Vacation rentals in Heartbreak Hill

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.

Annisquam Village Bunny Cottage

This beautiful Annisquam Village cottage was renovated to the highest level of quality by two artist's. Located just 5 minutes from Lighthouse Beach, Cambridge Beach and Talise Restaurant. Bunny Cottage has beautiful gardens, is surrounded by water on 3 sides, and has peek-a-boo views of Wingaersheek Beach from the bedroom window. The house is charming, with top notch amenities, like, heated floors, air conditioning (indoor/outdoor living). Mass Dept. of Revenue Certificate Number: #C0022781070

The Hideaway | Fireplace | Downtown | Theater

The Hideaway is a modern luxury suite located right in the center of it all. You can stroll a 1/2 mile to the beach, cozy up to the fireplace, walk downtown, catch a show at the theater, or discover Boston, Salem (2 miles away), or other quaint seaside towns. Tucked around the corner from downtown Beverly, in a quiet and historic neighborhood. This suite is located in the lower level of our home, and you’ll have your own private entrance, queen bed, fireplace, desk, fridge, and full bathroom.

Charming 2 Bedroom Apartment in Historic Ipswich.

In the heart of historic downtown Ipswich, the John Brewer house has been a family home since 1680! This fully renovated apartment features many modern amenities, like hi-speed internet, 50" and 55" televisions with streaming channels. There is parking for two cars, and we are a short walk to Market Street, the commuter rail to Boston, a large park for children, and many fantastic local restaurants. Drive to Boston or Maine in 45 mins; Salem or Gloucester in 30 mins; Crane Beach in 10 mins!

Live Like a Local, Just Steps From The Beach

Beautiful and private 2 bedroom suite, located on the upper floor of stylish 19th century beach house. Steps (literally steps) from Plum Cove Beach and Lanes Cove you'll have choices of where to swim or watch the sunset over the water. Guests will have the entire 2nd floor, with a private entrance and is western facing for beautiful sunset views. Located within a 15 minute drive to downtown Rockport, Gloucester, Wingaersheek and Good Harbor Beaches. 30 minutes from Salem for Halloween fun!

Stagehill Beach House

Spectacular water views from every room! 5 min walk to the beach and Pirate Park playground. Well stocked spacious kitchen, two family rooms, 4 BRs , dining room, deck and screened-in sun porch. Happily welcomes families, wedding guests and friends to enjoy my informal, livable, light infused beach house. Located on Great Neck in historic Ipswich, 4 miles to the charming downtown and a 15 minute drive to Crane Beach. Relax and enjoy! Ping pong table, corn hole, campfire! 2 driveways!

Amazing Ocean View In-Law Apt.

Step into a breath-taking magical seaside residence with 180-degree ocean views. This private in-law apartment has a sprawling lawn, steps to the ocean, and landscaped gardens. The apartment has one queen size bed with sliding doors opening out to the lawn, a queen pullout couch, granite counter-top complete kitchen including micro and dishwasher, ping-pong table, flat screen TV, home office and bathroom/ shower. The apartment has been thoroughly cleaned and meets all covid-19 standards.

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.

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!

French Flair "Pied a Terre" Cottage on the Marsh

Sunny cottage with marsh views, under 5 minute walk to town. Eat on the water in one of the many village restaurants, rent a kayak or paddle board. Go "down river" like a local! Shop the world renowned antique stores or enjoy the local beaches. There are many unique places to visit in Gloucester, Manchester, Rockport, Ipswich, Salem and of course Boston. There is a Visitor Manual for your convenience and we would be happy to answer questions that you might have.

Hillside

Perfectly situated within steps of Pavilion Beach and Pirate Park Playground. Makes for a great family getaway! Highchair and pack & play available! Wake up to this sun-filled home with water views from almost every window in the house! Enjoy the wraparound deck with lots of space for outdoor entertaining while taking in the spectacular views! The kitchen is well equipped with all new appliances, including a Viking range for those who love to cook.

Comfortable house, close to beach and downton IPSW

This home has all you need for your business or gateway in New England . With everything a Nice hotel has to offer ,this will be your home away from home. The Kitchen is fully equipped and you will have the entire place for yourself . You will be in walking distance to the train station in dowtown Ipswich and biking distance to the beach and Crane's Castle. Also you can explore Cannoing or paddling on the nearby Ipswich River.