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Vacation Rentals in Kingston, NY

Explore Red Cottageโ€™s 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 regionโ€™s best dining, arts, hiking, and four-season outdoor experiences.

Stay close to Uptownโ€™s 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.

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Features & Amenities

What Our Guests Are Saying About Their Kingston Stay

    Explore Kingston

      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 20โ€“34 Low $ ๐Ÿ”ฅ Fireside weekends, bookstore and gallery days
      February โ„๏ธ Coldest stretch, crisp and quiet 21-37 Low $ ๐Ÿฅพ Low key resets, winter walks, great dining without waits
      March ๐ŸŒจ๏ธ Late winter, early thaw 29-47 Low – Medium $$ ๐Ÿ”๏ธ Shoulder season hikes, uncrowded town weekends
      April ๐ŸŒจ๏ธ Cool spring, brighter days 40โ€“60 Low $ ๐Ÿš— Waterfalls, scenic drives, patio season starting
      May ๐Ÿƒ Mild and green 50-71 Medium $$ ๐Ÿฅพ Ashokan Reservoir walks, trail days, long lunches
      June ๐ŸŒค๏ธ Warm, early summer 58โ€“79 High $$$ ๐Ÿ”๏ธ Best all around weather, hiking plus waterfront evenings
      July โ˜€๏ธ Hot, peak summer 63โ€“83 Very High $$$$ ๐Ÿฅพ Long weekends, outdoor dining, day trips and late sunsets
      August โ˜€๏ธ Warm and humid, peak summer 62โ€“81 Very High $$$$ ๐Ÿก Lazy mornings, reservoir sunsets, relaxed town time
      September ๐ŸŒจ๏ธ Pleasant, cooler nightsย  54โ€“73 High $$$ ๐Ÿ”๏ธ Perfect hiking temps, wineries, best balance of energy and ease
      October ๐Ÿ Crisp and peak foliage 43-62 Very High $$$$ ๐ŸŽƒ Fall color drives, Minnewaska days, cozy dinners
      November ๐ŸŒจ๏ธ Cool, quiet off-season 34-50 Low $ ๐Ÿ  Slow weekends, best availability, calm trails
      December โ„๏ธ Cold, early snow feel 25-39 Medium $$ ๐ŸŽ„ Holiday escapes, fireside stays and winter walks

      Frequently Asked Questions

      How far is Kingston, NY, from NYC?

      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.

      Do I need a car in Kingston?

      Yes, and we highly recommend it. Uptown and the Rondout are fun to explore on foot once youโ€™re 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.

      Are there any Red Cottage homes in Kingston with a hot tub?

      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.

      What is the best area to stay in, Kingston or near the Ashokan Reservoir?

      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.

      When is the best time to visit Kingston?

      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.