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Guesthouse vacation rentals in Putnam County

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Top-rated guesthouse rentals in Putnam County

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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

5 out of 5 average rating, 4 reviews

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.

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.

Guesthouse in Beacon

4.95 out of 5 average rating, 401 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.

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.

Guesthouse in Beacon

4.92 out of 5 average rating, 72 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!

A round dining table with two transparent chairs is positioned near large windows that offer views of vibrant autumn foliage. A small vase with flowers decorates the table. Light enters through the open door, enhancing the bright and airy ambiance.

Guesthouse in Mahopac

4.95 out of 5 average rating, 247 reviews

Lakeview Guesthouse with Sauna

Art and light filled spacious studio with panoramic views overlooking lake Mahopac perched on a steep hill. A short 5 min walk down the hill to swimming/paddleboarding/canoeing. Walkable to an on-the-lake restaurant/ dining/ takeout options + boba tea! Drivable to farm fresh food markets, restaurants and art museums. Cedar dry Sauna on property for use. Nearby towns and hikes include Fahenstock Park, Pound Ridge, Cold Spring, Beacon, Ridgefield, or walk up the hill to trails of Volz park!

Top guest favorite

The exterior of a spacious two-story brick home is showcased, featuring a wide stone pathway leading to the front entrance. Large windows reflect the surrounding greenery, while a well-maintained lawn complements the serene country setting. A backdrop of trees adds to the tranquility.

Guesthouse in Cold Spring

5 out of 5 average rating, 16 reviews

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 woods. Plenty of parking for large groups.

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

4.94 out of 5 average rating, 150 reviews

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.

A black guesthouse features a covered deck with a dining area and seating, surrounded by gardens. Solar panels are installed on the roof, and a lush green lawn enhances the outdoor space. Tall plants and flowers add visual interest to the surroundings.

Guesthouse in Beacon

5 out of 5 average rating, 9 reviews

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!

Top guest favorite

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.

Guesthouse in Cold Spring

4.99 out of 5 average rating, 175 reviews

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.

Top guest favorite

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.

Guesthouse in Beacon

4.97 out of 5 average rating, 189 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!

A cozy bungalow exterior is framed by lush greenery, with a wooden deck featuring two outdoor chairs. The entrance is marked by a white door and an array of windows, inviting natural light into the space.

Guesthouse in Carmel Hamlet

4.89 out of 5 average rating, 83 reviews

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.

Top guest favorite

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.

Guesthouse in Philipstown

4.99 out of 5 average rating, 100 reviews

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.

A modern guesthouse structure features a sleek metal facade with a large window that invites natural light. Three garage doors are prominently displayed, set against a backdrop of lush green trees under a clear blue sky.

Guesthouse in Putnam Valley

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!

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Popular amenities for Putnam County guesthouse rentals

Free parking on premises

Air conditioning

Family-friendly guest house rentals

Top guest favorite

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.

Guesthouse in Philipstown

4.99 out of 5 average rating, 100 reviews

Historic 1 bedroom home in Cold Spring, NY

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

4.94 out of 5 average rating, 150 reviews

Sherwood Barn - close to ski mountain

A black guesthouse features a covered deck with a dining area and seating, surrounded by gardens. Solar panels are installed on the roof, and a lush green lawn enhances the outdoor space. Tall plants and flowers add visual interest to the surroundings.

Guesthouse in Beacon

5 out of 5 average rating, 9 reviews

The Beacon Woods

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.

Guesthouse in Beacon

4.95 out of 5 average rating, 401 reviews

Cozy Mountainside Suite - Minutes from Beacon

Top guest favorite

A spacious studio features a comfortable bed with a decorative throw blanket. A dining table is surrounded by patterned chairs. The kitchen area is visible in the background, and a staircase leads to a loft space. Natural light brightens the room, enhancing the wooden details.

Guesthouse in Beacon

4.98 out of 5 average rating, 42 reviews

Spacious Trailside Studio

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.

Guesthouse in Beacon

4.92 out of 5 average rating, 72 reviews

A modern barn on the Hudson River

Top guest favorite

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.

Guesthouse in Beacon

4.97 out of 5 average rating, 189 reviews

Beacon Modern victorian+garden—steps to mainstreet

A cozy bungalow exterior is framed by lush greenery, with a wooden deck featuring two outdoor chairs. The entrance is marked by a white door and an array of windows, inviting natural light into the space.

Guesthouse in Carmel Hamlet

4.89 out of 5 average rating, 83 reviews

Sweet lil' house among the boulders LONG TERM STAY

Guest house rentals with a patio

Top guest favorite

A private guest house is framed by lush greenery, with a gently sloping wooden ramp leading to the entrance. The exterior features a simple design harmonizing with its woodland surroundings, while tall trees and ferns create a peaceful atmosphere.

Guesthouse in New Milford

4.97 out of 5 average rating, 38 reviews

House in the Trees w/ Pool & Tennis

The exterior of a renovated farm cottage features a two-story structure with a red umbrella over a wooden deck. The landscaped surroundings include a stone wall and various greenery, creating an inviting atmosphere. A pathway leads to the entrance, immersed in a natural setting.

