Holiday houses in Heartbreak Hill

Incredible Views of Ocean, River, Sunrise & Sunset

1 bedroom home that can sleep 4. The house has sun filled rooms and vista scenery of the ocean, river and beach's. Located on a private road with Spectacular sunrises over the ocean with sunsets overlooking the river. Savor the steam room after a cross country ski or hike through the 100s of acres of manicured and marked trails only 5 miles away. The house has a large fireplace for you to enjoy Whether traveling with family friends or solo the seaside town of Ipswich has some great attractions

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

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.

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!

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.

The Raven!

Looking for the quintessential Salem stay? Look no further! The main bedroom is designed to get you in the Salem spirit, with its dark gothic decor. Take a reading break in the adjacent room, outfitted to look like a Victorian British library. A spacious living room, dining room, kitchen, and full bath complete this lovely property. Enjoy parking in a driveway in the typically-packed city. We are just a quick and enjoyable 12-minute walk to Essex street and all that downtown has to offer!

Charming Toe-Hold, A Short Walk to Town and Beach

Toe-Hold is a wonderful year-round 1846 home with plenty of rooms, reading nooks and quiet spaces for family and friends of all backgrounds to eat and play together. The gorgeous beaches and picturesque downtown, great restaurants, art galleries and shops for the whole family, are within 10-15 minute walk. Rockport is one of the oldest art colonies in the US, and home to generations of fishermen. Day trips by car or train to Boston and other beautiful historic towns.

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!

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.

Charming apt-2 Bedroom -Close to Beach/Sleeps 6

Our home is in the oldest neigborhood of New englad , surrounded by restaurants, art galleries and shopping. A short walk to the river and train station. This spacious apt has dramatic views of the Ipswich River thats is just across st . You will enjoy the whole place for yourself and the living room have 65" screen tv . A kitchen includes what you will need for your stay when you aren't enjoying various neighborhood restaurants.