Beach Retreat
Stay at this vacation home in Gloucester. Enjoy a garden, laundry facilities, and cable/satellite TV service. Popular attractions Good Harbor Beach and Cape ...
10/10 Exceptional! (2 reviews)

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! (39 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! (14 reviews)

Beach Life Bliss - steps to the beach
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! (40 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 ...
9.4/10 Exceptional! (32 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 ...
8.2/10 Very Good! (7 reviews)

Annisquam Singing Pines: Riverfront Splendor
Stay at this vacation home in Gloucester. Enjoy a garden, laundry facilities, and cable/satellite TV service. Popular attractions Wingaersheek Beach and Good ...
8/10 Very Good! (2 reviews)

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 ...
7.6/10 Good! (4 reviews)

Antique Cottage RARE PRIVATE SAUNA Lighthouse Beach Nearby Trails Firepit
$358 nightly
The price is $400 total per night from Nov 11 to Nov 12
$400 total
Nov 11 - Nov 12
Total with taxes and fees
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 ...
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.

