Holiday rentals in Simsbury

Hidden Cozy Waterfront Eco Cabin Nature Sanctuary

Welcome to Otter Falls Inn! Nestled in the trees directly above the brook and hidden off the main road sits our cozy, vintage eco cottage. Just 8 minutes from all major conveniences, our property is a hidden oasis- an urban nature sanctuary where we are restoring native habitat and the waterway. We lovingly restored and updated the cottage to offer a unique, relaxing, romantic getaway where guests can slow down and enjoy connecting to each other and nature in this stylish, eco conscious home.

Easy Living Modern Ranch-Garage & Central Air

This one floor easy living, peaceful, ranch home has an updated kitchen with an induction cooktop, new appliances +(all cookware etc.). The freshly remodeled modern master bathroom has a curb-less shower & overhead heat (to keep you warm) pristine hardwood floors are throughout the entire space, and the use of a 2 car garage for your safety and convenience. The home has new Central Air Conditioning. The The shops at Farmington Valley, The Fresh Market and Whole Foods are around the corner.

Newly Renovated Apartment

Welcome to Center Street Stay, your charming retreat in Simsbury, CT. This fully renovated, first-floor one-bedroom apartment blends modern comfort with convenience. The kitchen is equipped with modern appliances, perfect for culinary endeavors. Relax in the cozy living area with a smart TV or get some rest on the memory foam queen mattress. The renovated bathroom offers sleek fixtures and a rejuvenating shower. Enjoy amenities like in-unit washer/dryer, high-speed Wi-Fi, and free parking.

The Carriage House Wine Vineyards nearby

Newly built contemporary light filled spacious 700 ft carriage house/Loft. It is walking distance to the Farmington river and downtown historic Collinsville. Just off the cycling "rails to trails" river trail, you'll find places to also kayak, SUP, fish and swim. CT Wine Trail and Brignole Vineyards nearby where you'll find food trucks and live music along with award winning wine! Skiing nearby. Conveniently close to Farmington, Avon, Simsbury, West Hartford and 84 highway.

Linny's - Lakefront Retreat Private Dock & Firepit

🌲🌳 What Guests Love -> -Private waterfront dock -Swimming and lake access -Firepit with serene views -Peaceful morning coffee spot -Family-friendly setup -Fast WiFi for remote work or streaming -Bright open living space -Comfortable bedrooms -Fully equipped kitchen -Great lake views -Smart TV and high-speed internet -Clean, modern bathroom Spend your days on the water and your evenings grilling, relaxing on the dock, or enjoying wine at sunset while the kids play lakeside.

Farm Stay with Horses & Pool | Mountaintop Views

Come sleep above the horses at Bloombury Hill Farm. With stunning mountaintop views, this immaculate 2 BR apartment is spacious and boasts over 2000 square feet. Bask in the sunshine at the pool (open Memorial Day through Labor Day from 11a-5pm.) Close to thriving West Hartford Center with loads of restaurants and shopping. Hiking trails, local breweries and wineries, and farm stands are all located close by. All the ingredients for a magical weekend getaway.

Best River View, on Rail Trail in Collinsville!

This quaint and spotless home is perched on a knoll across the road from the Farmington River & Rails to Trails you can walk to restaurants, gift shops & antique shops; Canoe/Kayak/Paddleboard; go fishing; enjoy the Farmington River Rail Trail; hiking trails, and Ski Sundown close by; or just relax & enjoy the view! Enjoy the best view in Collinsville - one of "America's 10 Coolest Small Towns" by Arthur Frommer's Budget Travel Magazine. Beautiful year round!

Modern Farmhouse

This is a quaint, sun-filled farmhouse in the Farmington valley of Connecticut. Convenient to great antique shopping, Ski Sundown, farm stands, Farmington river inner-tubing and biking trails, kayak and canoe rentals, the sweet towns of Collinsville and New Hartford, and a 30 minute straight shot to Hartford itself. The house is also convenient to Torrington, Simsbury, Avon, Winsted, and a beautiful drive to Hartford-Bradley International Airport.

2 Bedroom Private Suite in West Hartford, CT

Private 2 BR Queen Suite Apartment with large LR, 1.5 baths and separate entrance. Newly renovated private kitchen. Ideal for families or two couples traveling together. Off street parking for 2 cars. Quiet residential area close to WH Center and Elizabeth Park. Quick drive to Univ. of Hartford, Trinity College, UConn Law, UConn Medical, St. Francis and Hartford Hospitals. Two blocks to pizza, bakery, market & liquor store.

Collinsville Overlook at LaSalle

Stay in the heart of Collinsville, above the historic Lasalle Market. Just steps to the Farmington River, Rails to Trails, restaurants, shopping, antiquing, concerts, walking, biking, fishing, canoeing and kayaking. Sleeping for 4 (including a queen bedroom and a queen air mattress). Enjoy breakfast in your private nook overlooking the village. Voted one of America's 10 Coolest Small Towns by Frommer's Budget Travel Magazine!

Windy Top Cottage ~ A Romantic "European" Getaway

The Windy Top Cottage is an old stone building constructed in 1932 by H. L. Bitter, a wealthy Hartford businessman. This area of Granby was a favorite of the Hartford elite for a place to 'summer' in the early part of the 20th Century. The cottage was the quarters for the domestic staff while the family was in North Granby. With an elevation of 970, we offer clean, fresh country air!

The Little Red Schoolhouse ~ Circa 1877

This wonderful old building is listed on the National Register of Historic Places and operated as the District 9 schoolhouse until 1948. Now, this beautiful piece of history is available for you to enjoy! Located in the picturesque West Granby, Connecticut, this little schoolhouse directly abuts hundreds of acres of open space, Granby Land Trust property, and several organic farms.