Pet-friendly vacation rentals in Gloucester

4.99 out of 5 average rating, 141 reviews

The open kitchen features a large island with seating for several guests. A cozy living area is visible, with a comfortable seating arrangement and large windows allowing natural light and ocean views. Warm wood flooring complements the airy atmosphere.

Apartment in Rockport

4 Bed 2.5 Bath Water view Downtown with 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.

4.95 out of 5 average rating, 176 reviews

A cozy outdoor patio features two bright red Adirondack chairs and a white circular table. The table holds two bowls of snacks and a glass of orange beverage. A backdrop of greenery creates a serene setting, enhancing relaxation.

Condo in Gloucester

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 spacious living area, perfect for gathering together after a day of exploring all that Gloucester has to offer. With its comfortable furnishings and modern amenities, this unit is designed to provide you with the ultimate vacation experience.

4.94 out of 5 average rating, 153 reviews

A private deck features comfortable green seating and a glass table, surrounded by colorful potted flowers. Ocean views extend beyond the railing, with trees visible in the background, creating a peaceful outdoor space for relaxation.

Apartment in Nahant

Ocean view studio with hot tub & access to Boston

All the amenities needed in a clean, spacious and modern apartment tucked away in a peaceful coastal town close to Boston. Studio with stunning ocean views, large private deck, hot tub, separate entrance, fast internet, granite kitchen, comfy couches, Breville Barista, bbq, and Sealy queen bed. Space is private with quiet residents in adjoining units. Off street parking. 2 sets of stairs to private entry, shared entrance by request. Use of hot tub at no additional cost. Short walk to beaches.

4.78 out of 5 average rating, 259 reviews

The exterior of a two-story building showcases a traditional design with white siding and dark blue shutters. A welcoming entrance is highlighted by a covered front porch and a set of stairs. Surrounding greenery adds to the inviting atmosphere.

Apartment in Amesbury

Lovely Downtown Oasis ~ Hospitals/Colleges/Beaches

Unwind in the modern 1BR 1Bath apt in the heart of downtown Amesbury, just a stone's throw away from tasty local restaurants and attractions. This charming oasis is perfect for leisure guests looking to explore nearby beaches and towns while also being close to hospitals and colleges, catering to traveling nurses and professionals. ✔ Comfortable King Bedroom ✔ Cozy Living Room ✔ Fully Equipped Kitchen ✔ Smart TV ✔ Workspace ✔ Washer/Dryer ✔ High-Speed Wi-Fi ✔ Free Parking Learn more below!

4.99 out of 5 average rating, 145 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

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!

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.

4.93 out of 5 average rating, 172 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.

Farm stay in North Andover

The spacious room features a king-sized bed with soft bedding and decorative pillows. Natural wood accents support a pitched ceiling, while a chandelier provides ambient lighting. A cozy gas fireplace and a flat-screen TV are visible. Large windows allow natural light and views of the surroundings.

4.95 out of 5 average rating, 272 reviews

Winery Studio w/ Private Hot Tub,Fireplace,Tasting

*A North Shore Favorite!* This former art studio is breathtakingly beautiful and is a true getaway to relax and feel at peace. It has great lighting and is located directly off of one of our historic barns. The space is perfect for a romantic retreat or the traveling professional looking for a place to call their home away from home. Located in an affluent neighborhood, minutes away from shopping and restaurants. Booking includes a wine tasting and 10% off all wine purchases!

A charming cape house is viewed from the street, featuring a covered porch with white railings. Large windows allow natural light to fill the interior. The surrounding yard is flat and grassy, bordered by trees that provide shade in a peaceful neighborhood.

4.92 out of 5 average rating, 134 reviews

Gloucester Beach House, near Good Harbor Beach!

Escape to this inviting, and pup friendly 4-bedroom Gloucester home, just a short walk to Good Harbor Beach! This classic coastal home blends comfort & convenience. All 4 bedrooms are air-conditioned, featuring a large eat-in kitchen, covered front porch perfect for relaxing or grilling, full bathroom plus refreshing outdoor shower. Stay connected with high-speed Wi-Fi, & enjoy the ease of on-site laundry. Openings for September and October. Ideal for weekend get aways!

Guest suite in Lakeside Marblehead

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.

4.9 out of 5 average rating, 289 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.

4.94 out of 5 average rating, 125 reviews

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

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.

4.97 out of 5 average rating, 469 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.

4.93 out of 5 average rating, 172 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.

Popular amenities for Gloucester pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.96 out of 5 average rating, 280 reviews

A well-equipped kitchen presents stainless steel appliances and an island with seating for four. Natural light floods the space through large windows, creating a bright and inviting atmosphere. The adjacent sunroom is visible through an open entryway, enhancing the home’s spacious feel.

Home in Wakefield

Welcoming 7-room house <15 miles to Boston & Salem

4.86 out of 5 average rating, 196 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

5 out of 5 average rating, 12 reviews

Lane's Cove Bijou

4.96 out of 5 average rating, 82 reviews

Two white rocking chairs sit invitingly along a stone walkway, facing a calm harbor. Reflections of colorful buildings and boats can be seen on the water's surface, framed by a vibrant sky during sunset.

