Escape to Connecticut: Discover Charming Vacation Rentals in Mystic, Kent, and Chester
Connecticut, a charming New England gem, offers a diverse range of vacation rentals that capture the essence of the region’s coastal beauty, rolling countryside, and historic small towns. Whether you’re seeking a cozy cottage by the sea in Mystic, a luxurious estate nestled in the Litchfield Hills near Kent, or a quaint farmhouse in the artistic enclave of Chester, Connecticut’s vacation rentals provide an inviting home base for exploring the state’s rich cultural heritage, scenic landscapes, and culinary delights. With options catering to serene getaways and adventurous escapes, Connecticut promises a relaxing and enriching vacation experience.
Explore Candlewood Lake
Candlewood Lake is the largest lake in the state and a beloved destination for both locals and visitors. Created in the 1920s by impounding the Rocky River, this freshwater reservoir spans over 8,500 acres and offers the ideal retreat for recreational activities. Boasting 85 miles of shoreline, Candlewood Lake is a haven for water enthusiasts, providing opportunities for boating, fishing, swimming, and water sports. The lake’s crystal-clear waters are stocked with various, making it a popular spot for anglers seeking bass, perch, and trout.
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Best time to visit
Best places to visit
Top Unique Facts About Connecticut
01
Yale University
Yale University was founded in 1707, making it the oldest and most prestigious university in Connecticut and the USA.
02
New Haven Pizza
Connecticut is renowned for its distinctive style of pizza, known as “New Haven-style pizza” or “apizza.” It often features a thin crust, a coal-fired oven, and a variety of creative toppings.
03
Connecticut River Shad
The annual migration of shad fish in the Connecticut River is a celebrated event. The fish return to the river each spring, drawing attention from locals and visitors alike.
Must See Attractions
Thimble Islands
Nature & Parks
Off the coast of Branford lies the Thimble Islands, an archipelago of small islands known for their scenic beauty and historic charm. These islands are accessible by boat, and tours offer a unique perspective on the area’s history and stunning landscapes.
The Mark Twain House & Museum
Speciality Museums
The Mark Twain House & Museum in Hartford, Connecticut, preserves the historic home where the iconic American author Samuel Clemens, known by his pen name Mark Twain, and offers visitors a glimpse into the life and creative inspiration of this literary giant.
Mystic Seaport Museum
Speciality Museums
This maritime museum and living history village provides a captivating journey into America’s maritime heritage, featuring historic vessels, interactive exhibits, and a recreated 19th-century coastal village.
Where to Sleep
Connecticut Lakes to Explore
2. Bantam Lake
37 Miles
Bantam Lake, with its peaceful atmosphere, is the largest natural lake in Connecticut and offers boating, fishing, and birdwatching opportunities.
3. Tyler Lake
38 Miles
Tyler Lake is a smaller, quieter lake known for its tranquil setting. It’s a great spot for kayaking, canoeing, and fishing, with limited motorboat activity.
4. Lake Quassapaug
38 Miles
Located in Middlebury, this lake is a popular recreational lake with a sandy beach and a range of water activities, including swimming, boating, and water skiing.
5. Lake Waramaug
45 Miles
Lake Waramaug is a scenic lake popular for boating, fishing, and camping; the state park along its shores provides many opportunities for outdoor recreation.
6. Mudge Pond
55 Miles
Mudge Pond is a peaceful lake surrounded by forests and hills and is an excellent location for fishing, paddling, or simply enjoying the natural beauty.
7. Squantz Pond
66 Miles
Squantz Pond, in the town of New Fairfield, is a beautiful lake known for its clear waters and sandy beach; it’s a favorite spot for swimming, fishing, and picnicking.
8. Candlewood Lake
67 Miles
Located in western Connecticut, this is the largest lake in the state and is a popular destination for boating, fishing, and water sports, surrounded by hills and forests.
Annual Events and Festivals
March 2025
Sugar Maple Festival
The Sugar Maple Festival in Hebron, Connecticut, is a vibrant showcase of New England’s maple syrup tradition, featuring a variety of activities that highlight the syrup-making process. Visitors can explore sugarhouses to witness the intricate methods involved in tapping maple trees and transforming the sap into the sweet golden syrup that is synonymous with the season. The festival also offers an array of maple-infused treats, from maple candies to hot pancakes drizzled with freshly harvested syrup. In addition to the culinary delights, attendees can enjoy live music, arts and crafts vendors, and educational demonstrations about the cultural and historical significance of maple sugaring.
