Search Gloucester pet friendly vacation rentals

Our top choices for a great stay

Private riverfront home with tidal dock, Annisquam Singing Pines

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)
Opens in a new windowPrivate riverfront home with tidal dock, Annisquam Singing Pines
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 Good ...
9.8/10 Exceptional! (36 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 Good Harbor Beach and Wingaersheek Beach are ...
9.8/10 Exceptional! (13 reviews)
Opens in a new windowLABOR DAY SPECIAL: Save 10%! Come enjoy last weekend of summah on PRIVATE 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! (31 reviews)
Opens in a new windowCape Ann, Annisquam panoramic ocean views from every room.
Beach Life Bliss - steps to the beach

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)
Opens in a new windowBeach Life Bliss - steps to the beach
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 Wingaersheek Beach and Good Harbor Beach are located ...
9.2/10 Wonderful! (5 reviews)
Opens in a new windowPeaceful centrally located home: w/ yard & walking distance to town
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 ...
Opens in a new windowCozy Beach cottage walkable to Good Harbor and Long Beach
Perrywinkle: Waterfront on Gloucester’s Rocky Neck.

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 ...
Opens in a new windowPerrywinkle: Waterfront on Gloucester’s Rocky Neck.
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
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 Good Harbor Beach are ...
Opens in a new windowWingaerchic: Woodsy retreat in West Gloucester
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.