Lodging Image

Search Guest Houses in Chester

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Next weekend
Oct 30 - Nov 1
In two weeks
Nov 6 - Nov 8
In one month
Nov 20 - Nov 22
In two months
Dec 18 - Dec 20
No exact matches found, but these alternatives could be just right

Recommended hotels in Chester

A hotel with a central entrance pavilion, a flag, and a landscaped garden.

1. 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, (1,000 reviews)
"Good place to stay."
United States
Stephanie
$111 nightly
The price is $137
Nov 18 - Nov 19
Total with taxes and fees
Holiday Inn Express Hotel & Suites Chester by IHG
A large, two-story white house with a wrap-around porch and a small front garden.

2. The Dominion House Bed & Breakfast

The Dominion House Bed & Breakfast
2.0 star property
Chester
9.2 out of 10, Wonderful, (238 reviews)
"The owners were so kind and attentive, and the grounds are absolutely beautiful! Delicious food, gorgeous mountain air, and the horses were adorable. Thank you for having us!"
United States
Sinead
$108 nightly
The price is $122
Nov 9 - Nov 10
Total with taxes and fees
The Dominion House Bed & Breakfast
A hotel room with a large bed, a desk, a chair, a desk lamp, a wall-mounted TV, and a window with curtains.

3. Sleep Inn & Suites Monroe - Woodbury

Sleep Inn & Suites Monroe - Woodbury
2.5 star property
Monroe
9.4 out of 10, Exceptional, (1,123 reviews)
"Parking was great, very clean, friendly and helpful staff, and some good breakfast. Thank you for making my stay enjoyable!"
United States
Natasha
$113 nightly
The price is $127
Nov 1 - Nov 2
Total with taxes and fees
Sleep Inn & Suites Monroe - Woodbury
A swimming pool with colorful umbrellas and lounge chairs.

4. LEGOLAND Hotel NEW York

LEGOLAND Hotel NEW York
3.0 star property
Goshen
8.2 out of 10, Very good, (131 reviews)
"We’re coming back. We loved our stay here it was perfect."
United States
Kylaia
$239 nightly
The price is $281
Oct 25 - Oct 26
Total with taxes and fees
LEGOLAND Hotel NEW York
A spacious hotel lobby with wooden beams, a central bar area, and seating arrangements.

5. Hampton Inn by Hilton Middletown

Hampton Inn by Hilton Middletown
2.5 star property
Middletown
8.4 out of 10, Very good, (1,000 reviews)
"Room was clean, bed was comfortable."
United States
Amanda
$80 nightly
The price is $94
Nov 19 - Nov 20
Total with taxes and fees
Hampton Inn by Hilton Middletown
A modern living room with a stone accent wall, a flat-screen TV, and a fireplace. There are multiple seating options including a sofa, chairs, and a table.

6. 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, (1,000 reviews)
"Clean rooms, nice staff, and convenience to Lego Land"
United States
Aeron
$129 nightly
The price is $159
Nov 1 - Nov 2
Total with taxes and fees
Fairfield Inn & Suites by Marriott Goshen Middletown
A breakfast area with a counter displaying hard-boiled eggs, a bowl of green apples, and various pastries.

7. Tru by Hilton Middletown

Tru by Hilton Middletown
2.5 star property
Middletown
8.6 out of 10, Excellent, (1,005 reviews)
"Everything was amazing! We really enjoyed our stay!"
United States
Rebecca
$89 nightly
The price is $106
Nov 2 - Nov 3
Total with taxes and fees
Tru by Hilton Middletown
A landscaped outdoor area with a fire feature, seating, and a pathway.

8. Courtyard by Marriott Middletown Goshen

Courtyard by Marriott Middletown Goshen
3.0 star property
Middletown
8.4 out of 10, Very good, (1,002 reviews)
"Great place"
United States
marc
$101 nightly
The price is $119
Nov 8 - Nov 9
Total with taxes and fees
Courtyard by Marriott Middletown Goshen
A modern hotel with a two-story structure, a covered entrance, and a parking lot with marked spaces.

9. Holiday Inn Express & Suites Middletown - Goshen by IHG

Holiday Inn Express & Suites Middletown - Goshen by IHG
2.5 star property
Middletown
8.8 out of 10, Excellent, (786 reviews)
"Super helpful staff. Great breakfast"
United States
Mignonne
$118 nightly
The price is $139
Oct 25 - Oct 26
Total with taxes and fees
Holiday Inn Express & Suites Middletown - Goshen by IHG
A modern hotel with a prominent 'La Quinta' sign, large windows, and a covered entrance area.

10. La Quinta Inn & Suites by Wyndham Middletown-Goshen

La Quinta Inn & Suites by Wyndham Middletown-Goshen
3.0 star property
Middletown
9.4 out of 10, Exceptional, (1,002 reviews)
"The room was clean staff was nice."
United States
Marvin
$109 nightly
The price is $129
Nov 8 - Nov 9
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Middletown-Goshen
Lobby

11. Comfort Suites Central Valley - Woodbury

Comfort Suites Central Valley - Woodbury
2.5 star property
Central Valley
8.4 out of 10, Very good, (197 reviews)
"Our stay was great !"
United States
Vu andyvu
$118 nightly
The price is $145
Nov 19 - Nov 20
Total with taxes and fees
Comfort Suites Central Valley - Woodbury
A multi-story hotel with a central courtyard, large windows, and a parking lot.

