Cottage vacation rentals in Tolland County

Waterfront Cottage in Thompson CT • Dogs Welcome

Escape to our beautifully renovated 1928 cottage on Quaddick Lake—your perfect retreat for relaxation and adventure. Just 60 minutes from Boston, Providence, and Hartford, this lakeside haven makes vacationing effortless. Start your day sipping coffee as the sunrise glows over the water and spend evenings by the crackling fire pit under the star filled sky. Whether paddling the lake or unwinding in cozy comfort, you'll feel miles away from the busy world, free to relax and make lasting memories.

Lakefront | Pvt Dock | Kayaks | Firepit | 1G | W/D

The Yellow • 1,750ft² (170m²), 2-level cottage • Open concept with 180° view from living room • 3 bedrooms (all queen size beds), 2 full baths • Fully equipped kitchen • Private dock & firepit • Canoe & 2 kayaks • 50" smart TV and 4 Google Smart Speakers • 1 Gigabit Wi-Fi 'gorgeous with amazing views' • Workspace with laptop stand upstairs • Additional full size bed upstairs • Additional queen size sofa bed downstairs • Additional twin trundle downstairs • Washer and dryer with laundry detergent

Vintage Bolton Lake

Experience the nostalgia of vintage lake charm and enjoy the calming lake waters! The Vintage is nestled on the shores of picturesque Middle Bolton Lake. Relax, unplug, and savor the good life of times past. The cottage has been tastefully updated and outfitted with period furnishings to allow for vacationing in comfort and style. As our guest, you will enjoy full use of the cottage, WiFi, property, propane grill, smokeless firepit, kayaks and much more. Come enjoy vintage lakefront lifestyle.

Welcome to The Holly at Amston Lake

Welcome to The Holly at Amston Lake! Great two-bedroom cottage situated in a peaceful lake community. Great place to enjoy time with family and friends. Take a stroll down to the main beach or enjoy the great views of the lake from the deck! Don't forget about the gas fire pit for those chilly evenings. We are located near numerous vineyards, a brewery, the Connecticut Airline Trail, and great local restaurants! Guests have access to the grill, fire pit, kayaks, and two main beaches.

Cozy Getaway | Pet Friendly | Litchfield Cty

Escape to the Cottage at the Grove - with a cozy wood burning fireplace and inviting sectional it is the perfect winter sanctuary. Well equipped with all the amenities; from a fully stocked kitchen to bath salts for the deep soaking tub. One bedroom w/ en-suite bath & pull-out full size sofa bed. Just 30 min to Mohawk or Southington Ski Mountains. Just 10 min to downtown Litchfield, close to local farms & vineyards. For security we have two exterior cameras facing the door & driveway.

Waterfront cottage overhanging the water!

Come relax at this cute and cozy cottage overhanging a large and beautiful lake! Whether it's a family trip, a couple's getaway, or a best friends reunion, this place has something for everyone. From relaxing on the deck with a beautiful view, to kayaking and canoeing, or swimming in the summer, there is much fun and peaceful relaxation to do at the cottage. Also, it's just a 10 minute drive to Mystic, wineries, orchards, the shoreline, restaurants, and 5 minutes to Foxwoods casino.

Clark Cottage in the historic village in Chaplin

Up to 14 day stays are OK. Cottage is empty several days between guests. Virus cleaning protocol in use. This little rustic cottage, circa 1850, has antique charm, yet modern comforts. In addition to a living and dining room, there is a full vintage kitchen, 2 bedrooms, 1 bathroom, plus laundry facilities. Very tall people will have to duck under door ways. Not suitable for children under 12. WiFi and a smart TV. Kitchen ceiling is 6'3.5".

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.

Cozy Cottage on Cedar Lake- "Cottage Cheeze"

Our petite (648 sq. ft.) lakeside cottage is the perfect place to unwind, relax and explore. Enjoy the spectacular unobstructed views of the sunset from the spacious deck (750 sq. ft.) from the comfort of your easy chair. The location of our cottage provides the tranquility of the lake, close to major routes and you will be minutes away from all that Sturbridge has to offer.