
Penzance Road, MA
10/12 – 10/23
$309/nighttotal: $3399 (11 )
Long Beach Suites: 3 Mins Toes To Sand!
1 3apartment , Gloucester
This Gloucester rental is conveniently located within one mile of Good Harbor Beach and Long Beach, and three miles from Cape Hedge Beach, offering easy access to Gloucester's popular coastal attractions.
The apartment features a fully equipped kitchen with a refrigerator, microwave, and dishwasher, a private balcony, in-unit laundry, and on-site parking; it also includes internet access and is perfect for travelers seeking a comfortable and convenient stay near Gloucester's beaches and Schooner Adventure.
The apartment features a fully equipped kitchen with a refrigerator, microwave, and dishwasher, a private balcony, in-unit laundry, and on-site parking; it also includes internet access and is perfect for travelers seeking a comfortable and convenient stay near Gloucester's beaches and Schooner Adventure.

Penzance Road, MA
10/16 – 10/23
$388/nighttotal: $2716 (7 )
The Bookstore|king Beds|walk2beach|private Parking
1 3apartment , Rockport
This Rockport apartment rental is centrally located in downtown, steps from Front Beach and Bearskin Neck, offering easy access to cafes, restaurants, shops, and the Shalin Liu Performance Center, and a 10-minute walk from the commuter rail to Boston. This two-bedroom, one-bathroom unit sleeps four guests and features a fully equipped kitchen, two king-size beds, off-street parking (a rare find!), and a convenient EV charging station nearby.

Penzance Road, MA
06/23 – 07/01
$557/nighttotal: $4456 (8 )
Downtown Coastal Views And Parking
1 4apartment , Gloucester
This Gloucester ground-floor apartment, located in historic Gloucester, is a short walk from downtown restaurants and shops.
This pet-friendly rental boasts two bedrooms, one bathroom, and sleeps up to six guests comfortably, featuring a queen bed, full-over-twin bunk bed, and a queen Murphy bed, along with a fully equipped kitchen, private deck with harbor views, in-unit laundry, and designated parking.
This pet-friendly rental boasts two bedrooms, one bathroom, and sleeps up to six guests comfortably, featuring a queen bed, full-over-twin bunk bed, and a queen Murphy bed, along with a fully equipped kitchen, private deck with harbor views, in-unit laundry, and designated parking.

Penzance Road, MA
10/16 – 10/23
$206/nighttotal: $1442 (7 )
Ocean Breeze / 8 Min Walk To Beach
1 3apartment , Gloucester
This Gloucester rental is a private lower unit in a two-unit house, located an 8-minute walk from Gloucester's beaches and a 50-minute drive from Boston.
The fully furnished one-bedroom apartment sleeps 4 guests, features a king-size bed, queen-size sofa bed, private backyard with grill and fire pit, free parking, and includes Wi-Fi, laundry, and all utilities.
The fully furnished one-bedroom apartment sleeps 4 guests, features a king-size bed, queen-size sofa bed, private backyard with grill and fire pit, free parking, and includes Wi-Fi, laundry, and all utilities.

Penzance Road, MA
10/16 – 10/23
$350/nighttotal: $2450 (7 )
Vintage Rockport Escape
3 3house , Rockport
This Rockport vacation home is conveniently located within a short walk of both Front Beach and Back Beach, offering easy access to the beautiful Rockport coastline. The house has earned excellent ratings for its location, cleanliness, and overall guest experience.
This 3-bedroom house can comfortably accommodate up to 6 guests and features a fully equipped kitchen, a private patio, and a children's playground. Enjoy amenities like air conditioning, a swimming pool, free Wi-Fi, and the option to bring your pets along.
This 3-bedroom house can comfortably accommodate up to 6 guests and features a fully equipped kitchen, a private patio, and a children's playground. Enjoy amenities like air conditioning, a swimming pool, free Wi-Fi, and the option to bring your pets along.

Penzance Road, MA
10/16 – 10/23
$391/nighttotal: $2737 (7 )
Family Friendly Home|walk To Ocean+downtown Rkpt
2 3house , Rockport
This Rockport vacation home is located 1.1 miles from Front Beach and offers easy walking access to downtown Rockport's shops and restaurants.
This spacious 1690 sq ft, 2-bedroom, 2-bathroom rental accommodates up to 7 guests and includes a fully equipped kitchen, free WiFi, and a private patio.
This spacious 1690 sq ft, 2-bedroom, 2-bathroom rental accommodates up to 7 guests and includes a fully equipped kitchen, free WiFi, and a private patio.

