Holiday rentals 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

Springtime waterviews in downtown Rockport

Come to Rockport this spring and stay at this renovated waterfront apartment in a historic home with onsite parking, yard and a private entrance. Our prime downtown location is steps from beaches, restaurants, coffee shops, live music, and shopping on Bearskin Neck. Features full kitchen and bathroom with new applicances and fixtures. Living room has a loveseat, swivel chair, dining table, coffee table, roku TV, games, puzzles & books. Kitchen has a fridge, stove, oven, microwave and Keurig.

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!

Comfy and Cozy Apartment

Relax with the whole family at this peaceful place to stay. A great spot to unwind and experience Cape Ann. You will enjoy the apartment all to yourself. Entrance to the apartment is same level as parking so no stairs. The apartment is located in the basement of our primary residence. The space is located 45 min from Boston and 5 min drive to the commuter rail with access to Boston and Rockport. Additionally, we are a short drive to Gordon and Endicott College.

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.

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.

Friendship Acres Barn Apt. A

Spending time at Friendship Acres is not just a vacation, but a way of life. Enjoy this peaceful country setting while close to everything Cape Ann has to offer. Watch the horses graze, listen to the chickens chat. Walk downtown for fun activities on the Essex River or eat at one our excellent restaurants. Close to Historic Gloucester. Beautiful beaches, boating, whale watching, sailing, Kayaking, SUP, hiking and much more.

2b apt loft downtown Ipswich

When you get in to this apt/loft you will be amazed by the comfort and cozy set up. This unit is located downtown Ipswich on the third floor with a beautiful view where you can enjoy sunsets and have a place to hang out. NOT RECOMMENDED for elderly people because of the stairs. there are three sets of stairs, also if you are traveling with young children or toddlers need to be aware of the height and the whereabouts.

Private Studio Near Downtown & Ocean

Take advantage of the thriving communities of the north shore with this cozy space just steps away from downtown Beverly. This room comes with a queen size bed, its own 3/4 bath, kitchenette and a private entrance in the back of our family home. Enjoy easy walking to the beach, multiple parks and restaurants and the train station to travel anywhere including Boston and downtown Salem.

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!

Lovely 1822 Wade House

Walk to train! The Lovely 1822 Wade House. Entire 2nd floor of Historic House in historic district. Located on the main road into town which is centrally located and convenient for easy access to many places. 10 minute walk to restaurants and train to Boston and Salem. 10 minute drive to Crane Beach. Owner occupied building. This is a non smoking unit.