Guesthouse vacation rentals in Putnam County

Find and book unique guesthouse rentals on Airbnb

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Popular amenities for Putnam County guesthouse rentals

Family-friendly guest house rentals

Guest favorite
A gravel pathway leads to a dark wooden fence, framing the entrance to the property. Lush greenery and trees surround the area, while a spacious lawn extends towards a cottage and rolling hills in the background, under a partly cloudy sky.
Guesthouse in Gaylordsville
4.96 out of 5 average rating, 111 reviews

Adorable Cottage in Pastoral Setting

KathleenRating, 5 stars1 month ago
This was our fourth or fifth time staying at the Farm Cottage. It’s our go to spot when we’re in town. Always consistently clean and comfortable and the location is perfect for us. Never had a need that wasn’t met by Irit.
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, 284 reviews

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

LisaRating, 5 stars1 day ago
Jonathan and Amy were the perfect hosts. Super friendly and resourcesful. The property is beautiful and so peaceful which was perfect for our down time as we were in town for a three-day wedding. We enjoyed breakfast with the family of deer that live in the back field and so many beautiful birds. The apartment is so quaint, very clean and has everything that we needed. The beds were super comfortable. It was decorated to the age of the property which we loved! It was a great find and we highly recommend the apartment and will surely book again if ever in the area.
Superhost
A charming cottage exterior is framed by lush greenery, featuring large front glass doors and a sloped roof. Potted flowers adorn the entrance, while a shaded sitting area with comfortable chairs is visible beside the pathway, inviting relaxation in a serene setting.
Guesthouse in Stormville
4.97 out of 5 average rating, 175 reviews

Hudson Valley Cottage with Pond Access

ChelseaRating, 5 stars2 months ago
If you're looking for a private retreat in a gorgeous setting, this is your place. The property is stunning, super walkable grounds, and a gorgeous back patio. S.A. is a super host, and when we ran into an issue, he was quick to respond and help. We recommend this place, and intend to stay again in the future.
Guest favorite
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
4.94 out of 5 average rating, 400 reviews

Cozy Mountainside Suite - Minutes from Beacon

AnthonyRating, 5 stars2 weeks ago
My fiancé and I stayed at Lambs hill to celebrate our anniversary. We had the most wonderful time. The views are breathtaking. The wrap around deck with jacuzzi and hammock made our stay calming and serene. I loved seeing the horses and donkeys throughout the day. They made the experience even more special and unique. Charlotte was super responsive and accommodating. We took cabs to Main Street at night for dinner and drinks and it was so close and convenient. I left my heart in lambs hill and can’t wait to return one day.
Guest favorite
A gravel area is framed by a rustic wooden fence and lush greenery. The parking space is bordered by low shrubs, and a glimpse of the neighboring cottages is visible in the background, surrounded by trees and a serene setting.
Guesthouse in New Milford
4.94 out of 5 average rating, 194 reviews

Charming Cottage w/Pastoral Views

JuneRating, 5 stars2 weeks ago
Irit is a very experienced host, in that she ore sees our needs and provides anything you may have missed. The cottage is cozy x10! The bed, linens, furniture are very comfy and welcoming, while also high quality. I highly recommend her cottages, she is a great hostess. We have stayed multiple times, and try to book her place every time we are visiting our home town. You will not be disappointed. Also, very clean and safe!

Guest house rentals with a patio

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, 97 reviews

Historic 1 bedroom home in Cold Spring, NY

AmyRating, 5 stars3 days ago
My husband and I stayed 2 nights for our anniversary and loved it! Pieter and Jackie were lovely people, and the place is even better than the photos. We had everything we needed, and while we had a car we didn't use it because it was so easy to walk everywhere - a hiking trail, restaurants, shops, the waterfront! We would definitely stay here again!
Superhost
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

ChloeRating, 5 stars5 months ago
Absolutely fantastic week at the cottage. Highly recommend and we will definitely be back !!
Superhost
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, 71 reviews

The Nest. Large studio in the Woods.

LiannRating, 5 stars2 days ago
Marianne is a wonderful host! The setting for this cottage is idyllic, the surrounding grounds and gardens are stunning. To address some concerns posted previously, yes, the driveway is steep and winding but it is well maintained and was not a problem for us at all. We arrived on a hot day in June and the studio cooled off quickly and remained comfortable with the AC. Didn’t miss the TV at all! This is a find! Will be back!
Superhost
A bright living area is framed by large windows showcasing a wooded view. A dark green sofa with white pillows is positioned alongside two light-colored armchairs. A wooden coffee table rests on a patterned area rug, with a dining table visible in the background.
Guesthouse in Pound Ridge
5 out of 5 average rating, 16 reviews

Renovated guesthouse on private 7 acre property

MattRating, 5 stars7 months ago
Can’t say enough good things about this place. Everything is exactly as described and photographed. Communication was also seamless. The perfect place if you want a quiet and peaceful stay that’s also a short drive to the Main Street in Pound Ridge. Highly recommended!
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, 54 reviews

Millie's Inn

AlexRating, 5 stars4 weeks ago
Millie’s Inn exceeded all of our expectations. It’s private, peaceful, comfortable, clean and so beautifully designed. Jackie & Lenny are responsive and dedicated hosts who made sure we had everything we needed our entire stay. We would stay here again and recommend it to anyone in a heartbeat.
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, 95 reviews

