Bed and breakfast holiday rentals in Orange County

Trestle - Caldwell House Bed & Breakfast

The Caldwell House is located in the heart of the lower Hudson Valley near West Point, Storm King Art Center, Brotherhood Winery and the Woodbury Common. This guestroom is named for the nearby historic landmark, the Moodna Viaduct Trestle, which crosses the local valley. The length of the trestle is nearly two thirds of a mile, and it hovers nearly 20 stories above the ground. The Trestle Room is furnished with a lovely queen-size maple bed, lush bedding, a stately antique maple bureau and a lovely elevated electric fireplace. The room’s private en-suite bath comes with a shower. Charming, comfortable, and evoking days gone by, this room is perfect for celebrating special occasions or simply enjoying some time away! After feasting on one of Dena’s famous breakfasts, you can take a leisurely stroll down to see the Moodna Viaduct Trestle and take in the breathtaking sight made famous by its appearance in the movie Michael Clayton starring George Clooney. After that, it’s onward to explore the beautiful Hudson Valley. Upon your return, you can play a game in the Living/Game Room, relax on the front porch, enjoy a wood fire in the parlor or simply lounge around the Trestle Room.

Indoor spaces · Hospitality · Comfort

Storm King - Caldwell House Bed & Breakfast

The Caldwell House is located in the heart of the lower Hudson Valley near West Point, Storm King Art Center, Brotherhood Winery and the Woodbury Common. The Storm King Room, named for the nearby Storm King Art Center – 500-acres of landscaped fields, hills, and woodlands recognized as one of the world’s greatest outdoor sculpture gardens – is located on the ground floor level of the Carriage House. Its rustic, yet romantic feel has quickly turned the room into a guest favorite. Most of the original wood and stonework (circa 1803) remains in place – giving the room a feel of a bygone era. An impressive queen-size bed, top-of-the-line mattress, and luxurious bedding will guarantee a blissful sleep. The room has a lingerie chest, a cherry wood framed floor mirror, comfy love seat and a beautiful antique chair as there is ample space for seating throughout the room, and plenty of space to snuggle up in front of the fireplace. Storm King’s spacious bathroom comes complete with a Jacuzzi tub for two, a separate shower, and beautifully appointed fixtures. In the morning, breakfast awaits in the B&B’s Main Dining Room.

Location · Breakfast · Amenities

Butter Hill - Caldwell House Bed & Breakfast

The Caldwell House is located in the heart of the lower Hudson Valley near West Point, Storm King Art Center, Brotherhood Winery and the Woodbury Common. Inspired by Dutch colonists’ original name for Storm King Mountain, the Butter Hill Room evokes the region’s history with beautiful 19th century details. This charming room offers a lovely queen-size sleigh bed, love seat, antique English armoire, Empire-style bureau, historic engravings hanging on the walls painted with colors that remind you of the buttercups that line the local fields, and a roomy private en-suite bathroom with a shower.

Location · Accuracy · Indoor spaces

Victorian Hideaway: Sparrow King Suite

Welcome to the only BNB located in the center of Montgomery Village. Get that rural feel while being able to walk to restaurants and shops. Close drive to Angry Orchard, Shawangunk Wine Trail, Hiking, U-Pick Farms, Storm King Sculpture Park and many other wonders of the Hudson Valley! The stately "Sparrow" room, the original master bedroom of the Borland House built in 1839, has a king-size bed and private bathroom. Please note breakfast is not included in Airbnb rates and stairs to access room

Family · Value · Backyard

Benmarl Vineyards/Winery bedroom #2

This room overlooks the winery and vineyard, has a double bed, dresser, vanity, television, refrigerator, Keurig, and PRIVATE BUT NOT CONNECTED BATHROOM. THE BATHROOM IS LOCATED DOWN THE HALLWAY, HOWEVER WE PROVIDE BATHROBES. Included in your stay is a free wine tasting, 10% off wine purchases, a Breakfast voucher for breakfast at The Valley Diner In Marlboro, NY, and a complimentary cheese platter. Taxes and cleaning fees are included. FYI: There is another room:Great Scenic Vineyard B&B #1

Location · Family · Access

Spacious & Private Hudson Valley Getaway

Welcome to Marlboro! This private space in our home features a private entrance, private bathroom with a nice standing shower, eating area (not a kitchen) with tea kettle and coffee machine, toaster, microwave and refrigerator with freezer. There is a table and chairs, love seat couch that transforms into a small cot, queen bed, walk in closet and 55 inch smart TV with a full motion TV stand. We are permitted to operate in the town of Marlboro and a yearly fire inspection is conducted.

Location · Family · Check-in

Glenwood Farmhouse Bed & Breakfast - Second Suite

Victorian farmhouse (c. 1855) minutes from the Village of Warwick, Mountain Creek Ski Resort, local orchards, wineries, and Appalachian Trail. This master room has a king-sized bed and en suite bathroom with soaking tub and separate shower stall. Your stay includes a country farm breakfast with eggs from our chickens, produce from our garden (in season) and other local ingredients. Swimming pool and lounge for guests. ATTENTION: THERE ARE TWO CATS ON THE PREMISES.Check in 2:00 pm.

Value · Family · Getting around

Timless Elegance: Hummingbird Queen Suite

Enjoy this charming Queen room with a private bath featuring a spacious walk-in shower, located on its own private floor in a home originally built in 1789. This cozy space blends historic character with modern comforts, including air conditioning, a flat-screen TV, complimentary Wi-Fi, a desk, and a comfortable sitting area—perfect for relaxing after a day of exploring the Hudson Valley. Please note, breakfast is not included in Airbnb rates and there are stairs to access this room.

Value · Family · Parks

Glenwood Farmhouse Bed & Breakfast

Victorian farmhouse (c. 1855) minutes from the Village of Warwick, Mountain Creek Ski Resort, local orchards, wineries, and Appalachian Trail. This one bedroom Empire Suite includes an adjoining bathroom and private sitting room. Your stay includes a country farm breakfast with eggs from our chickens, produce from our garden (in season) and other local ingredients. Swimming pool and lounge for guests. Attention : THERE ARE TWO CATS ON THE PREMISES. Check in time 2:00 pm.

Location · Family · Amenities

Windsong Retreat Bed & Breakfast

Close to Bethel Woods, Minniwaska State Park, Mohonk Mountain House, Forestburgh Playhouse, Shadowland Playhouse, art and culture, hiking and biking trails, fishing and much more! You’ll love my accomodations because of the quiet, peaceful and serene location nestled in the Catskills. Gourmet breakfasts will awaken you along with the sounds of nature and a beautiful garden. Newly renovated and ready to cater to your personal needs to make your stay most enjoyable.

Family Haven: Robin's Loft

This private 2-bedroom suite is part of the newly renovated side of the house. The 2-room suite has a private bathroom and can sleep up to 4 people. Please note, breakfast is not included in Airbnb rates. Breakfast is available for purchase in our Brunch House Restaurant located on the main floor at $20/person. Local Craft Beer and Wine available for purchase. Please note there are stairs to access this room.

Family · Location · Walkability

Villa Verde B&B, Suite, Greenwood Lake, NY

This stylish place is perfect for anyone who wants to rest and relax. The area offers a lot. Water sports, hiking, skiing attract many visitors. Good restaurants around with live music and lake view. Award winning wineries and craft breweries may be a nice complement. Just minutes to the beach, Harriman State Park, golf course, Renaissance Fair. Delicious breakfast with local products is served every morning.

Location · Hospitality · Indoor spaces