
Holiday rentals in Chester
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Top-rated holiday rentals in Chester
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Lakeview Cottage Near Restaurants & Wedding Venues
Enjoy lake views at this peaceful retreat just under an hour from NYC. Sip your morning coffee as the sun rises over the water, then unwind at night by the fire pit. Guests love how spotless, comfortable, & thoughtfully stocked the cottage is. Across the street from a marina - bring your boat! 5 min to beach-like swimming, watersports, & great restaurants, w/in 20 mins of popular wedding venues, 10 mins to Hopatcong State Park & Rockaway Mall, 35 mins to Mountain Creek, 40 min to MetLife (FIFA).

Ranch in the Woods | A Peaceful Designer Retreat
Welcome to @ranch_inthewoods No cleaning fee STR permit #34035 This newly built ranch-style home with thoughtfully designed wabi-sabi interiors sits in the woods of the Warwick Valley. It's located a short drive away from several lakes, hiking trails, breweries, and dining experiences. It features forest/creek views, designer furniture, modern appliances (dishwasher, washer/dryer, gas cooktop), smart 4k TV, gym & yoga studio, gas firepit, and ample deck with an outdoor kitchen & dining area.

Pickle Farm
Meticulously maintained private quiet gated enclave featuring a restored vintage 1800 historic farmhouse and pastoral land- 1 hour from NYC. Registered movie and film location, featured in movies, commercials, documentaries and photo shoots. Agent handles negotiations, Prices vary. Minutes to train, Hamilton Farm, Pingry , Gill & Willow schools. Willowwood Arboretum, Bamboo Brook, Natirar, Several well known golf courses surrounded by hundreds of acres of preserved open land and state park.

Coziest Creek Cabin- Idyllic, Authentic, Poconos
Deep within our psyche lies a romantic image, that of a log cabin tucked into the woods perched above a babbling trout laden stream. Perhaps inside there's a sheepskin rug laid before a grand fireplace, a reading nook, and a child's dreamy hideaway loft. Or maybe you're out on the deck, a crisp morning bundled and sipping cocoa on a rocking chair, or nights soaking sore bones and soaking up the sounds of the stream & kids below roasting smores by the fire. Now make that dream a reality!

Cranberry Cove Cabin - Lakefront Bright Oasis
Escape to a charming lakefront retreat on Cranberry Lake, just one hour from NYC. This cozy cabin features exposed beams, a comfortable living area with leather sofa, flat-screen TV, soundbar, and Roku, plus a fully stocked kitchen. Enjoy seasonal deck furniture, yard games, a charcoal grill, and fire pits by both the yard and the lake. Private lake access via stairs (over a hill) leading to your own dock, with folding chairs and a kayak—perfect for relaxing, paddling, and soaking in nature.

River Witch Cottage Frenchtown
Nestled in the heart of Frenchtown NJ, you'll find enchantment hidden in the lush gardens of River Witch Cottage. • Restore yourself in a luxe queen bed • Prep a simple meal in the fully equipped kitchen • Nourish yourself in the charm of an intimate dining area • Recline in cozy comfort beside a beautiful gas fireplace • Rejuvenate in the jets of the jacuzzi tub, soaking under the natural glow of skylights • Morning coffee or evening wine in the tranquil setting of the private outdoor patio

Luxury Cottage with Spectacular Lake Views
Ultra Chic Cottage set high above Greenwood Lake with Private beach and lake front community access. Minutes away from Mountain Creek Ski Resort, Spa & Water park, Mt. Peter Ski & Tubing, Warwick creameries, breweries & vineyards & apple picking. 1 BR, 1 Bath, play/office/common room. Huge wrap around fenced in deck with Mid century modern fireplace allows for scenic dining, lounging and around the fire gatherings. #LakeViewCottage_GWL Town of Warwick Short Term Rental Permit #P25-0245

Riverwood Bungalow- Bucks County Getaway
A small but cozy bungalow on a quiet property bordering a state park. Explore river towns along the Delaware including Frenchtown, New Hope and Lambertville. FRESH BAGEL DELIVERY included on first morning. It offers private parking (next to front door), EV charger for electric vehicles, QUEEN-SIZE bed, kitchenette and heated floors in bed & bath. Take a morning walk along the canal, enjoy a quiet dinner outside at the table for two, then end the night relaxing by the chiminea.

Boone Docks - lower level
Newly built in 2021 you’ll enjoy the entire basement level of this lake front home with private entrance. Hosts occupy the first floor of the home. It is located on the Northern end of Lake Hopatcong which is perfect for waterskiing, tubing, kayaking, fishing, or just sitting on the dock watching the sunset. We are minutes away from many hiking and biking trails. Rent a boat at Bridge Marina for a day and explore the largest lake in New Jersey. Only 5 miles from Interstate 80.

Secluded yellow farm house with Mountain View’s
Take it easy at this unique and tranquil getaway. Secluded but 3 miles from center of Hackettstown, shopping, restaurants, centenary college all within 3 miles. Good heat , air conditioning, wood stove. Many parks nearby to visit, long valley, historic Chester, and local farm markets with animals nearby. This building is stand alone. View our profile for our 4 other listings available for larger groups/events.

Idyllic 1 Bedroom Cottage in picturesque setting.
Nestled at the end of a long driveway just an hour from NYC and an hour and a half from Philly, experience peace and quiet in a pastoral setting while staying in this newly appointed sun filled cottage. You’ll get country views from every window while being minutes to Frenchtown, where you can peruse the great shops, and restaurants or visit Art Yard, bike down the towpath, and hike in Horseshoe Bend Park.

C&J Signature Stays Historic Renovated Apartment
Stay in your private, beautiful, bright two-bedroom unit with historical 1870s architectural details, including original brick walls, arched living room doorways, and stone kitchen walls. The unit was recently renovated to maintain its old charm while updating and modernizing the kitchen, living room, and two bedrooms. It is an excellent space for vacation or work. Fast Wi-Fi + Roku TV.
Popular amenities for Chester holiday rentals
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Destinations to explore
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- Times Square
- Madison Square Garden
- Central Park Zoo
- New York City Center
- Yankee Stadium
- Camelback Resort & Waterpark
- Columbia University
- Mountain Creek Resort
- Sesame Place
- Six Flags Great Adventure
- American Dream
- Bushkill Falls
- Rockefeller Center
- United Nations Headquarters
- Pocono Raceway
- MetLife Stadium
- Dorney Park & Wildwater Kingdom
- Empire State Building
- Blue Mountain Resort
- Bryant Park
- Citi Field
- Barclays Center
- Camelback Mountain Resort
- Statue of Liberty





