Vacation rentals in Chester

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Chester

Guests agree: these stays are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Top guest favorite

A two-story building is featured with large panoramic windows on the facade, allowing natural light to fill the interior. The first floor is occupied by an optical shop, while the surrounding area includes paved parking spaces and landscaped elements in front.

Loft in Warwick

4.96 out of 5 average rating, 301 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 favorite

Guest suite in Montgomery

4.95 out of 5 average rating, 490 reviews

Garden View Guest Cottage

Located under 15 min. to Stewart Airport...1 mile to City Winery , nearby Angry Orchards , 1/2 hour to West Point Charming cottage setting located in the village of Montgomery, NY, Come for the day or stay for a few to take in all this historic area has to offer. Walk to some of the best restaurants in Orange County or simply read a book in the gardens... Truly a great value since it's a true "apartment " like setting..not just a room, with all the conveniences and sleeps up to 6 people

Guest favorite

A private pool deck features two lounge chairs positioned by the pool's edge, accompanied by a small table. The area is surrounded by a fenced perimeter, with a grassy yard visible in the background, suggesting a serene outdoor space for relaxation.

Loft in Cornwall

4.85 out of 5 average rating, 543 reviews

Country Getaway - Close to Hiking & Storm King

Enjoy the countryside minutes away from downtown restaurants, bars and Main Street, in our private, cozy loft studio! Located on 1.5 acres, this clean and comfortable apartment includes a kitchenette with bar-style table, living room and two flat screen Roku TV’s with Netflix, Hulu as well as an electric fireplace, outdoor patio and fire pit. Guests have two parking spaces, a private first-floor entrance, private full bathroom, outdoor dining area, BBQ and fire pit! Pool available seasonably.

Guest favorite

A vibrant display of climbing roses adorns a trellis, featuring clusters of deep red blooms against a backdrop of light-colored siding. Green leaves intertwine with the flowers, enhancing the lush appearance of the outdoor space, providing a serene atmosphere.

Apartment in Goshen

4.82 out of 5 average rating, 260 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 favorite

A functional kitchen area is equipped with modern appliances, including a refrigerator and a microwave. Open shelving presents glassware and kitchen items, while a white tiled backsplash complements the wooden countertop. Natural light enters through the window above the sink, enhancing the space.

Cottage in Goshen

4.92 out of 5 average rating, 266 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 favorite

A spacious bathroom is showcased, featuring a claw foot tub with an elegant chrome faucet. A modern glass shower enclosure is visible, along with a wooden vanity and mirror. The floor displays a patterned tile design, and the walls are painted in calming shades of blue.

Guest suite in Chester

4.96 out of 5 average rating, 320 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 favorite

Apartment in Wallkill

4.89 out of 5 average rating, 406 reviews

Dream getaway apartment in the foot of Gunks Ridge

Beautifully decorated space full of original art located in the foot of Shawangunk Ridge on the side of a large farm field and a forest. Get together with friends at the handmade farm dining table, feel hygge next to a wood-fired place, enjoy nature tranquility, and recharge. We provide ALL you need: clean towels, cooking essentials, complimentary high-end loose tea /coffee, friendly atmosphere, and good local advice. Apartment is a half basement part of a house but has full privacy.

Superhost

A classic white fireplace with ornate detailing is highlighted in the foreground. In the background, a doorway leads to a bright, white space, suggesting a clean and modern bathroom area. A decorative rug adds warmth beneath the fireplace.

Apartment in Newburgh

4.86 out of 5 average rating, 190 reviews

Special Nest w Private Entrance River View Porches

Front and back porch, river views, spacious living areas, new & fresh kitchen, and *two* bathrooms make this apartment the ultimate landing spot for a fun vaycay! Located on a street filled with intricate historical homes, this first floor apartment offers an accessible and comfortable getaway. A large backyard is shared with other guests, and sweeping river views are only steps away from your front door. Private entrance, plus easy parking and an electric car charger if you need it!

Top guest favorite

A vibrant piece of artwork featuring sunflowers hangs above a wooden table. An orange juicer, a blue teapot, a navy kettle, and a white bowl of oranges are neatly arranged, showcasing a mix of colors and textures.

Apartment in Warwick

4.98 out of 5 average rating, 395 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

Top guest favorite

A young deer is seen amidst vibrant yellow flowers and lush green foliage. The deer, with its distinctive spots, stands calmly, showcasing its attentive posture and large ears. The background suggests a serene natural setting.

Apartment in Chester

4.98 out of 5 average rating, 107 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.

Guest favorite

Home in Chester

4.95 out of 5 average rating, 128 reviews

Millionaire Mansion Countryside Stay w/ 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.

Guest favorite

A family stands outdoors near a horse-drawn carriage. Two adults and two children are present, with the adult holding a child. The background features brick buildings and shop signage, adding to the lively street atmosphere.

Guest suite in Warwick

4.94 out of 5 average rating, 297 reviews

Suite on Longhouse Creek

Beautiful one bedroom private suite with comfy queen size bed. The suite includes a sitting room, overlooking the creek, full bath, coffee nook with small refrigerator, microwave and Keurig coffee maker. Coffee is provided. A spiral stair leads you to the private deck with a french door entrance. Enjoy your coffee sitting at the lovely bistro set overlooking the longhouse creek. Feel free to use yard seating by the creek. Town Permit # 33316

Vacation rentals for every style

Get the amount of space that is right for you

Villas

Luxurious estates for the ultimate escape

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Popular amenities for Chester vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Chester

Guest favorite

The kitchen area is designed with modern cabinetry and stainless steel appliances. Large windows frame the surrounding greenery, creating a bright atmosphere. A kitchen island with a wooden top provides additional workspace, while a small dining cart is positioned nearby.

