
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 963 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.

Incredible Views of Ocean, River, Sunrise & Sunset
1 bedroom home that can sleep 4. The house has sun filled rooms and vista scenery of the ocean, river and beach's. Located on a private road with Spectacular sunrises over the ocean with sunsets overlooking the river. Savor the steam room after a cross country ski or hike through the 100s of acres of manicured and marked trails only 5 miles away. The house has a large fireplace for you to enjoy Whether traveling with family friends or solo the seaside town of Ipswich has some great attractions
WalkabilityPetsIndoor spaces

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!
PetsOutdoor spacesKitchen

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
WalkabilityPetsView
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!
WalkabilityPetsBathroom

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!
Outdoor spacesWalkabilitySleep quality

Private Pool Retreat w/Fire Pit Near Singing Beach
Relax in a private coastal retreat with a pool and fire pit, minutes from Singing Beach. This updated suite features a modern layout, fireplace, and two queen beds—one in a private sleeping area. Ideal for relaxing or remote work, with a secluded backyard, private entrance, free parking, and fast Wi-Fi. Near downtown Manchester-by-the-Sea, dining, and coastal views. Seasonal pool: 5/20–9/8. Walk to local shops, restaurants, and the harbor, all from this peaceful setting.
Outdoor spacesPetsEV charging

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.
WalkabilityOutdoor spacesSolo travel

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."
PetsWalkabilityNearby

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.
PetsOutdoor spacesAmenities

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.
Outdoor spacesWalkabilityQuiet

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
Outdoor spacesWalkabilityAir conditioning

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.
WalkabilityOutdoor spacesBathroom
Popular amenities for Gloucester pet-friendly home rentals
Pet-friendly house rentals

Oceanfront Retreat | Salem 7 min by train
PetsWalkabilityLocation

Beverly Beach House- Upper Deck
Outdoor spacesPetsAir conditioning

Large, Comfortable & Conveniently located Home
PetsOutdoor spacesCleanliness

Walk to Everything Great about Marblehead!
WalkabilityOutdoor spacesComfort

Pirates Hideaway - Sanctuary on the Marsh
WalkabilityPetsKitchen

Quaint Little New Hampshire Lake House Getaway!
WalkabilityOutdoor spacesSleep quality

Newly Restored 1850’s farm house 3 bedroom 2 bath
WalkabilityOutdoor spacesBeach

Plum Island Cottage
WalkabilityPetsBackyard
Pet-friendly home rentals with a pool

Private Luxury Retreat | Pool · Gym · Parking
Outdoor spacesWalkabilityHospitality

Charming 2-story private Guesthouse
PetsOutdoor spacesView

Heated Pool Firepit Huge Screen Porch King bed
PetsOutdoor spacesSleep quality

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

Beautiful Spacious 4BRM House!
PetsWalkabilityKitchen

Luxury Modern Getaway (Near Salem/Boston)
CheckoutCleanlinessCheck-in

Brand New Luxury Retreat w/ Pool & Fitness Center
FamilyComfortIndoor spaces

“Luxury 2BR Cambridge | Pool + Parking”
WalkabilityGetting aroundLayout
Private, pet-friendly home rentals

Ipswich Apartment
Outdoor spacesPetsFamily

Mermaid Surf Bungalow on Good Harbor Beach
Outdoor spacesPetsTV

Oceanfront Retreat w/ Deck & Parking
WalkabilityOutdoor spacesCheck-in

East Gloucester Beach house
PetsWalkabilityDecor

Historic Oceanfront Home - Walk to Downtown
PetsWalkabilitySleep quality

Pavilion Beach Townhouse
Outdoor spacesPetsBeach

Eden Cove
WalkabilityOutdoor spacesParks

Waterfront Rockport Gem Steps to Shops and Beaches
PetsWalkabilityKitchen
When is the best time to visit Gloucester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | R 2,936 ZAR | R 3,208 ZAR | R 2,984 ZAR | R 3,610 ZAR | R 4,299 ZAR | R 5,117 ZAR | R 5,454 ZAR | R 5,711 ZAR | R 4,460 ZAR | R 4,893 ZAR | R 3,674 ZAR | R 3,561 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
- Boston Common
- Revere Beach
- Boston University
- Boston Convention and Exhibition Center
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- Freedom Trail
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