Lodging Image

Search Holiday Homes in Chester

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Save instantly and earn perks with One Key
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Chester holiday homes

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
9.0 out of 10, Wonderful, (18 reviews)
"Great value and beautiful room and In ."
United States
Paul E.
The price is £126
includes taxes & fees
21 Jul - 22 Jul
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town

Amazing Home Near West Point, Shopping, Skiing and Legoland

Amazing Home Near West Point, Shopping, Skiing and Legoland
Monroe
10.0 out of 10, Exceptional, (14 reviews)
"The host was welcoming and easy to reach. It’s a lovely, fully stocked house that had everything we needed. Check-in and check-out were a breeze. Nice, quiet location."
United States
Michael M.
The price is £374
includes taxes & fees
24 Jul - 25 Jul
Amazing Home Near West Point, Shopping, Skiing and Legoland

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, (10 reviews)
"Good stay, awesome place"
United States
Scott G.
The price is £304
includes taxes & fees
21 Jul - 22 Jul
House on the Babbling Brook- Quiet 2BR + King Bed!

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, (14 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 £127
includes taxes & fees
27 Jul - 28 Jul
Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town

Romantic Lakeview Escape w/ Fire Pit

Romantic Lakeview Escape w/ Fire Pit
Greenwood Lake
10.0 out of 10, Exceptional, (1 review)
"We had a wonderful stay at this house! It was clean, comfortable, and had everything we needed. The highlight was the beautiful backyard with its peaceful lake viewperfect for relaxing and enjoying the scenery. The host was fantastic, very friendly, and always quick to respond to any questions. We would happily stay here again and highly recommend this property to others!"
United States
yana b.
The price is £243
includes taxes & fees
29 Jul - 30 Jul
Romantic Lakeview Escape w/ Fire Pit

3-bedroom house in marvelous Goshen. Luxury cabin vibes for your getaway.

3-bedroom house in marvelous Goshen. Luxury cabin vibes for your getaway.
Goshen
8.0 out of 10, Very good, (1 review)
"The check-in process went smoothly. The property was very clean and comfortable. Location was close to many different small towns. "
United States
Kelly M.
The price is £369
includes taxes & fees
29 Jul - 30 Jul
3-bedroom house in marvelous Goshen. Luxury cabin vibes for your getaway.

Family Home Close to Warwick, 5 Mi to Lake!

Family Home Close to Warwick, 5 Mi to Lake!
Monroe
10.0 out of 10, Exceptional, (17 reviews)
"Clean, cozy home in a quiet and safe neighborhood. "
United States
Jillian C.
The price is £546
includes taxes & fees
2 Aug - 3 Aug
Family Home Close to Warwick, 5 Mi to Lake!

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, (10 reviews)
"Everything you could ask for!!"
United States
Elisabeth
The price is £313
includes taxes & fees
20 Jul - 21 Jul
3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King

Charming 2-bedroom house in Greenwood Lake with Central AC/Heat

Charming 2-bedroom house in Greenwood Lake with Central AC/Heat
Greenwood Lake
10.0 out of 10, Exceptional, (7 reviews)
"Very clean and really cute place. "
United States
Katie C.
Charming 2-bedroom house in Greenwood Lake with Central AC/Heat

Waterfront Home with Hot Tub, Kayaks, and Fast Wifi

Waterfront Home with Hot Tub, Kayaks, and Fast Wifi
Greenwood Lake
9.8 out of 10, Exceptional, (39 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 £522
includes taxes & fees
21 Jul - 22 Jul
Waterfront Home with Hot Tub, Kayaks, and Fast Wifi

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

3BR West Point Retreat-3min to Back Gate+ King Bed
Highland Falls
8.0 out of 10, Very good, (6 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 £375
includes taxes & fees
21 Jul - 22 Jul
3BR West Point Retreat-3min to Back Gate+ King Bed

