TOP 30 Cottage with historical charm in Connecticut

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Southbury Historic Homes Rentals is a prestigious real estate and travel agency located at 712 South Britain Road in the charming town of Southbury, Connecticut. Our agency specializes in renting out beautifully preserved historic homes that offer a unique and authentic experience for travelers looking to immerse themselves in the rich history of the area. Whether you are looking for a weekend getaway or a long-term rental, our dedicated team is here to help you find the perfect historic home for your stay. Experience the beauty and charm of Southbury with Southbury Historic Homes Rentals.

Windy Top Cottage is a charming lodging located at 80 Silkey Road in Granby, Connecticut. Nestled in the peaceful countryside, this cozy cottage offers a serene retreat for guests looking to escape the hustle and bustle of city life. With its picturesque surroundings and comfortable accommodations, Windy Top Cottage is the perfect destination for a relaxing getaway. Whether you're looking to explore the nearby attractions or simply unwind in nature, this quaint retreat is sure to provide a memorable experience for all who visit.

The Blackberry River Inn is a charming lodging establishment located at 538 Greenwoods Road West in Connecticut, United States. Nestled in the picturesque countryside, this inn offers a peaceful retreat for guests looking to escape the hustle and bustle of city life. The cozy rooms are tastefully decorated and provide all the comforts of home. Guests can enjoy a delicious breakfast in the morning and relax in the beautiful gardens or by the river. With its tranquil setting and warm hospitality, the Blackberry River Inn is the perfect destination for a relaxing getaway.

Located at 69 Maple Avenue in Connecticut, the Manor House Inn is a charming lodging institution that offers a perfect blend of relaxation and adventure. Situated on five acres in the beautiful Litchfield Hills, this historic property provides a tranquil retreat from the hustle and bustle of everyday life. Whether you are looking for a romantic getaway or a fun-filled excursion, the Manor House Inn is the ideal destination. As one of the few Green Hotels in Connecticut, the Manor House Inn prides itself on its commitment to sustainability. The property is adult-oriented and nonsmoking, creating a peaceful and serene atmosphere for guests to enjoy. With a focus on digital detox, the inn encourages guests to unwind and connect with nature and each other.

Hotel Hi-Ho is a charming lodging institution located at 4180 Black Rock Turnpike in Fairfield, Connecticut. This cozy hotel offers a comfortable and inviting atmosphere for guests looking for a relaxing stay in the beautiful New England countryside. With its convenient location, guests can easily explore the nearby attractions such as beaches, parks, and historic sites. The hotel features well-appointed rooms, friendly staff, and excellent amenities to ensure a pleasant and memorable stay. Whether you are visiting for business or pleasure, Hotel Hi-Ho is the perfect choice for your accommodations in Fairfield.

The Study at Yale is a sophisticated and elegant lodging option located in the heart of New Haven, Connecticut. Situated at 1157 Chapel Street, this upscale institution offers luxurious accommodations for visitors looking to experience the charm and culture of Yale University and the surrounding area. With stylish rooms, modern amenities, and exceptional service, The Study at Yale provides a unique and comfortable stay for guests seeking a memorable experience in this historic city. Whether visiting for business or pleasure, this boutique hotel is the perfect choice for those looking for a refined and upscale lodging option in New Haven.

The Avon Old Farms Hotel is a charming lodging institution located at 279 Avon Mountain Road in Avon, Connecticut, United States. Set in a picturesque location, this hotel offers guests a unique and memorable stay with its historic charm and modern amenities. The hotel features comfortable rooms, a restaurant serving delicious cuisine, and a variety of amenities such as a fitness center and outdoor pool. Whether you are visiting for business or leisure, the Avon Old Farms Hotel provides a relaxing and welcoming atmosphere for all guests.

