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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Chester vacation homes

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

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

Country House w/Hot Tub, Deck, Grill & Fire Pit
Goshen
9.8 out of 10, Exceptional, (67 reviews)
"We had a nice weekend at the Country House. I would recommend this property to friends and family. "
United States
Mike T.
The price is AED 1,036
AED 1,979 total
includes taxes & fees
1 Nov - 2 Nov
Country House w/Hot Tub, Deck, Grill & Fire Pit
A room with a bay window, a wooden table with a vase of flowers, and two upholstered chairs.

2. 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, (19 reviews)
"I absolutely loved my stay. A beautiful place with Victorian inspired, a big comfy bed, a really nice cozy reading nook with stone glass windows, and had an enjoyable stay!! Very easy check-in and check-out process. Great air conditioning during a heat wave!!"
United States
Daisy
The price is AED 347
AED 592 total
includes taxes & fees
4 Oct - 5 Oct
Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town
A kitchen with white cabinets, stainless steel appliances, a microwave, oven, and a refrigerator.

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

Amazing Home Near West Point, Shopping, Skiing and Legoland
Monroe
9.8 out of 10, Exceptional, (17 reviews)
"Very nice property in a nice neighborhood . Had all the amenities we needed and Ruth was super responsive. If we are in the area again, we will def stay at this location. "
United States
Kimberly R.
The price is AED 1,286
AED 2,729 total
includes taxes & fees
13 Oct - 14 Oct
Amazing Home Near West Point, Shopping, Skiing and Legoland
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

Renovated 5 Bedrm/3bath + Swim Spa & Huge Outdoor Space
Goshen
10.0 out of 10, Exceptional, (35 reviews)
"Great house, as advertised!"
United States
Steven K.
The price is AED 1,519
AED 2,690 total
includes taxes & fees
2 Nov - 3 Nov
Renovated 5 Bedrm/3bath + Swim Spa & Huge Outdoor Space
A room with a chandelier, a sofa, a table, and a cabinet.

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

Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
Warwick
8.8 out of 10, Excellent, (23 reviews)
"Great value and beautiful room and In ."
United States
Paul E.
The price is AED 360
AED 607 total
includes taxes & fees
2 Nov - 3 Nov
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
A hot tub with a view of a lake and houses in the background.

6. Waterfront Home with Hot Tub, Kayaks, and Fast Wifi

Waterfront Home with Hot Tub, Kayaks, and Fast Wifi
Greenwood Lake
10.0 out of 10, Exceptional, (42 reviews)
"We have stayed here a few times and the house is always perfect. Will stay here again in the future! "
United States
Lex S.
The price is AED 735
AED 1,882 total
includes taxes & fees
7 Oct - 8 Oct
Waterfront Home with Hot Tub, Kayaks, and Fast Wifi
A modern living room with a stone fireplace, large windows, and a cozy seating area.

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

Lakefront • 7BR Retreat • Sleeps 12 • Massage Chair
Monroe
10.0 out of 10, Exceptional, (5 reviews)
"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."
United States
Moshe F.
The price is AED 2,241
AED 4,558 total
includes taxes & fees
26 Oct - 27 Oct
Lakefront • 7BR Retreat • Sleeps 12 • Massage Chair
A deck with Adirondack chairs, a fire pit, and a grill.

8. 3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King

3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King
Cornwall
10.0 out of 10, Exceptional, (15 reviews)
"Everything you could ask for!!"
United States
Elisabeth
The price is AED 819
AED 1,627 total
includes taxes & fees
2 Nov - 3 Nov
3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King
A rural landscape with a barn, a silo, and a bridge with rocks and purple flowers in the foreground.

9. A Cozy Private Suite Near New Paltz: Farms, Nature, Hiking & Bike the rail trail

A Cozy Private Suite Near New Paltz: Farms, Nature, Hiking & Bike the rail trail
Wallkill
9.2 out of 10, Wonderful, (15 reviews)
"The room was super cute and clean. It had everything that I needed."
United States
Carrie
The price is AED 241
AED 497 total
includes taxes & fees
7 Oct - 8 Oct
A Cozy Private Suite Near New Paltz: Farms, Nature, Hiking & Bike the rail trail
A two-story house with a porch, a red door, and a small outdoor seating area with chairs and a table.

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

House on the Babbling Brook- Quiet 2BR + King Bed!
Highland Falls
9.8 out of 10, Exceptional, (13 reviews)
"We had a very comfortable stay. Nice quaint village. Area was quiet and easy to get to."
United States
Leann M.
The price is AED 481
AED 1,515 total
includes taxes & fees
6 Oct - 7 Oct
House on the Babbling Brook- Quiet 2BR + King Bed!
A room with a balcony overlooking a lake, featuring a small table and chairs.

11. Entire Lakeview House ~ Hot Tub ~ Firepit ~ Stunning View ~ 2 Decks

Entire Lakeview House ~ Hot Tub ~ Firepit ~ Stunning View ~ 2 Decks
Greenwood Lake
10.0 out of 10, Exceptional, (12 reviews)
"We had lovely and relaxing stay at this property! The surrounding area is beautiful and the crowd are amazing!"
United States
Susan R.
The price is AED 1,570
AED 3,168 total
includes taxes & fees
5 Oct - 6 Oct
Entire Lakeview House ~ Hot Tub ~ Firepit ~ Stunning View ~ 2 Decks
A lakeside dock with lounge chairs and a small table, surrounded by autumn foliage and a clear sky.

