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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
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, 175 reviews

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.

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, 91 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
A cozy seating area features a blue futon sofa and a matching chair with yellow accent pillows. A small coffee table sits on a decorative rug. A lighted lamp and artwork add charm, while a glimpse of the bedroom is visible in the background.
Loft in West Orange
4.99 out of 5 average rating, 282 reviews

*Fragrance Free-Clean Safe Cozy-Easy Commute NYC!

**The studio is private, entry is not private, it is through the hosts living area** (You will have your own keys and you and are free to come and go as early or late as you like) ***BEFORE REQUESTING TO BOOK*** please read my entire listing *As you can see by my photos, ratings and reviews this really is a lovely place to stay, I am an attentive host, but please indulge me and read on.... * I keep a fragrance free house and require that guests be fragrance free.

Guest favourite
A spacious living and dining area features a blend of comfortable furniture, including a green armchair and a sleek table with chairs. A small decorative rug lies on the tiled floor, and a television is mounted on the wall. Natural light enters through a window, accentuating the room's warmth.
Guest suite in Hackettstown
4.88 out of 5 average rating, 143 reviews

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.

Top Guest favourite
Home in Hopatcong
4.98 out of 5 average rating, 139 reviews

Lakeside Home w/Lake Access, Dock & Water Views!

Enjoy amazing lake views from this absolutely gorgeous, modern lakeside home! Perfect destination for a mini-vacation, couples retreat or a family getaway. "La Vida Lago" is a completely furnished, single family lakeside ranch home featuring 2 bedrooms, 1.5 baths, deck, patio, private lake access and dock directly across the street. The property is perched up from the road and nestled into the mountain surrounded by trees! The ideal environment to connect w/nature, yourself and loved ones.

Top Guest favourite
A serene outdoor area features two sets of blue Adirondack chairs positioned beside a gently flowing waterfall. Lush greenery surrounds the private pond, with a distant view of a white shed and the glistening pool, creating a peaceful retreat in nature.
Home in Mendham Township
4.98 out of 5 average rating, 57 reviews

Historic Cottage with Private Pond & Pool

Step back in time to 1760 with the old world charm of Colonial America. Pre-dating our country by over a decade, our beautifully renovated 260+ year old home sits on 5 acres with a detached studio and 2 separate water features. Experience the private pond teeming with koi, frogs, and other wildlife or take a dip in the refreshing pool just steps away. Whether you seek a relaxing getaway or a portal back to the days of our founding fathers, our historic home promises the ideal retreat.

Guest favourite
A cozy living area is highlighted by a blue sofa adorned with decorative pillows. Natural light fills the space through two windows, revealing wooden flooring and a light-colored rug. An air conditioning unit and two dining options are visible in the background.
Bungalow in Jefferson
4.91 out of 5 average rating, 418 reviews

2 Queen Sized Beds - Lake Hopatcong Cottage

This little house offers a lot for visitors to the area: - near Route 15 and minutes to US 80 - two comfortable queen sized beds - sofa bed that comfortably sleeps 2 - kitchen with basic cooking amenities - rear patio with grill and fire pit - walking distance to boat rentals - near trails and restaurants - popular wedding venues within 15 mile drive: Perona Farms, Waterloo Village, Crossed Keys Estate, Sussex Fairgrounds -Mountain Creek approximately 20 miles away.

Guest favourite
A living room features floral-patterned sofas with pink accent pillows, complemented by warm wooden flooring. A central coffee table is adorned with a decorative green vase. Artwork hangs on the walls, and natural light enters through a window dressed with soft curtains.
Apartment in Chester
4.98 out of 5 average rating, 96 reviews

Carriage House

Our place is close to the Gladstone train station, historic downtown Chester, Hacklebarney State Park, and several other parks. It's a great place to stay if you are coming to the area for business travel, visiting family in the area or leisure. You’ll love our place because it's large, tastefully decorated and comfortable. We have hiking trails, a stream, and a pond on our beautiful acreage that you can explore and enjoy. Friendly black lab on premises.

Guest favourite
A modern living room features light-colored furnishings with a spacious sofa and wooden coffee table. Textured curtains frame the windows, complementing the warm wooden floor. A small decorative tree adds a touch of nature, while a lamp and an art piece enhance the inviting environment.
Apartment in Bernardsville
5 out of 5 average rating, 25 reviews

Modern bright downtown apartment Unit B

This cozy and modern apartment is designed for your comfort and relaxation. This includes a modern kitchen with brand-new stainless-steel appliances, well-equipped kitchen, comfortable living areas, and a dedicated workspace for business travelers. The sunny living room with decorative fireplace flows into the ample sized dining room. The primary bedroom boasts an en-suite full bathroom with stall shower, walk-in closet, and patio access.

Top Guest favourite
A comfortable living area features a white sofa adorned with coordinating cushions, set against a neutral wall. A rustic coffee table with a weathered finish sits in the center, complemented by a patterned rug. Artwork is displayed above the couch, adding a contemporary touch.
Cottage in Upper Black Eddy
5 out of 5 average rating, 604 reviews

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.

Top Guest favourite
Two mini donkeys graze peacefully in a grassy field, surrounded by trees with green foliage. A blue sky with a few scattered clouds provides a bright backdrop, and wooden fences outline the pasture, enhancing the farm-like setting.
Farm stay in Frenchtown
4.95 out of 5 average rating, 591 reviews

DREAM BIG! Rustic Tiny Home on Hidden Farmlet

Ready to kick back and relax from your busy life? Have you ever dreamed of waking up on a farm? Then our charming 170 sq ft tiny home is perfect for you! Situated on 10 picturesque acres, and home to one horse, two mini donkeys, two goats, a pig, twenty-two chickens, five ducks, a goose and, of course, a barn cat. This is the place to disconnect and get back to nature!

Top Guest favourite
A spacious sleeping area features a bed with layered bedding and a decorative blanket. A chest of drawers and wardrobe provide storage options. Soft lighting from a nearby lamp creates a cozy ambiance, while a small chaise lounge adds extra seating.
Guesthouse in Morristown
4.96 out of 5 average rating, 248 reviews

Private Guest House

Private 600 square foot guest house on side of owners home. Private entrance. Recently renovated with all new bedding, furnishings, bathroom, appliances and fixtures. Located just 1 mile from center of Morristown. Walking distance to many restaurants, parks and shopping. 1 mile from Morristown Train Station, direct to NYC. Plenty of parking, pet friendly.

Popular amenities for Chester holiday rentals

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  2. United States
  3. New Jersey
  4. Morris County
  5. Chester