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 Long Beach and Good Harbor Beach are located ...
10/10 Exceptional! (9 reviews)
Opens in a new windowCozy Beach cottage walkable to Good Harbor and Long Beach
Joseph's Way: Quiet Beach Retreat

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 Long ...
10/10 Exceptional! (2 reviews)
Opens in a new windowJoseph's Way: Quiet Beach Retreat
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 Coffins Beach and Wingaersheek ...
9.8/10 Exceptional! (39 reviews)
Opens in a new windowSteps to Wingaersheek's Private 1.5 Mile White Dune Beach
LABOR DAY SPECIAL: Save 10%! Come enjoy last weekend of summah on PRIVATE beach!

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 Gray Beach and Coolidge Reservation are located ...
9.8/10 Exceptional! (14 reviews)
Opens in a new windowLABOR DAY SPECIAL: Save 10%! Come enjoy last weekend of summah on PRIVATE beach!
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 Plum Cove Beach and Halibut Point Reservation ...
9.6/10 Exceptional! (41 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 Plum Cove Beach and Wingaersheek Beach are located ...
9.4/10 Exceptional! (32 reviews)
Opens in a new windowCape Ann, Annisquam panoramic ocean views from every room.
Peaceful centrally located home:  w/ yard & walking distance to town

Peaceful centrally located home: w/ yard & walking distance to town

2 out of 5
Stay at this vacation home in Gloucester. Enjoy a garden, laundry facilities, and patios. Popular attractions Stage Fort Park and Half Moon Beach are located ...
8.6/10 Excellent! (8 reviews)
Opens in a new windowPeaceful centrally located home: w/ yard & walking distance to town
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 Dogtown ...
8/10 Very Good! (2 reviews)
Opens in a new windowAnnisquam Singing Pines: Riverfront Splendor
Wingaerchic: Woodsy retreat in West Gloucester

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 Coffins Beach are located ...
7.6/10 Good! (4 reviews)
Opens in a new windowWingaerchic: Woodsy retreat in West Gloucester
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 Plum Cove Beach and Wingaersheek Beach are located ...
Opens in a new windowAntique Cottage RARE PRIVATE SAUNA Lighthouse Beach Nearby Trails Firepit
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.