Search Gloucester pet friendly vacation rentals

Our top choices for a great stay

Cozy Beach cottage walkable to  Good Harbor and Long Beach

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! (10 reviews)
Opens in a new windowCozy Beach cottage walkable to Good Harbor and Long Beach
Salt Island Views: 4-Season Beach House

Salt Island Views: 4-Season Beach House

Stay at this vacation home in Gloucester. Enjoy a garden, patios, and cable/satellite TV service. Popular attractions Good Harbor Beach and Cape Ann are located ...
10/10 Exceptional! (5 reviews)
Opens in a new windowSalt Island Views: 4-Season Beach House
Beach Life Bliss - steps to the beach

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 ...
9.8/10 Exceptional! (52 reviews)
Opens in a new windowBeach Life Bliss - steps to the beach
Cape Ann, Annisquam panoramic ocean views from every room.

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! (47 reviews)
Opens in a new windowCape Ann, Annisquam panoramic ocean views from every room.
SAVE 10%…Last minute special for this sunny beach weekend of July 24-26!

SAVE 10%…Last minute special for this sunny beach weekend of July 24-26!

Stay at this vacation home in Gloucester. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Good Harbor Beach and Wingaersheek Beach are ...
9.6/10 Exceptional! (18 reviews)
Opens in a new windowSAVE 10%…Last minute special for this sunny beach weekend of July 24-26!
Wingaerchic: Woodsy retreat right by the beach

Wingaerchic: Woodsy retreat right by the beach

Stay at this vacation home in Gloucester. Enjoy a garden, laundry facilities, and patios. Popular attractions Wingaersheek Beach and Crane Beach are located ...
8/10 Very Good! (5 reviews)
Opens in a new windowWingaerchic: Woodsy retreat right by the beach
Steps to Wingaersheek's Private 1.5 Mile White Dune Beach

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 Crane ...
Opens in a new windowSteps to Wingaersheek's Private 1.5 Mile White Dune Beach
Antique Cottage RARE PRIVATE SAUNA Lighthouse Beach Nearby Trails Firepit

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 ...
Opens in a new windowAntique Cottage RARE PRIVATE SAUNA Lighthouse Beach Nearby Trails Firepit
Annisquam Singing Pines: Riverfront Splendor

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 ...
Opens in a new windowAnnisquam Singing Pines: Riverfront Splendor
Joseph's Way: Woodsy Beach Retreat by Good Harbor Beach

Joseph's Way: Woodsy Beach Retreat by Good Harbor Beach

Stay at this vacation home in Gloucester. Enjoy a garden, laundry facilities, and cable/satellite TV service. Popular attractions Good Harbor Beach and Cape ...
Opens in a new windowJoseph's Way: Woodsy Beach Retreat by Good Harbor Beach
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.