July 2025
Sailfest
Sailfest is a vibrant annual celebration that transforms the historic waterfront of New London into a bustling hub of maritime festivities. This multi-day event typically occurs in July and draws thousands from across the state. At the heart of Sailfest is a spectacular display of tall ships, sleek yachts, and various other nautical vessels that grace the shores of the Thames River. The festival embraces the spirit of New England’s maritime heritage, offering a diverse range of activities for all ages. Attendees can explore maritime exhibits, indulge in delectable seafood from local vendors, and enjoy live music performances that echo over the waterfront. The event culminates in a dazzling fireworks display that illuminates the night sky, reflecting on the rippling river below.
October 2024
The Apple Festival
Held in the charming town of Salem, this community gathering is a true ode to the apple, featuring various activities and attractions for all ages. Visitors can indulge in various apple-themed treats, from classic apple pies and cider donuts to innovative apple-infused dishes. The festival also boasts live music, craft vendors showcasing handmade goods, and a farmers’ market offering an assortment of fresh, locally-grown produce. Families often partake in traditional activities such as apple picking, hay rides, and face painting, creating a festive and wholesome atmosphere.
Top Hiking Trails
Ragged Mountain Blue and Red Blazed Loop
Ragged Mountain Trailhead, 437 West Ln, Berlin, Connecticut
This is a picturesque hiking trail that takes you through the scenic expanse of Ragged Mountain Memorial Preserve. This loop encompasses approximately 6.2 miles of well-maintained trails, offering outdoor enthusiasts a diverse and rewarding trek through woodlands, rocky ridges, and tranquil meadows over the three hours it takes to complete. As adventurers hike the loop, they encounter an array of native flora and fauna, including the occasional glimpse of the region’s wildlife. The summit of Ragged Mountain grants hikers breathtaking vistas, making it a popular spot to pause and appreciate the natural beauty of central Connecticut.
Bear Mountain Trail
Undermountain Trailhead Parking Area, 395 Under Mountain Rd, Salisbury, Connecticut
Part of the Appalachian Trail, this hike provides an invigorating hiking experience through the heart of the state’s northwest corner. Ascending 500 meters, hikers climb up to Connecticut’s highest peak, and the trail leading to its summit is a popular choice for hikers seeking both a challenging ascent and breathtaking views. Spanning approximately 6.7 miles, the Bear Mountain Trail winds through lush forests, over rocky terrain, and past cascading waterfalls, providing a diverse and immersive journey for nature lovers. It takes approximately four hours to complete. Hikers are rewarded at the summit with panoramic vistas of the surrounding Berkshire Mountains and Taconic Range, making the trek well worth the effort.
Salmon River Trail Loop from Comstock Bridge
11 Bridge St, East Hampton, Connecticut
The Salmon River Trail Loop, originating from the historic Comstock Bridge, is a hiking experience that unfolds along the scenic banks of the Salmon River. Approximately six miles long, this trail loop takes hikers through meadows, dense woodlands, and along the rushing waters of the Salmon River. The trail’s highlight is the scenic overlook at Day Pond State Park. The trail takes approximately three hours to complete.
Best Golf Courses
Alling Memorial Golf Course
35 Eastern St, New Haven, Connecticut
This course is a hidden gem for golf enthusiasts seeking a classic and challenging round of golf. Established in 1930, this course has stood the test of time, providing golfers with a traditional layout and a rich history. Designed by Geoffrey Cornish, the course offers a par-70 experience with tree-lined fairways, deliberately placed bunkers, and small, well-manicured greens. The layout is both forgiving for beginners and demanding for more seasoned players, making it the perfect destination for golfers of all skill levels. The course’s scenic beauty, with mature trees and gentle rolling hills, adds to the overall charm of the experience.
Wintonbury Hills Golf Course
206 Terry Plains Road, Bloomfield, Connecticut
Wintonbury Hills Golf Course is a championship-level golf facility that blends the natural beauty of Connecticut and the challenging play of a course by renowned golf architect Pte Dye. This 6,711-yard, par-70 course opened in 2003 and has since become a celebrated destination for golf enthusiasts. The course features rolling fairways, strategically placed bunkers, and greens that provide a fair yet demanding game for players of all levels. The course’s layout seamlessly integrates with the surrounding woodlands, offering stunning views of the Farmington Valley throughout the round. The clubhouse, with its modern amenities and panoramic vistas, complements the golfing experience.
Keney Park Golf Club
171 Windsor Ave, Windsor, Connecticut
This course is a historic and revitalized golf course that stands as a testament to the local’s commitment to providing accessible and enjoyable golfing opportunities. Established in 1927, the course underwent a comprehensive restoration in 2016, led by renowned golf architect Matthew Dusenberry. The result is a par-71, 18-hole layout that seamlessly blends classic design elements with modern amenities. The course features tree-lined fairways, advantageously placed bunkers, and challenging greens that offer both novices and seasoned golfers an engaging and rewarding golfing game. The Keney Park Golf Club holds historical significance, as it was one of the first golf courses in the United States to welcome players of all races.
