Holiday houses in Chester

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Top-rated holiday rentals in Chester

Guests agree: these stays are highly rated for location, cleanliness and more.

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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, 107 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.

Guest favourite
A charming cottage with a red roof and yellow siding stands in a lush green landscape. A front porch is bordered by steps leading to a vibrant garden area. Tall trees and a clear blue sky create a serene outdoor environment.
Farm stay in Frenchtown
4.98 out of 5 average rating, 115 reviews

The Summer Kitchen Cottage: Pastoral Elegance

Idyllic pastoral getaway on 26 acres of renowned landscape designer Paul Steinbeiser’s homestead. Stroll the walking paths framed by native plants, wildflower meadows and sculptures featured in annual HOBART show. By summer, pick-your-own organic berries, vegetables & flowers or, by winter, cozy up to the wood burning stove. Nestled outside of Frenchtown, 15 from New Hope/Lambertville, an hour from New York and Philly, the cottage is a utopian respite to decompress and connect with the land.

Top Guest favourite
Cabin in Byram Township
4.97 out of 5 average rating, 31 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.
Guesthouse 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

Top Guest favourite
A rustic wooden cabin is nestled among tall trees in a dense forest. A covered front porch is visible, featuring two yellow chairs and surrounded by natural landscaping. The cabin's exterior showcases a blend of wood tones and large windows, inviting natural light indoors.
Cabin in Dingmans Ferry
5 out of 5 average rating, 353 reviews

Charming Chestnut Cabin in Woods

*Winter bookings must have 4 Wheel or AWD Vehicle. This one-of-a-kind cabin borders the Delaware Water Gap National Recreation Area. Hike right behind the cabin, through the woods, to Dingmans Creek. A short hike upstream leads to George W. Childs Park with 3 tumbling waterfalls, a rustic trail system, and observation decks. A longer hike downstream will bring you to Dingmans Falls. DWGNRA offers swimming, fishing, hiking, biking, canoeing, and kayaking, all within minutes of the cabin.

Guest favourite
A charming kitchen area features a mix of natural stone and wooden elements. A countertop is complemented by a small dining table and rustic decor. Appliances include a refrigerator, microwave, and stove. Natural light fills the space through a nearby door and window.
Farm stay in Hackettstown
4.87 out of 5 average rating, 82 reviews

Cozy cottage, serene with views

lovely setting of this romantic spot in nature, with mountain views. You can hike and hunt right from the property as 100’s of acres of state land border me. Good for 2 adults , 2-children on pull out sofa.Also availablon site are 2-three bdrm units and a 2-bdrm unit. Within 3 miles is Hackettstown, all restaurants/stores u need. Our place has a spring fed pond right out the back, we provide snacks, coffee choices, chimenea,hammock, grill/patio. Secure monitored parking, air conditioning

Guest favourite
Home in Blairstown
4.93 out of 5 average rating, 28 reviews

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

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, 386 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
Guest suite in Columbia
5 out of 5 average rating, 306 reviews

DWG Mountain Oasis-Private Apt w/Frog Pond

Private family apartment built for relaxing comfort and views of nature 2 miles from Mount Tammany, Mount Minsi, and the Appalachian Trail Walk to a private brookside trail and a winery Private deck Includes: Bread, eggs, pancake mix, coffee, tea, milk, bananas, s'mores kit, and more AWARDS: Top 1% of all Airbnb & #1 "Most Hospitable NJ Host" in 2021 Little or no host interaction – your choice Host lives on-site and can provide customized recommendations for food and things to do

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, 338 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.

Guest favourite
A master bedroom features large double doors leading to a private balcony overlooking the lake. A spacious bed with a textured white coverlet is visible in the foreground. The scenic view of the water and distant landscape can be enjoyed from the room.
Home in Hopatcong
4.93 out of 5 average rating, 44 reviews

Lux Lakeview House Experience/Sleep 8

Welcome to our breathtaking lake-view retreat! This stylish 2,600 sq ft home is perfect for families and friends, featuring multiple living areas, large flat-screen TVs, cozy wood and pellet fireplaces, a game table (pool, ping-pong & air hockey), karaoke, a gourmet kitchen, and a spacious deck with stunning lake views. High-speed Wi-Fi for remote work, peaceful surroundings for relaxation, and parking for 1 car per 2 guests, up to 4 cars. Permit 2025-18

Popular amenities for Chester holiday rentals

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