Chester Vacation Rentals from ￥13,380: Search Short-Term Rentals

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

Cozy Cabin with Sauna & Firepit! : This vacation home rental near Chester offers a fireplace, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms in addition to a kitchen with a stovetop and a microwave.

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Our top choices for Chester vacation rentals

1. Serene 10BR Retreat w/Pool, Gym & Hot Tub

Chester

"We had an amazing stay! The house was even better than the pictures. There was plenty of space for our large group, and the 10 bedrooms made it comfortable for everyone. The pool and hot tub were definitely highlights, and the game room kept both the kids and adults entertained throughout the trip.One of the things we loved most was how private and secluded the property felt. It was the perfect place to relax, unwind, and spend quality time together without feeling crowded. The home was clean,...

Jacob F.

2. TRANQUIL MOUNTAIN SOLITUDE

Pine Bush

Michelle H.

￥38,093 total

includes taxes & fees

Aug 11 - Aug 12

3. The DeVita House Est. 1900

Gardiner

Christopher T.

￥70,500 total

includes taxes & fees

Aug 16 - Aug 17

4. Hudson Valley Retreat w/ Pool Near Greenwood Lake

Monroe

David

￥81,499 total

includes taxes & fees

Aug 11 - Aug 12

5. Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town

Warwick

Paul E.

￥23,664 total

includes taxes & fees

Sep 8 - Sep 9

Coffee/tea maker, fridge, microwave, oven

6. Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Goshen

Jessica C.

￥46,155 total

includes taxes & fees

Aug 14 - Aug 15

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

Warwick

Melissa V.

￥43,012 total

includes taxes & fees

Sep 9 - Sep 10

Design Apartment, Patio, Garden View | View from room

8. Historic Horse Barn Apartment in Goshen

Goshen

￥58,503 total

includes taxes & fees

Aug 19 - Aug 20

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Top Chester Hotel Reviews

Holiday Inn Express Hotel & Suites Chester by IHG

8/10 Good

"It has a good breakfast . I like they have coffee available 24 hours . I did not like that the room has a funny smell not pleasant."

Sleep Inn & Suites Monroe - Woodbury

10/10 Excellent

"We only needed one night before a stay at LegoLand. We needed a place with EV chargers and this hotel did not disappoint. There are many chargers and the overall condition of the property was wonderful. The room was clean and modern and the bathroom was large. The pull out sofa was very comfortable for the kids and the gentleman at the front desk was very kind when we asked for more blankets. The breakfast buffet was a big hit with the kids."

Crowne Plaza Suffern - Mahwah by IHG

10/10 Excellent

"Magnifique hôtel! Chambre propre mais les matelas sont usés et on a tendance à rouler au milieu! Le petit déjeuner est vraiment super!!! Diversifié, des omelettes cuites devant nous et à notre goût et j’en passe! Je suis vraiment satisfaite et j’y retournerai sans hésitation."

Find out more about Chester

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:

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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 Cabin with Sauna & Firepit!: This vacation home rental near Chester offers a fireplace, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms in addition to a kitchen with a stovetop and a microwave.

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?

Cultural attractions include Museum Village and Sugar Loaf Performing Arts Center, whereas The Rock Sports Complex is one spot to enjoy nature. 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.

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Check prices for these dates

Our top choices for Chester vacation rentals

1. Serene 10BR Retreat w/Pool, Gym & Hot Tub

2. TRANQUIL MOUNTAIN SOLITUDE

3. The DeVita House Est. 1900

4. Hudson Valley Retreat w/ Pool Near Greenwood Lake

5. Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town

6. Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

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

8. Historic Horse Barn Apartment in Goshen

9. Hudson Valley Retreat w/ Pool Near Greenwood Lake

10. Carriage House Apartment Goshen NY

11. Hay Loft Apartment in Barn - Goshen

12. Historic Cabin with Pool & Fire Pit

13. The Wine House, Sitting atop of Warwick's brand new Wine Bar

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

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

16. Hello Small Stone

17. Grant - A Tranquil One Bedroom Steps from River

18. Modern Hudson Valley Apt 202 - King/Queen/Twin

19. Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

20. Cabin in the heart of the Hudson Valley, Cabin 4

Find vacation rentals that suit your style

Top Chester Hotel Reviews

Holiday Inn Express Hotel & Suites Chester by IHG

Sleep Inn & Suites Monroe - Woodbury

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

Courtyard by Marriott Middletown Goshen

Crowne Plaza Suffern - Mahwah by IHG

Inn on the Hudson

Sleep Inn & Suites Middletown - Goshen

Hampton Inn Harriman Woodbury

Ramada by Wyndham Newburgh/West Point

Find out more about Chester

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