Water Sports
Lakeside Watersports
Boating and Water Sports
Whether you are new to water sports or have a lifetime of experience under your belt, enjoying a day at Candlewood Lake with the help of Lakeside Watersports is the way to go. Learn how to wake board, tube, water ski, or wake surf, or take a boat out on the lake with friends and family. You can also try more unique water sports, such as knee boarding, wakeboarding, and water skiing.
Thimble Island Cruises
Boat tours
Thimble Island Cruises offers a maritime experience along the picturesque Connecticut shoreline, exploring the archipelago of the Thimble Islands. The islands, numbering over 100, boast rich histories, ranging from pirate legends to grand summer estates. The cruise provides a front-row seat to this living history, with knowledgeable guides narrating tales of the islands’ past, wildlife, and the vibrant coastal ecosystem. Visitors can also opt for private charters, making it an ideal choice for special events or gatherings.
West Hill Pond Fishing
Fishing
Fishing at West Hill Pond in Connecticut is an experience for anglers of all levels. West Hill Pond offers a picturesque setting where you can fish in the summer or ice fish in the winter. This popular fishing destination is known for its diverse aquatic life, including largemouth bass, smallmouth bass, trout, and panfish. Anglers can cast their lines from the shore or venture out onto the water in boats, enjoying the peaceful atmosphere while trying to catch various fish species.
Resorts to Explore in Connecticut
Water’s Edge Resort & Spa
Luxury
1525 Boston Post Rd, Westbrook, Connecticut 06498
Saybrook Point Resort & Marina
Luxury, Recreational
Two Bridge Street, Old Saybrook, Connecticut, 06475
Winvian Farm
Couples, Retreats
155 Alain White Rd, Morris, Connecticut 06763
Tips on Vacationing in Connecticut
Plan Ahead
To make the most of your trip, research seasonal attractions and events in advance. For instance, autumn is perfect for visiting the state’s picturesque small towns and enjoying scenic drives through its vibrant foliage. Summer is ideal for exploring the coastline and enjoying water activities.
Explore Coastal Towns
Connecticut’s coastline is dotted with charming towns like Mystic, Old Saybrook, and Stonington. These towns offer a mix of maritime history, quaint shops, and delicious seafood. Don’t miss Mystic Seaport Museum and Mystic Aquarium for family-friendly attractions. Take the time to stroll through these towns, visit local boutiques, and dine at waterfront restaurants to fully experience coastal living.
Stay in Unique Accommodations
Connecticut offers a range of unique lodging options, from historic inns and bed-and-breakfasts to modern boutique hotels. Staying in a charming inn or a coastal B&B can add a special touch to your vacation experience. For a more rustic adventure, consider camping in one of the state’s beautiful state parks.
Frequently Asked Questions about Connecticut
When looking for vacation rentals in Connecticut, you have various options. Some popular websites include Lake, Rent By Owner™, Visit CT, Tripping.com, and Likibu. These sites provide many rental options, from beach houses to country cabins, ensuring you find the perfect place to stay.
The best time to visit Connecticut is May to October. During these months, the weather is plesant, and many activities and events are held.
To choose the perfect Connecticut rental for your stay, consider your budget, travel party size, desired amenities, and location preferences. Use filters on rental websites to narrow down the options and read reviews from previous guests to ensure a great experience. Don’t hesitate to contact the property owner for any questions or concerns about the rental before booking, as this can help you make a better-informed decision.
Finding an affordable beach or lake house in Connecticut may require some searching, as prices fluctuate based on the season and location. Be sure to compare websites like Lake. Additionally, consider choosing a rental away from popular tourist destinations or book your stay during the off-season.
To find luxury vacation rentals in Connecticut, search on websites like Lake and filter based on star ratings or customer reviews. Additionally, you can look for luxury properties labeled as “Grand Luxe” or featuring amenities such as heated private pools, golf carts, and upscale furnishings.
Yes, there are unique cabins available for rent in Connecticut. Use platforms like Lake to find one-of-a-kind cabins and country retreats that suit your tastes. Make sure to read reviews and pay attention to the details in each listing, as this will help you identify truly unique rental options.
Connecticut has a variety of lakes, trails, and outdoor activities for the whole family to enjoy. Waterparks, museums, and events are organized family activities when the family is not exploring one of Connecticut’s many parks.
Vacation Destinations Nearby
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