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Chester Vacation Rentals

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Check prices for these dates

In two weeks
Jul 10 - Jul 12
In two months
Aug 21 - Aug 23
In three months
Sep 18 - Sep 20
In four months
Oct 16 - Oct 18

Our top choices for Chester vacation rentals

Terrace/patio

House on the Babbling Brook- Quiet 2BR + King Bed!

House on the Babbling Brook- Quiet 2BR + King Bed!
Highland Falls
10.0 out of 10, Exceptional, (9 reviews)
"Good stay, awesome place"
United States
Scott G.
$351 nightly
The price is $371
Jun 23 - Jun 24
Total with taxes and fees
House on the Babbling Brook- Quiet 2BR + King Bed!
1 bedroom, free WiFi, bed sheets

Cozy Loft Cabin high above Bashakill Wildlife Refuge

Cozy Loft Cabin high above Bashakill Wildlife Refuge
Wurtsboro
9.4 out of 10, Exceptional, (29 reviews)
"Great weekend getaway, very communicative and easy to access"
United States
Marlon R.
$171 nightly
The price is $192
Jun 23 - Jun 24
Total with taxes and fees
Cozy Loft Cabin high above Bashakill Wildlife Refuge
Property grounds

TRANQUIL MOUNTAIN SOLITUDE

TRANQUIL MOUNTAIN SOLITUDE
Pine Bush
10.0 out of 10, Exceptional, (7 reviews)
"Such a quaint & cozy little hideaway! Hosts could not be more hospitable. Thank you for a great stay!"
United States
Michelle H.
$212 nightly
The price is $237
Jun 29 - Jun 30
Total with taxes and fees
TRANQUIL MOUNTAIN SOLITUDE
Living area

Cozy 2BR condo w/ valley views

Cozy 2BR condo w/ valley views
Vernon Township
9.6 out of 10, Exceptional, (28 reviews)
"Very nice stay really clean and beautiful views thanks a lot enjoyed snowboarding at creek for the 2 days "
United States
Jacqueline
$223 nightly
The price is $252
Jun 23 - Jun 24
Total with taxes and fees
Cozy 2BR condo w/ valley views
Interior

Dream getaway apartment in the foot of Gunks Ridge

Dream getaway apartment in the foot of Gunks Ridge
Wallkill
9.6 out of 10, Exceptional, (29 reviews)
"Clean and quiet."
United States
Ted
$182 nightly
The price is $184
Jun 29 - Jun 30
Total with taxes and fees
Dream getaway apartment in the foot of Gunks Ridge
Interior

Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town

Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town
Warwick
8.6 out of 10, Excellent, (12 reviews)
"The bed was very comfortable! Loved the sitting area in the room! The downstairs of this location is an excellent restaurant! "
United States
Annette L.
$138 nightly
The price is $156
Jul 19 - Jul 20
Total with taxes and fees
Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town
Smart TV, fireplace

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

Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out
Vernon Township
9.4 out of 10, Exceptional, (54 reviews)
"Great convenient stay for a few days in the mountain!!! "
United States
rebecca l.
$269 nightly
The price is $304
Jul 6 - Jul 7
Total with taxes and fees
Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out
Terrace/patio

Renovated 1 Bedroom Valley View

Renovated 1 Bedroom Valley View
Vernon Township
10.0 out of 10, Exceptional, (3 reviews)
"Room & Facilities are great."
United States
Elvis
$223 nightly
The price is $239
Jun 23 - Jun 24
Total with taxes and fees
Renovated 1 Bedroom Valley View
Terrace/patio

Cabin in the heart of the Hudson Valley, Cabin 3

Cabin in the heart of the Hudson Valley, Cabin 3
Newburgh
9.8 out of 10, Exceptional, (14 reviews)
"We had a great stay, everything you need is provided. Would recommend to anyone."
United States
Bill W.
$234 nightly
The price is $276
Jun 23 - Jun 24
Total with taxes and fees
Cabin in the heart of the Hudson Valley, Cabin 3
Property grounds

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

Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!
Wallkill
10.0 out of 10, Exceptional, (84 reviews)
"great location and nice host"
United States
christopher s.
$208 nightly
The price is $233
Jul 13 - Jul 14
Total with taxes and fees
Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!
Shower, hair dryer, towels, soap

Luxe Penthouse Loft on Main St- Steam Shower, Elevator, Parking, Views, Kitchen

Luxe Penthouse Loft on Main St- Steam Shower, Elevator, Parking, Views, Kitchen
Warwick
10.0 out of 10, Exceptional, (41 reviews)
"Absolutely ideal comfort, cleanliness, amenities that are top notch for the kitchen and bathroom and luxury at the heart of Main Street in Warwick."
United States
Melissa V.
$231 nightly
The price is $261
Jun 23 - Jun 24
Total with taxes and fees
Luxe Penthouse Loft on Main St- Steam Shower, Elevator, Parking, Views, Kitchen
Exterior

