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Find Romantic Hotels in Chester, NY from CA $166

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Check availability on Chester Romantic Hotels

Tonight
Aug 11 - Aug 12
Tomorrow
Aug 12 - Aug 13
This weekend
Aug 14 - Aug 16
Next weekend
Aug 21 - Aug 23

Our top choices for Chester romantic hotels

Exterior
Reception
Premium bedding, desk, iron/ironing board, WiFi (free)
Free daily on-the-go breakfast

1. Holiday Inn Express Hotel & Suites Chester by IHG

Holiday Inn Express Hotel & Suites Chester by IHG
Chester
United States
Christopher
CA $166
CA $204 total
includes taxes & fees
Sep 9 - Sep 10
Holiday Inn Express Hotel & Suites Chester by IHG
Room, 1 King Bed, Non Smoking
Free daily self-serve breakfast
Business center
Terrace/patio

2. Sleep Inn & Suites Monroe - Woodbury

Sleep Inn & Suites Monroe - Woodbury
Monroe
United States
Crysta
CA $157
CA $178 total
includes taxes & fees
Sep 1 - Sep 2
Sleep Inn & Suites Monroe - Woodbury
Lobby
Standard Room | Living area
Snack bar
Terrace/patio

3. Hampton Inn Harriman Woodbury

Hampton Inn Harriman Woodbury
Central Valley
United States
Danen
CA $170
CA $210 total
includes taxes & fees
Sep 1 - Sep 2
Hampton Inn Harriman Woodbury
Reception
Lobby
Terrace/patio
View from property

4. Fairfield Inn & Suites by Marriott Goshen Middletown

Fairfield Inn & Suites by Marriott Goshen Middletown
Goshen
United States
Kathleen
CA $180
CA $221 total
includes taxes & fees
Sep 9 - Sep 10
Fairfield Inn & Suites by Marriott Goshen Middletown
Exterior
Superior Double Room, Ensuite (Primrose) | Miscellaneous
Outdoor pool, sun loungers
Miscellaneous

5. The Dominion House Bed & Breakfast

The Dominion House Bed & Breakfast
Chester
United States
Anna
CA $299
CA $339 total
includes taxes & fees
Sep 7 - Sep 8
The Dominion House Bed & Breakfast
Courtyard
Lobby
Exterior
Premium bedding, in-room safe, desk, laptop workspace

6. Home2 Suites by Hilton Middletown

Home2 Suites by Hilton Middletown
Middletown
United States
Christian
CA $268
CA $321 total
includes taxes & fees
Aug 18 - Aug 19
Home2 Suites by Hilton Middletown
Exterior
Premium bedding, pillowtop beds, desk, laptop workspace
Property amenity
Fitness facility

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

La Quinta Inn & Suites by Wyndham Middletown-Goshen
Middletown
United States
Kelly
CA $173
CA $205 total
includes taxes & fees
Aug 31 - Sep 1
La Quinta Inn & Suites by Wyndham Middletown-Goshen
Free continental breakfast on weekdays
Lobby
Exterior
Indoor pool

8. Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen
Middletown
United States
Barbara
CA $148
CA $175 total
includes taxes & fees
Sep 10 - Sep 11
Sleep Inn & Suites Middletown - Goshen
Exterior
Free daily on-the-go breakfast
Pool
Desk, blackout drapes, iron/ironing board, cribs (free)

9. Holiday Inn Express & Suites Montgomery by IHG

Holiday Inn Express & Suites Montgomery by IHG
Montgomery
United States
Chime
CA $146
CA $166 total
includes taxes & fees
Aug 30 - Aug 31
Holiday Inn Express & Suites Montgomery by IHG
Property amenity
Lobby
Property amenity
Exterior

10. Courtyard by Marriott Middletown Goshen

Courtyard by Marriott Middletown Goshen
Middletown
United States
shanique
CA $147
CA $173 total
includes taxes & fees
Aug 23 - Aug 24
Courtyard by Marriott Middletown Goshen
View all properties

Top Chester Hotel Reviews

Courtyard by Marriott Montvale

Courtyard by Marriott Montvale

10/10 Excellent
"Little bit of a maze - had to get used to lay-out of property."
Suzanna 2-night trip
Posted 8 hours ago
Courtyard by Marriott Montvale
Crowne Plaza Suffern - Mahwah by IHG

Crowne Plaza Suffern - Mahwah by IHG

10/10 Excellent
"Great, clean and comfortable bed. No carpets anywhere which is a plus. Beautiful interior and lobby to hang out by"
pearl 1-night trip
Posted 1 day ago
Crowne Plaza Suffern - Mahwah by IHG
Inn on the Hudson

Inn on the Hudson

10/10 Excellent
"Nice place and convenient location in Peekskill"
Pedro 1-night trip
Posted 2 days ago
Inn on the Hudson

Frequently asked questions

Searching for romantic hotels in Chester?
Are you and your partner looking for a romantic vacation? Our guests also enjoy Chester for its restaurants and shopping. If you want to explore the area, you might head to Castle Fun Center, The Rock Sports Complex, or Museum Village. If you're interested in staying close to a certain attraction, you can sort by neighborhood or distance to top landmarks, so you'll be able to see everything on your list.
When is the best time of year for a romantic getaway to Chester?
If you're hoping to get lost in the rain on your romantic getaway, check out these details about year-round temperatures in Chester: The hottest months are usually July and August with an average temp of 70°F, while the coldest months are January and February with an average of 32°F. The snowiest months in Chester are January, February, March, and April, with each month seeing an average of 6 inches of snowfall.
What is there to do in Chester?
There's nothing better than seeing a new place with your sweetheart, so consider checking out all that Chester has to offer. If you're hoping to see some of the area's cultural attractions, you'll enjoy Chester for its shopping. A visit to Castle Fun Center, The Rock Sports Complex, or Museum Village might be just the ticket when you're checking out the sights.
What's the best way to get to Chester and around town during my romantic getaway?
This information about transportation options in Chester might help your romantic trip get off to a smooth start: To get to Chester, book a flight to Stewart Intl. Airport (SWF), which is the closest major airport, located 13.5 mi (21.7 km) from the city center. If you'd like to venture out around the area, you may want to rent a car for your trip.

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