Holiday rentals in Chester

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Top-rated holiday rentals in Chester

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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, 180 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
Home in Jefferson
4.97 out of 5 average rating, 148 reviews

Adorable quiet & cozy lakefront studio on dead end

Welcome to your lakeside escape! This charming studio offers breathtaking views of the water- perfect for relaxing and peaceful sunsets. Tucked away at the end of a quiet dead end, you’ll enjoy the sounds of the lake. Whether you’re here for a weekend getaway or a longer stay, this is the perfect place to unwind, recharge, or work remotely in a serene setting. A short trip from NYC w/ great eateries, hiking, & shopping nearby. Enjoy the simple joys of lakefront living- you won’t be disappointed!

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, 117 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.

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
4.87 out of 5 average rating, 150 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
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
4.99 out of 5 average rating, 110 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
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, 127 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 castle-style retreat is showcased, featuring a whimsical dragon statue and a large chess set in the foreground. A tranquil pond with a fountain is visible, alongside a magnificent castle structure designed with classic stone elements and a welcoming entrance, all set amidst lush greenery.
Castle in East Stroudsburg
4.99 out of 5 average rating, 438 reviews

Pocono Castle w/ Dungeon Escape Room &Private Pond

Sleep in a Fairy Tale at Pocono Castle! Live the dream in this 2,300 sq. ft storybook retreat, where you’ll sleep like royalty in a real fairy tale castle. Unwind in luxury with a bubbling hot tub, a cedar sauna, and endless magical touches. Dress up as Kings, Queens, or Knights and explore the grounds, featuring a private one-acre pond & maybe you’ll catch a Golden Fish! With enchanting bedrooms, outdoor adventures, and unforgettable charm, this is the OMG getaway you’ve been waiting for!

Top guest favourite
The charming cottage features a white exterior with a brown roof and brick chimney. Lush green trees and plants surround the home, providing a tranquil setting. A small garden area is visible in the foreground, enhancing the natural appeal of the landscape.
Home in New Hope
5 out of 5 average rating, 204 reviews

Charming cottage

Welcome to this over 100 yr young charming cottage located betw New Hope Boro and Peddlers Village. Completely updated and renewed, this stylish open floor plan cutie has all new appliances, offering Bertazonni stove, Pfisher & Pakel fridge &much more! Two generously sized bedrooms on the upper level, full bathroom on first floor. Exquisite views of the professionally landscaped spacious rear yard and in ground pool with lg deck overlooking the grounds & charming paths to guide you thru

Top 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
4.98 out of 5 average rating, 379 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

Guest favourite
The tranquil lake reflects a vibrant sunset, showcasing shades of pink, purple, and orange across the water's surface. The scene is framed by distant wooded hills and includes a dock extending into the lake, providing a serene setting.
Home in Hopatcong
4.92 out of 5 average rating, 228 reviews

Lakeside Style and Luxury

Tastefully appointed home on highly desirable deep water Davis Cove with stunning views of Lake Hopatcong. Fully updated home offers spacious bedrooms, two bathrooms, premium furnishings, beautiful landscaping, 50 Ft dock, lakeside deck/seating, hot tub, wood burning fireplace, game room, fully equipped kitchen, large outdoor grill, swimming, fishing, boating. Quiet side-street neighborhood. Outstanding guest service from your host. Don't just stay anywhere... make it memorable!

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
4.94 out of 5 average rating, 124 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.

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, 639 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.

Popular amenities for Chester holiday rentals

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