Home in Rockport

Charming waterfront home. Patio, AC, Shops, Dining

4.94 out of 5 average rating, 175 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!

5 out of 5 average rating, 227 reviews

A bright yellow two-family home is positioned amidst greenery, featuring a welcoming entry with a red door. A small flowering tree adds a splash of color in front, while a large deck is visible in the background, perfect for outdoor gatherings.

Home in North Chelmsford

Newly renovated, spacious, clean, 3 bedroom home.

4.92 out of 5 average rating, 108 reviews

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

Ocean Views at Casa de Mar near Salem & Boston

4.98 out of 5 average rating, 263 reviews

A two-story white house features a welcoming front porch and black shutters. Lush greenery surrounds the property, with a well-kept lawn and flower beds. A pathway leads from the road to the entrance, and a driveway is visible beside the house.

Home in Dedham

Cozy, historic 3 bedroom home close to Boston!

Pet-friendly home rentals with a pool

4.96 out of 5 average rating, 57 reviews

A spacious bedroom is presented, featuring a dark wooden bed frame with a light-colored bedding set. Two nightstands with lamps are positioned on either side. Natural light enters through three windows, complementing the warm tones of the wooden floor and subtle wall color.

Home in Kittery

Fantastic Kittery Home with Pool

An open-concept living area features large windows with city and water views. A modern kitchen island with a stainless steel sink is paired with blue cabinetry. A light blue area rug complements the spacious couch and coffee table, enhancing the area’s bright and airy feel.

Apartment in Mystic River

4.85 out of 5 average rating, 48 reviews

3BR 2BA Condo Spectacular Views in Every Direction

5 out of 5 average rating, 15 reviews

Home in Bedford

Bauhaus Retreat in Nature Preserve

4.92 out of 5 average rating, 26 reviews

A well-maintained backyard features a spacious pool surrounded by a green lawn and landscaping. The red house extends with multiple levels, showcasing a deck and seating area. Additional structures are visible, set against a bright sky, creating a serene outdoor environment.

Home in Rockport

Rockport Pool House|4BR/3BA Walk to Bearskin Neck

4.95 out of 5 average rating, 43 reviews

The exterior of a two-story house is displayed, featuring white siding and red shutters. A well-maintained front yard is visible, showcasing green grass and shrubs. A brick pathway leads to the front door, framed by two planters with greenery.

Home in Arlington

Beautiful Spacious 4BRM House!

Apartment in Manchester-by-the-Sea

A spacious living area features a large, sectional sofa with neutral upholstery, oriented towards a wooden coffee table. Bright light filters through multiple windows, illuminating the room. A dining area with wooden chairs is visible in the background, along with built-in storage cabinets.

4.9 out of 5 average rating, 177 reviews

Modern Space With Pool Close To Singing Beach

4.92 out of 5 average rating, 12 reviews

A charming home features a white exterior with red doors, framed by a well-manicured lawn. A tree casts gentle shade over the yard, while a pathway leads to the entrance. A garage is visible to the left, complemented by a classic streetlamp.

Home in North Andover

Peaceful New England Retreat Close to It All

4.95 out of 5 average rating, 64 reviews

A spacious outdoor pool is framed by lounge chairs and shaded by umbrellas. Neat rows of trees and landscaped gardens enhance the inviting atmosphere. The surrounding buildings feature large windows, reflecting the evening sky painted in soft hues.

Apartment in Everett

Elegant Oasis with Pool and Gym

Private, pet-friendly home rentals

4.84 out of 5 average rating, 144 reviews

An inviting living space features exposed wooden beams and a fireplace with a decorative mantle. A round dining table for four and comfortable seating are present. Two windows allow natural light to fill the room, providing views of the surroundings and enhancing the open layout.

Apartment in Salem

Historic House by the Gables

4.81 out of 5 average rating, 123 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

5 out of 5 average rating, 12 reviews

A serene waterfront scene captures calm waters reflecting clear blue skies. Boats are anchored in the bay, and a rocky shore is framed by lush greenery. In the distance, a quaint building with a blue roof stands on a pier, adding a touch of charm to the coastal view.

Home in Annisquam

Stroll to SeaView/Beach; Great Yard

Apartment in Lakeside Marblehead

A warm living area features a leather armchair with a cozy throw, accompanied by a small wooden side table. A fireplace is positioned against the wall, with decorative accents placed above it. Natural light enhances the hardwood flooring and walls.

4.98 out of 5 average rating, 55 reviews

Captain’s Quarters

5 out of 5 average rating, 13 reviews

A spacious living area is designed with large windows providing expansive views of the ocean. A comfortable white sofa faces a wooden coffee table, complemented by a cozy throw. Natural light fills the room, accentuating the warm wooden floors and tasteful decor.

Home in Nahant

Sea Forever - Oceanfront Home in Nahant!

Guest suite in Gloucester

5 out of 5 average rating, 61 reviews

The Artist Suite by Toi Moi

A three-story house is shown with light-colored siding and classic shutters. A small garden with shrubs and flowers is visible in front. A staircase leads to the entrance, where a welcoming flag hangs. The neighborhood features residential homes on either side.

5 out of 5 average rating, 8 reviews

Lobster Trap: Beauport, Pavilion Beach, Downtown

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.