Pet-friendly vacation rentals in Gloucester

4.9 out of 5 average rating, 121 reviews

Home in Ipswich

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

Outdoor spacesPetsFamily

4.99 out of 5 average rating, 162 reviews

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

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!

WalkabilityPetsKitchen

4.82 out of 5 average rating, 137 reviews

The exterior of a summer cottage is showcased, with a light grey wooden structure resting on a rocky landscape. Stairs lead up to the entrance, flanked by greenery. A deck with railings is visible on the upper level, complemented by large windows allowing natural light.

Cottage in Rockport

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

Outdoor spacesPetsBiking

4.93 out of 5 average rating, 192 reviews

Home in Gloucester

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!

Outdoor spacesPetsAccess

4.99 out of 5 average rating, 172 reviews

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

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 spacesPetsCheckout

Apartment in Manchester-by-the-Sea

4.91 out of 5 average rating, 200 reviews

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 spacesWalkabilityAccess

4.94 out of 5 average rating, 124 reviews

A quaint stone cottage is surrounded by lush greenery and colorful flowers, with a well-maintained garden featuring clusters of purple blooms. The cottage's rustic charm is complemented by a sloped lawn and mature trees, creating a serene outdoor atmosphere.

Guesthouse in Gloucester

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.

Outdoor spacesWalkabilityTV

A vibrant sunset casts warm orange and yellow hues across the ocean's surface, reflecting on gentle waves. Silhouetted rocks line the shore, while distant land appears along the horizon, creating a serene coastal scene.

4.81 out of 5 average rating, 101 reviews

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."

WalkabilityOutdoor spacesAccess

4.97 out of 5 average rating, 501 reviews

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

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.

Outdoor spacesWalkabilityCondition

4.98 out of 5 average rating, 113 reviews

A panoramic view reveals the tranquil ocean, with soft waves lapping against the shore. Green trees and distant sandy areas are visible, enhancing the natural scenery. Several rooftops in the foreground provide a sense of elevation and perspective towards the coastline.

Home in Gloucester

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 spacesWalkabilityHeating

4.99 out of 5 average rating, 265 reviews

The living area features a mix of comfortable seating, including a floral-patterned sofa and a plaid armchair. A round coffee table sits atop a light blue area rug, and large windows allow natural light to fill the space, enhancing the cozy ambiance.

Condo in Marblehead

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

PetsWalkabilityView

4.94 out of 5 average rating, 203 reviews

An aerial view captures a spacious coastal home, surrounded by lush trees with changing leaves. The structure showcases a wraparound deck, and the sloped lot offers a rocky edge, enhancing the natural setting. Nearby residences are partially visible through the foliage.

Apartment in Rockport

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.

Outdoor spacesWalkabilityCleanliness

Popular amenities for Gloucester pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.93 out of 5 average rating, 142 reviews

Home in Swampscott

Oceanfront Retreat | Salem 7 min by train

PetsOutdoor spacesNearby

4.86 out of 5 average rating, 221 reviews

Colorful stacked kayaks are arranged on a grassy area overlooking the water. A sandy beach is visible in the foreground, leading to a stone jetty extending into a calm body of water. A clear blue sky with scattered clouds fills the background.

Home in Beverly

Beverly Beach House- Upper Deck

Outdoor spacesWalkabilityCheck-in

4.99 out of 5 average rating, 136 reviews

A large tree with a broad canopy dominates the lush backyard, surrounded by greenery. The area features a stone border outlining a patch of grass, with glimpses of the landscape beyond, including wooded areas and a play structure in the distance.

Home in Danvers

Large, Comfortable & Conveniently located Home

WalkabilityPetsParking

4.77 out of 5 average rating, 190 reviews

The exterior of a spacious antique house is shown, featuring a yellow facade with green shutters. A large deck is visible in front, complemented by a white picket fence. The house is set against a clear blue sky, adding a bright and welcoming appearance.

Home in Marblehead

Walk to Everything Great about Marblehead!

Outdoor spacesWalkabilityGetting around

5.0 out of 5 average rating, 121 reviews

A modern blue house is nestled within lush greenery, featuring multiple large windows and a rooftop deck with an umbrella. The tranquil marshland, dotted with tall grasses, stretches into the distance under a sky filled with soft clouds.

Home in Salisbury

Pirates Hideaway - Sanctuary on the Marsh

Outdoor spacesPetsValue

4.94 out of 5 average rating, 195 reviews

A serene view of the lake is framed by two bright blue chairs and a small white table topped with a pot of yellow flowers. Lush greenery surrounds the water, with residential homes visible in the distance.

Home in Salem

Quaint Little New Hampshire Lake House Getaway!

WalkabilityPetsQuiet

5.0 out of 5 average rating, 118 reviews

A modern kitchen features dark stone countertops and antique-style cabinetry. A large island with seating is positioned at the center, complemented by stylish bar stools. High-end appliances are visible, and a window allows natural light to brighten the space.

