Connecticut Vacation & Cabin Rentals
Trade the pace of the city for the quiet elegance of Connecticut. Red Cottageโs 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 youโre planning a group getaway, a family trip, or a quiet reset for two, youโll find a comfortable home base with Red Cottage, and the kind of calm youโll want to return to.
What Our Guests Are Saying About Their Stay in Connecticut
โBeautiful home with plenty of space to spread out. My whole family stayed here for just under a week, and we had a wonderful experience. The property is peaceful and filled with natural light. We also loved the wood stove.
โYes, this place looks exactly like the pictures, and it truly is that stunning Connecticut getaway with a picture-perfect lawn view and a sleek, modern pool. What the photos donโt show you is how it feels: like youโre staying at your impossibly chic friendโs house while theyโre away traveling (probably in Paris for Fashion Week and staying at Costes).โ
โWe spent Thanksgiving weekend at this Cornwall home and absolutely loved it. The kitchen was equipped beyond our expectations, and there were plenty of extra linens and pillows in the closets. The whole place was so cozy, we felt right at home all weekend. Highly recommend! We would love to be back.โ
โGorgeous property. Wonderful peaceful location with plenty of hiking and natural beauty. I would love to go back.โ
โAn absolutely wonderful stay. The house was beautiful, well equipped and very conveniently located close to Mohawk Mountain! We would love to return again soon!โ
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, itโs easy to build a weekend that matches your pace. Whether you want to stay active or take it slow, youโll find plenty of ways to make the trip feel easy.
For a quick escape in the Litchfield Hills, start at Lake Wononscopomuc, stop by Kent Falls for an easy waterfall visit, and add a golden hour loop around Lake Waramaug if you have time.
For a simple culture day, choose one: The Aldrich Contemporary Art Museum in Ridgefield for modern exhibits, Yale University Art Gallery in New Haven for a top museum stop, or the Florence Griswold Museum in Old Lyme for art history in a scenic setting.
Keep it light and wander. Lakeville and Salisbury are great for antiques and small town charm, Kent is perfect for a walkable Main Street, and Redding or Ridgefield make an easy Fairfield County day for browsing and lunch.
For flexible trails with river views, go to Steep Rock Preserve in Washington. For the quickest big scenery, choose Kent Falls. In Fairfield County, Collis P. Huntington State Park is a calm option for wooded trails.
Pick one or two stops and keep it relaxed: Hopkins Vineyard on Lake Waramaug for wine with a view, Sunset Meadow Vineyards in Goshen for a polished afternoon, Kent Falls Brewing Company for a casual beer stop, or Litchfield Distillery for a local tasting.
For skiing and riding, base your day at Mohawk Mountain, then keep the rest simple with a coffee stop, a scenic drive, and an early cozy night back at a beautiful Red Cottage home.
For a truly special night out, book Arethusa al tavolo in Bantam for an elevated experience that feels celebration-worthy. In Kent, The Fife โn Drum is an enduring icon when you want a lively, traditional evening. For a polished dinner in the Litchfield Hills, try West Street Grill. And for a more relaxed but still destination worthy meal, add Kingsley Tavern in Kent.
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 | 14โ30 | Medium – High | $$ | ๐ Skiing, snow tubing, and relaxing evenings by the fire |
| February | โ๏ธ Cold, peak winter | 16-33 | Medium – High | $$ | ๐ Ski days and fireside nights |
| March | ๐จ๏ธ Chilly, late winter | 23-42 | Medium | $$ | ๐ Less crowded ski runs, morning hikes |
| April | ๐จ๏ธ Cool, bright spring | 34โ56 | Low | $ | ๐ง Waterfall hikes, museum stops, and better value travel weeks |
| May | ๐ธ Mild, green and fresh | 45-67 | Medium | $$ | โฐ๏ธ Hiking adventures, biking days, and small town strolling |
| June | ๐ค๏ธ Warm, early summer | 53โ75 | High | $$$ | ๐ถ Relaxed lake days, easy hikes, and a farm to table meal |
| July | โ๏ธ Hot, peak summer | 58โ80 | Very High | $$$$ | ๐ฃ Lake and pool season, Tanglewood concerts, and easy family escapes |
| August | โ๏ธ Warm, peak summerย | 57โ78 | Very High | $$$$ | ๐๏ธ Long weekends, outdoor dinners |
| September | ๐จ๏ธ Pleasant, cooler nightsย | 50โ71 | Medium High | $$$ | ๐ต๐ป Great temps, fewer people, and hiking plus museum days |
| October | ๐ Crisp, fall color | 39-58 | High | $$$ | ๐ Colorful fall views, scenic routes, and harvest season stops |
| November | ๐จ๏ธ Cool, quiet off-season | 30-47 | Low | $ | ๐ Peaceful weekends, museum days, and warm, cozy meals |
| December | โ๏ธ Cold, early snow, cozy | 21-36 | Medium | $$ | ๐ Festive escapes, early season skiing, and a fresh reset |
Frequently Asked Questions
If skiing is part of your plan, youโll 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.
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.
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.
Driving is usually the easiest way to get from NYC to Connecticut. Depending on where youโre headed in the state, the trip is commonly about 1.5 to 3 hours, and traffic can make a big difference, especially on weekends.
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.