Chester Vacation Rentals from AED 334: Search Short-Term Rentals

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Our top choices for Chester vacation rentals

A patio with stone flooring, a grill, outdoor furniture, and a house with white siding and green trim.

1. Historic Sugar Loaf Farmhouse | 5BR | Sleeps 8

Chester

jolene j.

A two-story house with a porch, a table, and chairs outside.

2. Historic Horse Barn Apartment in Goshen

Goshen

AED 606 total

includes taxes & fees

12 Nov - 13 Nov

A hot tub in a lush garden with a stone wall and outdoor furniture.

3. Country House w/Hot Tub, Deck, Grill & Fire Pit

Goshen

Mike T.

AED 1,891 total

includes taxes & fees

18 Nov - 19 Nov

A circular outdoor seating area with a fire pit, surrounded by a stone border, set in a lush green forest.

4. Renovated 5 Bedrm/3bath + Swim Spa & Huge Outdoor Space

Goshen

Steven K.

A spacious living room with a fireplace, a ceiling fan, and a large window.

5. Hudson Valley Retreat w/ Pool Near Greenwood Lake

Monroe

Scott

AED 1,981 total

includes taxes & fees

30 Nov - 1 Dec

A kitchen with white cabinets, stainless steel appliances, a microwave, oven, and a refrigerator.

6. Amazing Home Near West Point, Shopping, Skiing and Legoland

Monroe

Kimberly R.

AED 2,590 total

includes taxes & fees

11 Nov - 12 Nov

A grey sectional sofa with patterned cushions, a round wooden coffee table with a green plant, and a window with a view of trees.

7. Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Goshen

Jessica C.

AED 990 total

includes taxes & fees

12 Nov - 13 Nov

A spacious living room with a stone fireplace, two white sofas, a glass coffee table, and large windows.

8. Villa Verde B&B, bsm, Greenwood Lake NY

Greenwood Lake

Tara

AED 985 total

includes taxes & fees

11 Nov - 12 Nov

A modern kitchen with wooden flooring, a dining area with a table and chairs, and a kitchen counter with appliances.

9. The Wine House

Warwick

Robin

AED 1,012 total

includes taxes & fees

11 Nov - 12 Nov

10. Luxe Loft 2 on Main St.Steam Shower, ZeroG King Bed, Designer Kitchen, Elevator!

Warwick

Francis

AED 877 total

includes taxes & fees

16 Nov - 17 Nov

A stone pathway leading to a stone wall with a potted plant.

11. Villa Verde B&B, Greenwood Lake NY, 1

Monroe

Thomas

AED 1,122 total

includes taxes & fees

11 Nov - 12 Nov

12. Hudson Valley Retreat w/ Pool Near Greenwood Lake

Monroe

Marc

AED 1,913 total

includes taxes & fees

30 Nov - 1 Dec

A room with a bay window, a wooden table with a vase of flowers, and two upholstered chairs.

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

Warwick

Joseph

AED 569 total

includes taxes & fees

16 Nov - 17 Nov

A two-story building with a porch, surrounded by greenery and a visible rainbow in the sky.

14. Top of the tower penthouse suite in Village of Warwick

Warwick

Lisi M.

AED 1,479 total

includes taxes & fees

11 Nov - 12 Nov

A modern living room with a stone fireplace, large windows, and a cozy seating area.

15. Lakefront • 7BR Retreat • Sleeps 12 • Massage Chair

Monroe

"The combination of an antique, old-style house with a modernized interior featuring all the amenities you could dream of made for an enjoyable and cozy experience. The house is located right at the back of the lake in a quiet neighborhood and comes fully equipped with:- A spacious layout- High-speed Wi-Fi- Useful massage chair - Fun recreational areas- Lovely decorThis house will truly become a staple in the area."

Moshe F.

AED 4,242 total

includes taxes & fees

11 Nov - 12 Nov

A circular fire pit with chairs and tables, surrounded by a stone deck, near a lake with string lights.

