Holiday houses in Essex County

Lakefront cottage for a fun, relaxing getaway.

Enjoy a cozy stay in a lake front cottage. Located in Essex, on chebacco lake, this 3 bedroom, 1.5 bathroom home has everything you could need. Fully stocked kitchen, comfortable living space with wifi and a large TV, and a comfy couch overlooking the lake. We have a external monitor with a keyboard and mouse to set up a workstation if needed. A large deck and seasonal dock to hang out on. Close to the ocean if you get tired of the lake. It's an excellent home base on Boston's North Shore.

Value · Location · Getting around

Blue Magnolia

High in the treetops, this spacious apartment is only two blocks from the Atlantic Ocean! You'll enjoy 1400+ square feet with beautiful hardwood floors, an all-new kitchen, and your choice of two comfortable bedrooms -- one king and one queen. With a sleeper sofa, the apartment can sleep six total. This is a 2-flight walkup with private entrance, plus access to a large patio and well-established plantings including roses & a grassy yard. Offstreet parking in back if needed, thru driveway gates.

Location · Family · Checkout

Direct Waterfront on Plum Island Sound Sunsets

Create lasting family memories at this unique direct waterfront home on Plum Island Sound in Ipswich’s peaceful Great Neck neighborhood. This 2 bed 2 baths offers stunning water views from nearly every room, ideal for family sunset dinners, open-concept living area with sunroom perfect for game nights or relaxing together. Spot wildlife along the shore or head to nearby Crane Beach one of New England’s most beautiful stretches of white sand with dunes, swimming, and endless family adventures.

Location · Family · Getting around

Comfy-Spacious-private 1BR conveniently located

This stylish, private place is perfect for a couple, small family or groups of 4. Just minutes from Boston or the North Shore. Travel by car, Uber, or local train to enjoy Boston excursions, Salem witches, Cape Ann antiquing, sand beaches, fall leaf peeping, skiing, historical sights, sporting events, graduations, and retail therapy at nearby malls, outlets, or ionic Newbury St. A multitude of local and city restaurants and breweries provide an array options for your pleasure. YMCA next door!

Value · Location · Amenities

private suite w/king bed

Enjoy a comfortable stay in our private and spacious sun-filled loft. Nestled on a scenic hill in a beautiful corner of Topsfield, this cozy studio suite is 30 minutes from Boston; 25 minutes from Salem; less than 20 minutes from local beach towns, Endicott College and Gordon College; and approx. five minutes from the Topsfield Fair Grounds, the Ipswich river, Mass Audubon hiking trails, and wedding venues like Peirce Farm at Witch Hill, The Commons 1854, Willowdale Estate and Moraine Farm.

Location · Family · Sleep quality

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!

Family · Value · Sleep quality

Marblehead Tiny House

This new 360 square foot tiny house sleeps four comfortably. A mile from old town, down town, and just steps from Salem Harbor for breathtaking sunsets. The house is located in private, wooded back yard of our home. Kitchen is outfitted with small refrigerator, instant pot, air fryer, hot plate with pots and pans, microwave oven, blender, toaster, coffee maker, and electric tea kettle, as well as glasses, plates, flatware, etc for eating in. Kitchen table and chairs comfortably seats four.

Location · Value · Walkability

Winter Island Retreat

Effective 4/1/23, NON Owner occupied listings have a 3% impact fee that is charged on the total expenses associated with the rental. Winter Island Retreat is a OWNER OCCUPIED listing that is the place; For total relaxation. Watch the sunrise and experience the Atlantic Ocean. Enjoy your favorite beverage while rocking in an Adirondack chair on the patio. Inhale the smell of the ocean breeze and fragrant sea roses. Winter Island Retreat is an experience like no other in the Witch City.

Location · Value · Bathroom

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

Family · Value · Outdoor spaces

Unit 2~Garden Getaway Close to Beach & Downtown

Holly House 2 is our 2nd floor Victorian vacation rental within close proximity to downtown, beaches, train, hiking, kayaking, biking, restaurants & shopping! Enjoy a stylish experience in this lovely home away from home with dedicated work space, comfy bedrooms/living room, in unit laundry & well stocked kitchen. A great retreat for couples, families, remote working/learning, nature enthusiasts, beach lovers, corporate stays, girl's weekends, holidays stays & more!

Family · Value · Parks

Large, Comfortable & Conveniently located Home

You will be close to everything when you stay at this centrally-located private, updated historical home. 4 bedrooms & 2 baths w/plenty of extra space for large families or groups. Fenced-in spacious patio with huge backyard. Sizable, private parking area. Near Routes 95 & 128. Only 25 mins to Boston. Perfect for trips to picturesque points, including Boston, Gloucester, Newburyport, Rockport, Cape Ann, historic Salem & Maine coastal towns and cities. Dog friendly.

Location · Value · Access

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.

Family · Location · EV charging