12. Latitude Lake House | Lake Access • Fire Pit

Latitude Lake House | Lake Access • Fire Pit
Greenwood Lake
10.0 out of 10, Exceptional, (7 reviews)
"Great property and loved the lake access!"
United States
Dan and Kristen L.
Latitude Lake House | Lake Access • Fire Pit
Two wine glasses on a wooden deck with a view of a lake and forested hills.

13. Romantic Lakeview Escape w/ Fire Pit

Romantic Lakeview Escape w/ Fire Pit
Greenwood Lake
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful home...it is clear that much thought and time went into the decor and functionality....complete with welcomed amenities."
United States
andrea e.
Romantic Lakeview Escape w/ Fire Pit
A blue house with a white porch, a welcome sign, and a mailbox.

14. 3BR West Point Retreat-3min to Back Gate+ King Bed

3BR West Point Retreat-3min to Back Gate+ King Bed
Highland Falls
8.4 out of 10, Very good, (7 reviews)
"Space was excellent, the multiple bedrooms with the extra bathroom was great. Kitchen was stocked with utensils, bathrooms were clean, living space was comfortable and cozy."
United States
Christine T.
The price is AED 503
AED 1,784 total
includes taxes & fees
6 Oct - 7 Oct
3BR West Point Retreat-3min to Back Gate+ King Bed
A bedroom with a bed, a ceiling fan, a nightstand, a window with curtains, and a wall with framed pictures.

15. Sleek Escape: Modern 3 BR- 4 Min from West Point !

Sleek Escape: Modern 3 BR- 4 Min from West Point !
Highland Falls
9.4 out of 10, Exceptional, (8 reviews)
"Great location and super host. "
United States
James U.
The price is AED 558
AED 1,730 total
includes taxes & fees
6 Oct - 7 Oct
Sleek Escape: Modern 3 BR- 4 Min from West Point !
A hotel with a swimming pool, green lawns, and a hilly backdrop.

16. 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, (61 reviews)
"The area is very convenient for doing outdoor activities. Room was clean."
United States
Siyu
The price is AED 526
AED 1,124 total
includes taxes & fees
4 Oct - 5 Oct
Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out
A spacious living room with a high ceiling, large windows, a flat-screen TV, a grey sofa, a small round table, and a wooden deck visible through the glass door.

17. Hike & Fish: Outdoor Retreat Near Trails

Hike & Fish: Outdoor Retreat Near Trails
Wurtsboro
9.6 out of 10, Exceptional, (10 reviews)
"Came in to town for a bachelor party weekend and had a great time. Rooms were clean and nice, scenery was beautiful, and the host was very responsive. Beds were comfy but could use some more pillows. Kitchen/dining room was convenient but could definitely use a bigger fridge for people who want to bring stuff for meals. Overall great experience!"
United States
Nate R.
The price is AED 606
AED 1,292 total
includes taxes & fees
4 Oct - 5 Oct
Hike & Fish: Outdoor Retreat Near Trails
A hallway with wooden flooring, white walls, a staircase with white railings, and a door at the end.

18. Walkable Village 5BR Home, 2 Full Kitchens, King Beds - Great for Groups.

Walkable Village 5BR Home, 2 Full Kitchens, King Beds - Great for Groups.
Montgomery
The price is AED 2,006
AED 3,119 total
includes taxes & fees
5 Oct - 6 Oct
Walkable Village 5BR Home, 2 Full Kitchens, King Beds - Great for Groups.
A modern kitchen with white cabinets, stainless steel appliances, and wooden flooring.

19. Luxury 3BR with King Beds in Montgomery Village

Luxury 3BR with King Beds in Montgomery Village
Montgomery
10.0 out of 10, Exceptional, (5 reviews)
"Excellent location! Very clean and the hosts were quick to respond to communication. We would definitely stay here again. "
United States
Barbara M.
The price is AED 1,200
AED 2,012 total
includes taxes & fees
4 Oct - 5 Oct
Luxury 3BR with King Beds in Montgomery Village
A modern kitchen with white cabinetry, a central island with stools, a built-in oven, and a stainless steel refrigerator.

20. New Farmhouse-Hot Tub, King Beds, Game Room, Pro Golf Sim & Amazing Valley View!

New Farmhouse-Hot Tub, King Beds, Game Room, Pro Golf Sim & Amazing Valley View!
Montgomery
10.0 out of 10, Exceptional, (20 reviews)
"Beautiful home, attentive hosts, and the hot tub was great!"
United States
Kyle F.
The price is AED 2,838
AED 5,038 total
includes taxes & fees
5 Oct - 6 Oct
New Farmhouse-Hot Tub, King Beds, Game Room, Pro Golf Sim & Amazing Valley View!
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

Crowne Plaza Suffern - Mahwah by IHG

Crowne Plaza Suffern - Mahwah by IHG

10/10 Excellent
"The hotel was great. The only problem was there is an internal bar that was supposed to close at 11:00 pm but there was a lot of noise from the bar until after midnight."
Douglas 2-night trip
Posted less than an hour ago
Crowne Plaza Suffern - Mahwah by IHG