Holiday houses in Rondout

4.97 out of 5 average rating, 260 reviews

The Ivy on the Stone

The oldest house you can stay at in the historic heart of Kingston! Walkable! This landmark 1680 stone house has been featured in Upstate Diary and Houzz. Enter this 350 sq ft luxe apartment through a secret garden and a shared porch. The private spa-like bathroom features a clawfoot tub, and rain shower. Featuring an organic queen bed, an electric fireplace, workspace, William Morris wallpaper, and a Nespresso maker. If you want to stay in the larger house visit: https://abnb.me/EexspArCAIb

4.87 out of 5 average rating, 118 reviews

Home in Kingston

Historic 1800s Kingston Waterfront Townhouse

Welcome to our newly renovated two story home in beautiful scenic Kingston, NY. This 3 bedroom, 2 bath loft style home is perfect for many occasions! It boasts a full kitchen stocked with modern stainless steel appliances and style for days. Marvel at the open Brooklyn loft style designing that will impress with its exposed brick and white wood ceiling rafters and light gray floors. Very chic! It is fully furnished with posh sofas and tables that lend beautifully to the sophisticated ambience.

4.97 out of 5 average rating, 115 reviews

Majestic! 3000 sq ft 2BR 2Bath

More room then you can ever imagine in our 3000 sq foot, 2 BR retreat In the heart of Kingston NY. 90 minutes from NYC. We offer modern amenities, cozy blankets, games and endless star gazing from our many windows at night. Just a 5 min walk to Ulster Performing Arts Center where you can catch a show, walking distance to local breweries, restaurants, bakery & coffee shop. Explore the boutiques in uptown or stroll the waterfront this winter where you can also Ice skate @ The Rondout Ice Rink.

4.94 out of 5 average rating, 212 reviews

Guesthouse in Kingston

Campfire Cottage: Fireplace, fire pit & no chores!

Escape the city and unwind at this beautifully designed home. Just 90 minutes from Manhattan, this is the perfect place to relax and reconnect with nature, or work remotely. Enjoy downtown attractions, hiking, and the Hudson River Maritime Museum nearby. The home features a cozy living area, full kitchen, electric fireplace, and no chore list for checkout. The yard has a grill and fire pit facing the woods. Book today to retreat to your private house and enjoy the beauty of Upstate New York!

4.9 out of 5 average rating, 230 reviews

Dog Friendly Hudson Valley Escape with Hot Tub

Welcome home! The unit in our fully renovated 19th-century colonial combines modern finishes with the historic charm centrally located in Kingston. This unit features a fully fenced-in backyard, you’ll find the following - Hot Tub - Fire Pit - Hammock - Grill - Outdoor Games If you’re looking to experience Kingston, you’ll be a short walk from some of the best the Hudson Valley has to offer! This is one of two private units that have been individually decorated and thoughtfully curated.

4.96 out of 5 average rating, 121 reviews

The Zen Den in Historic Rondout District

Escape to charming Kingston, NY and stay in the garden apartment of our historic brick home built in 1880. The womb like studio has heated clay floors and a floating cabin bedroom that will envelop and soothe. The private backyard with stonescaping and fire pit is yours alone to enjoy. Walk down the waterfront promenade to the Strand district with shops, restaurants, and museums, or drive to the surrounding swimming holes and nature trails of Woodstock, Rosendale, High Falls, and Saugerties.

4.91 out of 5 average rating, 144 reviews

Condo in Kingston

Cozy & walking distance to cafés *spring avails*

Perfect for friends, couples, families, or solo-travelers looking for a comfortable home that’s centrally located and near some of Kingston’s best restaurants and shops! This historic two-unit home is walking distance to the waterfront and a short drive to incredible hikes and farms! *Pet-friendly (no extra fee) *Family-friendly (highchair + Pack n Play for babies, games for kids). Note: Parking onsite or arrive via Metro North to Poughkeepsie, Amtrak to Rhinebeck, or bus to Kingston

4.96 out of 5 average rating, 238 reviews

DeMew Townhouse in Historic Kingston

DeMew Townhouse is beautiful duplex apartment located in a renovated 1850s building overlooking Hideaway Marina in the Rondout district of Kingston. The building boats a rich history: the main floor of the building served as a speakeasy during Prohibition. It has hand rubbed oak floors, a renovated kitchen and bath and 14 windows providing views of the Rondout. With a spacious open plan, the DeMew Townhouse is the perfect location from which to explore Kingston and the Hudson Valley.

4.98 out of 5 average rating, 165 reviews

Lovely 1 bedroom apt. with free parking in Rondout

Large 1 bedroom apartment with 10 foot ceilings, located in Kingston Historic Rondout District. Queen size bed and one large futon conversation, there are large pocket doors that separate the bedroom from the living room, pool table, lots of natural light, blackout curtains , air conditioning, claw foot tub, small private patio, 60 inch wall tv, walk to the historic Rondout water front, restaurants, boat rides, trolly, art galleries, Kingston Point Beach and Hudson Brickyards.

