Pet-friendly vacation rentals in Essex County

Newly Finished Guest Haven in Woburn

Welcome to our newly finished in-law lower level suite in Woburn! This private 1-king bed bedroom, 1-bath retreat features a cozy living room, a well-equipped kitchenette with a private entrance. Located on a quiet dead-end street, it’s just 5 minutes from Woburn Center, 15 minutes from Encore Boston Harbor, and a 20-minute drive to downtown Boston. Perfect for business travelers or couples, enjoy a peaceful stay with easy access to dining, shopping, and entertainment. Book your stay today!

Winery Studio w/ Private Hot Tub & Wine Tasting

Private Hot Tub, Vineyard Guesthouse at Winery. This former art studio is a true getaway to relax & feel at peace. Filled with natural light, it sits beside one of our historic 1800s barns on the winery property with vineyard views. Perfect for a romantic retreat or the traveling professional seeking a peaceful home away from home. Located in an affluent neighborhood minutes from shopping & restaurants. Your stay includes a complimentary wine tasting and 10% off all wine bottle purchases

Oceanfront Oasis:Stunning &Spacious 1st Fl 1BR #1

Escape to the coast and stay in this beautiful and bright 1BR apartment across the street from the ocean and Dane’s Street Beach. Enjoy the best of both worlds with views of the ocean and charming courtyard from your first-floor retreat. This spacious and stylish apartment will take your breath away with its pretty decor and comfortable furnishings. Whether you're here for a solo adventure or a romantic getaway, you'll feel right at home in this stunning home away from home.

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.

Hillside Ocean View 2BR with Private Beach Access

Cozy, light-filled home just a 10-min walk to Pavilion Beach with access to private Clark Beach too. Open living space with ocean views, comfy seating, fast WiFi, and streaming. Enjoy sunrises from the queen bed in the main bedroom; second bedroom also has a queen. Fully equipped kitchen with lobster pot and dishwasher. Relax in the ocean-facing sunroom or grill on the balcony with stunning views. Perfect for families or small groups seeking a relaxing beach escape.

Private Downtown Suite 1805 Home

Completely Private- No shared living spaces. Plush mattress + fresh linens •Down & down-alternative comforters for chilly October nights •Spacious bedroom with decorative fireplace •Cozy sitting room with 42″ TV •Free street parking with guest pass Attic loft (queen bed, 6-ft peak – see photo): •Perfect for school-aged kids •Comfortable for adults who don’t mind stairs + lower ceilings •Historic charm with modern comfort right in Salem

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.

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

Winnie's Place - Freshly Renovated 1800s Farmhouse

Welcome to Winnie's! Set in the picturesque New Hampshire countryside, Winnie's is a charming traditional New England 3 bedroom, 2 bath 1890s farmhouse with modern amenities. The home is newly renovated and updated with WiFi and smart TVs, but retains its historic character. It is perfect for a family getaway, romantic weekend or change of pace for those working from home. It is a “get away” without getting too far!

Sunny & private cottage in Lanesville Village

Sunny private 2 bedroom cottage with large garden, deck,and great Lanesville location near the ocean. Living room with large flat screen smart TV with Roku, fast internet, and lounge with pull out couch and pocket door for privacy. Now with mini-split A/C throughout and new windows in the bedrooms! Dogs under 55 lbs allowed (no more than 2 ) no cats. Yard is not fenced in.

Ipswich Apartment

This apartment has a private entrance in downtown Ipswich, close to restaurants and the commuter rail for Salem and Boston. From May to September, the nearby CATA shuttle makes it easy to reach Crane Beach and the town of Essex, known for its clams and antique shops. Ipswich also offers river cruises, kayaking, canoeing, and fishing. Enjoy the local attractions!

Quirky room above convenience store, near water.

Gorgeous view of the Mill River just behind the house. Hiking, boating, marine activities and city life just minutes away. Spacious, bright, private room in funky apartment building, with grocery/convenience store right downstairs. Private entrance (from common hallway), private bath. Best suited for easy going, laidback people.