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, (55 reviews)
"Great convenient stay for a few days in the mountain!!! "
United States
rebecca l.
The price is £232
includes taxes & fees
26 Jul - 27 Jul
Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out

Hike & Fish: Outdoor Retreat Near Trails

Hike & Fish: Outdoor Retreat Near Trails
Wurtsboro
9.6 out of 10, Exceptional, (9 reviews)
"Nice, clean little property in a secluded area. Great to get away."
United States
David F.
The price is £302
includes taxes & fees
26 Jul - 27 Jul
Hike & Fish: Outdoor Retreat Near Trails

Luxe Waterfront Retreat w/ Infrared Sauna & Red Light. Near New Paltz

Luxe Waterfront Retreat w/ Infrared Sauna & Red Light. Near New Paltz
wallkill
9.8 out of 10, Exceptional, (59 reviews)
"This is a wonderful property. Very clean and well maintained. It was centrally located to everything we needed. The outdoor area is amazing! We really enjoyed sitting by the river and having coffee in the morning"
United States
Nate B.
The price is £306
includes taxes & fees
20 Jul - 21 Jul
Luxe Waterfront Retreat w/ Infrared Sauna & Red Light. Near New Paltz

Highland Lakes Cabin | Huge Yard • Sleeps 8

Highland Lakes Cabin | Huge Yard • Sleeps 8
Highland Lakes
10.0 out of 10, Exceptional, (10 reviews)
"Nice place with very responsive and gracious hosts."
United States
Chris O.
The price is £384
includes taxes & fees
20 Jul - 21 Jul
Highland Lakes Cabin | Huge Yard • Sleeps 8

Marvelous 6-bedroom house with AC in Monroe

Marvelous 6-bedroom house with AC in Monroe
Monroe
The price is £2,618
includes taxes & fees
10 Aug - 11 Aug
Marvelous 6-bedroom house with AC in Monroe

Private Mountain Creek Getaway!

Private Mountain Creek Getaway!
Vernon Township
8.4 out of 10, Very good, (8 reviews)
"This place is fantastic, Charlie was extremely helpful and went above and beyond to ensure our stay was satisfactory. This place includes a lot in your stay such as towels soap/shampoo and even cotton swabs. This place is a great location and will 100% recommend for anyone staying in the area. We will definitely book again at this place and so should you if you want privacy and a great stay with a fantastic host. Thank You Charlie for the warm welcome."
United States
Cristian S.
The price is £308
includes taxes & fees
29 Jul - 30 Jul
Private Mountain Creek Getaway!

Perfect and Spacious Hudson Valley Escape!

Perfect and Spacious Hudson Valley Escape!
Cornwall
8.0 out of 10, Very good, (2 reviews)
"Great host, very responsive and accommodating. The house was very clean and comfortable."
United States
Joseph S.
The price is £613
includes taxes & fees
19 Jul - 20 Jul
Perfect and Spacious Hudson Valley Escape!

3BR Hudson Valley home perfect for families!

3BR Hudson Valley home perfect for families!
Wallkill
10.0 out of 10, Exceptional, (5 reviews)
"My wife and I traveled to West Point this weekend with my brother-in-law and sister-in-law to see our son compete in Army Navy track meet. I the house was perfect for us and an easy drive to West Point. House was clean, and well organized. We would stay again."
United States
Ronnie S.
The price is £399
includes taxes & fees
22 Jul - 23 Jul
3BR Hudson Valley home perfect for families!

Lakefront Couples Escape | Dock • Kayaks • Firepit

Lakefront Couples Escape | Dock • Kayaks • Firepit
Hewitt
The price is £420
includes taxes & fees
26 Jul - 27 Jul
Lakefront Couples Escape | Dock • Kayaks • Firepit
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Chester Hotel Reviews

Find out more about Chester

Chester Holiday Homes information

Number of reviews
252
Accommodation
352 Holiday Homes
Lowest Price
£126
Highest Price
£2,618