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Check prices for these dates

This weekend
12 Jun - 14 Jun
Next weekend
19 Jun - 21 Jun

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Our top choices for Chester hotels

Exterior

Holiday Inn Express Hotel & Suites Chester by IHG

Holiday Inn Express Hotel & Suites Chester by IHG
2.5 star property
Chester
8.6 out of 10, Excellent, (1,007 reviews)
"The hotel is very clean and the staff was very friendly and helpful."
United States
Pasquale
The price is NZ$246
includes taxes & fees
16 June - 17 June
Holiday Inn Express Hotel & Suites Chester by IHG
Exterior

The Dominion House Bed & Breakfast

The Dominion House Bed & Breakfast
2.0 star property
Chester
9.2 out of 10, Wonderful, (235 reviews)
"I had a perfect stay with my girlfriend for a long weekend. Eric and Susie were amazing hosts, serving delicious breakfast each day. The hot tub was luxurious and the area was beautiful. I’d 100% come back."
United States
Anna
The price is NZ$419
includes taxes & fees
11 June - 12 June
The Dominion House Bed & Breakfast
Lobby

Comfort Suites Central Valley - Woodbury

Comfort Suites Central Valley - Woodbury
2.5 star property
Central Valley
8.4 out of 10, Very good, (53 reviews)
"Clean nice new hotel"
United States
Amjad
The price is NZ$221
includes taxes & fees
17 June - 18 June
Comfort Suites Central Valley - Woodbury
Exterior

Tin Brook Bed & Breakfast

Tin Brook Bed & Breakfast
3.0 star property
Walden
9.4 out of 10, Exceptional, (122 reviews)
"Very nice accommodations & staff."
United States
Laurie
The price is NZ$268
includes taxes & fees
10 June - 11 June
Tin Brook Bed & Breakfast
Exterior detail

Borland House Inn

Borland House Inn
3.0 star property
Montgomery
9.2 out of 10, Wonderful, (168 reviews)
"Did you ever want to experience what it would be like to stay at a bed in breakfast? Well this is the place to go! So quaint and cute! Located right in the heart of the town of Montgomery. Plenty of things to walk to and see in the area. Brianna the manager was wonderful. Very helpful and informative. The breakfast choices were delicious. Would definitely stay here again and recommend it to others."
United States
roxanne
The price is NZ$205
includes taxes & fees
10 June - 11 June
Borland House Inn
Suite, 1 King Bed, Non Smoking

Quality Inn & Suites Fishkill South near I-84

Quality Inn & Suites Fishkill South near I-84
2.5 star property
Fishkill
9.0 out of 10, Wonderful, (1,008 reviews)
"Clean, comfortable, safe, nice breakfast"
United States
Brett
The price is NZ$209
includes taxes & fees
22 June - 23 June
Quality Inn & Suites Fishkill South near I-84
Restaurant

Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain
2.5 star property
Bear Mountain
8.4 out of 10, Very good, (1,018 reviews)
"Gorgeous setting, beautiful and comfortable room and easy access."
United States
Gwen
The price is NZ$308
includes taxes & fees
10 June - 11 June
Overlook Lodge at Bear Mountain
Suite, 1 King Bed, Non Smoking (1 Bedroom)

Days Inn by Wyndham Wurtsboro

Days Inn by Wyndham Wurtsboro
2.0 star property
Wurtsboro
7.6 out of 10, Good, (624 reviews)
"Very clean and staff helpful "
United States
Kaiden
The price is NZ$232
includes taxes & fees
14 June - 15 June
Days Inn by Wyndham Wurtsboro
Room, 1 King Bed, Non Smoking

Sleep Inn & Suites Monroe - Woodbury

Sleep Inn & Suites Monroe - Woodbury
2.5 star property
Monroe
9.4 out of 10, Exceptional, (1,092 reviews)
"The room was pristine, breakfast great, ample and easy parking, very warm staff!"
United States
Akunna
The price is NZ$219
includes taxes & fees
16 June - 17 June
Sleep Inn & Suites Monroe - Woodbury
Reception