Home in New Windsor

4.91 out of 5 average rating, 121 reviews

View House

JamieRating, 5 stars1 week ago

A fantastic stay: totally private yet with expansive views. Birds galore, June was the perfect time to spot them all. House is gorgeous and unique. Fantastic hosts, stayed here 8 years ago and I very much hope to be back before another 8 years passes. Thank you to Lisa and Nafeeza!

Superhost

The historic property features a classic two-story facade with a spacious porch, supported by white columns. Surrounding greenery includes neatly trimmed bushes and vibrant trees, creating a serene outdoor space. A welcoming red door is accentuated, enhancing the home's charm.

Apartment in Goshen

4.84 out of 5 average rating, 62 reviews

Private 1 bedroom apartment Village of Goshen

BrittneyRating, 5 stars3 weeks ago

We had a great stay at Marty’s place! We were in town for a wedding and it was the perfect accommodation for a long weekend, especially if you love historic architecture and peaceful surroundings. Walkable to breakfast and lunch spots which was a plus! Very friendly and helpful host as well. Would definitely recommend!

An outdoor seating area features a striped lounge chair and two white chairs surrounded by greenery. A glass table rests on a chevron-patterned rug. The bright blue sky and sunlight create an inviting space for relaxation.

Place to stay in Goshen

4.7 out of 5 average rating, 89 reviews

Groovy Digs for a unique stay on Murray Hill

JayleeRating, 5 stars1 month ago

Very glad I found Groovy Digs!! Loved the decor and how well put the together the host has the place. Great neighborhood with many things to do nearby. Would definitely recommend this place to others :) We hope to back again!

Guest favorite

A minimalist entryway is presented, featuring a black-framed glass door leading to a well-lit living space. A simple bench with a light-colored cushion is positioned against the wall, alongside a tall potted plant. Natural wood accents are noted in the ceiling and flooring.

Cabin in Greenwood Lake

4.99 out of 5 average rating, 90 reviews

Modern Nordic Designed Cabin

FeRating, 5 stars2 weeks ago

The Nordic Cabin was the perfect setting for my husband and I to celebrate our 22nd wedding anniversary. The cabin is beautiful and the modern design, furnishings, and decor really stand out. Instructions of how to get into the cabin and the pitcures provided made check in and check out a breeze. The kitchen was well stocked. A bottle of white wine and a few treats were left for us. The kitchen offered different spices, oils, milk, and eggs. Kitchen utensils, pots/pans, dishes, cups, glasses, etc are provided, as well as cleaning supplies. The bathroom was stocked with toiletries. We spent a lot of time relaxing in the cozy living room and slept well in the beautiful bedroom. Last, I have to say that the first time we opened the gate at night, after dinner in Warwick, and saw all of the outdoor lights on, really made it feel like we were entering an enchanted garden. Would definitely come back!! Thank you Kamil and Margaret!!

Guest favorite

A wooden deck features a patterned outdoor rug and a dining table with four chairs, surrounded by green grass and trees. The area is enclosed by a wooden fence, creating a sense of privacy and openness. Steps lead down from the deck to the backyard.

Apartment in Chester

4.82 out of 5 average rating, 17 reviews

“The Loaf” in Sugar Loaf NY

ElizabethRating, 5 stars3 weeks ago

We planned a trip to Legoland for my son’s birthday and discovered this place was only 10 min away! I grew up visiting Sugar Loaf and it was just as quiet, peaceful and beautiful as I remembered. This place was way more unique and spacious than I expected. Really cool layout, super cozy, everything we could possibly need and more. It was just such a special spot. The host made some dinner recommendations and we had so much fun going out to the Tap House across the street! Such a fun vibe and great food and service. We loved strolling around and coming back to this spot to crash. Beds are super comfy, lots of room, so much character. I wish we could’ve explored Sugar Loaf more but it was a short getaway and we had a great day at Legoland which was such a quick ride. If you visit be sure to visit The Candle Shop. The owner Peter was one in a million. Next time we’ll account for extra time to check out the amazing local businesses. What a special, memorable weekend away. We’ll be back!

Guest favorite

Home in Greenwood Lake

5 out of 5 average rating, 23 reviews

Lakeview House ~ Hot Tub, Firepit, Stunning Views

ScottRating, 5 stars5 days ago

The home was pristine and beautifully designed, feeling like a brand new home. Everything was purposely placed to have exactly what you would think you’d need. The host is extremely friendly and super responsive. The views of the lake are awesome. The bedrooms are huge and the beds and bedding are extremely cozy (we all slept like babies). The duel decks are a really cool set up with the hot tub on the bottom such a cool vibe with really nice ceiling lights hanging. We came for a work escape as a team, and this was a great stay for us. The bedrooms upstairs also had their own little balconies, which is great to enjoy a morning cup of coffee before getting our day started. They also had all the amenities in the kitchen you could ever need.

Top guest favorite

An above-ground pool is surrounded by a wooden deck and features an attached ladder. Lounge chairs sit on a patterned rug nearby, with a sun umbrella providing shade. Lush greenery and trees frame the background, contributing to a serene outdoor space.

Home in Chester

5 out of 5 average rating, 9 reviews

4 Bedroom Home with Hot-Tub

corrineRating, 5 stars1 week ago

The house is fantastic and had everything we needed for a family filled weekend. Spacious, clean and tons of amenities. We didn’t get to use the pool because it was cold, but it was very clean and inviting. We would definitely return.

Superhost