Pet-friendly vacation rentals in Gloucester

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Top-rated pet-friendly home rentals in Gloucester

Guests agree: these pet-friendly homes are highly rated for location, cleanliness, and more.

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Guest favorite
Condo in Gloucester
4.96 out of 5 average rating, 180 reviews

KeyWest Vibe, PrivatePatio, Close2Salem, WalkDWNTN

🏖️Looking for the perfect Gloucester retreat for your group or family?🌴 Look no further than this spacious and inviting 2-bedroom unit🛏️, ideal for families and groups seeking comfort, style, and ample room to relax🛋️✨. Step inside and be greeted by a bright and airy living area🛋️, perfect for gathering together after a day of exploring all that Gloucester has to offer 🚤🏞️. With comfortable furnishings 🪑 and modern amenities📺🍽️, this unit provides the ultimate vacation experience🌴🍹.

Top guest favorite
A spacious studio features a queen bed dressed in soft linens against a wooden beam ceiling. A cozy sofa provides seating, while a dark coffee table sits in the center. Two windows allow natural light to enter, alongside artwork adorning the walls.
Apartment in Salem
4.96 out of 5 average rating, 563 reviews

Charming Studio downtown Salem, MA *Parking

This adorable renovated studio is everything you need for your stay in Salem,MA. Centrally located, within 2 blocks from the train station -that takes you to the North Station in Boston in about 35 minutes - walking distance to most attractions, museums, restaurants, coffee shops... Queen bed, sofa, TV/internet, bathroom and fully equipped kitchen! Self check in with keypad. Private entrance in the back of the building. REG ID#1027 OCCUPANCY:2 GUESTS 1 OFF STREET PARKING during your stay 24-3

Superhost
A comfortable living area features a plush L-shaped sofa adorned with decorative pillows. A stylish coffee table is situated on a patterned area rug. A full-size mirror and a workspace with a desk and chair are visible, providing a functional and inviting atmosphere.
Apartment in Beverly
4.84 out of 5 average rating, 194 reviews

Charming Downtown Gem ~ 2min to Salem ~ Workspace!

Step into the modern and comfortable 2BR 1Bath apartment nestled in the picturesque downtown of Beverly, MA. It offers a relaxing getaway near excellent restaurants, shops, attractions, landmarks, major hospitals, and colleges, making it ideal for leisure and business guests. Stylish design and a rich amenity list will satisfy your every need. ✔ Two Comfortable Bedrooms ✔ Fully Equipped Kitchen ✔ Smart TV ✔ Workspace ✔ High-Speed Wi-Fi ✔ Free parking but only on Street; No dedicated parking

Guest favorite
A light-filled living area is arranged with a spacious sofa adorned with colorful cushions. A round coffee table sits at the center, complemented by a textured area rug. There are large windows allowing natural light, and decorative elements enhance the cozy ambiance.
Apartment in Rockport
4.98 out of 5 average rating, 114 reviews

Downtown 1 bedroom w parking

Enjoy our fully refurbished historical home located in the heart of the coastal town of Rockport, Massachussetts. Perfect for couples or small families. This cozy basement unit offers a comfortable stay with with parking and a new kitchen, bathroom and washer and dryer, Our unit features a bedroom with a comfortable king size bed, The living space is tastefully decorated with a queen sofa bed. Walk to the beach, Bearskin neck, restaurants, Shalin Liu music center, art galleries and shops.

Top guest favorite
A cozy living area features a gray sofa adorned with assorted pillows. A natural wood coffee table sits in front, complemented by a minimalist dining table and chairs. Exposed brick walls and wooden beams create a rustic backdrop, with natural light streaming through nearby windows.
Apartment in Rockport
4.9 out of 5 average rating, 147 reviews

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!

Top guest favorite
A cozy outdoor seating area overlooks the water, featuring two wicker chairs and a matching sofa arranged around a low table. A striped area rug anchors the space. The railing provides an unobstructed view of the rocky coastline and distant shoreline.
Apartment in Rockport
4.99 out of 5 average rating, 145 reviews

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!

