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Connecticut Vacation & Cabin Rentals

Trade the pace of the city for the quiet elegance of Connecticut. Red Cottageโ€™s collection of vacation homes set in Connecticut, where lake days, wooded trails, and classic New England towns make it easy to slow down and settle in. From refined country homes to warm, design-forward retreats, each stay is curated for weekends away that feel effortless and elevated.

Connecticut is a year-round escape with a little something in every season. Plan summer around lakes and long evenings outside, fall for crisp drives and foliage, winter for ski days at Mohawk Mountain and cozy nights in, and spring for hiking, farm stands, and small-town afternoons. Whether youโ€™re planning a group getaway, a family trip, or a quiet reset for two, youโ€™ll find a comfortable home base with Red Cottage, and the kind of calm youโ€™ll want to return to.

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What Our Guests Are Saying About Their Stay in Connecticut

    Explore Connecticut

    Connecticut is perfect for a quick escape that feels like a real reset. From small towns and scenic drives to hiking, museums, and cozy spots to eat and drink, itโ€™s easy to build a weekend that matches your pace. Whether you want to stay active or take it slow, youโ€™ll find plenty of ways to make the trip feel easy.

      Connecticut Through The Seasons

      The best time to visit depends on your plans. Use the guide below to compare typical weather, crowd levels, and nightly rates by month so you can choose the ideal time for lake days, foliage drives, cozy small-town weekends, farm-to-table dining, cultural stops, and ski season escapes.

      Month Typical Weather Avg Temp (ยฐF) Crowd Level Nightly Rates Best For…
      January โ„๏ธ Cold, snowy, classic winter 14โ€“30 Medium – High $$ ๐Ÿ‚ Skiing, snow tubing, and relaxing evenings by the fire
      February โ„๏ธ Cold, peak winter 16-33 Medium – High $$ ๐Ÿ‚ Ski days and fireside nights
      March ๐ŸŒจ๏ธ Chilly, late winter 23-42 Medium $$ ๐Ÿ‚ Less crowded ski runs, morning hikes
      April ๐ŸŒจ๏ธ Cool, bright spring 34โ€“56 Low $ ๐Ÿ’ง Waterfall hikes, museum stops, and better value travel weeks
      May ๐ŸŒธ Mild, green and fresh 45-67 Medium $$ โ›ฐ๏ธ Hiking adventures, biking days, and small town strolling
      June ๐ŸŒค๏ธ Warm, early summer 53โ€“75 High $$$ ๐Ÿ›ถ Relaxed lake days, easy hikes, and a farm to table meal
      July โ˜€๏ธ Hot, peak summer 58โ€“80 Very High $$$$ ๐ŸŽฃ Lake and pool season, Tanglewood concerts, and easy family escapes
      August โ˜€๏ธ Warm, peak summerย  57โ€“78 Very High $$$$ ๐Ÿ”๏ธ Long weekends, outdoor dinners
      September ๐ŸŒจ๏ธ Pleasant, cooler nightsย  50โ€“71 Medium High $$$ ๐Ÿšต๐Ÿป Great temps, fewer people, and hiking plus museum days
      October ๐Ÿ Crisp, fall color 39-58 High $$$ ๐ŸŽƒ Colorful fall views, scenic routes, and harvest season stops
      November ๐ŸŒจ๏ธ Cool, quiet off-season 30-47 Low $ ๐Ÿ  Peaceful weekends, museum days, and warm, cozy meals
      December โ„๏ธ Cold, early snow, cozy 21-36 Medium $$ ๐ŸŽ„ Festive escapes, early season skiing, and a fresh reset

      Frequently Asked Questions

      How close are Red Cottageโ€™s Connecticut homes to skiing?

      If skiing is part of your plan, youโ€™ll want to stay near Cornwall. Mohawk Mountain Retreat is just 5 minutes from Mohawk Mountain, making it easy to fit in full ski days while keeping the rest of the weekend relaxed and cozy.

      Does Red Cottage offer vacation rentals in Connecticut with private pools?

      Yes. Select homes offer pool time as part of the experience, including Meeker Hill House and Lakeville Lodge. Check each listing for seasonal availability and pool details so you can plan the perfect summer stay.

      How do I pick the best Connecticut area for my trip?

      Pick the location that matches your weekend style. Choose Salisbury and Lakeville for lake days, antiques, and a classic small-town rhythm, Cornwall for Mohawk Mountain ski weekends and hiking, and Redding for a polished Fairfield County escape with the easiest access from NYC.

      How far is Connecticut from NYC, and whatโ€™s the easiest way to get there?

      Driving is usually the easiest way to get from NYC to Connecticut. Depending on where youโ€™re headed in the state, the trip is commonly about 1.5 to 3 hours, and traffic can make a big difference, especially on weekends.

      What should I pack for a Connecticut vacation?

      Pack for comfort and the outdoors. Bring layers, proper footwear, and a weatherproof jacket, plus slippers or cozy socks for the house. In summer, add a swimsuit for pool days and a light layer for cooler nights. In fall and winter, pack warm boots, gloves, and a hat. If you plan to hike, bring trail shoes and consider tick repellent for warmer months.