The Scranton Seahorse Inn is a charming lodging located at 818 Boston Post Road in the picturesque town of Madison, Connecticut. This cozy inn offers a peaceful and relaxing atmosphere for guests looking to escape the hustle and bustle of everyday life. The rooms are tastefully decorated and equipped with modern amenities to ensure a comfortable stay. Guests can enjoy a delicious breakfast in the morning and relax in the beautiful garden or cozy lounge area. The inn is conveniently located near the beach, shops, and restaurants, making it the perfect destination for a weekend getaway or a longer vacation. Experience the warmth and hospitality of the Scranton Seahorse Inn during your next visit to Connecticut.

Cave Hill Resort, located at 138 Leesville Road in East Haddam, Connecticut, is a charming lodging establishment that has been family-owned and operated since the 1920s. The resort prides itself on providing guests with a warm and welcoming atmosphere, combined with a touch of nostalgia and charm that sets it apart from other accommodations. Nestled high in the rolling hills of the Connecticut River Valley, Cave Hill Resort offers guests a peaceful and serene setting to relax and unwind. The resort's expansive grounds feature lush lawns, shady trees, and plenty of opportunities for outdoor activities. Guests can relax in hammocks, gather at picnic tables, or take a dip in the picturesque pool.

Getaway Machimoodus Cabins is a lodging institution located at 298 East Haddam Moodus Road in East Haddam, Connecticut, United States. Nestled in Moodus, CT, this Outpost features secluded cabins with lush forest views, a scenic 1-mile nature trail, and a dog park for your furry friends. Just 2 hours from Boston and 2.5 hours from NYC, it's the perfect escape from city life. Explore the historic Gillette Castle, hike Machimoodus State Park, or adventure around the waterfall at Devil's Hopyard State Park — all just minutes away from the Outpost. With a location just 34 minutes from Hartford, it's a convenient destination for a weekend getaway.

The Inn at Woodstock Hill is a charming bed and breakfast located in Woodstock, Connecticut. With 21 individually decorated guest rooms, each offering a variety of amenities such as private baths, televisions, telephones, radios, wireless internet access, and air conditioning, this inn provides a comfortable and relaxing stay for guests. Some rooms even feature four-poster beds and gas fireplaces for added luxury. Conveniently located near the town of Putnam and within easy reach of Hartford, Boston, and Providence, The Inn at Woodstock Hill is the perfect destination for a weekend getaway or special event. The inn boasts a fine dining kitchen and banquet space, making it an ideal location for wedding receptions and other gatherings.

Located at 3 Williams Avenue in Stonington, Connecticut, the Inn at Mystic offers a picturesque getaway overlooking the Mystic Harbor and Fishers Island Sound. With over 15 acres of beautiful outdoor space, guests can enjoy a variety of activities such as walking trails, kayaking, basketball, and private picnics. The newly renovated rooms feature upgraded amenities, fireplaces, and Jacuzzi tubs, ensuring a comfortable and relaxing stay. The historic property, once a private estate, now includes a hotel, restaurant, mansion, and banquet facilities. With colonial cottage-style guest rooms and stunning water views, the Inn at Mystic provides a charming and memorable experience. Named the most famous hotel in Connecticut, the resort offers three unique lodging options including the Main Building, East Wing, and Haley Mansion. The property has been a popular choice for weddings, with the elegant Haley Mansion providing a beautiful backdrop for ceremonies and receptions. Guests can also enjoy dining at Rocks 21 Restaurant & Bar, which serves fresh seasonal cuisine, wood-fired pizza, craft beers, cocktails, and more. Experience personalized service, top-tier accommodations, and unforgettable events at the Inn at Mystic. Make your reservation online today to discover the magic of this enchanting destination.

The Whaler's Inn is a charming lodging establishment located at 20 East Main Street in historic Stonington, Connecticut. Situated in a picturesque coastal town, this inn offers guests a cozy and comfortable retreat with a touch of nautical charm. The rooms are tastefully decorated and equipped with modern amenities, ensuring a relaxing stay for visitors. The Whaler's Inn is the perfect place to unwind after exploring the nearby attractions, such as the Mystic Seaport Museum and Stonington Vineyards. Whether you're looking for a romantic getaway or a peaceful escape by the sea, The Whaler's Inn is the ideal destination for your next vacation.

