
Pet-friendly vacation rentals in Gloucester
Find and book unique pet-friendly homes on Airbnb
Quick stats about vacation rentals that are pet-friendly in Gloucester

Total vacation rentals
Explore 180 vacation rentals in Gloucester

Nightly prices starting at
Gloucester vacation rentals start at R 961 ZAR per night before taxes and fees

Verified guest reviews
Over 6,640 verified reviews to help you choose

Family-friendly vacation rentals
140 properties offer extra space & kid-friendly amenities

Rentals with dedicated workspaces
90 properties have a dedicated workspace

Wi-Fi availability
180 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!
Top-rated pet-friendly home rentals in Gloucester
Guests agree: these pet-friendly homes are highly rated for location, cleanliness, and more.

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.

Oceanfront Retreat | Salem 7 min by train
Relax at Casa de Mar, our 3 bedroom / 3 full bathroom oceanfront North Shore home with panoramic views of Swampscott Bay to Nahant. Walk to the train — downtown Salem in 7 min, Boston in 23 min. Enjoy a bright great room with 25’ ceilings, 70” TV, and modern kitchen. The master bedroom has a king bed, sitting area, TV, private balcony, and en suite bath. The first floor queen bedroom has a private balcony. The third queen bedroom has en suite bath. Perfect for family getaways and group trips.

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!

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
Waterfront Rocky Neck Cottage | Gloucester Harbor
Wake up directly on Gloucester Harbor in the heart of historic Rocky Neck. This charming 2-bedroom home with loft features incredible harbor views from a four-season porch with 8 sliding windows overlooking the water. Enjoy morning coffee while watching fishing boats and sailboats pass by, or relax with a good book and your fur baby. Restaurants, art galleries and the beach are just a short walk away. Includes 3 private off-street parking spaces. A true Gloucester waterfront experience!

Historic Carriage House | Dog Friendly | Hot Tub
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, kitchen, queen sized bed with en-suite bathroom and sun room that converts to an extra sleeping space perfect for kids. A short walk to the train for day trips to Salem, Gloucester, and Boston!

Plum Cove Cottage with king suite!
A quaint 1900's cottage Plum Cove beach is just 500 ft away! The full gourmet kitchen has granite counters and stainless steel appliances. There is also a spa shower, romantic king bedroom with maple spiral stairs and 3 skylights which provide amazing light throughout. Watch the spectacular sunsets voted one of the best in the world by National Geographic. This is the premier location to begin your exploration of Cape Ann. Beach umbrellas and chairs provided.

Sea Vagabond - Watch the waves, stroll to the sand
"The Sea Vagabond House is an expanded 1932 summer cottage, with spectacular views of the ocean waves, with the tidal Saratoga Creek offering a mesmerizing and changing scenes from inside and outside this charming vacation home. The home sleeps eight comfortably in beds. Each level offers a full bathroom with a bathtub/shower. There are plenty of bath towels and beach towels for each guest. "Comfortable, clean and close to the beach, we will return."

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.

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.

Harbor View Suite
Harbor View Suite is a beautifully decorated two story Unit within a newly renovated Victorian house on the harbor located in Historic Old Town Marblehead, Massachusetts. This accommodation offers a rooftop terrace with panoramic views of the Harbor. Views of the harbor also from the kitchen deck. Perfect for families & friends. One dog allowed no cats please PLEASE note - parking on site is very tight small cars compact SUVs only

Hidden Gem! Short term rental steps from 2 beaches
Hidden Gem! Short term seaside rental. Lovely 1 bed 1 bath unit located on private wooded property, steps away from 2 beaches. Private unit amenities include deck with gorgeous year round 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.
Popular amenities for Gloucester pet-friendly home rentals
Pet-friendly house rentals

Beverly Beach House- Upper Deck

Incredible Views of Ocean, River, Sunrise & Sunset

Large, Comfortable & Conveniently located Home

Walk to Everything Great about Marblehead!

Pirates Hideaway - Sanctuary on the Marsh

Quaint Little New Hampshire Lake House Getaway!

Newly Restored 1850’s farm house 3 bedroom 2 bath

Quick walk to the beach, dog friendly w/ full yard
Pet-friendly home rentals with a pool

Private Pool Retreat w/Fire Pit Near Singing Beach

Private Luxury Retreat | Pool · Gym · Parking

Charming 2-story private Guesthouse

Heated Pool Firepit Huge Screen Porch King bed

Pool is Open thru Sept+Walking Trails+Dead End St.

Brand New Luxury Retreat w/ Pool & Fitness Center

Beautiful Spacious 4BRM House!

Luxury Modern Getaway (Near Salem/Boston)
Private, pet-friendly home rentals

Ipswich Apartment

Mermaid Surf Bungalow on Good Harbor Beach

Oceanfront Retreat w/ Deck & Parking

East Gloucester Beach house

William Haskell House First Period Colonial Home

Historic Oceanfront Home - Walk to Downtown

Pavilion Beach Townhouse

Eden Cove
When is the best time to visit Gloucester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | R 2,930 ZAR | R 3,202 ZAR | R 2,978 ZAR | R 3,602 ZAR | R 4,291 ZAR | R 5,107 ZAR | R 5,443 ZAR | R 5,699 ZAR | R 4,451 ZAR | R 4,883 ZAR | R 3,666 ZAR | R 3,554 ZAR |
| Avg. temp | -1°C | 0°C | 4°C | 9°C | 15°C | 20°C | 23°C | 23°C | 19°C | 13°C | 7°C | 2°C |
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- Fenway Park
- Ogunquit Beach
- Hampton Beach
- Harvard University
- Wells Beach
- TD Garden
- Boston Seaport
- Gillette Stadium
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