The Hamlet Inn at Warwick

The Hamlet Inn at Warwick
2.5 star property
Warwick
7.6 out of 10, Good, (165 reviews)
"The location was very convenient"
United States
Stephen
The price is NZ$167
includes taxes & fees
10 June - 11 June
The Hamlet Inn at Warwick
Indoor pool

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

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
2.0 star property
New Windsor
8.4 out of 10, Very good, (1,008 reviews)
"We stopped here for the night and it was perfect. Clean room and courteous staff."
United States
Kathleen
The price is NZ$191
includes taxes & fees
23 June - 24 June
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
Exterior

Holiday Inn Express & Suites Montgomery by IHG

Holiday Inn Express & Suites Montgomery by IHG
2.5 star property
Montgomery
8.8 out of 10, Excellent, (866 reviews)
"Our stay for a day was great."
United States
Chime
The price is NZ$242
includes taxes & fees
5 July - 6 July
Holiday Inn Express & Suites Montgomery by IHG
Comfort Room, 2 Double Beds

High Point Motel

High Point Motel
2.0 star property
Sussex
9.2 out of 10, Wonderful, (148 reviews)
"Nice, clean motel. Chairs outside to enjoy the mountain view. Would definitely stay here again if in the area."
United States
Gregory
The price is NZ$177
includes taxes & fees
16 June - 17 June
High Point Motel
Lobby

Hampton Inn by Hilton Middletown

Hampton Inn by Hilton Middletown
2.5 star property
Middletown
8.6 out of 10, Excellent, (1,010 reviews)
"It was a pleasant and comfortable one night stay for us. Everything was as advertised with nice breakfast, supportive staff, and friendly ambience."
United States
Soumyadeep
The price is NZ$228
includes taxes & fees
16 June - 17 June
Hampton Inn by Hilton Middletown
Classic Quadruple Room, 2 Queen Beds, Non Smoking, Refrigerator & Microwave

Rolling Hills Motel

Rolling Hills Motel
2.0 star property
Sussex
8.6 out of 10, Excellent, (213 reviews)
"Very homey, clean and excellent customer service. Went above and beyond, I will absolutely be staying here again. Highly recommend!! "
United States
Jess
The price is NZ$155
includes taxes & fees
21 June - 22 June
Rolling Hills Motel
Lobby

Quality Inn near Mountain Creek

Quality Inn near Mountain Creek
2.5 star property
Vernon
7.6 out of 10, Good, (1,001 reviews)
"Breakfast menu was poor at best."
United States
Constance
The price is NZ$192
includes taxes & fees
23 June - 24 June
Quality Inn near Mountain Creek
Double Room | Bathroom

Appalachian Motel

Appalachian Motel
2.0 star property
Vernon
7.6 out of 10, Good, (535 reviews)
"The rooms are very basic, but we had everything we needed for our stay. A really nice surprise was how comfortable the beds were. The motel is close to hiking trails. The parking lot for hiking Stairway to Heaven was a 2 minute drive from the motel. If you stay here in the winter, it is only a 5 minute drive from Mountain Creek ski resort. We would stay here again."
United States
Lorrie
The price is NZ$133
includes taxes & fees
10 June - 11 June
Appalachian Motel
Reception

Fairfield Inn & Suites by Marriott Goshen Middletown

Fairfield Inn & Suites by Marriott Goshen Middletown
3.0 star property
Goshen
9.0 out of 10, Wonderful, (1,001 reviews)
"100% recommend this hotel. The continental breakfast was delicious. The staff was amazing and the location was ideal."
United States
Megan
The price is NZ$305
includes taxes & fees
11 June - 12 June
Fairfield Inn & Suites by Marriott Goshen Middletown
Business centre

Americas Best Value Inn at Central Valley-Woodbury

Americas Best Value Inn at Central Valley-Woodbury
2.0 star property
Central Valley
7.2 out of 10, Good, (1,008 reviews)
"Safe area not too far from restaurants and stores."
United States
Richard
The price is NZ$212
includes taxes & fees
10 June - 11 June
Americas Best Value Inn at Central Valley-Woodbury
Towels

