
Guest house holiday rentals in Putnam County
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Top-rated guest house rentals in Putnam County
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Popular amenities for guest house rentals in Putnam County
Family-friendly guest house rentals

Adorable Cottage in Pastoral Setting
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.

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

Hudson Valley Cottage with Pond Access
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.

Cozy Mountainside Suite - Minutes from Beacon
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.

Charming Cottage w/Pastoral Views
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

House in the Trees w/ Pool & Tennis
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.

Historic 1 bedroom home in Cold Spring, NY
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!

The Nest. Large studio in the Woods.
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!

Millie's Inn
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.

French Guest House in Waccabuc
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.

The Ciderhouse Cottage - private escape in Wilton
We had a fantastic stay at Heather’s place. The cottage was beautiful and perfect for our long weekend.

The Cottage in Redding
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.

Adorable 1-Bedroom Cottage w/ Mezzanine Weston, CT
Jacques is a delightful host. Very responsive. He wants to ensure that you have a good time and are comfortable. The Cottage is very inviting with private and peaceful surroundings. The bed is comfortable. The living room is cozy and has a large screen TV and sofa with good lighting. There is a mezzanine that provides a special hideaway or office space. The kitchen is well equipped with everything you might need to fix meals. We have enjoyed this beautiful Airbnb twice and look forward to more visits.
Guest house rentals with a washing machine and dryer

Red Barn Retreat - Shawangunk Mountains Getaway
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.

Entire Guest House at Fox Pond Farm.
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

Spacious Trailside Studio
A lovely spot! Clean, comfortable and well equipped. Connie left us snacks, water and even dog biscuits. Very thoughtful. We didn’t hike, because of a major heat wave, but it would be a great base camp for hiking the many trails on the mountain behind the house. Highly recommend!

Renovated guesthouse on private 7 acre property
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!

Tranquil getaway cottage in charming neighborhood
Can’t say enough good things about Erika’s place. Clean, spacious, well-stocked, comfortable, no surprises. Since we had already been traveling for two weeks when we arrived, we really appreciated the washer and dryer. When she asked for private feedback, all I could think to say was “just keep doing what you are doing.” We will definitely book with her again when we return to Bethel.

1723 Guesthouse
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.

Charming 2 bedroom Cottage w/ patio & yard.
I have been staying at the cottage several times and every time it's perfect! A wonderful place that fits myself, my husband and our dog! Patricia is always responsive and alerted us that she was having some workers around which didn't bother us nor did we ever see them. Will absolutely keep staying there to visit my parents.

The Perch, a luxe cottage with pool 1h from NYC
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.
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- Times Square
- Bryant Park
- Madison Square Garden
- Grand Central Terminal
- Empire State Building
- Columbia University
- Fairfield Beach
- Yale University
- Rye Beach
- Citi Field
- MetLife Stadium
- Yankee Stadium
- Mountain Creek Resort
- United Nations Headquarters
- Central Park Zoo
- USTA Billie Jean King National Tennis Center
- Radio City Music Hall
- Rockefeller Center
- Bronx Zoo
- The Metropolitan Museum of Art
- Rye Playland Beach
- Astoria Park
- Minnewaska State Park Preserve
- Walnut Public Beach