16. Lakefront Paradise Pool + Paddle Boats Sleeps 12

Monroe

"We had a wonderful week long stay. The house is beautiful and right on the lake, with beautiful views and sunsetsWe were there for a West Point Graduation and was about a 30 minute drive to the school, even on the busy days of the parade and graduation dayThe house had plenty of room for our group and the host was easy to get ahold of. There are 4 official bedroom and 4 bathrooms and a basement and 2 office/den, 2 washer and dryers - one in the top floor and another in the basement which has...

Courtney D.

AED 5,055 total

includes taxes & fees

17 Nov - 18 Nov

A hot tub with a view of a lake and houses in the background.

17. Waterfront Home with Hot Tub, Firepit, and Kayaks

Greenwood Lake

Lex S.

AED 1,774 total

includes taxes & fees

1 Dec - 2 Dec

A house with a view of a bridge and mountains.

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

Fort Montgomery

Jasmine

AED 1,115 total

includes taxes & fees

16 Nov - 17 Nov

A deck with Adirondack chairs, a fire pit, and a grill.

19. 3BR Home with Fireplace & Hudson Valley views near Woodbury Commons, West Point

Cornwall

Elisabeth

AED 1,532 total

includes taxes & fees

16 Nov - 17 Nov

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Top Chester Hotel Reviews

La Quinta Inn & Suites by Wyndham Middletown-Goshen

10/10 Excellent

"Love It"

Holiday Inn Express Hotel & Suites Chester by IHG

10/10 Excellent

"The hotel is new so everything is fresh, clean and beautiful. My husband and I are retired seniors and loved the fact that it was only a shower. Often a tub does not have a rough surface on the bottom to prevent slipping. So the shower was just perfect. We were upgraded to a suite that was just gorgeous. Could not have been better."

Inn on the Hudson

8/10 Good

"Clean room with a balcony that overlooks the Hudson but I didn’t consider that we were so close to be train tracks that you would hear the trains constantly haha. I would have liked to be able to turn off the balcony lights because they filtered through the door window all night but other wise is fine. Breakfast is very basic, as in a boiled egg, some bagels, cup cereals and the ability to make a waffle."

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 Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views: This vacation home rental near Chester is located on a lake and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

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. While here, Castle Fun Center 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.

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Check prices for these dates

Our top choices for Chester vacation rentals

1. Historic Sugar Loaf Farmhouse | 5BR | Sleeps 8

2. Historic Horse Barn Apartment in Goshen

3. Country House w/Hot Tub, Deck, Grill & Fire Pit

4. Renovated 5 Bedrm/3bath + Swim Spa & Huge Outdoor Space

5. Hudson Valley Retreat w/ Pool Near Greenwood Lake

6. Amazing Home Near West Point, Shopping, Skiing and Legoland

7. Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

8. Villa Verde B&B, bsm, Greenwood Lake NY

9. The Wine House

10. Luxe Loft 2 on Main St.Steam Shower, ZeroG King Bed, Designer Kitchen, Elevator!

11. Villa Verde B&B, Greenwood Lake NY, 1

12. Hudson Valley Retreat w/ Pool Near Greenwood Lake

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

14. Top of the tower penthouse suite in Village of Warwick

15. Lakefront • 7BR Retreat • Sleeps 12 • Massage Chair

16. Lakefront Paradise Pool + Paddle Boats Sleeps 12

17. Waterfront Home with Hot Tub, Firepit, and Kayaks

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

19. 3BR Home with Fireplace & Hudson Valley views near Woodbury Commons, West Point

Find vacation rentals that suit your style

Top Chester Hotel Reviews

La Quinta Inn & Suites by Wyndham Middletown-Goshen

Sleep Inn & Suites Middletown - Goshen

Hampton Inn & Suites Mahwah

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

Sleep Inn & Suites Monroe - Woodbury

Holiday Inn Express Hotel & Suites Chester by IHG

Inn on the Hudson

The Thayer Hotel at West Point

Studio 6 Extended Stay Fishkill Westage Center NY

Frequently asked questions

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