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.

%{current} / %{total}1 / 1
Top guest favourite
A spacious loft area features high ceilings accented by exposed wooden beams. A queen size bed is fitted with a soft blanket, while a colorful area rug complements the white furniture. A dining table with chairs and a cozy sitting area are visible in the background.
Guest house in Warwick
4.93 out of 5 average rating, 412 reviews

Rustic Loft Space with Distinctive Artistic Charm

Beautiful spacious and bright artist loft on the second floor of a newly renovated Warwick barn behind our 1893 Warwick Village home. More information The space We offer our furnished live and work artist loft on a daily or weekly basis. The loft : -is 400 sqf -is located on the second floor -has nicely designed bathroom -has a very comfortable queen size bed -has high speed internet access -is very tidy and clean The neighborhood: -one blocks from the NJ Transit bus to Manhattan. -great restaurants and cafés nearby This loft is wonderful is perfect for 2-4 visitors. You are in the middle of lovely village neighborhood, but get the comfort of a cozy retreat. Guests will have access to the entire SECOND FLOOR space. Situated in the lower Hudson Valley, the town of Warwick is just over an hour’s bus ride New York City. Explore its numerous orchards and wineries, head to the drive-in movie theater, or grab a bite from one of the village restaurants. The loft is just one block from the NJ Transit bus that leaves from Port Authority.

Top guest favourite
A spacious studio features a king bed with white linens, complemented by wood nightstands with lamps. Large glass doors lead to a balcony, allowing natural light to fill the room. A kitchen with modern appliances is visible, alongside a dining area with a wooden table.
Loft in Warwick
4.96 out of 5 average rating, 337 reviews

Luxe Penthouse Studio MainSt Warwick, SteamShower!

Relax & Indulge in our Luxe Penthouse Studio with Elevator & Parking! Beautifully furnished on Main St. in Warwick- Walk to Everything! Panoramic windows with amazing views over Warwick. Spa steam shower with bluetooth speakers, luxury bath toiletries, Heavenly King bed with Egyptian cotton linens, 65 in. HD Smart TV, reclining leather theater seats, velvet loungers convert into sleepers, fully stocked designer kitchen with all appliances, Nespresso & Keurig, coffee, tea, bottled water included.

Guest favourite
A spacious studio apartment features a large bed with a striped coverlet and soft lighting from bedside lamps. A round dining table is positioned near a flat-screen TV, while two windows allow natural light to brighten the room, enhancing the cozy ambiance.
Flat in Goshen
4.8 out of 5 average rating, 280 reviews

Great apartment- closest to Legoland

Large studio apartment in an historic luxury setting. Guests have a private entrance with parking to a first floor, fun studio. Our property boasts a private tennis/pickleball court for guest use and is situated directly on the Heritage Trail, which is perfect for biking and jogging. Our home borders several hundred acres of scenic rural property, yet we are conveniently located in the charming, historic Village of Goshen - within walking distance to restaurants and the Trotting Horse Museum

Guest favourite
A light-filled space features a well-equipped kitchen with modern appliances and a minimalist design. The wooden staircase, adorned with potted plants, leads to a cozy upper area. Natural light streams in through the window, illuminating the warm wooden flooring and vibrant area rug.
Flat in Newburgh
4.84 out of 5 average rating, 346 reviews

Unwind in a Bespoke Downtown Studio W Laundry

A bright & creative studio apartment welcomes you! Totally renovated by us for our family, and now available to you. Pros: ♥Automated check in (no waiting!) ♥ Comfy queen sized murphy bed with a real mattress ♥ Open space hang out, work, play, etc ♥Walkable neighborhood ♥Custom design with unique features (hand made tile, Murphy bed, commissioned mural) Cons: ☆Second floor apartment (one flight of stairs) ☆Rooftop not available in late fall/winter ☆ Studio apartment Welcome home!

Guest favourite
The cottage is surrounded by lush green grass and mature trees, offering a serene outdoor setting. A well-maintained pathway leads to the inviting entrance, while the structure features light-colored siding and large windows, creating a seamless connection with nature.
Cottage in Goshen
4.92 out of 5 average rating, 298 reviews

Cheery & Peaceful Farm Cottage, 10 Min to LEGOLAND

When you're looking to get away from it all and experience some peace and quiet surrounded in nature, this Cottage fits the bill. Whether it's enjoying fireflies over the field at dusk or enjoying cheerful birds in the morning, this beautiful Cottage sets the stage for you to be refreshed and renewed by the time you check out. While it feels like a secluded oasis, this place is also 10 minutes from LEGOLAND, Target, and all your other favorite conveniences. We look forward to hosting you.

Guest favourite
A cozy living area is showcased with two accent chairs, one in a warm terracotta tone and another in vibrant red, featuring a playful design. The wooden floor complements the inviting atmosphere, while framed artwork adorns the walls, adding visual interest to the space.
Guest suite in Chester
4.96 out of 5 average rating, 356 reviews

Adorable Guest Apartment in Victorian Mansion

This lovely 3rd floor private apartment is in an 1883 Victorian Mansion in Blooming Grove, NY for 1 - 6 people. It is beautifully furnished, has luxurious beds, so let us know if you need one, two or three bedrooms! The apartment has a private entrance, a claw foot tub, French door shower, and a kitchenette with sunny breakfast nook. It's freshly renovated and spacious. You will have to take 2 staircases. Our land has a nice view of a field of wildflowers, and our neighbor has cows.

