Holiday rentals in Chester

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Top-rated holiday rentals in Chester

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Guest favourite
The image captures a serene sunset over the lake, with warm hues illuminating the sky. Properties and trees frame the scene, while boats are visible on the water. Power lines traverse the foreground, connecting the area with the surrounding landscape.
Cottage in Jefferson
4.97 out of 5 average rating, 185 reviews

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).

Top guest favourite
A soft, textured sofa in a light neutral tone is positioned against a warm, smooth wall. A single floor lamp provides gentle lighting beside a small black side table. An adjacent window is dressed with sheer curtains, allowing natural light to filter softly into the space.
Cottage in Warwick
4.99 out of 5 average rating, 128 reviews

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.

Top guest favourite
A serene landscape features a large farmhouse set against a clear blue sky, with lush green grass surrounding a tranquil pond. Reflections of trees and the farmhouse are visible on the water's surface, complemented by a rustic barn in the background.
Home in Far Hills
4.99 out of 5 average rating, 108 reviews

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.

Top guest favourite
The inviting living area features wooden beams and a stone fireplace, surrounded by comfortable seating arrangements. Large windows illuminate the space, showcasing rustic decor and a cozy sheepskin rug on warm-toned wooden floors. A dining table is visible in the background, enhancing the communal atmosphere.
Cabin in East Stroudsburg
4.93 out of 5 average rating, 446 reviews

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!

Top guest favourite
Cabin in Byram Township
4.97 out of 5 average rating, 34 reviews

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.

Top guest favourite
A cozy seating area features a richly colored sofa adorned with patterned cushions, paired with a small circular table. A comfortable armchair complements the space, surrounded by floral wallpaper and natural light filtering through nearby windows.
Guest house in Frenchtown
4.98 out of 5 average rating, 150 reviews

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

Guest favourite
An outdoor area is illuminated by a vibrant red fireplace, surrounded by cozy seating arrangements with cushions and throws. Potted flowers add color, while string lights gently glow above, enhancing the serene atmosphere of the deck. A natural stone backdrop is visible in the distance.
Cottage in Greenwood Lake
4.97 out of 5 average rating, 387 reviews

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

Top guest favourite
A comfortable sofa is positioned against a neutral wall, complemented by an abstract artwork above. The kitchen area is visible in the background, featuring dark cabinetry and a wall clock. Soft lighting is provided by two lamps flanking the sofa.
Guest suite in Upper Black Eddy
5 out of 5 average rating, 341 reviews

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.

Top guest favourite
A colorful sunset fills the sky with shades of orange, pink, and purple, reflecting on the calm waters of Lake Hopatcong. In the foreground, a dock extends towards the water, with a charming blue house visible across the lake.
Guest suite in Jefferson
5 out of 5 average rating, 22 reviews

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.

Top guest favourite
Home in Hackettstown
5 out of 5 average rating, 13 reviews

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.

Top guest favourite
A welcoming entrance is presented with double doors bordered by potted plants. The exterior is complemented by a balcony above, and stone steps ascend to a lush garden area, surrounded by trees and natural landscaping, creating a serene and inviting approach.
Guest house in Frenchtown
4.98 out of 5 average rating, 167 reviews

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.

Guest favourite
The exterior of the unit showcases a blend of white and gray siding with large windows framing the entrance. A black door is set between stone accents at the base. Flower pots filled with various plants are arranged along the pathway, enhancing the welcoming appearance.
Guest house in Morristown
4.95 out of 5 average rating, 130 reviews

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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