Chester Vacation Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Vacation Rentals in Chester

Cottage Suites
Luxury Studio | Private kitchen | Full-size fridge, microwave, oven, stovetop
Cottage Suites
3.0 star property
8.0 out of 10, Very Good, (1)
"The actual room was excellent, compfy bed. Shower door was hard to open. No handle on the outside. Loud cars going through the neighborhood and my room was up 3 flights of stairs. "
Cottage Suites
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
1 bedroom, desk, iron/ironing board, travel crib
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
9.8 out of 10, Exceptional, (35)
"This is a cozy property in a very rural setting. The host is extremely responsive and very thorough. It is quiet and private. The furniture and bed are very comfortable. The wood burning stove is a pellet stove which provides enough heat to take the edge off. The hot tub could comfortably fit 4 people. The Village of Cold Spring is less than 10 minutes away, as is the Interstate 84 bridge across the Hudson. If you want to make your own food, bring it. There is no grocery store nearby."
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Property grounds
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
9.8 out of 10, Exceptional, (96)
"Comfortable apartment with a phenomenal view! The space could use a deep clean and some decluttering, but that view!!! Did I mention that the view was A-mazing?!?"
The price is ￥32,075
￥45,440 total
includes taxes & fees
Jun 10 - Jun 11
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Rustic Chic at Mountain Creek! Pool, Hot Tub, Sauna, Open ALL Year Round!
Outdoor pool, a heated pool
Rustic Chic at Mountain Creek! Pool, Hot Tub, Sauna, Open ALL Year Round!
10.0 out of 10, Exceptional, (38)
"Great location: clean and comfy."
The price is ￥20,493
￥39,019 total
includes taxes & fees
Jun 3 - Jun 4
Rustic Chic at Mountain Creek! Pool, Hot Tub, Sauna, Open ALL Year Round!
Lakefront Luxury on Greenwood Lake
Property grounds
Lakefront Luxury on Greenwood Lake
10.0 out of 10, Exceptional, (116)
"We spent a much needed relaxing weekend at this location. I can't say enough good things about this property. It was beautifully decorated, perfectly supplied, and very clean. We would rent this property again."
Lakefront Luxury on Greenwood Lake
Cozy Countryside Cottage with Spa/Fireplace//Enclosed Yard/Fire Pits
Property grounds
Cozy Countryside Cottage with Spa/Fireplace//Enclosed Yard/Fire Pits
9.6 out of 10, Exceptional, (35)
"Three nights here as we toured the area. Check in was easy. We were able to access the VRBO app 30 minutes prior to our arrival. By the time we reached the driveway, Ruben had sent the access code.The road to the house is gravel and only wide enough for one car. We were glad we had arrived during the day.The house has an antique store vibe. Lots of books for a rainy day activity. FYI, the photos on the listing are a bit different from what we saw in the rooms. The dining table is larger with...
Cozy Countryside Cottage with Spa/Fireplace//Enclosed Yard/Fire Pits
Hudson River View Suite-idyllic getaway with fireplace & private deck-75 min NYC
Property grounds
Hudson River View Suite-idyllic getaway with fireplace & private deck-75 min NYC
10.0 out of 10, Exceptional, (36)
"Very nice. A lot of attention to detail"
Hudson River View Suite-idyllic getaway with fireplace & private deck-75 min NYC
Updated Getaway w/ Pool & Hot Tub on < 3 Acres!
Fridge, microwave, stovetop, dishwasher
Updated Getaway w/ Pool & Hot Tub on < 3 Acres!
10.0 out of 10, Exceptional, (22)
"My family and I had a wonderful weekend at the property. It rained most of the time, but we made the best of it. It was all over too fast. It's a nice, relaxing property."
Updated Getaway w/ Pool & Hot Tub on < 3 Acres!
Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out
Smart TV, fireplace
Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out
9.6 out of 10, Exceptional, (12)
"Great location and communication! Very clean and nice!"
The price is ￥25,142
￥50,713 total
includes taxes & fees
Jun 3 - Jun 4
Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out
Cabin in the heart of the Hudson Valley, Cabin 4
Exterior
Cabin in the heart of the Hudson Valley, Cabin 4
8.4 out of 10, Very Good, (11)