12. Microtel Inn & Suites by Wyndham Middletown

Microtel Inn & Suites by Wyndham Middletown
2.0 star property
Middletown
6.8 out of 10, (1,005 reviews)
"It was okay for one night. Room was clean but dated and had a musty smell; toilet was very low. The floor had a musty/smoky smell."
United States
Peggy
$94 nightly
The price is $110
Nov 15 - Nov 16
Total with taxes and fees
Microtel Inn & Suites by Wyndham Middletown
A modern dining area with a large fish tank, sofas, and wooden tables and chairs.

13. Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen
2.5 star property
Middletown
8.8 out of 10, Excellent, (1,241 reviews)
"Great stay"
Canada
Justine
$101 nightly
The price is $119
Nov 10 - Nov 11
Total with taxes and fees
Sleep Inn & Suites Middletown - Goshen
A hotel sign for Candlewood Suites, an IHG hotel, with a parking lot and cars in front.

14. Candlewood Suites Middletown Goshen by IHG

Candlewood Suites Middletown Goshen by IHG
2.5 star property
Middletown
9.4 out of 10, Exceptional, (87 reviews)
"Great hotel to stay very clean and friendly"
United States
Antonio
$110 nightly
The price is $130
Oct 26 - Oct 27
Total with taxes and fees
Candlewood Suites Middletown Goshen by IHG
A lobby with a fireplace, seating area, and a reception desk.

15. Hampton Inn Harriman Woodbury

Hampton Inn Harriman Woodbury
2.5 star property
Central Valley
9.2 out of 10, Wonderful, (1,149 reviews)
"Close to restaurants and shopping, grocery store close as well."
United States
Timothy
$118 nightly
The price is $145
Nov 18 - Nov 19
Total with taxes and fees
Hampton Inn Harriman Woodbury
A hotel lobby with two sofas, a coffee machine, and a view of the parking lot.

16. 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, (1,003 reviews)
"Great place, clean quiet, helpful staff"
United States
Marlon
$99 nightly
The price is $122
Nov 3 - Nov 4
Total with taxes and fees
Americas Best Value Inn at Central Valley-Woodbury
A hotel room with a bed, two bedside tables with lamps, a wall-mounted telephone, and a large black and white windmill painting.

17. Super 8 by Wyndham Middletown

Super 8 by Wyndham Middletown
2.5 star property
Middletown
6.0 out of 10, (1,004 reviews)
"Very friendly and you are close to all the main attractions."
United States
Katelynn
$71 nightly
The price is $83
Nov 1 - Nov 2
Total with taxes and fees
Super 8 by Wyndham Middletown
A hotel room with a kitchenette, including a microwave, coffee maker, and sink.

18. Home2 Suites by Hilton Middletown

Home2 Suites by Hilton Middletown
3.0 star property
Middletown
9.0 out of 10, Wonderful, (796 reviews)
"My stay with my family here was fantastic."
United States
Carl
$161 nightly
The price is $193
Oct 27 - Oct 28
Total with taxes and fees
Home2 Suites by Hilton Middletown
A Holiday Inn Express & Suites building with a covered entrance, stone facade, and a parking area with a bench.

19. 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, (937 reviews)
"Good stay"
United States
Mike
$120 nightly
The price is $142
Nov 15 - Nov 16
Total with taxes and fees
Holiday Inn Express & Suites Montgomery by IHG
A brick exterior with outdoor seating, tables covered with white tablecloths, and brick walls.

20. The Orange Inn Boutique Hotel

The Orange Inn Boutique Hotel
2.0 star property
Goshen
9.8 out of 10, Exceptional, (180 reviews)
"Perfect place to stay for a weekend getaway."
United States
DENISE
$275 nightly
The price is $339
Oct 29 - Oct 30
Total with taxes and fees
The Orange Inn Boutique Hotel
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chester Hotel Reviews

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

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

8/10 Good
"Great location for the price. Comfortable enough. Nice terrace overlooking the lake but they do not maintain it well."
Jill 2-night trip
Posted 2 hours ago
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

Find out more about Chester

Chester Guest Houses information

Number of reviews
8,520
Accommodation
3 Guest Houses
Lowest Price
$83
Highest Price
$339

Frequently asked questions

What is the nightly rate for a guest house in Chester?
Rates for Chester guest houses vary, but travelers can find great-value prices from $83 with Expedia. A range of factors can affect nightly rates, such as the location, the breakfast offering, and the range of amenities. Travelers looking for a good deal should consider looking for a midweek stay, as weekend rates at Chester guest houses tend to be higher. Remember to also use our filters to sort prices from low to high.
What's the difference between a Chester guest house and a B&B?
A guest house in Chester is typically a larger establishment with more rooms, offering a more hotel-like experience, and may provide additional amenities including luxury bedding. In contrast, a B&B is usually a smaller property that focuses primarily on providing a room and breakfast. A B&B is often more personal, and breakfast is typically included as part of the stay, but other services might be more limited compared to a guest house.

Explore a world of travel with Expedia