Hotel holiday rentals in Dutchess County

1967 Hotel Caravana: For Those Who Want Amazing

*Ranked top 8 world’s best vintage caravan hotels- Lonely Planet *Featured in the Travel section of The Guardian *Seen on the Meghan Kelly Show and Good Morning America Nestled in the heart of Amenia, Hotel Caravana offers a world-class boutique airstream experience like no other. First, in the Hudson Valley, we offer a relaxed stay ​and an opportunity to escape life. Stay in an airstream, hotels are boring. *Includes 4 movie tickets to our Drive-In theatre (double feature) *Includes Mini Golf

Grace and Favor - welcoming one bedroom suite

Centrally located to all attractions, yet just far enough removed to offer the best of country life. The Grace and Favor Suite offers a large one bedroom (queen size bed) with seating area and private bath on the ground level. We make every effort to offer the best in hospitality while allowing our guests the most amount of privacy. Mini fridge, Keurig coffee maker, fresh fruit, cream, yogurt and fresh bake good are found in your room at checkin. Friendly sheep will greet you on arrival.

Village Inn - Tribeca suite - Saugerties NY

The Village Inn is the ideal hotel alternative. We offer well appointed private suites with a bit of luxury. Both of our accommodations include Cable TV, WiFi, and A/C. The Tribeca suite is a luxurious loft space with original post & beam construction. It features a queen bed, kitchenette, breakfast bar with exposed brick detail, Mudroom, living area with a twin pullout and a private custom tiled bathroom. Private parking lot to accommodate our guests, and all rooms have private entrances.

Prime Location! Near Kingston Point Beach

Experience a relaxing stay in a cabin near the Hudson River! If you're looking for something to do, you should check out Birch Body Care and El Paso Winery, while those looking to take in the area's natural beauty might visit Forsyth Park and Falling Waters Preserve. While in town, are you looking to take in an event or a game? Check out the events at Dietz Stadium or think about spending the evening at The Chateau. There are many water adventures nearby, including kayaking and boat cruises.

The Gables of Rhinebeck Inn, Sugarloaf Suite

The Gables of Rhinebeck, a 4-suite Inn located 1 block from main street. This historic Inn is a fifteen-gable 1860 Gothic Revival Victorian in the heart of Rhinebeck Village. Guests have full access to our half-acre fenced-in yard with perennial and ornamental gardens, + plenty of indoor space. "Sugarloaf" is a 1BR Suite at The Gables of Rhinebeck. About Your Room: -Queen Bed, Cable TV, Full Bath on the 2nd floor with claw foot tub. AC'd in the summer https://www.TheGablesRhinebeck.com/

Village Inn - Chelsea suite - Saugerties NY

The Village Inn is the ideal hotel alternative. We offer well appointed private suites with a bit of luxury. Both of our accommodations include Cable TV, WiFi, and A/C. The Chelsea suite features a private bedroom with a king sized bed. A kitchenette, with breakfast area and a living area with a twin pullout. Spa soaking tub to help relax and rejuvenate after a long day. Private parking lot to accommodate our guests, and all rooms have private entrances.

The Eliza at The Beacon Hotel

The Beacon Hotel is a short term rental style property, we do not employ a hotel staff. It is located right on Main Street in the middle of one of the Hudson Valley's most exciting cities, Beacon! Within the past 10 years Beacon has completely redeveloped and brought in a whole new population. Main street is filled with art galleries, shops, restaurants, antiques, nightlife and the Beacon Hotel is right in the middle of it all.

The Harlow House: Marque Suite

Welcome to The Harlow House, a serene inn nestled in the picturesque town of Rhinebeck, NY. The inn features 6 elegantly appointed suites, every suite boasts a private bathroom and a cozy bedroom. No children under the age of 12 or pets allowed. The Marque Suite has a dedicated work desk, a smart TV and a cozy reading corner. It also has a King sized bed and futon. It is on the 2nd floor and accessed via one flight of stairs.

Catskills Getaway - Spacious Comfortable Room

This room will delight your senses with oak surround and forest mural, this third floor gem offers tranquility and peace. Queen brass bed, 47" LED Cable TV, WiFi, antique oak table, plush chairs, cozy arm chair and private one and a half bathrooms (shower) both fully tiled and with skylights. Note:there is also an optional add-on room for up to two additional guests, ask about this option if interested.

The Reclaimed Motel, Hudson Valley - Three Farmers

Moving the past forward The Reclaimed Motel was built in 1960, and we wanted to respect its mid-century bones while making thoughtful modern upgrades. And the list of upgrades was long! From a new roof, to all new plumbing and electric, we've kept the integrity of this Red Hook landmark while investing in meaningful improvements to make this motel appealing and memorable for the modern traveler.

The Millbrook Inn Emerson 2 Queens

Located on the second floor of our Hudson Valley Inn, the Emerson is our best (and only) double room. And with a double vanity in the bathroom and a generous closet and dresser, it’s the perfect room for two friends traveling together. The room features two full beds; a sitting area with wing chairs, and a sunny marble bathroom with a walk-in shower.

Upstate Getaway

Cozy, clean, and just 90 minutes from NYC, our small upstate motel offers the perfect escape. Surrounded by nature, it’s ideal for hiking, exploring local farms, or enjoying a peaceful weekend away. With nearby trails and small-town charm, it's a great base for adventure or relaxation. Simple, affordable, and welcoming—your upstate retreat awaits.