Top guest favorite
The historic carriage house is presented in a charming turquoise color, surrounded by lush greenery and flowering plants. Tall windows provide ample natural light. A spacious yard is visible, framed by a low stone wall and iron fence.
Guesthouse in Rockport
4.99 out of 5 average rating, 149 reviews

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!

Top guest favorite
A charming white house is positioned along a rocky shore, showcasing a four-season porch with large windows that provide views of the harbor. Lush greenery surrounds the property, complementing the tranquil water scene with boats in the distance.
Home in Gloucester
4.93 out of 5 average rating, 175 reviews

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.

Top guest favorite
The great room is highlighted by 25-foot ceilings and panoramic windows offering views of the ocean. A large sectional sofa surrounds a coffee table, while a flat-screen TV is mounted above the fireplace. Sliding glass doors lead to an outdoor space, enhancing the airy feel.
Home in Swampscott
4.91 out of 5 average rating, 117 reviews

Ocean Views at Casa de Mar near Salem & Boston

Relax and unwind at Casa de Mar - our 3 bedroom, 3 full bathroom ocean front home on the North Shore. Close to Salem and Boston, overlooking Swampscott Bay to Nahant. The great room has 25' ceilings, a 70" flat screen TV, and 2 seating areas. Modern kitchen. The master bedroom has a king-sized bed, sitting area, flat screen TV, private balcony, and en suite bath. The first floor bedroom has a queen bed and a private balcony. The third bedroom has a queen bed and en suite bath.

Guest favorite
A light-filled living area features a pull-out sofa adorned with striped cushions and a coffee table with a decorative book and lamp. A sliding glass door opens to a sleeping area with a spacious bed, while bright curtains frame the window, offering a view of the exterior.
Guest suite in Lakeside Marblehead
4.9 out of 5 average rating, 293 reviews

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.

Guest favorite
A bright living area features large windows allowing natural light to fill the space. A comfortable sofa and a cozy armchair sit on a patterned rug, with a wooden coffee table in between. A dining table is visible in the background, creating a welcoming atmosphere.
Apartment in Gloucester
4.93 out of 5 average rating, 128 reviews

Walk to Good Harbor Beach

Newly renovated ground floor efficiency apartment with sliders/walkout to fenced backyard. Wifi and Netflix included. Most dogs okay, some breed restrictions apply. If you want to bring your dog please contact us prior to booking. Three night minimum for all stays. Space includes 1 bedroom with Queen size bed and Living Area with pull out couch. 2 adults will be most comfortable. 5 minute walk to Good Harbor Beach or Bass Rocks. 15 minute walk to Rocky Neck.

Top guest favorite
A charming log cabin is surrounded by lush greenery. Two miniature horses graze leisurely on the grass in front of the cabin, which features a covered porch and simple landscaping with flowers. Sunlight filters through the trees, highlighting the serene woodland setting.
Cabin in Rockport
4.97 out of 5 average rating, 482 reviews

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.

Popular amenities for Gloucester pet-friendly home rentals

When is the best time to visit Gloucester?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceR3,110 ZARR2,934 ZARR2,966 ZARR3,607 ZARR4,008 ZARR5,066 ZARR5,451 ZARR5,707 ZARR4,457 ZARR4,890 ZARR3,671 ZARR3,559 ZAR
Avg. temp-1°C0°C4°C9°C15°C20°C23°C23°C19°C13°C7°C2°C

Quick stats about vacation rentals that are pet-friendly in Gloucester

  • Total vacation rentals

    Explore 170 vacation rentals in Gloucester

  • Nightly prices starting at

    Gloucester vacation rentals start at R962 ZAR per night before taxes and fees

  • Verified guest reviews

    Over 6,520 verified reviews to help you choose

  • Family-friendly vacation rentals

    120 properties offer extra space & kid-friendly amenities

  • Rentals with dedicated workspaces

    80 properties have a dedicated workspace

  • Wi-Fi availability

    160 of Gloucester vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Gloucester rentals

  • 4.8 Average rating

    Gloucester stays are highly rated by guests—averaging 4.8 out of 5!