The Best Romantic Hotels in Chester, NY from ￥18,185 in 2026

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Our top choices for Chester romantic hotels

1. Holiday Inn Express Hotel & Suites Chester by IHG

Chester

Donald

￥18,142

￥22,337 total

includes taxes & fees

Sep 8 - Sep 9

Room, 1 King Bed, Non Smoking | Desk, laptop workspace, blackout drapes, iron/ironing board

2. Sleep Inn & Suites Monroe - Woodbury

Monroe

Crysta

￥17,641

￥19,956 total

includes taxes & fees

Aug 31 - Sep 1

One King Bed Studio | Living area | 55-inch LCD TV with cable channels, TV, pay movies

3. Hampton Inn Harriman Woodbury

Central Valley

Danen

￥19,275

￥23,733 total

includes taxes & fees

Aug 31 - Sep 1

4. Fairfield Inn & Suites by Marriott Goshen Middletown

Goshen

Kathleen

￥20,543

￥25,293 total

includes taxes & fees

Sep 8 - Sep 9

Superior Double Room, Ensuite (Primrose) | Miscellaneous

5. The Dominion House Bed & Breakfast

Chester

Anna

￥33,918

￥38,370 total

includes taxes & fees

Aug 13 - Aug 14

Premium bedding, pillowtop beds, desk, laptop workspace

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

Middletown

Kelly

￥19,594

￥23,146 total

includes taxes & fees

Aug 31 - Sep 1

Efficiency, Suite, 1 King Bed, Non Smoking | Premium bedding, desk, soundproofing, iron/ironing board

7. Sleep Inn & Suites Middletown - Goshen

Middletown

Barbara

￥16,762

￥19,801 total

includes taxes & fees

Sep 8 - Sep 9

8. Tru by Hilton Middletown

Middletown

Anurag

￥16,170

￥19,101 total

includes taxes & fees

Sep 1 - Sep 2

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Top Chester Hotel Reviews

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"

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

10/10 Excellent

"Very nice staff and clean room."

Inn on the Hudson

10/10 Excellent

"Nice place and convenient location in Peekskill"

Courtyard by Marriott Montvale

10/10 Excellent

"Helpful staff, location convenient, would stay again!"

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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Check availability on Chester Romantic Hotels

Our top choices for Chester romantic hotels

1. Holiday Inn Express Hotel & Suites Chester by IHG

2. Sleep Inn & Suites Monroe - Woodbury

3. Hampton Inn Harriman Woodbury

4. Fairfield Inn & Suites by Marriott Goshen Middletown

5. The Dominion House Bed & Breakfast

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

7. Sleep Inn & Suites Middletown - Goshen

8. Tru by Hilton Middletown

9. Hampton Inn by Hilton Middletown

10. Courtyard by Marriott Middletown Goshen

Top Chester Hotel Reviews

Crowne Plaza Suffern - Mahwah by IHG

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

Inn on the Hudson

Courtyard by Marriott Montvale

Frequently asked questions

Explore a world of travel with Expedia

Find Romantic Hotels in Chester, NY

Change your mind

Treat yourself

Be picky

Check availability on Chester Romantic Hotels

Our top choices for Chester romantic hotels

1. Holiday Inn Express Hotel & Suites Chester by IHG

2. Sleep Inn & Suites Monroe - Woodbury

3. Hampton Inn Harriman Woodbury

4. Fairfield Inn & Suites by Marriott Goshen Middletown

5. The Dominion House Bed & Breakfast

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

7. Sleep Inn & Suites Middletown - Goshen

8. Tru by Hilton Middletown

9. Hampton Inn by Hilton Middletown

10. Courtyard by Marriott Middletown Goshen

Top Chester Hotel Reviews

Crowne Plaza Suffern - Mahwah by IHG

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

Inn on the Hudson

Courtyard by Marriott Montvale

Frequently asked questions

Explore a world of travel with Expedia