Guesthouse holiday rentals in Putnam County

4.98 out of 5 average rating, 42 reviews

A bright living space is highlighted by large windows allowing ample natural light. A wooden table with four chairs is positioned near the window. A comfortable seating area features a dark sofa and a light armchair, complemented by decorative accents and a potted plant on the coffee table.

Guesthouse in Brewster

Hidden Hope Cottage

Hidden Hope Cottage is on a 19 acre working farm with walking trails and access to the East Branch River and The Great Swamp. Centrally located just minutes to hiking, the Empire Rail Trail, Thunder Ridge Ski and the Southeast train station with direct lines to New York City. The 2 bed 1 1/2 bath private fully renovated cottage boast a private deck, vaulted ceilings with beams, huge windows and great natural light. Sleeps 4 comfortably although can be adjusted to accommodate more upon request.

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Guesthouse in Philipstown

Modern Hudson Valley Loft | Foliage Views, 1hr NYC

No hustle or bustle here — just quiet, sky, and some of the best sunsets in the Hudson Valley. The Garrison Loft is a modern, design-forward guesthouse tucked beside Fahnestock State Park & 1hr from NYC. The open-concept loft is bright and intentional: spiral staircase, west-facing views, and a private balcony made for watching the fog lift off the valley each morning and the hills turn gold every evening. Cold Spring 10min, Beacon 20min. Perfect for couples, close friends, or a solo reset.

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5.0 out of 5 average rating, 16 reviews

The exterior of the Equestrian Suite is showcased, featuring a two-story structure with a blend of brick and wood. A wrap-around balcony offers scenic views, and lush greenery surrounds the property, complementing the tranquil mountain setting.

4.95 out of 5 average rating, 420 reviews

Cozy Mountainside Suite - Minutes from Beacon

The Equestrian Suite at Lambs Hill is a private estate with panoramic views overlooking the Hudson River & downtown Beacon. This beautifully-designed luxury suite sits atop a barn home to Icelandic horses & miniature donkeys, & features an outdoor hot tub, red light therapy, gourmet kitchen, & wrap-around decks. 1 mile to Beacon's Main St, 2 miles to Metro North train station & DIA: Beacon. We can host a max of 2 guests & have some dangerous features for kids so guests should be adults only.

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5.0 out of 5 average rating, 5 reviews

The Greenhouse in the Hudson Highlands (Beacon)

Unwind after a hike or a day out on the town at The Greenhouse, nestled in the foothills of the Hudson Highlands. Conveniently located in-between Beacon and Cold Spring, and close to all hiking trails in the area. This private 1 bed (queen-sized)/ 1 bath guesthouse is independent from the main house, has keyless entry, and a parking spot. Bay windows and skylights bring the outside in, further immersing you in nature. Great opportunity to disconnect from technology as there is no Wi-Fi or TV.

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A winding pathway leads towards a modern, dark-colored barn-style structure surrounded by greenery, with a panoramic view of the mountains in the background. The cloudy sky adds a soft, diffused light to the scene, highlighting the natural landscape.

4.94 out of 5 average rating, 96 reviews

A modern barn on the Hudson River

Welcome to your perfect getaway in the heart of picturesque Beacon, NY! Nestled amidst the tranquil beauty of HV, this newly renovated one-bedroom offers a unique blend of historic charm and modern comfort. The barn is conveniently located close to downtown Beacon. Step into your own private oasis, where you'll be greeted by the breathtaking views of the majestic Hudson River and be transported to world of peace and tranquility. Immerse yourself in the serene beauty this barn oasis offers!

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4.95 out of 5 average rating, 192 reviews

A rustic black barn is showcased, featuring wooden doors and exterior lighting. A paved driveway leads up to the entrance, bordered by a well-maintained lawn and trees. The surrounding natural landscape enhances the barn's secluded charm.

