Vacation rentals in Heartbreak Hill

4.96 out of 5 average rating, 268 reviews

Guesthouse in Gloucester

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

4.96 out of 5 average rating, 45 reviews

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!

4.99 out of 5 average rating, 158 reviews

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!

4.98 out of 5 average rating, 196 reviews

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!

4.87 out of 5 average rating, 292 reviews

Ipswich Apartment

The apartment, with a private entrance is located in downtown Ipswich. We are within walking distance to restaurants and the commuter rail, which services Salem, Boston etc. May - September, the CATA shuttle stops at the commuter rail station, a 3 minute walk. Some CATA services include Cranes Beach, and the town of Essex (famous for its clams and antique shops). You can also enjoy a river cruise down the Essex River there. Kayaking, canoeing, and fishing are also available in Ipswich.

4.98 out of 5 average rating, 384 reviews

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.

4.96 out of 5 average rating, 293 reviews

The Creaky Cauldron-Wizards and Witches Welcome!

Welcome to The Creaky Cauldron--an enchanting escape inspired by the world of witches and wizards--located in the heart of Salem! We have put a lot of love into creating a truly special and unique experience for visitors to the Witch City who love magic and Salem as much as we do. Each room has been carefully themed after a magical house or subject to give our guests an immersive experience. Each of our 7 rooms also reflects each of the 7 books in our favorite magical fantasy series.

4.96 out of 5 average rating, 162 reviews

The Ghoul’s Attic at The Creaky Cauldron

No ghoulies or ghosties here--just a unique and magical escape inspired by everyone's favorite school of magic--located upstairs at The Creaky Cauldron B&B in the heart of Salem! We have put a lot of love into creating a truly special and unique experience for visitors to the Witch City who love magic and Salem as much as we do. Each room has been carefully themed after a magical house and/or subject to give our guests an immersive experience in the world of witchcraft and wizardry.

4.94 out of 5 average rating, 683 reviews

Apartment in Beverly

Beverly Farms Apartment “Homeport”

"Homeport" - A nautical themed apartment, nestled in the small coastal village of Beverly Farms. The village has cafes, restaurants, beaches and nearby to “Witch City” Salem MA. Homeport has a private entrance, den, two bedrooms, 1.5 baths with essential amenities and guest parking. The local area is famous for beaches, museums, galleries, eateries and many historic attractions. Explore the North Shore or take a commuter train to explore Boston, saving time and expense of driving.

4.95 out of 5 average rating, 44 reviews

Apartment in Essex

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.

4.99 out of 5 average rating, 132 reviews

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!

4.95 out of 5 average rating, 256 reviews

Cottage in Essex

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.

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Popular amenities for Heartbreak Hill vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Heartbreak Hill

5 out of 5 average rating, 10 reviews

Great Neighborhood Home close to Ips River & Town

RachelRating, 5 stars7 months ago

Lisa's place was very comfortable, spacious, and clean for myself and my friends' stay. We appreciated the quiet location and quick drive to the train station, where we were able to easily commute to Salem for Halloween events without having to brave the traffic. We did have a couple of issues arise during our stay, and Lisa was very quick to respond and resolve them. She even kindly offered to ship a small item that we forgot back to us!

4.87 out of 5 average rating, 206 reviews

Guesthouse in Hamilton

Lake View New England Cottage in Hamilton, MA

ElaineRating, 5 stars2 weeks ago

Walking into Andy’s place was like coming home. Very pleasant and clean. Off the beaten path but easy driving distance to all Boston’s North Shore has to offer. Excellent restaurants nearby and interesting activities. Andy was friendly and accommodating. A pleasure. We look forward to returning soon!

5 out of 5 average rating, 3 reviews

Ipswich Waterfront Getaway

CatherineRating, 5 stars5 days ago

We really enjoyed staying at David's place. Everything was as advertised in the listing. The space was clean and comfortable, and check-in was a breeze. We were looking for something peaceful, and this place was perfect. The neighborhood was quiet, and the views of the sound from the sitting area and back patio were great. It was a short drive (a few miles) into Ipswich, which provided us with enough to do to see the area. Great overall visit.

5 out of 5 average rating, 14 reviews

Home in Salem

Cottage-style home in Salem

MishondaRating, 5 stars7 months ago

Beautiful home and well located to explore. Rewan is an amazing host! Truly exceptional

4.95 out of 5 average rating, 19 reviews

Cottage in Ipswich

2 Mi to Crane Beach: Waterfront Ipswich Escape!

LorettaRating, 5 stars7 months ago

Probably one of the most beautiful properties I’ve ever seen. Cozy nights and beautiful views

4.97 out of 5 average rating, 91 reviews

The 1870 Langmaid House Suite

JamesRating, 5 stars1 week ago

A great historic property in easy reach of all the attractions Salem has to offer. 20 minutes walking to the waterfront, and maybe another 5 minutes on to the Peabody Essex museum. The apartment was perfect, well equipped, with your own front door, a small seating area and nice kitchen space. We were personae by Tyna and shown round the space. Breakfast provisions are a great extra touch! Highly recommended!

5 out of 5 average rating, 67 reviews

The Cottage at 78

AnnRating, 5 stars1 week ago

Peter's home is beautiful, clean and well equipped for our weeklong visit. The view is amazing and we spent several evenings on the front porch watching the tide in the marshes. We came to visit family and enjoy my husband's hometown and this was a great spot to do it.