"Everything was as it says it was. Place was spotless. In the evening and morning you didn’t hear any traffic noise at all. Was quiet and peaceful. Communication with the property owner was outstanding."
The price is ￥17,138
￥25,677 total
includes taxes & fees
Jun 2 - Jun 3
Cabin in the heart of the Hudson Valley, Cabin 4
Fenced Yard Private Lakes 7 Beaches Huge Fire Pit
Lake
Fenced Yard Private Lakes 7 Beaches Huge Fire Pit
9.8 out of 10, Exceptional, (91)
"My family was down for the Spartan race weekend. The property is in a perfect location for proximity to the mountain, as well as Beaches and playgrounds for the kids. It comfortably fit four adults and two kids, and the fenced yard was great for the dog. Michael is a thoughtful and responsive owner, and we are looking forward to staying again next time we are down."
Fenced Yard Private Lakes 7 Beaches Huge Fire Pit
Renovated 1850's Cottage on Storm King Mountain
Property grounds
Renovated 1850's Cottage on Storm King Mountain
9.8 out of 10, Exceptional, (8)
"It was a beautiful setting with water fall. The home itself needs a little work. It is well used and needs some TLC. Photos look much better then actual home."
Renovated 1850's Cottage on Storm King Mountain
Cabin in the heart of the Hudson Valley, Cabin 2
Exterior
Cabin in the heart of the Hudson Valley, Cabin 2
9.4 out of 10, Exceptional, (3)
"Great tiny house for a stay upstate. Check in was easy and the place is clean!"
The price is ￥17,138
￥25,677 total
includes taxes & fees
Jun 3 - Jun 4
Cabin in the heart of the Hudson Valley, Cabin 2
Cozy family-friendly home!
Fridge, microwave, oven, stovetop
Cozy family-friendly home!
10.0 out of 10, Exceptional, (3)
"Older manufactured home has been updated. We appreciated that each area had its own mini split unit for individual climate control. Area felt safe and quiet. Good hot water and water pressure. Kitchen was stocked for stovetop cooking but not much for baking, and no water glasses. (We just drank everything from the coffee cups.) Split bedroom layout was good for two couples. "
The price is ￥21,855
￥44,976 total
includes taxes & fees
Jun 10 - Jun 11
Cozy family-friendly home!
Spectacular Log Home Estate North Wing Apt
Property grounds
Spectacular Log Home Estate North Wing Apt
10.0 out of 10, Exceptional, (25)
"All as represented. Had everything we needed for a lovely home away from home!"
Spectacular Log Home Estate North Wing Apt
Luxurious & Peaceful ~ Pool ~ Fire Pit ~ Backyard!
Fridge, microwave, oven, stovetop
Luxurious & Peaceful ~ Pool ~ Fire Pit ~ Backyard!
6.4 out of 10, (5)
"This host is very irresponsible knowing 8 months in advanced about the reservation and not having the pool ready or even communicating that the pool would not be ready for use is just unexceptable. Also property has many things wrong with it. The oven doesn't work, the gas tank for the grill was left empty, all shower heads need to be replaced, the tv and mini Fridge in the basement bedroom dont work, the power outlet in the master bedroom doesn't work and the wall fixture above jacuzzi is just...
The price is ￥80,187
￥152,010 total
includes taxes & fees
Jun 2 - Jun 3
Luxurious & Peaceful ~ Pool ~ Fire Pit ~ Backyard!
Royal Garden Main Cabin
Interior
Royal Garden Main Cabin
Royal Garden Main Cabin
Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!
Beach
Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!
10.0 out of 10, Exceptional, (35)
"I needed a place in Wallkill NY to stay. This VRBO was perfect!"
The price is ￥20,283
￥36,465 total
includes taxes & fees
Jun 12 - Jun 13
Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!
Located next to the Ski Resort, Bike Park and Water Park
Outdoor pool, a heated pool
Located next to the Ski Resort, Bike Park and Water Park
10.0 out of 10, Exceptional, (143)
"Comfortable one bedroom condo. Pleasant and clean. Mountaintop ceremony was unique and beautiful."
Located next to the Ski Resort, Bike Park and Water Park
Quaint village, walk to restaurants and shops.
Property grounds
Quaint village, walk to restaurants and shops.
The price is ￥29,088
￥47,995 total
includes taxes & fees
Jun 2 - Jun 3
Quaint village, walk to restaurants and shops.
Don't see what you're looking for?
See all available properties in Chester
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other types of properties in Chester you may be interested in