French Guest House in Waccabuc

AndrewRating, 5 stars1 week ago
Lori's guest studio was magical. Located on a French Country estate in a beautiful rural area near Cross River, NY, the studio fronted a lovely pond with the rhythmic sound of the aerating fountain and nightly chorus of bullfrogs that transport you to another time and place. The studio is beautifully decorated and perfect for our short stay. The Keurig coffee maker was well stocked but came in a distant second place to Lori's recommended cafe and patisserie just 10 mins away. Next time we return (and we do plan to return!), we'll try to make some time to explore the area and leave the ever-rushing world behind.
Guest favorite
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, 45 reviews

The Ciderhouse Cottage - private escape in Wilton

OdalysRating, 5 stars2 weeks ago
We loved our stay at this beautiful private cottage! It was perfect for our long weekend getaway since we were in the area for a wedding and grad celebration. Very clean, tidy, and spacious—plenty of room to get ready!
Guest favorite
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, 54 reviews

The Cottage in Redding

RyanRating, 5 stars7 months ago
Cozy guest cottage in a gorgeous New England setting. The perfect launch-point for exploring the historic towns and rolling hills and mountains of western Connecticut / eastern New York. The chickens were a charming addition. ;) Would be happy to stay again! The fall colors were stunning.

Guest house rentals with a washer and dryer

Top guest favorite
Guesthouse in New Milford
4.97 out of 5 average rating, 34 reviews

House in the Trees w/ Pool & Tennis

SaraRating, 5 stars1 month ago
We had a great stay here for the weekend of a wedding in the area. The area is so beautiful, and the spot was just what we needed! Pristine and so comfortable, with lovely views all around from your balcony. The family had a lovely time.
Top guest favorite
Guesthouse in Gardiner
4.99 out of 5 average rating, 175 reviews

Red Barn Retreat - Shawangunk Mountains Getaway

GretchenRating, 5 stars1 month ago
Great experience! 2 wineries within 1 mile. Close to great hiking. William, was very accommodating with check in & check out time. Would highly recommend staying here. Very cute , clean and comfortable with get amenities.
Guest favorite
An outdoor fire pit is surrounded by wooden adirondack chairs, offering a cozy space for gathering. The sun sets in the background, casting a warm glow over the lush tree line. A stone border surrounds the fire pit, providing a natural aesthetic.
Guesthouse in Easton
4.84 out of 5 average rating, 103 reviews

Entire Guest House at Fox Pond Farm.

ColinRating, 5 stars1 week ago
A group of us stayed here for a wedding nearby. Durelle was super communicative and helpful the whole time we were there. We didn't get to spend much time there and due to the weather we didn't hang outside too much but the property was beautiful and seemed like a great place for a summer getaway with the pool & firepit
Top guest favorite
An aerial view of the spacious studio showcases a cozy seating area with a green sofa and a red armchair. A wooden dining table with chairs is visible alongside a decorative area rug. Nature-themed artwork is displayed on the walls, enhancing the open atmosphere.
Guesthouse in Beacon
4.97 out of 5 average rating, 35 reviews

Spacious Trailside Studio

AndrewRating, 5 stars1 week ago
Wonderful host, had an amazing time, and the place was very clean with great accommodations!
Top guest favorite
A clean kitchen countertop is displayed with a tray holding decorative hand soap and dish soap. A roll of paper towels is presented on a holder, with a piece creatively folded into a bow shape. The backsplash features light blue tiles, enhancing the modern aesthetic.
Guesthouse in Bethel
5 out of 5 average rating, 19 reviews

Tranquil getaway cottage in charming neighborhood

EuripidesRating, 5 stars1 month ago
"Lovely, peaceful stay! Erika was a responsive and kind host. The place was clean, cozy, and perfect for relaxing. Would definitely return!" Highly recommend !
Guest favorite
A bright bathroom features a bathtub with a shower curtain and subtle tile accents. Natural light filters through the window, illuminating the space. Soft bath mats are positioned on the floor, complementing the white cabinetry and countertops.
Guesthouse in Wappingers Falls
4.91 out of 5 average rating, 11 reviews

1723 Guesthouse

JenniferRating, 5 stars4 weeks ago
This guesthouse was a perfect fit for our weekend visit to the Hudson Valley. It had plenty of space and was very clean. The house had a lot of charm and was a good value for the price. The host was friendly and helpful.
Guest favorite
A panoramic view showcases the Hudson River flanked by vibrant autumn foliage. A bridge spans the waterway, connecting the two banks, while rolling hills covered in colorful trees extend into the distance under a clear sky.
Guesthouse in Cortlandt
4.87 out of 5 average rating, 79 reviews

Charming 2 bedroom Cottage w/ patio & yard.

JulieRating, 5 stars1 month ago
The cottage was a great weekend stay, and the aesthetic details and care that has been put into the space was not expected. Very well done! Patricia's place was definitely dog-friendly - extra cleaning supplies, furniture covers, and more made us feel comfortable having our pup. As described, it is not private and you'll run into neighbours and hear traffic, but it's a great retreat to cook some meals and wind down after a day exploring the area.
Top guest favorite
A spacious main room includes a king-size canopy bed and a cozy seating area. Large windows frame the lush greenery outside, while a wood-burning stove adds warmth. A small table with games and books is set next to the seating, inviting relaxation amid nature.
Guesthouse in Bedford Hills
5 out of 5 average rating, 47 reviews

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

GabrielleRating, 5 stars1 day ago
Lovely getaway outside of NYC. We came up here with our toddler and dog —both magical creatures were very content. Super peaceful with lots of great restaurants and bakeries nearby plus parks. Jennifer’s book has all the great spots. We really enjoyed it and got to relax, disconnect. Highly recommend coming up to the Hudson valley and staying at The Perch.

Destinations to explore