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Search Guest Houses in Chester

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Check prices for these dates

Next weekend
Nov 6 - Nov 8
In two weeks
Nov 13 - Nov 15
In one month
Nov 27 - Nov 29
In two months
Dec 25 - Dec 27
No exact matches found, but these alternatives could be just right

Recommended hotels in Chester

A Holiday Inn Express hotel with a covered entrance, a parking lot, and a well-lit facade.

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, (1,005 reviews)
"Good place to stay."
United States
Stephanie
$114 nightly
The price is $140
Nov 22 - Nov 23
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 patio with stone flooring, a grill, outdoor furniture, and a house with white siding and green trim.

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

Historic Sugar Loaf Farmhouse | 5BR | Sleeps 8
Chester
9.0 out of 10, Wonderful, (2 reviews)
"Host was very nice and accommodating. The house was clean and comfortable. There is a beautiful tub in the master bath but I was wishing there was a shower there. Master bed was very comfortable but also very tall for a shorter person like myself. Overall very nice."
United States
jolene j.
$670 nightly
The price is $791
Oct 27 - Oct 28
Total with taxes and fees
Historic Sugar Loaf Farmhouse | 5BR | Sleeps 8
Room

4. Alpine Lodge

Alpine Lodge
2.0 star property
Vernon
9.0 out of 10, Wonderful, (2 reviews)
"It was a pleasure staying at the lodge we all enjoyed the continental breakfast very comfortable place to stay"
United States
Kathleen
$68 nightly
The price is $78
Nov 1 - Nov 2
Total with taxes and fees
Alpine Lodge
A hotel room with a large bed, a desk, a chair, a desk lamp, a wall-mounted TV, and a window with curtains.

5. Sleep Inn & Suites Monroe - Woodbury

Sleep Inn & Suites Monroe - Woodbury
2.5 star property
Monroe
9.4 out of 10, Exceptional, (1,118 reviews)
"Parking was great, very clean, friendly and helpful staff, and some good breakfast. Thank you for making my stay enjoyable!"
United States
Natasha
$106 nightly
The price is $120
Nov 22 - Nov 23
Total with taxes and fees
Sleep Inn & Suites Monroe - Woodbury
A hotel entrance with a covered walkway, a prominent sun logo, and a modern facade.

6. 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)
"Very new and clean hotel with good choice break fast."
United States
aziz h
$105 nightly
The price is $125
Nov 18 - Nov 19
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Middletown-Goshen
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, (1,007 reviews)
"Convenient to the mall, convenient to the highway, reasonably priced and elegant, helpful people at the front desk."
United States
Barry
$77 nightly
The price is $91
Nov 8 - Nov 9
Total with taxes and fees
Tru 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.

8. 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, (1,002 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 brick exterior with outdoor seating, tables covered with white tablecloths, and brick walls.

9. 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
$255 nightly
The price is $314
Nov 26 - Nov 27
Total with taxes and fees
The Orange Inn Boutique Hotel
A swimming pool with colorful umbrellas and lounge chairs.

10. LEGOLAND Hotel NEW York

LEGOLAND Hotel NEW York
3.0 star property
Goshen
8.2 out of 10, Very good, (135 reviews)
"Love this place and so does my kids. The food is not good so make sure you eat off the resort and out of the park"
United States
danielle
$239 nightly
The price is $281
Nov 1 - Nov 2
Total with taxes and fees
LEGOLAND Hotel NEW York
A lobby with a fireplace, seating area, and a reception desk.

11. 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
$114 nightly
The price is $140
Nov 16 - Nov 17
Total with taxes and fees
Hampton Inn Harriman Woodbury
An outdoor patio area with seating, a fire feature, and a view of the surrounding buildings.

12. 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
$112 nightly
The price is $136
Nov 4 - Nov 5
Total with taxes and fees
Home2 Suites by Hilton Middletown
A hotel with a modern facade, multiple floors, and a covered entrance area.