Penzance Road, MA
10/16 – 10/23
$410/nighttotal: $2870 (7 )
The Bookstore · Private Parking · King Beds · Downtown Rockport
2 3apartment , Rockport
This Rockport apartment, located in a renovated historic bookstore in downtown Rockport, offers unparalleled access to Front Beach, Bearskin Neck's shops and restaurants, and the Shalin Liu Performance Center.
The two-bedroom, one-bathroom unit sleeps four guests and features a fully equipped kitchen, high-speed Wi-Fi, a 4K Smart TV, in-unit laundry, and two reserved off-street parking spaces—a rare find in downtown Rockport—plus convenient access to an EV charging station.
The two-bedroom, one-bathroom unit sleeps four guests and features a fully equipped kitchen, high-speed Wi-Fi, a 4K Smart TV, in-unit laundry, and two reserved off-street parking spaces—a rare find in downtown Rockport—plus convenient access to an EV charging station.

Penzance Road, MA
10/12 – 10/23
$339/nighttotal: $3729 (11 )
The Orca – Modern Coastal Comfort Awaits
2 3apartment , Rockport
This Rockport apartment rental is located on Bearskin Neck, steps from the harbor and within walking distance of Front Beach, Old Garden Beach, and the Shalin Liu Performance Center.
The one-bedroom unit, featuring a queen bed and bunk beds, sleeps four and includes a kitchen, air conditioning, parking, and internet access; enjoy easy access to shops, restaurants, and the area's many attractions.
The one-bedroom unit, featuring a queen bed and bunk beds, sleeps four and includes a kitchen, air conditioning, parking, and internet access; enjoy easy access to shops, restaurants, and the area's many attractions.

Penzance Road, MA
06/24 – 07/04
$1403/nighttotal: $14030 (10 )
Secluded, 180 Degree View Of Wingaersheek Beach From High Up On The Dunes
1 2apartment , Gloucester
This modern home is located on a hilltop overlooking Wingaersheek Beach, just a 500-yard walk through sand dunes from the beach. The apartment is rated excellent by previous guests.
The home has 3 bedrooms and 2 bathrooms, comfortably accommodating up to 6 guests. Enjoy the spacious outdoor living area, complete with a deck, gas grill, fire pit, and a fully equipped kitchen with a dishwasher.
The home has 3 bedrooms and 2 bathrooms, comfortably accommodating up to 6 guests. Enjoy the spacious outdoor living area, complete with a deck, gas grill, fire pit, and a fully equipped kitchen with a dishwasher.

Penzance Road, MA
06/23 – 07/01
$461/nighttotal: $3688 (8 )
Charming Central Apartment On Bearskin Neck
1 4apartment , Rockport
This Rockport apartment rental is centrally located on Bearskin Neck in the historic colonial district, steps from beaches and close to shops, restaurants, and galleries.
The three-bedroom, one-bathroom unit sleeps five, features a kitchen with a fridge and microwave, in-unit laundry, air conditioning, and is near kayaking, schooner tours, and whale watching.
The three-bedroom, one-bathroom unit sleeps five, features a kitchen with a fridge and microwave, in-unit laundry, air conditioning, and is near kayaking, schooner tours, and whale watching.

Penzance Road, MA
06/23 – 07/01
$1394/nighttotal: $11152 (8 )
Mansion In Gloucester With Pool
1 4apartment , Gloucester
This luxurious home is located in a quiet, coveted neighborhood in Gloucester, just a short walk from the waterfront and Niles Beach. The property has received excellent ratings for location, cleanliness, and overall user experience.
This four-bedroom, four-bathroom mansion can comfortably accommodate up to 12 guests. Enjoy the private pool, tennis/pickleball court, spacious deck, and a fully equipped kitchen with modern appliances.
This four-bedroom, four-bathroom mansion can comfortably accommodate up to 12 guests. Enjoy the private pool, tennis/pickleball court, spacious deck, and a fully equipped kitchen with modern appliances.

Penzance Road, MA
06/23 – 07/01
$824/nighttotal: $6592 (8 )
Stately 2br Apartment With Walls Of Windows & Ac
2 4apartment , Gloucester
This downtown Gloucester condo offers a prime location, just steps from dining, shopping, and entertainment, with proximity to beachcombing and whale watching excursions.
This 2-bedroom, 2-bathroom condo sleeps 4 guests and features central air conditioning, complimentary WiFi, a full kitchen with a dishwasher and microwave, and free parking for one vehicle.
This 2-bedroom, 2-bathroom condo sleeps 4 guests and features central air conditioning, complimentary WiFi, a full kitchen with a dishwasher and microwave, and free parking for one vehicle.