Home in Greenland

Newly Restored 1850’s farm house 3 bedroom 2 bath

WalkabilityOutdoor spacesAmenities

4.93 out of 5 average rating, 103 reviews

A bright living room features a white sofa adorned with striped pillows, complemented by a wooden coffee table holding decorative items. Earth-toned curtains frame the window, which offers a glimpse of the outside. Natural light enhances the space, while woven wall hangings add texture.

Home in Plum Island

Plum Island Cottage

WalkabilityOutdoor spacesCondition

Pet-friendly home rentals with a pool

4.93 out of 5 average rating, 121 reviews

Apartment in Everett

Private Luxury Retreat | Pool · Gym · Parking

WalkabilityOutdoor spacesPool

4.94 out of 5 average rating, 255 reviews

A spacious outdoor area features a dining table surrounded by chairs, complemented by loungers and a hot tub. An umbrella provides shade over the seating area, while lush greenery and well-maintained landscaping create a peaceful environment. The in-ground pool is visible in the foreground.

Guesthouse in Newton

Charming 2-story private Guesthouse

PetsOutdoor spacesSleep quality

5.0 out of 5 average rating, 26 reviews

A spacious outdoor area features a heated pool surrounded by a paved patio. White lounge chairs and a dining table are positioned nearby, offering ample seating. A large umbrella provides shade, while a well-maintained lawn and wooden fence create a private retreat.

Home in Essex

Heated Pool Firepit Huge Screen Porch King bed

PetsOutdoor spacesBeach

4.89 out of 5 average rating, 54 reviews

Home in Marblehead

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

Outdoor spacesWalkabilityBackyard

4.93 out of 5 average rating, 58 reviews

A well-maintained swimming pool is featured in the backyard, surrounded by a patio. Lush greenery and mature trees offer privacy. The two-story house is visible in the background, with large windows allowing light to enter. A basketball hoop is positioned adjacent to the pool area.

Home in Arlington

Beautiful Spacious 4BRM House!

WalkabilityPetsIndoor spaces

Superhost

Guest suite in Peabody

5.0 out of 5 average rating, 8 reviews

Luxury Modern Getaway (Near Salem/Boston)

HospitalityCleanlinessCheckout

4.88 out of 5 average rating, 8 reviews

Apartment in Dorchester

Brand New Luxury Retreat w/ Pool & Fitness Center

AccuracyAccessCheck-in

4.93 out of 5 average rating, 27 reviews

Condo in Cambridge

“Luxury 2BR Cambridge | Pool + Parking”

WalkabilityAccuracySleep quality

Private, pet-friendly home rentals

4.89 out of 5 average rating, 368 reviews

A three-story house features a light-colored exterior with multiple windows and a welcoming front porch. The surrounding yard is neatly maintained, with grassy areas and a fire hydrant visible on the edge of the sidewalk. Neighboring houses can be seen in the background.

Apartment in Ipswich

Ipswich Apartment

Outdoor spacesPetsShared spaces

4.97 out of 5 average rating, 76 reviews

Bungalow in Gloucester

Mermaid Surf Bungalow on Good Harbor Beach

WalkabilityPetsParking

4.99 out of 5 average rating, 91 reviews

Apartment in Rockport

Oceanfront Retreat w/ Deck & Parking

Outdoor spacesWalkabilityTV

4.87 out of 5 average rating, 78 reviews

A wooden boardwalk stretches over a serene body of water towards a sandy beach. The calm sea, with gentle waves, meets a cloudy sky, and a rocky outcrop is visible in the distance. A figure can be seen walking along the shore.

Apartment in Gloucester

East Gloucester Beach house

PetsWalkabilityLocation

4.98 out of 5 average rating, 41 reviews

Historic Oceanfront Home - Walk to Downtown

Outdoor spacesWalkabilityGrill

4.97 out of 5 average rating, 75 reviews

The exterior of a newly constructed townhouse is depicted, showcasing a dark shingle facade. A wide staircase leads to the entrance, while garage doors are visible below. Surrounding structures and utility poles are present, indicating a well-developed neighborhood.

Home in Gloucester

Pavilion Beach Townhouse

Outdoor spacesWalkabilitySleep quality

A spacious deck is adorned with a round table and four chairs featuring red cushions. In the background, vibrant yellow flowers contrast against the blue ocean, with Thatcher Island's twin lighthouses visible in the distance. The scene captures a serene view of water and natural beauty.

5.0 out of 5 average rating, 46 reviews

Eden Cove

PetsWalkabilityFamily

The living room features comfortable seating arranged around a round coffee table. Large sliding doors provide access to a waterfront view, while natural light illuminates the space. A smart TV is mounted on the wall, and a mirrored wall adds depth to the open-concept area.