Apartment holiday rentals in Gloucester

Captains Quarters- Coastal Retreat Walk To Beach

Stay just steps from Rockport’s beautiful beaches, shops, and dining in this charming coastal retreat. Perfect for couples or small families, Captain’s Quarters offers comfort, convenience, and classic seaside charm in an unbeatable walkable location. Spend your days at Front Beach, exploring Bearskin Neck’s galleries and boutiques, or enjoying fresh seafood by the harbor — all within easy walking distance. Return to a peaceful space designed for relaxation after a day by the ocean. Inside you

Family · Value · Bathroom

4 Bed Water View w/ Parking

Your family and friends will be close to everything when you stay at this centrally-located home. Steps to the Ocean and walk into historic Bearskin Neck. Enjoy panoramic coastal views from the family room, kitchen and master bedroom. Deck space to enjoy outdoor dining, glass of wine, or a morning cup of coffee. Everything to do in Rockport is a short walk from this downtown home. Restaurants and coffee shops, Art Galleries, shopping and the town beaches are steps away. Parking spots included.

Family · Location · Pets

The Bookstore|King Beds|Walk2Beach|Private Parking

Inquire about our winter rental rates! KEY FEATURES: • Newly furnished and professionally designed space! • Steps to Front Beach, Bearskin Neck cafes, restaurants, boutiques, art shops, and the Shalin Liu Performance Center. • Private off street parking spots for 2 cars • High Speed Wi-Fi • 10 minute walk from commuter rail to Boston • Smart TV equipped to stream all your favorites • Fully stocked kitchen • 2 Comfortable KING memory foam beds • Convenient EV charging right across the street!

Location · Family · Wifi

3 Bedroom Apartment with parking on Bearskin Neck

Built in 1822, the Sound House is conveniently located on Bearskin Neck. The upstairs apartment is renovated with brand new oak floors, new bathrooms, and updated living area. The unit features 3 bedrooms and 2 full bathrooms, with laundry as well as 3 parking spaces in the back of the building. The kitchen includes cooking utensils, with an electric grill and butane burner for outdoor cooking on the new deck overlooking Cape Ann. Enjoy Rockport while creating new memories at the Sound House!

Family · Value · Heating

Amazing Ocean View In-Law Apt.

Step into a breath-taking magical seaside residence with 180-degree ocean views. This private in-law apartment has a sprawling lawn, steps to the ocean, and landscaped gardens. The apartment has one queen size bed with sliding doors opening out to the lawn, a queen pullout couch, granite counter-top complete kitchen including micro and dishwasher, ping-pong table, flat screen TV, home office and bathroom/ shower. The apartment has been thoroughly cleaned and meets all covid-19 standards.

Location · Value · Long stay

Old Harbor

Right on the Old Harbor on Bearskin Neck, a 2 story light, airy apartment just steps from shops, restaurants, and beaches-the top two floors of the building. Amazing views from large bay windows, enormous deck complete with table and chairs. Two beds (1 Queen, 1 Full) + a full-size pullout sofa. One on-site parking space for a small to mid-size car. Mini-split A/C units on each floor. Bring your kayak or paddleboard, step down 3 stairs and you are in the water! Have a good swim!

Value · Location · Indoor spaces

Mary's By The Sea

A unique 650 square foot ground floor apt across the street from Front Beach. 6 minute walk from the Rockport MBTA . There is a separate bedroom with a queen mattress and a pullout sofa bed in the living area. The pullout sofa is best for teens or smaller kids . There is a bathroom with a sink and toilet. There is another room with a sink and shower. The kitchen area is more like a kitchenette than a full-size kitchen. We provide one parking spot next door at The Cove parking lot.

Family · Location · Hiking

The Crows Nest | Near Shops & Beaches

This charming New England style apartment, located on Main Street has lots to offer. Features include a full kitchen, living room, a bedroom with queen sized bed and soft décor, plus a fully private bathroom and plush towels. Enjoy the spacious living room filled with natural light. Includes a private entrance and wrap-around porch overlooking beautifully maintained grounds. Parking. A 10 minute walk to the Bearskin Neck, shops and beaches, and a 5 minute walk to the train station.

Location · Value · Parking

Walk To Downtown and Ocean, Large Private Yard

Private Two Bedroom with Backyard -1 mile walk to historic downtown Rockport; shops and restaurants -1 mile walk to Front Beach, very family friendly -Fast Wifi, 2 Queen Beds, kitchenette with coffee and tea -Quiet, private yard space with firepit - very cozy! -Family friendly space! -Off street parking for 2 cars -Walking distance to town EV chargers Follow us @highsthavenrockport

Family · Location · Beach

Long Beach Suites: Steps Away From Surf!

Recently built, Long Beach Suites is ready to welcome you this summer. With peaks of Long Beach, come stay in one of our two bedroom apartment suites. Expertly built with summer visitors in mind. Long Beach Suites is just steps away from Long Beach in Rockport and only ten minutes to Good Harbor. You will be staying one of four similar apartments, photos may not be of exact unit.

Location · Value · Indoor spaces

The Gilbert: 1-Bed downtown suite, walk to beach.

Come stay in Gloucester’s historic downtown district, in St. Peter’s Square, just one block from Pavilion Beach, Stacey Boulevard and the historic West End of Main Street. The Gilbert sleeps two (up to 3 with an air mattress). A perfect getaway for those in love with history and seaside living. The unit has a private entrance, king sized bed, kitchenette and private bath.

Location · Comfort · Indoor spaces

Prime location to Beauport Hotel & Beach, Glo Apt

Located in the heart of historic Gloucester this two bedroom, fully furnished apartment is a 5 minute walk to the Beauport Hotel, beach, museums, shops, restaurants, train , boat shuttle, the famous "Man at the Wheel" Statue and much more. Dunkin Donuts and a mini mart on the same street. Please inquire about transportation options. Best Location on the island!

Location · Family · Laundry