Guesthouse holiday rentals in Putnam County

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.

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.

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!

Modern & Chic Hudson Valley Loft w/ Views, 1hr NYC

Welcome to the Garrison Loft, a modern Hudson Valley loft with West–facing views, 1 hr from NYC. Backing onto Fahnestock State Park, this serene, sun-drenched retreat is made for slowing down and reconnecting. Enjoy your private balcony, fire pit, and peaceful setting—just 10 min to Cold Spring and 20 min to Beacon, 5 minutes to Bird & Bottle + incredible hikes onsite. Perfect for couples, friends, & solo escapes. Baby gear available upon request. 25+ only. No pets — the wildlife thanks you!

Cold Spring Woodland Retreat 5 Bed 2.5 Bath

Enjoy being away from it all while still being minutes from the charm of the village of Cold Spring. This 2700 s.f. home was fully renovated in 2024 and boasts 5 bedrooms and 2.5 baths on a wooded and quiet country road. This home comes with an on-site host who lives in the attached in-law apartment. Invite the whole family and enjoy dining together in the large kitchen and dining table, roasting marshmallows in the backyard, and relaxing in the peaceful and shaded backyard with hot tub.

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.

The Beacon Woods

Welcome to paradise! Located just minutes away from Beacon's thriving Main Street, our homestead is nestled in a quiet little hamlet next to a monastery and just steps away from a waterfall that sits at the mouth of a hiking trail meandering to the shores of the Hudson River. The three-bedroom guesthouse with work space, deck, and yard is at your disposal. Enjoy views of Mt. Beacon as well as the extensive vegetable and flower gardens. Come to rest or play and make yourself at home!

Modern+Bright Forest Escape : Near Village & 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.

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!

Sweet lil' house among the boulders LONG TERM STAY

This cozy modern bungalow is set adjacent to our home with a separate entrance from the driveway on 8 acres isolated on a back country road with no neighbors visible anywhere. You are a bike ride away from Fahnestock Park, the Appalachian Trail, the Zen Monastery, White Pond and a small country deli. It's a 20 minute drive to Cold Spring with antiques and restaurants, 15 minutes to Carmel with first run movies, bowling, restaurants and a mall.

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.

Modern Compound Guesthouse

This private and modern guesthouse sits in a beautiful compound with walk-on/off access to the Appalachian Trail on the Garrison/Putnam Valley border. Gorgeous wooden floors, underfloor bathroom heat, full open kitchen, air-conditioning, dining area and luxurious Restoration Hardware furnishings. Plenty of parking and access to grounds. Possible transfers available to/from train stations. Not your average spot!