Holiday Rentals in Chester

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Holiday Rentals in Chester

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 €257
per night
7 May - 8 May
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
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."
The price is €247
per night
6 May - 7 May
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
Located next to the Ski Resort, Bike Park and Water Park
10.0 out of 10, Exceptional, (142)
"The condo was great - clean, all the appliances we needed, and very convenient since we needed to be right in Vernon!"
Located next to the Ski Resort, Bike Park and Water Park
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Cottage Suites
3.0 star property
The price is €238
per night
5 May - 6 May
Cottage Suites
Luxury Waterfront Retreat near New Paltz & the Gunks: Hike, Bike, or Relax!
9.6 out of 10, Exceptional, (29)
"Family trip with teens and grandma. Beautiful home but unprepared for the gnats outside. Quiet location. Peaceful to sit outside around the fire pit. Kelly quickly responded to all questions and concerns. Kids enjoyed the ping pong table and grandma enjoyed the sunsets. Thank you for a great getaway!"
The price is €373
per night
6 May - 7 May
Luxury Waterfront Retreat near New Paltz & the Gunks: Hike, Bike, or Relax!
Cozy country efficiency in the Hudson Valley
9.8 out of 10, Exceptional, (38)
"This property is beautiful!! Spotless, functional and private. We absolutely loved the experience and will DEFINITELY be back again."
The price is €199
per night
4 Jun - 5 Jun
Cozy country efficiency in the Hudson Valley
Cabin in the heart of the Hudson Valley, Cabin 4
8.4 out of 10, Very good, (10)
"Pleasant overbite getaway. Cabin fit the bill!"
The price is €156
per night
5 May - 6 May
Cabin in the heart of the Hudson Valley, Cabin 4
Lakefront Luxury on Greenwood Lake
10.0 out of 10, Exceptional, (114)
"EXCELLENT"
Lakefront Luxury on Greenwood Lake
Renovated 1850's Cottage on Storm King Mountain
10.0 out of 10, Exceptional, (7)
"Great location, very clean. Check in was easy and convenient. Will stay there again. Perfect for a family gathering."
Renovated 1850's Cottage on Storm King Mountain
Cozy Countryside Cottage with Spa/Fireplace//Enclosed Yard/Fire Pits
9.6 out of 10, Exceptional, (34)
"Comfy place and great communication. Would stay again!"
The price is €327
per night
6 May - 7 May
Cozy Countryside Cottage with Spa/Fireplace//Enclosed Yard/Fire Pits
Rustic Chic at Mountain Creek! Pool, Hot Tub, Sauna Open ALL Year Round!
10.0 out of 10, Exceptional, (37)
"We were only staying for the one night and we found the whole process between checking in, parking and communicating with Stacey was very easy and welcoming. While the facility itself didn't have a ton of other guest (based on the season I assume), all of the amenities were working away i.e. the heated pool, sauna, hot tub etc. The apartment was cozy and had a lovely welcome package with loads of tips for food and activities nearby which we made use of. Thanks for your quick communication...
The price is €198
per night
8 May - 9 May
Rustic Chic at Mountain Creek! Pool, Hot Tub, Sauna Open ALL Year Round!
Cozy family-friendly home!
10.0 out of 10, Exceptional, (2)
"The property was beautiful and just as pictured. The host was more than attentive and helpful. He went above and beyond to make sure my stay was fantastic. I highly recommend this property!"
Cozy family-friendly home!
2 bedroom cozy condo with parking on premises
9.8 out of 10, Exceptional, (8)
"Our group had a great time at Fabiola's property. She was responsive and helpful and the unit was clean, cute and had everything we needed for a great stay. Thanks for having us!"
The price is €276
per night
7 May - 8 May
2 bedroom cozy condo with parking on premises
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 €801
per night
7 May - 8 May
Luxurious & Peaceful ~ Pool ~ Fire Pit ~ Backyard!
Catskills Cabin over waterfall with views & hot tub
9.8 out of 10, Exceptional, (57)
"We had a wonderful week of relaxing and recharging, such a cozy cabin! The views are amazing! Definitely recommend!"
Catskills Cabin over waterfall with views & hot tub
Hudson River View Suite-idyllic getaway with fireplace & private deck-75 min NYC
10.0 out of 10, Exceptional, (33)
"Very nice property, immaculately clean and very close to the Riverside Art Venue. Both quiet and convenient for my time in Newburgh. I would definitely stay here again."
The price is €168
per night
19 May - 20 May
Hudson River View Suite-idyllic getaway with fireplace & private deck-75 min NYC
Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out
9.6 out of 10, Exceptional, (10)
"Great for skiing. Easy to get to lifts. Clean, well equipped 1 bedroom. Good layout. Highly recommend. "
The price is €303
per night
8 May - 9 May
Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out
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
Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.
10.0 out of 10, Exceptional, (27)
"Weather was not so great to be outside but the game room made up for it!"
Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.
Spectacular Log Home Estate North Wing Apt
10.0 out of 10, Exceptional, (24)
"The place was amazing! It was a very beautiful place and was close to everything I was needing to do. It was extremely clean and cozy and I would stay again for sure!"
Spectacular Log Home Estate North Wing Apt
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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
2.5 star property
8.4 out of 10, Very good, (1002)
"The staff was amazing! Soon as we arrived the front desk person was very nice, There was no waiting to check in. We were checked in and got our room key. Not so happy about the room and for the price for 2 nights I expected better. We were given a room in the second floor facing the front of the hotel. There was a road nearby so we could hear when cars were passing by.you could also hear the engine of the bikes that belong to some people staying at the hotel.The room when we arrived was a bit...
The price is €127
per night
7 May - 8 May
Holiday Inn Express Hotel & Suites Chester, an IHG Hotel
DoubleTree by Hilton Hotel Nanuet
4.0 star property
8.4 out of 10, Very good, (1005)
"I want to compliment Chole, the woman at the front desk. Always pleasant and helpful."
The price is €131
per night
2 Jun - 3 Jun
DoubleTree by Hilton Hotel Nanuet
La Quinta Inn & Suites by Wyndham Middletown
2.5 star property
9.2 out of 10, Wonderful, (367)
"Clean, friendly staff Only negative: Breakfast! Only a few items available. Most everything needed to be restocked. Coffee too weak...tasted like hot water."
The price is €139
per night
9 May - 10 May
La Quinta Inn & Suites by Wyndham Middletown
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.

Everything you need to know about Chester holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chester holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chester holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Chester holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chester. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chester holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chester holiday rentals we have selected for you start as low as €156 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chester rentals

At Expedia, we put the best Chester holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Chester rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chester holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Chester?

Yes, there are holiday rentals in Chester close to Castle Fun Center, or you can select a more secluded option if you're looking for a relaxing stay. The shops and restaurants are several reasons why visitors like Chester. Make sure you have time to check out the ski areas and coffee shops during your trip.

What are some of the best holiday rentals that Chester has to offer?

Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits: This holiday home rental outside of Chester is located on a lake, and has a fireplace, a patio and a BBQ 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 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals are there in Chester?

Expedia has 11 holiday 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 favourite places to visit such as LEGOLAND® New York and Woodbury Common Premium Outlets in the wider area.

What are holiday rentals like in Chester?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chester. Holiday rentals provide amenities like laundry facilities and kitchens so you'll have all the conveniences of home. If you're concerned about a sanitised environment, holiday rentals can provide a sense of seclusion away from shared hotel lifts and busy front desks while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental an attractive option for a family trip or a small group gathering.

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