Vacation rentals in Heartbreak Hill

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Top-rated vacation rentals in Heartbreak Hill

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Guest favorite

Apartment in Beverly

4.92 out of 5 average rating, 448 reviews

Private apartment 10 min to Salem!

This private entrance basement apartment is within a 1/2 mile to several beautiful Beverly beaches. Downtown Beverly is about a 10 to 15 minute pleasant walk. It offers great restaurants and cafes. Live entertainment is happening almost nightly at the Larcom and Cabot theaters. Endicott College is 1 mile away. Downtown Salem is about a ten minute drive from here. The train to Boston, Salem, or Rockport is about a mile away. Plenty of safe street parking is available in front of my house.

May 6 – 13

ﺩ.ﺇ500 per night

Guest favorite

Apartment in Ipswich

4.98 out of 5 average rating, 121 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!

Jan 17 – 24

ﺩ.ﺇ578 per night

Superhost

Guest suite in Beverly

4.85 out of 5 average rating, 658 reviews

Historic North Shore, private suite & bathroom

Minutes from Salem! Relax in historic Beverly (walk to Beverly shops) in your private suite; bedroom, living room, and small bathroom, connected to our home, but private entrance. Just minutes from Salem. Commuter line to Boston and close to beautiful North Shore beaches and historic sites. Beaches within biking and driving distances, downtown, parks, hiking. Comfy, soft king bed, queen pull out couch, and plenty of linens. Great for couples, solo adventurers, business travelers, and families.

Aug 31 – Sep 7

ﺩ.ﺇ450 per night

Guest favorite

Home in Ipswich

4.98 out of 5 average rating, 170 reviews

Stagehill Beach House

Cozy year round beach house within 5 min walk to beach and playground. Views of Plum Island, Crane beach, Ipswich River and marsh from every room. 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, walk to beaches, 4 miles to the charming downtown and a 15 minute drive to Crane Beach.

Jan 1 – 8

ﺩ.ﺇ1,893 per night

Guest favorite

Apartment in Salem

4.97 out of 5 average rating, 300 reviews

The Salem House Too

An 1850’s built home with a modern interior and revitalized exterior. It’s the perfect spot to relax and unwind or take work on the road. Located one mile from downtown Salem and away from the traffic, our goal is to provide a classy, upscale experience with all of the comforts of home. Pair a sparkling clean private space with off street parking, unlimited coffee, and a fridge stocked with drinks and snacks and you’ve got The Salem House! Come stay with us and see what Salem is all about!

Feb 9 – 16

ﺩ.ﺇ484 per night

Guest favorite

Apartment in Ipswich

4.88 out of 5 average rating, 227 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.

Dec 14 – 21

ﺩ.ﺇ368 per night

Guest favorite

Guest suite in Gloucester

4.98 out of 5 average rating, 375 reviews

SplashLanding Private Beach Getaway in Gloucester

Jan-March 2024 open for monthly rentals. Must Book Summer 2024 via Airbnb website not the APP! *Our 2nd unit SquishInn has openings beginning April 2024 airbnb.com/h/squishinn-gloucester-ma Long walks on a private beach. Get sun-kissed; toes in the sand. Romantic dinners on the deck. Cozy in Winter (Energy Star home and Radiant heat throughout). TRAVELING WITH ANOTHER COUPLE? Book Private Beach Getaway SquishInn. Our 2nd unit for adult couples. Now another 2 friends can join you!

Dec 19 – 26

ﺩ.ﺇ1,051 per night

Guest favorite

Guest suite in Peabody

4.98 out of 5 average rating, 177 reviews

Cozy West Peabody Guest Suite

Come enjoy this renovated studio guest suite in the quiet neighborhood of West Peabody! An easy drive to Salem or Boston, close to a woodsy bike trail, and a short drive to local shops and restaurants. Features a fully equipped kitchenette and an outdoor space with a fire pit and charcoal grill. Make use of a Roku TV and fast, reliable WiFi to keep yourself entertained. This is a great space whether you are looking to explore the Boston North Shore or simply embark on a quiet getaway.

Aug 12 – 19

ﺩ.ﺇ403 per night

Guest favorite

Loft in Gloucester

4.9 out of 5 average rating, 167 reviews

Rocky Neck Studio/Loft, Gloucester, Mass.

Welcome 2024! We look forward to you visiting RockyNeck in Gloucester. You will be sure to enjoy various special activities and events this summer and fall. We are located in the "quiet end", on a private residential dead end street in a historic artist colony . Nearby public transportation, Audubon sites, cultural events, the Gloucester Stage Co and beaches . Parking is on street with a parking lot nearby, if needed. PLEASE NOTE: the yard is private Bring your passcodes for TV

Jan 23 – 30

ﺩ.ﺇ451 per night

Guest favorite

Apartment in Beverly

4.94 out of 5 average rating, 617 reviews

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.

Dec 27 – Jan 3

ﺩ.ﺇ616 per night

Guest favorite

Cottage in Essex

4.97 out of 5 average rating, 212 reviews

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.

Aug 22 – 29

ﺩ.ﺇ737 per night

Superhost

Apartment in Ipswich

4.86 out of 5 average rating, 226 reviews

Confortable and confy , close to beach /sleeps 6

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.

Feb 26 – Mar 5

ﺩ.ﺇ524 per night