
Holiday houses in Rondout
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Top-rated holiday rentals in Rondout
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Large 2-BR apartment in historic waterfront home
This sophisticated, cozy, pet-friendly historic home in Kingston's beautiful, walkable downtown waterfront (Rondout National historic district) is close to restaurants, sidewalk cafes, boutiques, parks, a beach, museums, galleries, and more. It features a beautiful front porch and back deck, fenced-in yard, living room, master bedroom (queen bed), 2nd bedroom with (full-sized bed), and den/study adjacent to the second bedroom. It is the perfect retreat for a couple, friends, or a small family.
4.94 out of 5 average rating, 135 reviews
Luxury Catskills A-Frame Cabin | Hot Tub & Sauna
Nestled in the serene woods of Saugerties, NY, this luxurious A-frame cabin offers modern comfort and natural beauty. Just 10 mins from Woodstock and 2 hrs from NYC, NJ. it sits on a private 2-acre lot. Easy Access. Featuring premium queen Casper mattresses, a Breville espresso machine, a 4K projector, a firepit, grill, a cedar wood-fired hot tub & Sauna. Dog friendly! A cozy & stylish retreat near hiking, skiing, and top dining spots in the Catskills. Visit our ig ‘highwoodsaframe’ for more!
4.99 out of 5 average rating, 159 reviews
Near-Kingston Staycation Home
This is a newly renovated home in a two-unit house in Port Ewen, 5 min to historic Kingston. We have carefully planned and renovated this home with a work/leisure lifestyle in mind. The space is designed for an individual, a couple, close friends, or a small young family. There are swimming places and parks walking distance as well as amazing coffee, shopping, art, attractions, events, etc. Note that this place has noise from traffic on the main road (ear buds and white noise machine provided).
4.86 out of 5 average rating, 143 reviews
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.
4.87 out of 5 average rating, 149 reviews
Garden apt with river views in downtown Kingston
Lovingly restored garden level apt in 1870's Victorian. Sweeping Hudson River views (with private patio) and just steps away from the entrance for the Kingston Point Rail Trail. Quick 1/2 mile walk to restaurants, shops and boats in Kingston's downtown historic West Strand. One mile walk to events at Hutton Brickyards. California king bed, Central A/C, washer-dryer. and full kitchen in unit! Designed by dog lovers (dogs 45 lbs and under are typically most comfortable due to size of space).
5.0 out of 5 average rating, 129 reviews
Chic, Private Cabin with Stunning River Views
Private, fully renovated cabin with high-end finishes and stunning views of the Hudson River. All creature comforts including full kitchen, expansive living room, stylish bathroom and cozy bedroom, along with firepit and large deck to watch the eagles from. Nestled on a wooded corner of the owner's property but completely independent with separate driveway, parking and fenced yard for privacy. Just minutes from shopping/dining in Kingston, as well as world world class hiking and nature.
4.99 out of 5 average rating, 187 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.
4.95 out of 5 average rating, 320 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.
4.98 out of 5 average rating, 237 reviews
Historic Rondout Home | Walk to Waterfront
Welcome to our comfortable two-bedroom home in Kingston’s historic Rondout neighborhood. It’s an easy home base for couples, friends, families, and solo travelers—just a short walk from the waterfront and some of Kingston’s best restaurants and shops. *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
4.88 out of 5 average rating, 179 reviews
Tangerine Dream~king suite/ perfect for two
You will enjoy easy access to everything from this centrally located apartment. Your right next door to Ulster Performing Arts Center & Tubbys where you will find amazing shows and live music! West Kill Brewing is walking distance as well as many restaurants and coffee shops. Downtown Hudson River waterfront packed with restaurants and water views is a 5 minute drive. Grab a pair of skates and go ice skating at The Rondout Rink right on the waterfront.
4.9 out of 5 average rating, 162 reviews
Charming Historic Home Near Waterfront Restaurants
The best of both worlds: our 1870s house fits right into its historic Rondout neighborhood, but with funky modern design, style, comfort and amenities. Relax in a beautiful zen-like outdoor oasis with pond and dining and lounging areas. Walk just a few blocks down to the waterfront where you’ll find cafes, restaurants, antique stores, boutiques, and museums; grab a freshly fried donut and coffee, and watch the boats go by from a bench in the park.
4.94 out of 5 average rating, 179 reviews
Union House - Kingston's Rondout - 1 bedroom
Once called "Carpenter's Mate," this 1850s brick carriage house was recently gutted and rebuilt brick by brick. Only a block from Kingston's bustling waterfront, the first floor apartment has an open concept living/dining area with French doors leading to the cozy bedroom. We've decorated with a collection of inherited antiques and gems from our travels and the kitchen has everything you need to cook a great meal.
4.94 out of 5 average rating, 157 reviewsPopular amenities for Rondout holiday rentals
Other great holiday rentals in Rondout

Airy Two-Bedroom in a 1735 Stone Landmark
4.98 out of 5 average rating, 787 reviews
Hudson Valley Hygge House~ comfort in the country!
4.95 out of 5 average rating, 374 reviews
Stunning 2-Bedroom A-Frame in the Woods with Sauna
4.98 out of 5 average rating, 298 reviews
Noa’s Ark Float-House
5.0 out of 5 average rating, 75 reviews
Hudson Waterfront Mid-Century Modern Home
4.97 out of 5 average rating, 86 reviews
The Bosun's Crack, Coziness in the Rondout
4.91 out of 5 average rating, 55 reviews
The Quaint House: Modern Heritage in Kingston
4.95 out of 5 average rating, 40 reviews
Designer Retreat with a garden in Kingston NY
4.97 out of 5 average rating, 32 reviewsDestinations to explore
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- Hunter Mountain
- Belleayre Mountain Ski Center
- Bear Mountain State Park
- Minnewaska State Park Preserve
- Thunder Ridge Ski Area
- Bethel Woods Center for the Arts
- Resorts World Catskills
- Windham Mountain
- Catamount Mountain Ski Resort
- Butternut Ski Area and Tubing Center
- Storm King Art Center
- Taconic State Park
- Plattekill Mountain
- Mohonk Preserve
- Peekamoose Blue Hole
- Hunter Mountain Resort
- Kent Falls State Park
- Bash Bish Falls State Park
- Brotherhood, America's Oldest Winery
- Harriman State Park
- Mount Peter Ski Area
- Mohawk Mountain Ski Area
- Millbrook Vineyards & Winery
- Storm King Art Center