Guest favourite
A modern living area features a light grey sectional sofa accompanied by two matching chairs. A sleek wooden coffee table sits on a patterned rug. A flat-screen television is mounted on the wall, and natural light filters through the window, illuminating the space.
Home in Warwick
4.87 out of 5 average rating, 183 reviews

Renovated 2 Bedroom Apartment in Heart of Village

Our newly renovated apartment is the lower level of a 1920 Victorian in the heart of the Village of Warwick. It boasts 650 sq ft of space with 2 bedrooms, and a full kitchen and bath. You can walk to beautiful shops, parks, and restaurants, or drive (free off-street parking) only minutes to ski, golf, hike, or enjoy our local orchards and wineries. There's even a doughnut shop across the street! All this with a huge backyard with it's own babbling creek! Welcome to 69 South St.

Top guest favourite
A modern kitchen features a round table surrounded by four wooden chairs. The walls are tiled in white, and a stainless steel stove is visible alongside a countertop with kitchen appliances. A vibrant painting of sunflowers adds a splash of color to the space.
Flat in Warwick
4.97 out of 5 average rating, 411 reviews

Warwick Village Apt w Off St Parking

2 minutes to Warwick Village Farmers Market Our lovely apartment has earned 5 star reviews from over 300 guests. You'll love this private suite w private entrance Large kitchen, bedroom & stunning sun room loaded with plants Loved by gardeners, bicyclists, runners, artists, writers, diners, & shoppers. Visit Brew Pubs & Wineries, Woodbury Common, West Point, Catskills, Mt Peter, Mountain Creek, Heated bathroom floor & large shower Beautiful gas stove 300 MBPS Washer & dryer

Guest favourite
A spacious main room is featured with high ceilings and a skylight. The kitchenette is visible alongside a dining table and chairs. A wooden coffee table sits in the living space, adorned with decorative items. Natural light flows through large windows framed by greenery.
Flat in Chester
4.98 out of 5 average rating, 141 reviews

Private Country Getaway

This family-friendly apartment is an hour from NYC, with a private driveway and entrance. The location is ideal for a getaway in any season. In the Warwick Valley, the property is 10 min from Legoland, and 13 min from the NY Renaissance Festival, surrounded by vineyards, orchards, farms, breweries, state parks, skiing, and the Appalachian Trail. 5 minutes from historic Sugar Loaf and the Sugar Loaf Performing Arts Center. 15 min from Woodbury Commons Premium Outlets.

Top guest favourite
Home in Chester
4.96 out of 5 average rating, 146 reviews

Mountainview Mansion Countryside Stay / Lrg Hottub

You'll be staying in a millionare mansion in the town where cream cheese was invented. Immerse in the fresh upstate NY nature nearby farms! Sugarloaf antique village, famous vineyards, luxury shopping, amusement parks, hiking, swimming, and restaurants. Surround yourself with mountain views through floor-to-ceiling windows spilling shimmering light into spacious rooms. Every room flows effortlessly into the next, naturally creating the space for deep connections.

Superhost
A cozy sleeping area is featured, highlighting a spacious bed with crisp white linens and a gray blanket. A decorative honeycomb shelf hangs on the dark blue wall, providing an artistic accent. Soft lighting enhances the peaceful ambiance.
Home in Goshen
4.9 out of 5 average rating, 211 reviews

Goshen House: hot tub, fenced yard, by downtown

Escape to The Goshen House. Enjoy relaxation, convenience, and open space in our new well-stocked and centrally-located home. This home was designed with comfort in mind: you'll love the radiant heat floors, open floor-plan, and modern kitchen. Let Fido get the zoomies out in the fenced-in yard or take her out on Heritage Trail, just steps away. Or just relax in the zen backyard, including a hot tub, fire pit and grill. Only 1 hour drive to Manhattan.

Top guest favourite
The exterior of a two-story home is presented, featuring a welcoming front porch with two chairs. A distinctive copper-colored roof complements the white siding and black shutters, while tall windows create a bright atmosphere. A stone pathway leads to the front entrance amidst landscaped grass.
Flat in Chester
4.96 out of 5 average rating, 408 reviews

Luxury Apt/Sugar Loaf/10 Min To LEGOLAND

This lovely modern space was just built in 2015. The space is located in the quaint Hamlet of Sugar Loaf, New York Artisan Village, which is surrounded by the town of Warwick and Chester with Greenwood Lake just minutes away...and NYC is just 75 minutes. It's a second floor apartment with private front and back entrances. Rear deck overlooks spacious fenced in yard with pond view. Walking distance to 2 restaurants and deli. LEGOLAND just 8 miles!

Popular amenities for Chester holiday rentals

Quick stats about holiday rentals in Chester

  • Nightly prices starting at

    Chester holiday rentals start at $635 SGD per night before taxes and fees

  • Verified guest reviews

    Over 60 verified reviews to help you choose

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Chester rentals

  • 4.9 Average rating

    Chester stays are highly rated by guests – averaging 4.9 out of 5!

  1. Airbnb
  2. United States
  3. New York
  4. Orange County
  5. Chester