Chester Holiday Rentals

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Holiday Rentals in Chester

Our top choices for Chester holiday rentals

Charming 1-bedroom Rekindled Farmhouse Historic Sugar Loaf, NY

9.6 out of 10, Exceptional, (4)
"The farmhouse is clean, comfortable, has modern updates to a rustic house. The owner/host was very pleasant and unobtrusive. We would definitely stay here again."
Charming 1-bedroom Rekindled Farmhouse Historic Sugar Loaf, NY

Mountain Creek Resort Condo - Golf, Hike, Legoland, Bike, NYC 1 Hour

10.0 out of 10, Exceptional, (47)
"Excelente place to stay and the host was very attentive.Will definitely be back "
The price is AU$431
includes taxes & fees
29 Sept - 30 Sept
Mountain Creek Resort Condo - Golf, Hike, Legoland, Bike, NYC 1 Hour

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

9.8 out of 10, Exceptional, (29)
"Great place for a quiet stay"
The price is AU$512
includes taxes & fees
21 Sept - 22 Sept
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

9.8 out of 10, Exceptional, (120)
"It has an incredible mountain and water view. "
The price is AU$476
includes taxes & fees
1 Sept - 2 Sept
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views

10.0 out of 10, Exceptional, (305)
"The lake views at this house are absolutely worth the trip and the money. It's a beautiful spot. And the host, Don, is super responsive, thoughtful and accommodating. Highly recommend!"
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views

Resort Getaway ! Mtn Creek Ski-In Ski-Out -Pool-Hot Tub-Sauna

10.0 out of 10, Exceptional, (63)
"We had a great stay."
The price is AU$444
includes taxes & fees
1 Sept - 2 Sept
Resort Getaway ! Mtn Creek Ski-In Ski-Out -Pool-Hot Tub-Sauna

Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out

9.4 out of 10, Exceptional, (36)
"Nice and clean"
The price is AU$475
includes taxes & fees
1 Sept - 2 Sept
Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out

Ann Creek: Charming 2 BR fully renovated house at Greenwood Lake. Dog friendly.

10.0 out of 10, Exceptional, (6)
Ann Creek: Charming 2 BR fully renovated house at Greenwood Lake. Dog friendly.

Waterfront Home with Hot Tub, Kayaks, and Fast Wifi

9.8 out of 10, Exceptional, (19)
"Clean, comfortable, beautiful views, cute little town. Super accommodating host. Couldn’t have asked for more. "
The price is AU$862
includes taxes & fees
16 Sept - 17 Sept
Waterfront Home with Hot Tub, Kayaks, and Fast Wifi

Cabin in the heart of the Hudson Valley, Cabin 4

9.2 out of 10, Wonderful, (25)
"Exactly as advertised "
The price is AU$272
includes taxes & fees
3 Sept - 4 Sept
Cabin in the heart of the Hudson Valley, Cabin 4

Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9

9.8 out of 10, Exceptional, (11)
"The place was wonderful! Even before check-in, Don was very communicative and made sure to ask about our preferences for one of the rooms.We had a fantastic stay — the home was very spacious, and the layout was perfect for a large family.The highlight for us was the beautiful lake view. We loved the outdoor seating area right by the water — perfect for relaxing with a coffee in the morning or unwinding in the evening. The kayaks were a great bonus and made for some fun time on the lake.We will...
Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9

Lake Glenwood A-Frame Cabin stunning views, fire pit, game room, Pet Friendly

10.0 out of 10, Exceptional, (31)
"We had a nice and relaxing time in beautiful surroundings. Thank you for having this cabin. We really enjoyed the sunsets reflecting off the lake!"
Lake Glenwood A-Frame Cabin stunning views, fire pit, game room, Pet Friendly

Cabin in the heart of the Hudson Valley, Cabin 2

9.6 out of 10, Exceptional, (22)
"Perfect for a getaway weekend for my wife and I! Easy check-in, clean, and although it's off a busy road, we found it peaceful and quiet. Would definitely stay again!"
The price is AU$272
includes taxes & fees
8 Sept - 9 Sept
Cabin in the heart of the Hudson Valley, Cabin 2

Modern penthouse suite in a restored grain tower with private roof deck.

10.0 out of 10, Exceptional, (23)
"Wonderful stay!"
The price is AU$826
includes taxes & fees
1 Sept - 2 Sept
Modern penthouse suite in a restored grain tower with private roof deck.

Condo at Mtn Creek 1 Bdr 1 Bath sleep 4 Mtn view #234

10.0 out of 10, Exceptional, (4)
"This property was comfortable, quaint and clean. Perfect little weekend getaway. We definitely plan on staying here again. "
The price is AU$377
includes taxes & fees
8 Sept - 9 Sept
Condo at Mtn Creek 1 Bdr 1 Bath sleep 4 Mtn view #234

Rustic Cabin in Fishkill!

10.0 out of 10, Exceptional, (1)
"Beautiful property with many different areas to explore. We originally intended to spend more time in beacon but decided it was more fun hanging out here. "
The price is AU$648
includes taxes & fees
2 Sept - 3 Sept
Rustic Cabin in Fishkill!

A luxurious stay.

6.0 out of 10, (2)
"If you want to go to a diagusting neighborhood then this is your place. We felt so unsafe we didn’t even stay there. We got a hotel. It is that bad. As nice as the inside is, the outside and neighborhood will have you running. Music blasting stinks of weed homeless people all over. Do not book this place. The owner didn’t even refund us our cleaning fee. Trust me STAY AWAY."
The price is AU$438
includes taxes & fees
12 Sept - 13 Sept
A luxurious stay.

Large,Cozy,Bright Apartment, Business Themed.

8.8 out of 10, Excellent, (15)
"Very cozy stay with responsive host"
The price is AU$1,053
includes taxes & fees
2 Sept - 3 Sept
Large,Cozy,Bright Apartment, Business Themed.

Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!

10.0 out of 10, Exceptional, (65)
"The yard and river are so beautiful. It’s a wonderful place to stay!"
The price is AU$323
includes taxes & fees
4 Sept - 5 Sept
Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!

Stylish & Peaceful Getaway on 3 Private Acres

2.0 star property
8.6 out of 10, Excellent, (7)
"The steps upstairs were worrisome, if you have any knee issues - this may not be the best option for a VRBO.This home was super clean, and beautiful however. Plenty of parking space for your guest.All supplies were provided."
The price is AU$664
includes taxes & fees
1 Sept - 2 Sept
Stylish & Peaceful Getaway on 3 Private Acres
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.
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Top Chester Hotel Reviews

Find out more about Chester

Find out more about Chester

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, 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 favourite 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 depend 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 AU$272 per night. Entering your travel dates in the search wizard might find you 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?

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo: This holiday home rental outside of Chester offers a fireplace, a patio and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with an oven, a microwave and an electric kettle, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many holiday rentals are there in Chester?

Expedia has 10 holiday rentals for your stay in Chester.

What can I see and do in Chester?

Family-friendly attractions include Castle Fun Center, whereas The Rock Sports Complex is a spot to enjoy the outdoors. 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.