13. 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, (788 reviews)
"Staff was welcoming, room was clean and spacious for a family with little ones. Breakfast had a nice variety of options. Pool was lovely to enjoy. Our family enjoyed the stay while visiting for a wedding!"
United States
Andrea
$122 nightly
The price is $144
Nov 8 - Nov 9
Total with taxes and fees
Holiday Inn Express & Suites Middletown - Goshen by IHG
A landscaped outdoor area with a fire feature, seating, and a pathway.

14. Courtyard by Marriott Middletown Goshen

Courtyard by Marriott Middletown Goshen
3.0 star property
Middletown
8.4 out of 10, Very good, (1,003 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 dining area with a large fish tank, sofas, and wooden tables and chairs.

15. Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen
2.5 star property
Middletown
8.8 out of 10, Excellent, (1,246 reviews)
"Great stay"
Canada
Justine
$101 nightly
The price is $119
Nov 18 - Nov 19
Total with taxes and fees
Sleep Inn & Suites Middletown - Goshen
Lobby

16. Comfort Suites Central Valley - Woodbury

Comfort Suites Central Valley - Woodbury
2.5 star property
Central Valley
8.4 out of 10, Very good, (203 reviews)
"Our stay was great !"
United States
Vu andyvu
$112 nightly
The price is $137
Nov 22 - Nov 23
Total with taxes and fees
Comfort Suites Central Valley - Woodbury
A compact hotel room with two beds, a kitchenette, a dining area, and a view of a rocky landscape.

17. Rolling Hills Motel

Rolling Hills Motel
2.0 star property
Sussex
8.6 out of 10, Excellent, (238 reviews)
"Niki was wonderful. Thank you."
United States
Kimberly Arlene
$90 nightly
The price is $100
Nov 24 - Nov 25
Total with taxes and fees
Rolling Hills Motel
A modern hotel room with a large bed, a seating area with leather chairs, and a view of the outdoors through large windows.

18. Luxe Penthouse Loft on Main St- Steam Shower, Elevator, Parking, Views, Kitchen

Luxe Penthouse Loft on Main St- Steam Shower, Elevator, Parking, Views, Kitchen
Warwick
10.0 out of 10, Exceptional, (48 reviews)
"Always a pleasure staying here."
United States
Natalie M.
$210 nightly
The price is $238
Nov 1 - Nov 2
Total with taxes and fees
Luxe Penthouse Loft on Main St- Steam Shower, Elevator, Parking, Views, Kitchen
An outdoor patio with a dining table and chairs, a barbecue grill, and a fire pit.

19. Residence Inn by Marriott Middletown Goshen

Residence Inn by Marriott Middletown Goshen
3.0 star property
Middletown
9.4 out of 10, Exceptional, (352 reviews)
"The place is great and staff are above and beyond. Definitely coming back"
United States
jubert cruz
$188 nightly
The price is $222
Nov 8 - Nov 9
Total with taxes and fees
Residence Inn by Marriott Middletown Goshen
A room with a chandelier, a sofa, a table, and a cabinet.

20. The Warwick Inn Boutique Amity Room 3 an Hour from NYC

The Warwick Inn Boutique Amity Room 3 an Hour from NYC
Warwick
8.8 out of 10, Excellent, (18 reviews)
"We had a great time! The room was clean and quaint. Easy walk to town. There is music playing majority of the day so if that’s not your vibe, this isn’t the place for you. We’ll be returning."
United States
Benjamin
$181 nightly
The price is $205
Nov 3 - Nov 4
Total with taxes and fees
The Warwick Inn Boutique Amity Room 3 an Hour from NYC
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

The Thayer Hotel at West Point

The Thayer Hotel at West Point

10/10 Excellent
"Great experience and location! Loved my stay."
Clay 1-night trip
Posted 2 hours ago
The Thayer Hotel at West Point

Find out more about Chester

Chester Guest Houses information

Number of reviews
7,130
Accommodation
3 Guest Houses
Lowest Price
$78
Highest Price
$791

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 $78 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.

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