Pet-friendly holiday rentals in Gloucester

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.

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!

Gingerbread House | Hot Tub | Dog Friendly

Our historic carriage house in Downtown Rockport has everything you need for the perfect getaway, all year long! A two-minute walk to beaches, shops, galleries, parks, and playground. A peaceful family and pet-friendly space with all the amenities you need for a comfortable stay: laundry, full kitchen, queen sized bed with en-suite bathroom and a sun room that converts to an extra sleeping space perfect for kids. A 5 minute walk to the train for day trips to Salem, Gloucester, and Boston!

Retreat in the Trees- walk to Cape Hedge Beach

Cozy and comfortable summer home with lots of natural light and everything you need to make your stay enjoyable. Fully equipped kitchen, washer & dryer, air conditioning, gas grill, 3 decks, outdoor showers, high speed internet , over the air TV, Netflix, Prime Video. A short 5 minute walk to Cape Hedge Beach, 45 minute walk to Bearskin Neck. There is also lots of great sightseeing, history, boating, and restaurants all a short drive away. MA Room Occupancy Tax certificate C0104592520

Winery Studio w/ Private Hot Tub & Wine Tasting

Private Hot Tub, Vineyard Guesthouse at Winery. This former art studio is a true getaway to relax & feel at peace. Filled with natural light, it sits beside one of our historic 1800s barns on the winery property with vineyard views. Perfect for a romantic retreat or the traveling professional seeking a peaceful home away from home. Located in an affluent neighborhood minutes from shopping & restaurants. Your stay includes a complimentary wine tasting and 10% off all wine bottle purchases

Wonderful Rocky Neck home on Gloucester harbor

2 Bedroom with Loft, 1 Bathroom fully furnished Home on Gloucester harbor. Dead end street with 3 off street parking spots. Restaurants, local art gallery's, the beach all just a short walk away. Wake up with the sweet smell of ocean air and the sound of seagulls calling. Enjoy your breakfast with a million dollar view on the 4 season porch with 8 sliding windows overlooking the harbor. You could spend hours watching the boats go by as you read a good book with your fur baby on your lap.

Ocean Park Retreat

Bright and cheery 1 bedroom ground floor apartment with two+ car parking on quiet street in Marblehead's Ocean Park neighborhood, just steps from the ocean. Full size bed and pull-out full-size sofa in living room, private bathroom with in-floor heating, kitchenette with microwave, dishwasher, sink, double induction cook-top, refrigerator, and toaster oven. Laundry access. Walk to the waterfront, watch the sailboats drift by. Fifteen- minute walk to Historic town center.

Hillside Ocean View 2BR with Private Beach Access

Cozy, light-filled home just a 10-min walk to Pavilion Beach with access to private Clark Beach too. Open living space with ocean views, comfy seating, fast WiFi, and streaming. Enjoy sunrises from the queen bed in the main bedroom; second bedroom also has a queen. Fully equipped kitchen with lobster pot and dishwasher. Relax in the ocean-facing sunroom or grill on the balcony with stunning views. Perfect for families or small groups seeking a relaxing beach escape.

The Solar Powered Dogtown Cabin at Applecart Farm

Beautiful hand built very private cabin with master bedroom and large loft located deep in the woods of Cape Ann. Walking distance to down town Rockport and waterfront. Friendly miniature horses just 200 feet away that children love to visit. Applecart Farm is happy to have guests of diverse backgrounds and interests. Pets are allowed only with advanced request to ensure safety of guest and residents pets. NEM 1450 plug for EV charging.

Private Pool Retreat w/Fire Pit Near Singing Beach

Relax in a private coastal retreat with a pool and fire pit just minutes from Singing Beach. This updated suite offers a clean, modern layout with fireplace, comfortable sleeping space, and is ideal for relaxing stays or remote work. Enjoy a secluded backyard—rare this close to the beach. Located in Manchester-by-the-Sea near downtown, dining, and coastal views. Private entrance, free parking, and fast WiFi. Seasonal pool (5/20–9/8).

Ocean views! Welcome to Sea Breeze! Winter rates!

Sea Breeze offers a spacious, newly renovated, 4 bedroom escape, that smiles down upon Good Harbor beach. Take in the refreshing salt air breezes while enjoying the solitude of being situated at the end of a quiet cul de sac. A short 3-5 minute drive gets you into the Good Harbor parking lot or take a 20 minute walk instead. Close-by downtown Gloucester is teeming with spectacular restaurants and activities for the whole family.

Sweet short term rental in Rockport

Lovely hilltop unit located on private wooded property, steps away from 2 beaches. Built on a massive granite boulder, the property is one of kind with stunning seasonal views of the Atlantic. Fully equipped kitchen, flat screen TV, WiFi, and everything to make your stay pleasant and comfortable. We're a 7 minute drive from downtown Rockport and Gloucester, a 7 minute walk to Cape Hedge and Long Beaches.