Guesthouse in Chester

4.94 out of 5 average rating, 17 reviews

1786 Farm Cottage "Honeymoon Suite" Renovated 2022

Top guest favorite

An open-concept area features warm wood flooring and soft lighting from hanging lamps. A kitchen space is visible with a small island equipped with seating. A spacious bed is situated in the corner, dressed in patterned linens. Large windows allow natural light to brighten the room.

Guesthouse in Wallkill

5 out of 5 average rating, 58 reviews

Millie's Inn

Top guest favorite

The exterior of the guest house is framed by manicured gardens, featuring two decorative statues positioned beside a pea gravel walkway. A small patio area includes a round table with two chairs, creating a serene spot for outdoor relaxation.

Guesthouse in Waccabuc

4.99 out of 5 average rating, 103 reviews

French Guest House in Waccabuc

The cottage is surrounded by lush greenery, featuring a charming entrance with a white door and a stone chimney. A greenhouse sits alongside, filled with plants. The front yard is lined with vibrant shrubs and framed by blooming trees under a clear blue sky.

Guesthouse in Wilton

4.98 out of 5 average rating, 46 reviews

The Ciderhouse Cottage - private escape in Wilton

The exterior of the cottage is shown with a welcoming porch featuring a red umbrella over a dining table. Potted plants are arranged along the walkway, while a grill and a trash bin are visible nearby. Lush greenery surrounds the property, enhancing the serene environment.

Guesthouse in Cortlandt

4.88 out of 5 average rating, 84 reviews

Charming 2 bedroom Cottage w/ patio & yard.

A charming cottage is nestled among lush greenery, surrounded by vibrant trees and shrubbery. The exterior features a white façade with large black-framed windows and a distinctive barn door design, complementing the serene natural setting.

Guesthouse in Redding

4.93 out of 5 average rating, 58 reviews

The Cottage in Redding

A cozy living area is visible from the mezzanine, featuring a beige sofa with two dark cushions. Artwork hangs on the wall above the sofa, complemented by modern floor lamps. Natural light filters through the window shutters, illuminating the wooden flooring.

Guesthouse in Weston

5 out of 5 average rating, 71 reviews

Adorable 1-Bedroom Cottage w/ Mezzanine Weston, CT

Guest house rentals with a washer and dryer

Top guest favorite

A bright sitting room features a cozy sofa adorned with colorful pillows. A wooden sideboard stands against the wall, while a small side table holds reading materials. Natural light filters in through two windows, illuminating the room's warm, wooden flooring and vibrant area rug.

Guesthouse in South Salem

4.94 out of 5 average rating, 294 reviews

1795 colonial w private 2 bd rm, 1 bth,LR,Kit apt

Top guest favorite

A lush green field extends towards the horizon, framed by clusters of trees. The sky is filled with varying shades of clouds, reflecting a soft light from the setting sun. The peaceful rural landscape evokes a sense of tranquility.

Guesthouse in Gardiner

4.99 out of 5 average rating, 178 reviews

Red Barn Retreat - Shawangunk Mountains Getaway

The exterior of the guest house features a stone facade complemented by a sloped roof. Lush greenery surrounds the property, and the driveway is lined with gravel. Two white planters with flowers are positioned in front of the entrance, while the sky displays a mix of clouds and blue.

Guesthouse in Easton

4.85 out of 5 average rating, 106 reviews

Entire Guest House at Fox Pond Farm.

A rustic exterior of a large studio is framed by trees showcasing fall colors. The structure features a unique design with a gabled roof and wooden paneling. A gravel driveway and a stone patio are visible, providing access to the entrance amid a serene natural setting.

Guesthouse in Southbury

4.93 out of 5 average rating, 75 reviews

The Nest. Large studio in the Woods.

Top guest favorite

A spacious living area features a comfortable dark sofa complemented by patterned armchairs. Natural light enters through large windows adorned with sheer curtains, illuminating the neutral walls. A small coffee table and decorative elements add to the inviting setup.

Guesthouse in Bethel

5 out of 5 average rating, 22 reviews

Tranquil getaway cottage in charming neighborhood

Top guest favorite

A charming red exterior features white window treatments and a rustic door. Decor elements include a wooden wagon wheel and an artistic iron wall hanging. Lush greenery and flowers are visible in the garden area, enhancing the welcoming entryway.

Guesthouse in Newtown

4.99 out of 5 average rating, 80 reviews

Guest Suite at Wisteria Gardens

Top guest favorite

The cottage is tucked amidst vibrant autumn foliage, framed by trees. A large front deck, furnished with two chairs, provides a serene entry, while the three expansive windows invite natural light. The wooden exterior blends harmoniously with the surrounding woodland.

Guesthouse in Bedford Hills

5 out of 5 average rating, 53 reviews

The Perch, a luxe cottage with pool 1h from NYC

A cozy living area features a light-colored sofa adorned with decorative pillows. Two dark wooden tables flank the sofa, each holding a potted plant. A textured area rug covers the hardwood floor, and large windows are dressed with light curtains that softly filter sunlight.

Guesthouse in Tomkins Cove

4.84 out of 5 average rating, 25 reviews

The cottage at Oasis Cove

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