Budget Motor Inn - Stony Point

Budget Motor Inn - Stony Point
1.5 star property
Stony Point
5.2 out of 10, (560 reviews)
"Excellent "
United States
Tariq
The price is NZ$119
includes taxes & fees
10 June - 11 June
Budget Motor Inn - Stony Point
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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Stay near popular Chester attractions

The Rock Sports Complex

4.0/5 (18 reviews)
This dedicated sports venue hosts baseball and softball tournaments on well-maintained turf fields. Bring portable chairs and sun protection to enjoy the games in comfort at this local athletic hub.
See properties

Learn more about Chester

Lace up your hiking boots and hit the trails at Goosepond Mountain State Park for stunning views. After working up an appetite, head to Castle Fun Centre for go-karts, mini-golf, and arcade games.

See all hotels in Chester
The Queens Park Bridge, a landmark of Chester

Top Chester Hotel Reviews

Studio 6 Extended Stay Fishkill Westage Center NY

Studio 6 Extended Stay Fishkill Westage Center NY

2/10 Terrible
"The man working overnights for yall needs a raise but one of the worst hotel experiences I’ve had, never even got a room but I got my refund"
Kameron 1-night trip
Posted 10 hours ago
Studio 6 Extended Stay Fishkill Westage Center NY

More cheap accommodation in Chester

Studio 6 Extended Stay Fishkill Route 9 NY

Studio 6 Extended Stay Fishkill Route 9 NY

25 Merritt Blvd Fishkill NY
The price is NZ$143 per night from 7 July to 8 July
NZ$143
7 July - 8 July
includes taxes & fees
6.6/10 (1,005 reviews)

Frequently asked questions

What's the best place to stay in Chester?
Based on our traveller data, Holiday Inn Express Hotel & Suites Chester by IHG is one of the top choices for your stay. This hotel offers free breakfast and an indoor pool. Other good choices for your stay in the area are Spark by Hilton Fishkill and DoubleTree by Hilton Hotel Nanuet. See all available top hotels, or vacation rentals in Chester.
What are some of the best holiday rentals that Chester has to offer?
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo: This holiday home rental outside of Chester offers a fireplace, a patio and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with an oven, a microwave and a coffee maker, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games. See all vacation rentals in Chester.
If I need to cancel my hotel reservation in Chester, will I receive a refund?
Yes! You'll find that most room reservations are refundable if you cancel prior to the hotel's cancellation deadline, which is often 24 or 48 hours before the scheduled arrival. If you have a reservation that's non-refundable, you might still have the option to cancel and receive a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Chester.
What's the best family accommodation in Chester?
The Dominion House Bed & Breakfast is a B&B with an outdoor pool and free parking, and it's a top choice on Expedia for families. Also, children of all ages will enjoy a visit to Castle Fun Center. Find more child-friendly accommodations in Chester.
What is the favourite LGBTQ-friendly accommodation in Chester?
Holiday Inn Express Hotel & Suites Chester by IHG is a top LGBTQ-friendly hotel that features free breakfast and free Wi-Fi. The Dominion House Bed & Breakfast is another good option for your trip. See all available hotels listed as LGBTQ-friendly in Chester.
What are some accommodation options with pools in Chester?
Holiday Inn Express Hotel & Suites Chester by IHG is a top hotel with a pool, free on-the-go breakfast and free WiFi. View all hotels with pools in Chester.
What is staying in Chester like?
Visitors to Chester will definitely enjoy the shopping and restaurants. Tourists can also enjoy the city's ski areas and coffee shops. Top sights around the area include LEGOLAND® New York and Woodbury Common Premium Outlets. In Chester, there are 18 hotels and other accommodation options to choose from. Find out more about Chester.
What are the top places to visit in Chester?
Favourite places to visit include Castle Fun Center, The Rock Sports Complex and Museum Village. Additionally, you'll find LEGOLAND® New York and Woodbury Common Premium Outlets in the area. Take a look at what more there is to see and do in Expedia's Chester guide.
What's the seasonal weather like in Chester?
The hottest months are usually July and August, with an average temperature of 21°C, while the coldest months are January and February, with an average of 0°C. The snowiest months in Chester are January, February, March and April, with each month seeing an average of 16 cm of snowfall.

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