
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).

Isaac Read Cottage—historic Hope property near DWG
The Isaac Read Cottage offers a peaceful respite in the northwestern heart of the Garden State, minutes from the historic township of Hope, NJ, and the Poconos. Here you will find a cozy retreat thoughtfully curated with unique antiques, original artwork, premium linens, and local provisions. 1:10 hours from NYC, nearby attractions include Jenny Jump State Forest, Shawnee Mountain Ski Area, Delaware Water Gap National Rec Area, and the Appalachian Trail, plus antiques, wineries, farm stands...

Private farm loft
Secluded farm with Mountain View’s surrounded by hundreds of acres of state land to hunt and hike right off our land, but still have the convenience of the town of Hackettstown, all the stores/restaurant choices you need all within 3 miles. Enjoy 2700 square feet of open concept space at the loft, with fully stocked kitchen, coffee choices, snacks. Enjoy board games, air hockey table, multi game table. Outside fire pit, grilling, areas to relax, walk our wildflower fields, manicured landscape

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.

Carriage House in The Valley
A quiet, safe countryside lifestyle 1 hour from Manhattan, NJ beaches, or the Delaware Water Gap. Walk, Bike, fish watch birds and see historical sites where George Washington marched. Senior couple's 2 acre lot among huge trees. The rustic outside of the unit gives way to a comfortable living space on the top floor and the bottom floor is a wide open utility room with a second bath, electric stove, full laundry and a place to store things while in transit or if moving in or out of the area.

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!

Full Apartment near Hackettstown
Enjoy this private apartment connected to an 18th century stone house. It comes furnished with 1 1/2 bathrooms, a fully equipped kitchen, large living/dining room, and one bedroom with closet and a queen sized bed. We are located in the beautiful highlands of northwest NJ--about 60 miles from Lincoln Tunnel and 75 miles from Philadelphia. Nearby are historical sights, great hiking and skiing areas restaurants, brew pubs, and a train station. Private parking provided next to entrance.

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

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.

Riverwood Cottage• borders Bucks County state park
Wake up to fresh bagels and quiet countryside views. This charming guest cottage sits in the heart of Bucks County, surrounded by picturesque river towns and rolling hills. Enjoy fresh bagels delivered to your door on your first morning. Take a 5 minute drive along the Delaware River into Frenchtown for a day of exploring and dining. Close to New Hope, Lambertville and Doylestown. ***No pets allowed - please book our dog-friendly bungalow (on same property) if you’d like to bring your dog.

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

Lakefront | Kayaks | 200-Acre Estate | Tennis
✓ Lakefront on a private gated 200-acre estate ✓ 5-acre lake with kayaks, pedal boats & boat slip ✓ Tennis court, hiking trails & outdoor fire pit ✓ 1 hour to NYC, 20 minutes to ski resorts Set on a 200-acre private gated farm with a 5-acre lake, this property offers complete privacy and access to a tennis court, hiking trails, fishing, swimming, and breathtaking views. We provide kayaks, life vests, tennis rackets, and firewood. Everything you need for a relaxing or adventurous getaway
Popular amenities for Chester holiday rentals
Other great holiday rentals in Chester

Modern bright downtown apartment Unit B

Boone Docks - lower level

Studio Glamping Pod - Hickory

Rare find! Poconos log cabin with indoor sauna

Beautiful Lakefront Retreat w/ Deck & Views!

The Scout House - Hot Tub/Sauna/Fire Pit/Projector

Cozy and peaceful Studio apt

Modern Luxe Lakefront Cabin
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- Times Square
- Central Park Zoo
- New York City Center
- Camelback Resort & Waterpark
- Yankee Stadium
- Mountain Creek Resort
- Columbia University
- Sesame Place
- Six Flags Great Adventure
- American Dream
- Bushkill Falls
- MetLife Stadium
- Rockefeller Center
- United Nations Headquarters
- Pocono Raceway
- Dorney Park & Wildwater Kingdom
- Empire State Building
- Blue Mountain Resort
- Bryant Park
- Camelback Mountain Resort
- Barclays Center
- Citi Field
- Statue of Liberty
- Grand Central Terminal





