Holiday rentals in Chester Township

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Top-rated holiday rentals in Chester Township

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Top guest favourite
A spacious lawn is framed by natural rock formations, leading to a deck with chaise loungers. The gently sloping pathway is lined with greenery and provides access to the lakefront. In the background, a multi-level house is set against a clear blue sky.
Home in Jefferson
5.0 out of 5 average rating, 29 reviews

Lakeside Lux and Laughs!

Newly renovated 4BR/3.5BA lakefront property with multiple sitting areas, both inside and outside, is the perfect spot for relaxing and having fun with family and friends. It boasts a full game-room in the basement, a 10-person outdoor dining table, a firepit - and a fully covered bar down by the water. Sleeps 12 and is centrally located on "main lake" affording access to local restaurants, mini-golf and retail. Short-haired / non-shedding dogs (1) allowed. This home is truly something special!

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, 110 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 rustic carriage house is featured, surrounded by lush greenery and trees. A neatly maintained lawn leads up to the structure, which has a symmetrical façade with multiple windows. An American flag is displayed prominently in front of the house.
Guest house in Bridgewater
4.95 out of 5 average rating, 130 reviews

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.

Guest favourite
An 18th-century stone house is depicted, showcasing multiple stories and large windows that offer bright views. Surrounding trees and greenery create a natural setting, while a small outdoor patio area with a table and chairs is visible at the front of the building.
Guest suite in Hackettstown
4.88 out of 5 average rating, 156 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.

Superhost
Home in Chester
4.84 out of 5 average rating, 31 reviews

Private Home - 2 acres

Take it easy at this unique and tranquil getaway. 2 beautifully landscaped very private acres. Over 1 acre of backyard fenced - dog friendly. Two Tesla Level 2 Chargers available for an extra charge. 60' x 120' playing field for soccer or any sport. Close to downtown Chester - easy access to Rt 206, Rt 24, Rt 80, Rt 287 and Rt 78. The landscaped yard blooms throughout the seasons. This is a completely smoke-free property, indoors and out, to ensure a clean and comfortable stay for all guests.

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, 475 reviews

Pocono Castle: 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
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
4.96 out of 5 average rating, 76 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.

Superhost
Flat in Franklin Township
4.86 out of 5 average rating, 179 reviews

Spacious 2 Bed | Clubhouse Amenities, Somerset

Settle into your two bedroom, two bathroom apartment, perfect for business trips, golf getaways, or a family visit to New Brunswick and Somerville. The apartment includes a full kitchen, dedicated work area, and a king bed in each bedroom. Unwind at our resort-style pool and fire pit lounge, with quick access to golf courses and NYC transit. AVE Somerset is a garden-style community featuring walk-up residences across three floors. Please note that our buildings do not have elevators.

Top guest favourite
A spacious exterior view of a two-story home features a blend of stone and stucco. Arched windows and doors create a welcoming entrance, while the surrounding area is landscaped with shrubs and trees. The driveway is paved, leading up to the inviting entrance.
Home in Hackettstown
4.93 out of 5 average rating, 59 reviews

Charming Rustic Retreat

Discover timeless luxury wrapped in rustic charm. This home blends vintage character with upscale comfort, offering a warm, nostalgic atmosphere and refined touches throughout. From antique wood beams to handpicked vintage décor, every detail invites relaxation and emotional connection. Whether you're enjoying a serene morning or a cozy evening, this space promises a uniquely rich and elegant stay that feels like a heartfelt escape into classic sophistication.

Top 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
4.94 out of 5 average rating, 48 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

Superhost
A bright dining area features a wooden table surrounded by cushioned chairs, with place settings arranged thoughtfully. Large windows offer unobstructed views of the lake, filling the space with natural light and showcasing reflections on the water.
Home in Hopatcong
4.93 out of 5 average rating, 166 reviews

Lakefront Hopatcong w/dock kayaks fishing near NYC

3800 sqt 4b 2.5b, stunning lakefront house on the largest lake in NJ. Breathtaking lake views from every room. Sunrise coffee at bedroom balcony. Grill in the sunset at the spacious patio, fishing off the private dock. two spacious living rm for multi family, well equipped kitchen, large washer dryer, 3 kayak, fishing rods, grill, everything you need for your group to have a comfortable lake retreat and make some beautiful memories. 1 hr to NYC.

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.
Flat in Bernardsville
4.98 out of 5 average rating, 46 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.

Popular amenities for Chester Township holiday rentals