2 Full Beds | Non-Smoking, Kitchen

2 Full Beds | Non-Smoking, Kitchen
Fishkill
9.8 out of 10, Exceptional, (19 reviews)
"great place tostay"
United States
Anonymous traveler
$110 nightly
The price is $127
Jun 28 - Jun 29
Total with taxes and fees
2 Full Beds | Non-Smoking, Kitchen
1 bedroom, iron/ironing board, free WiFi, bed sheets

Cozy country efficiency in the Hudson Valley

Cozy country efficiency in the Hudson Valley
Newburgh
9.8 out of 10, Exceptional, (68 reviews)
"Comfy cozy weekend retreat"
United States
Michael M.
$246 nightly
The price is $291
Jun 23 - Jun 24
Total with taxes and fees
Cozy country efficiency in the Hudson Valley
Exterior

Premium Studio with Stunning Mountain & Sunset Views at The Appalachian #263

Premium Studio with Stunning Mountain & Sunset Views at The Appalachian #263
Vernon
9.8 out of 10, Exceptional, (15 reviews)
"It was all good but I think they could have the restaurant available for visitors not to many restaurants around but the stay all in all was good"
United States
Donna
$242 nightly
The price is $273
Jun 23 - Jun 24
Total with taxes and fees
Premium Studio with Stunning Mountain & Sunset Views at The Appalachian #263
Exterior detail

Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen

Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen
Beacon
9.8 out of 10, Exceptional, (53 reviews)
"Have stayed a few times now… absolutely wonderful!! Clean, cozy, and comfortable! "
United States
Daniela C.
$208 nightly
The price is $239
Jul 8 - Jul 9
Total with taxes and fees
Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen
Lobby

1 King Bed | Non-Smoking, Kitchen, Shower

1 King Bed | Non-Smoking, Kitchen, Shower
Fishkill
10.0 out of 10, Exceptional, (16 reviews)
"Great rooms and service,"
United States
Anonymous traveler
$90 nightly
The price is $102
Jul 13 - Jul 14
Total with taxes and fees
1 King Bed | Non-Smoking, Kitchen, Shower
Property grounds

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Fort Montgomery
9.8 out of 10, Exceptional, (139 reviews)
"The space was comfortable and clean with a great view of the Hudson River valley. Perfect for 2 people on a weekend getaway. "
United States
Meredith C.
$277 nightly
The price is $327
Jun 23 - Jun 24
Total with taxes and fees
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Smart TV

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Goshen
9.8 out of 10, Exceptional, (13 reviews)
"Great place to stay when visiting Legoland. Convenient location and comfortable and clean."
United States
Jessica C.
$284 nightly
The price is $296
Jul 5 - Jul 6
Total with taxes and fees
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Cottage (2 Bedrooms) | Interior

Hudson Valley Retreat w/ Pool Near Greenwood Lake

Hudson Valley Retreat w/ Pool Near Greenwood Lake
3.0 star property
Monroe
10.0 out of 10, Exceptional, (3 reviews)
"fantastic accommodations"
United States
David
$455 nightly
The price is $515
Jun 28 - Jun 29
Total with taxes and fees
Hudson Valley Retreat w/ Pool Near Greenwood Lake
1 bedroom, iron/ironing board, free WiFi, bed sheets

Cabin in the Heart of the Hudson Valley, Cabin 1

Cabin in the Heart of the Hudson Valley, Cabin 1
Newburgh
10.0 out of 10, Exceptional, (34 reviews)
"Cute, clean and perfect for our needs"
United States
Richard H.
$234 nightly
The price is $276
Jun 24 - Jun 25
Total with taxes and fees
Cabin in the Heart of the Hudson Valley, Cabin 1
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

Sonesta Simply Suites Nanuet

Sonesta Simply Suites Nanuet

8/10 Good
"Room was clean but seems then clean room once a week, which was not expected. Hence will avoid in future"
GYANESHWAR 3-night trip
Posted 1 hour ago
Sonesta Simply Suites Nanuet

Find out more about Chester

Everything you need to know about Chester vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chester vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chester vacation 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 low season months. For more hustle and bustle, you may prefer to visit Chester in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $233 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Chester rentals

At Expedia, we put the best Chester vacation 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 vacation.

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.

Explore a world of travel with Expedia

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?

Lakefront Paradise Pool + Paddle Boats Sleeps 12: This vacation home rental near Chester offers an outdoor pool, a balcony, and air-conditioning to help you feel perfectly comfortable in your new surroundings. You can relax into your vacation with a garden and a pool table.

How many vacation rentals are there in Chester?

Expedia has 9 vacation 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. While here, Museum Village and Goosepond Mountain State Park are other places worth a visit.

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.