Holiday 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.

Location · Family · Access

Ipswich Riverfront Lodge|Sleeps 10|Kayak+Canoe

Enjoy a secluded retreat in nature all while being conveniently close to all the North Shore has to offer at The Ipswich River Lodge. The rustic style combined with modern amenities and multiple gathering spaces makes this the perfect spot for groups and families alike. Just minutes to downtown Ipswich and Crane Beach/Estate it's the perfect landing spot to explore all that Cape Ann has to offer! 10 Min Drive to Crane Beach 30 Min Drive to Salem Experience Ipswich With Us & Learn More Below!

Family · Location · Sleep quality

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!

Location · Value · TV

Parker River House Two Bedroom

This is a private two bedroom one bathroom second floor suite in the owner occupied Tudor style Parker River House. Minutes from downtown Newburyport, the train to Boston, The Governor’s Academy and many outdoor recreational opportunities, the unit overlooks the Parker River and the Great Marsh. It offers a seasonal sleeping porch, a luxurious marble bathroom, large outside deck with a dining table, in unit laundry, refrigerator, microwave and Keurig. Private entrance and adjacent parking.

Location · Family · Hospitality

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.

Family · Location · Cleanliness

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 · Value · Nearby

Ipswich Inn | Staniford Quarters

Welcome to Staniford Quarters, a spacious second-floor apartment tucked behind the main house. This charming cottage-style unit features a king bedroom, a queen bedroom, and a full bath with a tub and shower. The open concept living area includes a full kitchen, dining space, and Smart TV for relaxing nights in. Perfect for families or groups, this home offers comfort and convenience. Enjoy a peaceful stay with easy access to local attractions, shops, and dining just a short drive away!

Family · Location · Indoor spaces

Northridge View

Escape the everyday in this spacious, serene retreat on Great Neck. Wake to breathtaking sunrises and unwind with glowing sunsets. This three-level home offers a bright, fully equipped kitchen, dining area, comfortable bedrooms, and a full bath, plus sunny workspaces and a relaxing deck. Walk to private Clark Beach or public Pavilion Beach, and enjoy walking, biking, and kayaking. Seven miles from the stunning Crane Estate and Beach, with excellent restaurants and live music nearby.

Location · Value · TV

Modern Studio Beverly – Private & Peaceful Retreat

Welcome to your quiet getaway in the heart of Beverly, MA. This stylish, modern minimalist studio is perfect for solo travelers or couples seeking comfort, convenience, and a touch of calm. With a private entrance, full bathroom, and space designed to inspire focus or relaxation, it’s ideal for both short stays and work-from-anywhere escapes. 🚫 Please Note: NO smoking - NO pets Book your stay and enjoy a peaceful home base close to beaches, coffee shops, art, and adventure!

Value · Location · Getting around

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 · Nearby

William Haskell House First Period Colonial Home

A First Period Colonial American experience in beautiful Gloucester, Massachusetts! As you step through the threshold of this sensitively restored 1680 residence, you are transported to an earlier time—immersed in the history of the home and the area. This listing reserves all four rooms in the house: Parlor Chamber, North Ell, the Spinning Room and The Gambrell Bedroom. As well as access to the kitchen and lounge area that has a television.

Location · Family · Hospitality

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.

Family · Location · Condition