4.92 out of 5 average rating, 116 reviews

Apartment in Rosendale

Shack in the Heart of Rosendale

This unique, centrally located 500 sq ft ground-floor, 1.5 story apartment is in an ideal location to explore Rosendale and the surrounding areas. Located in a 1890s Brownstone, the Shack is a comfortable refurbished studio with hand hewn beams, brick walls and a wood burning stove. Sleep in a queen Murphy bed (pulls down) and prepare food in the kitchenette. Keep in mind nobody above you and the town shuts down at 10 PM so you have a decent amount of peace and quiet.

4.89 out of 5 average rating, 577 reviews

Apartment in Stone Ridge

Cozy Apartment with Sauna in Historic Stone Ridge

First floor apartment in historic colonial house in the middle of Stone Ridge, NY. It offers perfect mixture of rustic and modern styles and is decorated with original pieces of art. It has a fireplace stove and a wood fired sauna in the backyard. Full kitchen is equipped with everything guests need to prepare a great meal. It is perfect for all seasons. New Paltz, Woodstock, Minnewaska, Mohonk Preserves, Shawangunk Ridge are all within the short 20 min drive.

4.99 out of 5 average rating, 315 reviews

Treehouse in Wallkill

The Treecastle at the Roundhouse Homestead

The Treecastle started as a vision when I was a child, but came to life during the quarantine of 2020. Escaping into the woods and surrounded by nature, the treecastle is supported on one end completely by a mature pin oak with hardware from Treehouse Masters TV show. Attention to detail shows in this romantic stay that will surely be a memory to last a lifetime. For more photos and videos check out our social media pages : treehouseandchill

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4.88 out of 5 average rating, 43 reviews

Home in Kingston

Charming Two-Bedroom, One-Bath Kingston Retreat!

AshlieRating, 5 stars2 weeks ago

Great location, could walk to a few places, convenient! Fenced in yard with a little groundhog friend! Comfy beds and an overall nice stay. Thanks again for the stay!

4.98 out of 5 average rating, 97 reviews

Cottage in Port Ewen

Relaxing Cottage block from peaceful river view

Leanne MarieRating, 5 stars4 days ago

This cozy cottage was perfect for our weekend with two couples. Everything was in place for us to make some of our meals at the house and we so enjoyed the Kingston waterfront with beautiful views and great restaurants. Dawn-Marie was a wonderful host with very helpful instructions left for us and promt responses to any communication.

4.98 out of 5 average rating, 40 reviews

Cozy Uptown Getaway

DanielRating, 5 stars1 week ago

Shaun's place is a good value. Bed is comfortable, bathroom is clean, and many thoughtful touches to make your stay comfortable. The apartment was spacious enough not to feel cramped. I would stay here again.

4.93 out of 5 average rating, 27 reviews

Home in Port Ewen

Hudson Riverfront Mid-Century Modern Home

KevinRating, 5 stars3 weeks ago

A beautiful, comfortable house right on the Hudson with stunning views. We loved watching all the life on the river, herons and loons and ducks, as well as boats from tiny crafts to massive barges. There are great hikes just a short distance away. It is a perfect place to rest, write, draw, and make music.

5 out of 5 average rating, 81 reviews

Home in Staatsburg

Boulder Tree House

SanjayRating, 5 stars1 week ago

This house was absolutely spectacular. The gorgeous, architectural design highlighted its natural surroundings while providing all the thoughtful comforts of a home away from home. Each window is carefully placed to frame the greenery and let in the perfect amount of light throughout the day. From the steam shower to the towels to the linens, the amenities provided were comparable to those offered at a luxury hotel. The hosts were super responsive and welcoming. We couldn’t recommend it more!

5 out of 5 average rating, 27 reviews

Cottage in Kingston

Empire Bicycle Lodge

MarciaRating, 5 stars2 weeks ago

Samantha’s place was great and I would stay there again. It’s clean and comfortable with two separate sleeping spaces, so great to share with a friend or family members. Proximity to the different zones of town is very convenient. The neighborhood is walkable / residential with some local amenities right nearby. The outdoor eating zone is a bonus !

4.97 out of 5 average rating, 94 reviews

Home in Kingston

Large 2-BR apartment in historic waterfront home

TriciaRating, 5 stars3 weeks ago

Jennifer's place was charming and you felt at home there. She met us when we checked in and was very friendly and lots of recs! My mom, sister and I had a lovely stay. Wonderful back patio, front porch and comfortable beds. Close to some nice cafes and restaurants.