Banner Estates is a premier real estate agency located at 24 Augusta Circle in the picturesque town of East Haddam, Connecticut, United States. With a team of dedicated professionals, we specialize in helping clients buy, sell, and rent properties in the area. Whether you are looking for a charming historic home, a waterfront property, or a cozy cottage in the woods, our experienced agents are here to assist you every step of the way. Trust Banner Estates to help you find your dream home in beautiful East Haddam.

Shore & Country Real Estate is a premier real estate agency located at 249 Shore Road in Old Lyme, Connecticut. With a reputation for excellence and personalized service, our team of experienced agents is dedicated to helping clients buy, sell, and rent properties in the beautiful coastal town of Old Lyme and the surrounding areas. Whether you are looking for a charming beachfront cottage, a historic New England home, or a luxurious waterfront estate, Shore & Country Real Estate is here to assist you every step of the way. Contact us today to start your real estate journey!

Country Manor - Pomfret is a premier real estate agency located in the picturesque town of Pomfret, Connecticut. Situated at 120 Putnam Road, our team of experienced agents are dedicated to helping clients find their dream homes in this charming New England setting. Whether you are looking for a cozy cottage, a historic farmhouse, or a luxurious estate, Country Manor - Pomfret is here to assist you every step of the way. With a commitment to personalized service and a deep knowledge of the local market, we strive to make the home buying process as seamless and stress-free as possible. Contact us today to start your journey towards finding the perfect property in Pomfret.

Country Manor-Woodstock is a premier real estate agency located in the charming town of Woodstock, Connecticut. Situated at 150-154 Harrisville Road, our expert team of agents is dedicated to helping clients find their dream home in this picturesque New England town. Whether you are looking for a cozy cottage, a historic farmhouse, or a sprawling estate, Country Manor-Woodstock has a diverse portfolio of properties to suit every taste and budget. With a reputation for personalized service and attention to detail, we strive to make the home buying process as seamless and stress-free as possible. Contact us today to start your journey to finding the perfect property in Woodstock, Connecticut.

The Carriage House at 26 Pearl is a charming lodging establishment located in the historic town of Groton, Connecticut. Situated at 26 Pearl Street, this cozy inn offers guests a comfortable and inviting atmosphere with beautifully decorated rooms and modern amenities. Whether you are visiting for business or pleasure, the Carriage House provides a peaceful retreat in a convenient location. Experience the warmth and hospitality of this unique accommodation during your stay in Groton.

26 School House is a charming institution located at 26 School House Road in Stonington, Connecticut, United States. This historic house, built in 1946 by the owner's grandparents, has been lovingly renovated and decorated over the past decade to provide a comfortable and inviting space for guests. Dedicated to offering a great experience for all visitors, 26 School House prides itself on personal communication with guests and ensuring a memorable stay. With a focus on providing a secluded and peaceful waterfront setting surrounded by wetlands and wildlife, this institution is perfect for those seeking a tranquil retreat.

William Pitt Sotheby's International Realty - Stamford Brokerage is a prestigious real estate agency located at 3 Roxbury Road in Stamford, Connecticut, United States. Specializing in the North Stamford area, known for its blend of small-town charm and urban convenience, the agency offers a wide range of properties including grand mansions, luxury condominiums, historic homes, and new construction. Stamford itself is a vibrant city with a high quality of life, attracting celebrities, artists, and professionals alike. With its close proximity to New York City, residents benefit from easy access to world-class amenities such as dining, shopping, the arts, and beaches. The agency's experienced team of real estate professionals is dedicated to providing exceptional service to clients in Stamford and neighboring communities in Fairfield County. William Pitt Sotheby's International Realty is committed to upholding the Fair Housing Act and the Equal Opportunity Act, ensuring a fair and inclusive real estate experience for all.