
Holiday rentals in Chester
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Chester
Guests agree: these stays are highly rated for location, cleanliness and more.

Lakeview Cozy Cottage w/ 2 bedrooms & 1 bath
Start your morning with a fresh cup of coffee while watching the sunrise over the lake. Less than 1 hour from NYC, enjoy your staycation in this updated cottage in a peaceful lake community. Relax on the patio while enjoying the tranquility of nature and creating wonderful memories. Less than 5 minute drive to swimming, watersports, boating, farms, wineries, and lots of great restaurants & bars. Less than 10 mins to Hopatcong State Park, 10 mins from Rockaway Mall, and 30 mins to Mountain Creek.

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.

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.

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.

Luxury forest cabin w/private trails
Welcome to picturesque spacious luxury: this fully renovated cabin, tucked away on an expansive 200+ acre property w/ private trails. The spectacular 1 bedroom features: vaulted ceilings, brand new kitchen & appliances, granite counter island w/ seating, dining room, powder room & bathroom with walk in shower & soaking bathtub, King bed, blackout curtains, large windows with nature views, Smart TV, BBQ, hot tub option(available in summer) & direct access to the serene forest & walking paths.

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

Cabinessence -on Greenwood Lake, NY #34370
"Cabinessence" is Year Round Comfort in a Chestnut Cabin by Greenwood Lake with a little touch of "glamping". Hiking, biking, strolling, paddle boarding, kayaking , canoeing. Restaurants, shopping, Drive-in movies, antiquing in nearby Warwick. Fall color, apple picking, gas fireplace (in season). Winter, ski, snowboard, tubing. Spring is watching the natural world wake up :) Hanging at the cabin- year round- is special here! Every season has its magic! ( + Covid Enhanced cleaning!)

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

Historic Tiny Cottage on the Delaware Canal
This renovated home, dating back to 1900, is located right along the picturesque Delaware Canal, offering stunning views and plenty of opportunities for outdoor activities like kayaking and biking. Inside are modern amenities like a new heating/AC system, hardwood floors, a new bathroom, W/D, and a fully equipped kitchen. The loft area features a queen bed and a desk area perfect for remote work. The yard has outdoor seating to enjoy the scenery.

Romantic New Hope Cottage
Whether you’re visiting for business or pleasure, you will feel right at home in our private cottage tucked away on a quiet country road in historic Bucks County. From the moment you pull into the driveway and meander along the stone pathway, you will feel a sense of tranquility, warmth, and comfort. The cozy environment is perfect for a romantic getaway, a relaxing weekend, or a solo work trip (exceptional wifi on premises).

Lake Hopatcong hide away
Private cottage in Lake Hopatcong Nj. Cottage is NOT on the lake and there is no direct access from the property. Enjoy fishing, boating and swimming in the largest lake in NJ. Cottage is in a quiet Neighborhood less then 1/4 mile from the lake. Enjoy outside lake view dining at the many restaurants the lake has to offer. Located 30 miles from PA and 40 miles from NYC. There is a ring camera doorbell.

Cozy guest cottage with indoor fireplace
Take it easy at this unique getaway in the Poconos! This vintage one room cottage is the perfect space for soaking in nature, getting creative, or exploring the attractions of the Pocono Mountains. The cozy cottage is within 20 minutes of ski resorts, Kalahari, and the Delaware Water Gap national recreation park. Reach downtown Stroudsburg and it’s restaurants and nightlife within 7 minutes.
Popular amenities for Chester holiday rentals
Other great holiday rentals in Chester

Secluded Private Retreat Entire House and Woodland

A-Frame Modern House w/ Private Pond

Cranberry Cove Cabin - Lakefront Bright Oasis

Secluded Cabin w/ Boats < 6 Mi to Jenny Jump!

“Scenic Riverside Retreat – A Unique Getaway”

Commuter's Dream | Resort Amenities

Private Cottage 1 BR 1BA on a quiet farm in NJ

2BR Apt in North Brunswick Rutgers/RWJ @10 Minutes
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Tuckahoe Holiday rentals
- Long Island Holiday rentals
- Boston Holiday rentals
- Washington Holiday rentals
- East River Holiday rentals
- Hudson Valley Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- South Jersey Holiday rentals
- Pocono Mountains Holiday rentals
- Times Square
- Madison Square Garden
- New York City Center
- Columbia University
- Central Park Zoo
- MetLife Stadium
- Camelback Resort & Waterpark
- Mountain Creek Resort
- Bronx Zoo
- Brooklyn Bridge
- Yankee Stadium
- Rockefeller Center
- United Nations Headquarters
- Sesame Place
- Blue Mountain Resort
- Six Flags Great Adventure
- Camelback Mountain Resort
- Empire State Building
- Citi Field
- Grand Central Terminal
- Bryant Park
- Pocono Raceway
- Radio City Music Hall
- Statue of Liberty