Holiday Inn Express Hotel & Suites Chester, an IHG Hotel
Exterior
Holiday Inn Express Hotel & Suites Chester, an IHG Hotel
2.5 star property
8.4 out of 10, Very Good, (1000)
"The staff was friendly and accommodating, room was clean spacious. Overall a pleasant stay."
The price is ￥22,500
￥25,453 total
includes taxes & fees
Jun 2 - Jun 3
Holiday Inn Express Hotel & Suites Chester, an IHG Hotel
La Quinta Inn & Suites by Wyndham Middletown
Exterior
La Quinta Inn & Suites by Wyndham Middletown
2.5 star property
9.2 out of 10, Wonderful, (388)
"The staff was nice. Checking in was very quick and the place is clean. "
The price is ￥19,965
￥23,583 total
includes taxes & fees
Jun 3 - Jun 4
La Quinta Inn & Suites by Wyndham Middletown
HYATT house Fishkill/Poughkeepsie
Fridge, microwave, coffee/tea maker, cookware/dishes/utensils
HYATT house Fishkill/Poughkeepsie
3.0 star property
8.6 out of 10, Excellent, (1000)
"Liked how the room was a suite! They we’re accommodating and let us check in a little early, too. Would recommend for a good spot in the area!"
The price is ￥22,308
￥25,012 total
includes taxes & fees
Jun 17 - Jun 18
HYATT house Fishkill/Poughkeepsie
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Search for holiday rentals in Chester on Expedia! You can easily find your home rentals, villas, holiday apartments in Chester using one of the methods below:

  • View our selection of featured holiday rentals in Chester
  • Use the map to find apartments and other holiday homes in the Chester neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chester while they last

Look no further and take a look at our great range of rental properties in Chester!

Frequently asked questions

Are there vacation rentals in Chester?

Yes, you can find vacation rentals in Chester close to Castle Fun Center, or you can go with a more remote option if you'd like a relaxing place to stay. The shops and restaurants are several reasons why visitors like Chester. Make sure you have time to check out the ski areas and coffeehouses during your trip.

What are some of the best vacation home rentals in Chester?

Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits: Located near Chester, this vacation home rental is located on a lake and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. It offers a garden, a selection of games, and a spa tub so you can immerse yourself in your vacation.

How many vacation rentals are there in Chester?

Expedia has 11 vacation rentals for your stay in Chester.

What can I see and do in Chester?

The Rock Sports Complex and Goosepond Mountain State Park are a couple of scenic spots to enjoy the outdoors, whereas Museum Village is one of the cultural attractions. You’ll find favorite places to visit like LEGOLAND® New York and Woodbury Common Premium Outlets in the larger area.

What are vacation rentals like in Chester?

Vacation rentals are privately owned properties you can reserve for several days or more in Chester. Vacation rentals provide amenities such as hot tubs, fire pits, and patios so you'll have everything you need. If you're concerned about a sanitized environment, a vacation rental can provide a sense of security away from shared hotel elevators and busy concierge desks while still allowing you a great travel experience. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental a popular option for a family trip or a small group gathering.

Recent reviews of Chester properties
Expedia verified reviews

Sleep Inn & Suites Monroe - Woodbury

Sleep Inn & Suites Monroe - Woodbury

5/5 Excellent
"Got the reservation last minute and was impressed by quality of the accommodations."
A verified traveler stayed at Sleep Inn & Suites Monroe - Woodbury
Posted 13 hours ago
Sleep Inn & Suites Monroe - Woodbury