Guesthouse in Brewster

Sherwood Barn - close to ski mountain

Our guests stay on the SECOND floor of the barn in a 1200 Sq Ft, fully reno'd apt that sleeps 6. Located about 1 hour from NYC you will find peace and serenity in the middle of nature on this 4 acre estate (that also contains our main home) where you can get away from it all. unwind this way or visit local attractions like Thunder Ridge Ski Mountain, snowshoe/ X Country skiing, hike/bike/running trails, restaurants and local cafe's. Great oasis to kick back and spend time with family.

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Guesthouse in Cold Spring

A sunlit open space features a light-colored wooden floor and white walls. Two large windows invite natural light, while a patterned area rug adds warmth. A small table and chairs are arranged nearby, creating a versatile area for dining or work.

Bright Modern Escape: Near Village, Forest & Train

Modern, efficient, and elegant private flexible garden apt. Guesthouse can be used as a studio apartment, or as a private personal retreat space for art/work/rest/meditation. Hiking trails available right out the door, and just a few minutes walk to Cold Spring's vibrant Main Street and Metro North train station to NYC and beyond. Comfortable bed, all modern amenities. Private patio. Native pollinator gardens and forest surround. Solar orientation brings in natural light.

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4.99 out of 5 average rating, 239 reviews

A navy blue sofa with bright yellow accent pillows is centered in the image. Behind the sofa, a well-organized shelving unit displays various books, decorative items, and plants. The light-colored walls and patterned rug contribute to a cozy living area.

4.98 out of 5 average rating, 231 reviews

Beacon Modern victorian+garden—steps to mainstreet

Hey there! Welcome to style and ease at our GUESTHOUSE in the heart of the creative and vibrant Beacon NY. Central air and heat (new!). Retreat to your 1000 square foot GH with your own private entrance, 2 bedrooms, (King sized bed!), queen bed, and plush queen pull out sofa in the living room (with door for privacy), and microwave, toasteroven, kettle, mini fridge, glasses, plates/utensils (no stove or kitchen sink). Streaming tv, WiFi, workstation, garden!

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Guesthouse in Philipstown

A cozy sitting room features exposed wooden beams and a brick fireplace. Two comfortable leather chairs are arranged around a wooden coffee table. Natural light enters through multiple windows adorned with sheer curtains, illuminating the space, which is enhanced by decorative touches like artwork and plants.

Historic 1 bedroom home in Cold Spring, NY

This lovingly restored home, built in 1826,is located within the hamlet of Nelsonville within walking distance of the village of Cold Spring. This home has its own entrance and private courtyard and is attached to the owners main residence. Space is curated with antiques and is intended for a couple. This is cozy any time of the year. This home is near trailheads of spectacular hikes in the Hudson Highlands and at the base of Bull Hill.

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4.99 out of 5 average rating, 155 reviews

4.99 out of 5 average rating, 330 reviews

The interior features large windows allowing natural light to illuminate the space. A spiral staircase leads to the loft. A cozy seating area includes a white sofa and a decorative fireplace. Lake views are visible through the glass doors, enhancing the serene atmosphere.

Guesthouse in Brewster

The Cottage by the Lake: Hudson Valley Indulgence

The Cottage by the Lake is a cozy, secret get-away on the scenic banks of the Croton Watershed. About an hour from NYC, it’s on the property of an 1850 farmhouse & has a fully equipped kitchen & bath, cathedral ceiling, working fireplace & cozy sleeping loft. The patio has a fire pit and gas bbq. It’s the ideal place for those seeking to work from home.

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4.97 out of 5 average rating, 30 reviews

Newly renovated guest house in the heart of Beacon

Private, newly renovated, clean and calming - welcome to our guest house in the heart of Beacon, NY. Located in a gorgeous, leafy neighborhood, we're a short walk from the train, and ideally located for exploring the best stores and restaurants in Beacon. Come and enjoy a long weekend of hiking, reading, playing boardgames and more!

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