Hotels in Chester, Orange County

  • Overview

    Chester is a charming town located in Orange County, New York. Situated in the Hudson Valley, Chester offers a perfect blend of small-town charm and natural beauty. The area is known for its picturesque landscapes, historic buildings, and vibrant community.

  • When to visit

    The best time to visit Chester is during the spring and fall seasons when the weather is mild and the foliage is at its peak. Springtime brings blooming flowers and rejuvenated green landscapes, while autumn offers stunning foliage colors. The town also celebrates its seasonal beauty with events like the Chester Fall Festival, making these seasons a particularly delightful time to explore the area.

  • Reasons to Visit

    There are several reasons to visit Chester. Nature enthusiasts can explore the nearby Black Rock Forest and enjoy hiking, birdwatching, and wildlife spotting. History buffs will appreciate the well-preserved 18th-century buildings and museums that showcase the town's rich heritage. Chester also offers a range of recreational activities like fishing, boating, and golfing. Moreover, the town hosts various festivals and events throughout the year, providing visitors with a chance to experience the local culture and traditions.

  • Nearby Attractions

  • Storm King Art Center

    Storm King Art Center is a renowned outdoor sculpture park spread across 500 acres. It features a vast collection of contemporary art installations set against a backdrop of rolling hills, forests, and meadows. Visitors can wander through the park, marvel at the unique sculptures, and enjoy the tranquil surroundings.

  • Goosepond Mountain State Park

    Goosepond Mountain State Park offers nature lovers a serene escape with its peaceful trails, lush forests, and scenic lakes. The park is ideal for hiking, picnicking, and birdwatching. It is home to a diverse range of flora and fauna, including various species of birds and wildflowers.

  • Erie Station Museum

    Erie Station Museum is a historical museum housed in a beautifully restored train station. It showcases the town's history, railroading heritage, and the development of Chester and its surroundings. Visitors can explore the exhibits, learn about the area's transportation history, and admire the authentic period artifacts.

  • Hotels

  • 1786 Farm Cottage Honeymoon Suite Renovated 2022

    - Located in Chester in the New York region, 1786 Farm Cottage Honeymoon Suite Renovated 2022 provides accommodation with free WiFi and free private parking. The property is around 33 km from Bear Mount Next available price is on . 1786 Farm Cottage Honeymoon Suite Renovated 2022

  • Craftsman Hideaway at the 1841 Farmhouse

    - Situated in Chester, 38 km from St George s Episcopal Church and 40 km from Michie Stadium, Craftsman Hideaway at the 1841 Farmhouse offers a garden and air conditioning. With free private parking, th Next available price is on . Craftsman Hideaway at the 1841 Farmhouse

  • Fairfield Inn & Suites by Marriott Goshen Middletown

    - Make yourself at home in one of the 95 guestrooms featuring refrigerators and microwaves. Complimentary wired and wireless internet access keeps you connected, and cable programming provides entertain Next available price is 122.55 on Sept. 14, 2025. Fairfield Inn & Suites by Marriott Goshen Middletown

  • Holiday Inn Express Hotel & Suites Chester, an IHG Hotel

    - Make yourself at home in one of the 80 guestrooms featuring refrigerators and microwaves. Wired and wireless internet access is complimentary, while 42-inch flat-screen televisions with cable programm Next available price is on . Holiday Inn Express Hotel & Suites Chester, an IHG Hotel

  • LEGOLAND New York Resort

    - Located in Goshen, 22 km from Metro-North Harriman Station, LEGOLAND New York Resort provides accommodation with a seasonal outdoor swimming pool, private parking, a fitness centre and a garden. Featu Next available price is on . LEGOLAND New York Resort

  • Sleep Inn & Suites Monroe - Woodbury

    - Make yourself at home in one of the 82 air-conditioned rooms featuring refrigerators and flat-screen televisions. Complimentary wireless internet access keeps you connected, and cable programming is a Next available price is 156.74 on Sept. 14, 2025. Sleep Inn & Suites Monroe - Woodbury

  • Stagecoach Inn

    - Stay in one of 5 guestrooms featuring flat-screen televisions. Your pillowtop bed comes with Egyptian cotton sheets. Wireless internet access (surcharge) keeps you connected, and cable programming is Next available price is on . Stagecoach Inn

  • The Dominion House Bed & Breakfast

    - Make yourself at home in one of the 3 guestrooms. Next available price is on . The Dominion House Bed & Breakfast

  • The Orange Inn Boutique Hotel

    - Make yourself at home in one of the 31 individually furnished guestrooms, featuring iPod docking stations and Smart televisions. Your memory foam bed comes with premium bedding. Complimentary wireless Next available price is on . The Orange Inn Boutique Hotel
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9 hotels in Chester