Vacation Rentals in Kingston, NY
Explore Red Cottageโs collection of Kingston, NY vacation rentals, featuring design-forward homes, historic retreats, and modern escapes. Each home is thoughtfully selected for exceptional comfort and easy access to the regionโs best dining, arts, hiking, and four-season outdoor experiences.
Stay close to Uptownโs Stockade District for bookstores, galleries, and dinner out, then spend your days on the Rondout waterfront or out by the Ashokan Reservoir for wide-open views and quiet miles on the trail. From a renovated cape just minutes to Kingston with a hot tub to modern, design-forward retreats near the reservoir, these homes make it simple to plan a weekend that feels elevated, unhurried, and worth repeating.
What Our Guests Are Saying About Their Kingston Stay
“This is a beautiful and thoughtfully designed house โ full of character, natural light, and cozy corners. Every spot is photogenic; the kind of place where youโll end up taking photos for Insta, and everyone will ask you for the link!
โSuch a wonderful spot, when can we come back? The cottage is the perfect getaway. Has everything you need for a cozy, restful trip to the mountains. This authentic log cabin has all the amenities of a luxury hotel, plus a wood stove, a stone fireplace, and a well-stocked kitchen. The Red Cottage hosts were exceptionally responsive, and the location is pretty terrific, with views of the Catskills and a creek running through the property. Itโs an easy drive into Stone Ridge for restaurants and a good launch point for visiting other charming towns in the area.โ
โMy fiancรฉ and I, along with our goldendoodle, had a lovely stay at Red Cottage. The house was in a perfect location for us as it was central to several towns and had breathtaking fall foliage surrounding it. We were very cozy and felt right at home. Red Cottage responded very promptly and was so helpful.โ
โGorgeous house and serenity abound. Meticulous attention to detail. We found it to have the best cookware selection of any Airbnb Iโve ever stayed in (which was perfect for a Thanksgiving stay). One of the few spaces Iโd truly like to return to!โ
โThis was such a lovely and cozy getaway! The space is charming, the kitchen is well stocked, the beds are extremely comfortable, and the hot tub is fantastic! My friends and I had a beautiful time taking in the scenery and cooking meals together.ย โ
โWhat a beautiful home! Gorgeous, comfortable furnishings. Chefโs dream kitchen. Amazing river views. Peaceful setting. Perfect for our family gathering.โ
Explore Kingston
For the simplest โresetโ with a big payoff, head to the Ashokan Reservoir for wide-open water views and mountain silhouettes. Pair it with a walk or bike ride on the Ashokan Rail Trail, then come back to your Red Cottage home for a slow late lunch and an early evening.
Uptown Kingston, especially the Stockade District, is made for wandering: galleries, bookstores, and beautiful old buildings that make even a casual stroll feel like an outing. When you want a change of scene, the Rondout waterfront adds boats, river air, and a slightly dressier dinner rhythm.
Do Kingston in two parts. Start Uptown for shopping and coffee, then head to the Rondout for waterfront browsing and a golden-hour walk. If you are staying closer to the reservoir, add a quiet stop like West Shokan or Olivebridge for a slower, more local feel.
For nearby views and a quick nature break, go to Shaupeneak Ridge. For a more dramatic scramble and cliffy scenery, pick Bonticou Crag. For an all-day park experience with lakes, waterfalls, carriage roads, and big ridge views, spend the day at Minnewaska State Park Preserve. If you are staying near the Ashokan corridor, add Vernooy Kill Falls for a rewarding, close-to-home outing.
Keep it winery-forward and easy. For a vineyard afternoon, drive to Robibero Family Vineyards, Whitecliff Vineyard & Winery, or Benmarl Winery for Hudson Valley views and tastings. If you want to stay close to Kingston afterward, add a local spirits stop at Wiltwyck Spirits Company for cocktails and a bottle to take back to your Red Cottage stay.
Book one standout meal and build the rest around it. For a polished dinner, Restaurant Kinsley is a strong choice when you want a night that feels special. For daytime, Rough Draft is a favorite for coffee and pastries with a bookstore atmosphere that encourages lingering.
Kingston Through The Seasons
Kingston feels different every time of year. Summer is for walks by the water and long dinners outside. Fall brings scenic drives, cool-weather hikes, and cozy nights at local restaurants. Winter is made for ski days and warm fires at home. In spring, the trails are quiet, afternoons by the reservoir feel fresh again, and patios around town start to come back to life.
| Month | Typical Weather | Avg Temp (ยฐF) | Crowd Level | Nightly Rates | Best For… |
|---|---|---|---|---|---|
| January | โ๏ธ Cold and snowy, cozy indoors | 20โ34 | Low | $ | ๐ฅ Fireside weekends, bookstore and gallery days |
| February | โ๏ธ Coldest stretch, crisp and quiet | 21-37 | Low | $ | ๐ฅพ Low key resets, winter walks, great dining without waits |
| March | ๐จ๏ธ Late winter, early thaw | 29-47 | Low – Medium | $$ | ๐๏ธ Shoulder season hikes, uncrowded town weekends |
| April | ๐จ๏ธ Cool spring, brighter days | 40โ60 | Low | $ | ๐ Waterfalls, scenic drives, patio season starting |
| May | ๐ Mild and green | 50-71 | Medium | $$ | ๐ฅพ Ashokan Reservoir walks, trail days, long lunches |
| June | ๐ค๏ธ Warm, early summer | 58โ79 | High | $$$ | ๐๏ธ Best all around weather, hiking plus waterfront evenings |
| July | โ๏ธ Hot, peak summer | 63โ83 | Very High | $$$$ | ๐ฅพ Long weekends, outdoor dining, day trips and late sunsets |
| August | โ๏ธ Warm and humid, peak summer | 62โ81 | Very High | $$$$ | ๐ก Lazy mornings, reservoir sunsets, relaxed town time |
| September | ๐จ๏ธ Pleasant, cooler nightsย | 54โ73 | High | $$$ | ๐๏ธ Perfect hiking temps, wineries, best balance of energy and ease |
| October | ๐ Crisp and peak foliage | 43-62 | Very High | $$$$ | ๐ Fall color drives, Minnewaska days, cozy dinners |
| November | ๐จ๏ธ Cool, quiet off-season | 34-50 | Low | $ | ๐ Slow weekends, best availability, calm trails |
| December | โ๏ธ Cold, early snow feel | 25-39 | Medium | $$ | ๐ Holiday escapes, fireside stays and winter walks |
Frequently Asked Questions
Most guests drive, and it is an easy weekend trip at about 2 hours in normal conditions, often around 1 hour 50 minutes to 2 hours 10 minutes depending on traffic and whether your stay is closer to Kingston or farther out toward the Ashokan Reservoir.
Yes, and we highly recommend it. Uptown and the Rondout are fun to explore on foot once youโre there, but having a car makes it easy to reach the best hikes, the Ashokan Reservoir, and nearby small towns whenever you feel like it.
Yes. Some Kingston-area Red Cottage homes include a hot tub, which is especially perfect after a day at the Ashokan Reservoir or a hike in the Catskills. Check each listing for the exact amenity details and any seasonal notes so you can plan for hot tub nights as part of the stay.
Choose Kingston if you want the easiest access to restaurants, shops, and the Uptown and Rondout neighborhoods. Choose the Ashokan Reservoir corridor if you want a quieter setting and a more nature-forward trip, with quick access to reservoir walks and trailheads.
Peak color typically hits in October, with crisp days that are ideal for scenic drives, reservoir views, and hikes at places like Minnewaska. Book early if you want prime weekends.