Pet-friendly vacation rentals in Gloucester

4.99 out of 5 average rating, 175 reviews

Apartment in Rockport

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.

WalkabilityOutdoor spacesParking

4.99 out of 5 average rating, 165 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!

PetsWalkabilityGrill

4.83 out of 5 average rating, 138 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

PetsOutdoor spacesLocation

4.93 out of 5 average rating, 193 reviews

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 spacesPetsIndoor spaces

4.99 out of 5 average rating, 176 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 spacesWalkabilityBackyard

4.99 out of 5 average rating, 93 reviews

Apartment in Rockport

Oceanfront Retreat w/ Deck & Parking

• Private deck with ocean view • Parking • Steps to Front Beach • Walk to Bearskin Neck • Pet friendly • 15-minute walk to commuter rail • Contemporary art gallery on site Beautifully renovated, light-filled top-floor apartment on the water in historic downtown Rockport. Enjoy a private ocean-view deck, one dedicated parking space, and seasonal private access to Front Beach. One of three guest apartments at The Pearl, located just behind Thalassa, our contemporary art gallery.

WalkabilityOutdoor spacesLocation

4.94 out of 5 average rating, 48 reviews

Lane's Cove Bijou

Kick back and relax by the cozy gas fireplace as you take in spectacular sunsets over the ocean. This calm, stylish space features a gourmet kitchen and a luxurious master bedroom suite that make this jewel of a house the perfect retreat for a couple. The spa-like master bath includes a large walk-in shower and a clawfoot tub with views of the cove. A second bedroom provides space for an additional guest. The dining table expands to comfortably seat eight for shared meals.

WalkabilityOutdoor spacesDecor

Apartment in Manchester-by-the-Sea

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.

WalkabilityOutdoor spacesAmenities

4.91 out of 5 average rating, 202 reviews

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.

WalkabilityOutdoor spacesView

4.97 out of 5 average rating, 502 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.

PetsOutdoor spacesHiking

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.

4.98 out of 5 average rating, 115 reviews

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 spacesWalkabilityBackyard

4.99 out of 5 average rating, 267 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

WalkabilityPetsAir conditioning

Popular amenities for Gloucester pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.86 out of 5 average rating, 222 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 spacesWalkabilityPool

4.8 out of 5 average rating, 102 reviews

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.

Home in Rockport

Sea Vagabond - Watch the waves, stroll to the sand

WalkabilityPetsComfort

4.93 out of 5 average rating, 144 reviews

Home in Swampscott

Oceanfront Retreat | Salem 7 min by train

PetsOutdoor spacesFamily

4.9 out of 5 average rating, 121 reviews

Home in Ipswich

Incredible Views of Ocean, River, Sunrise & Sunset

Outdoor spacesPetsGrill

4.87 out of 5 average rating, 101 reviews

A cozy seating area features two armchairs facing large windows that provide a clear view of the lake. Natural light enters, illuminating the wooden floor and a round coffee table adorned with a small plant. The decor emphasizes tranquil lakefront living.

Home in Amesbury

2 bedroom waterfront retreat all seasons

Outdoor spacesWalkabilityKitchen

4.99 out of 5 average rating, 137 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

Outdoor spacesWalkabilityGetting around

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!

WalkabilityOutdoor spacesCondition

4.94 out of 5 average rating, 197 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!

Outdoor spacesPetsCheck-in

Pet-friendly home rentals with a pool

4.92 out of 5 average rating, 130 reviews

Apartment in Everett

Luxury Grand Oasis | Pool · Gym · Parking · 2BR

Outdoor spacesWalkabilityNearby

4.94 out of 5 average rating, 257 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

Outdoor spacesPetsCheck-in

4.89 out of 5 average rating, 55 reviews

Home in Marblehead

4-Bed+Walking Trails+Dead End St.+Dog-Friendly

WalkabilityOutdoor spacesParking

4.91 out of 5 average rating, 11 reviews

Apartment in Dorchester

Brand New Luxury Retreat w/ Pool & Fitness Center

Check-inHospitalityLocation

4.93 out of 5 average rating, 59 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!

WalkabilityPetsValue

4.93 out of 5 average rating, 27 reviews

Condo in Cambridge

“Luxury 2BR Cambridge | Pool + Parking”

WalkabilityBathroomLocation

Superhost

Apartment in Downtown

2BR Penthouse Boston Common DT Indoor Pool & Gym

PetsWalkabilityAccess

4.89 out of 5 average rating, 9 reviews

5.0 out of 5 average rating, 18 reviews

Apartment in Somerville

Luxury Stay in Somerville | River & City View

WalkabilityAccuracyKitchen

Private, pet-friendly home rentals

4.97 out of 5 average rating, 77 reviews

Bungalow in Gloucester

Mermaid Surf Bungalow on Good Harbor Beach

Outdoor spacesWalkabilityQuiet

A historic Colonial home is depicted with dark wooden siding and multiple windows. The structure features a central door, surrounded by evenly spaced windows on the front facade. Trees and greenery are visible in the surrounding yard, under a bright blue sky.

5.0 out of 5 average rating, 37 reviews

William Haskell House First Period Colonial Home

Outdoor spacesPetsCheck-in

Superhost

Home in Rockport

Halibut Point Retreat

PetsWalkabilitySleep quality

5.0 out of 5 average rating, 3 reviews

4.87 out of 5 average rating, 79 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

5.0 out of 5 average rating, 7 reviews

Home in Ipswich

Direct Waterfront on Plum Island Sound Sunsets

KitchenLocationIndoor spaces

Superhost

Cottage in Gloucester

Charming New England cottage

WalkabilityPetsAmenities

4.79 out of 5 average rating, 14 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.

4.96 out of 5 average rating, 76 reviews

Pavilion Beach Townhouse

WalkabilityOutdoor spacesKitchen