Vacation rentals in Northeastern Connecticut Planning Region

Historic Railroad Caboose - Unique CT Farm Escape

🚂 Authentic 1906 SOO-Line Caboose on our working CT horse farm! Queen Murphy bed + two bunks, WiFi, Roku, microwave, fridge, Keurig, deck, and cozy bathroom. Note: The historic 22" doorways limit accessibility. Explore nearby: Mashamoquet Brook trails, antique shops, wineries, and Putnam's arts district. Farm life starts early! Fall asleep to railroad dreams, wake to countryside serenity. Note: historic charm means cozy dimensions. Book today—before this experience leaves the station! 🌿

Family · Location · Heating

The Barn at Pondview

Reconnect with nature at this unforgettable escape. Enjoy pond views and incredible sunsets from the top patio deck. This property is on the 2nd & 3rd floors of the barn, so there are stairs. Also the "bedroom area" picture is a loft area with a trundle bed, (2 twin beds) - the room is open to the downstairs main living area. The game room has pool, shuffle and foosball tables, darts and a bar area. There is also a basketball court in the back yard. Inground pool in the summer.

Location · Family · Indoor spaces

Handcrafted Timber Frame Cabin Retreat

Escape to the woods and slow things down at this beautifully handcrafted timber frame cabin, tucked away among towering trees and nature’s quiet. Built with exposed beams, natural wood, and timeless craftsmanship, this cabin blends rustic charm with modern comfort—perfect for a romantic getaway, creative retreat, or unplugged weekend escape. Whether you’re looking to reconnect, recharge, or simply enjoy the beauty of the forest, this timber frame cabin offers a warm and memorable escape.

Location · Sleep quality · Comfort

Little Rest Studio

Little Rest Studio overlooks 100 acres of conservation land, primarily oak and hickory forest. Recently renovated by the owners and full of personal, handmade touches, this apartment was originally conceived as a temporary ARTIST’S residence and occupies the top story of an English-style BARN otherwise used as a photographer's WORKSHOP. We offer a chance to slow down and meet the season, relax in the warmth of the wood stove or the bath, and be a human in a lovingly handmade retreat.

Family · Location · Comfort

Lake House w/Game Rm 5 Min From Foxwoods & Mohegan

Relax and enjoy the breathtaking views of this new contemporary lakefront home. Kayaks & paddleboards await you, 5 min from Foxwoods, 10 min from Mohegan Sun with multiple-choices of hiking, boating, shopping and dining. Stunning cathedral, ceilings, fully equipped kitchen, with granite countertops, tiled showers with full amenities and a game room/theater. You cannot get any closer to the water. This two bedroom 2 1/2 bath sleeps eight, 2200 square-foot house completed in 2024.

Location · Value · Sleep quality

Clark Cottage in the historic village in Chaplin

Up to 14 day stays are OK. This rustic cottage, circa 1850, has antique charm, yet modern comforts. In addition to a living and dining room, there is a vintage kitchen, 2 bedrooms, 1 bathroom, 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". An exterior camera is installed to observe wild life passing through the yard. A switch in the laundry turns it off.

Family · Location · Hiking

Waterfront Home | Newly Renovated | Chef's Kitchen

Wake up to a private pond. Step onto your deck and the water is right there. This cottage is a newly renovated (2026) waterfront home on Aspinook Pond in Jewett City, CT. Two bedrooms plus a pull out couch, a chef-outfitted kitchen built to actually cook in, and a breathtaking master bathroom. Two kayaks, a canoe and a skiff, a public boat launch, and a fully stocked pond ideal for fishing. Dogs welcome. Self check-in. Foxwoods + Mohegan Sun Casino: 20 min.

Location · Family · Comfort

Wings & Wildflowers at the Glen

Relax with family or friends. Whether attending a wedding at one of the area's fabulous venues, visiting family or just looking for some peace and quiet in rural Connecticut, this is the place for you. Tucked away off the road with The Little River across the street, we are serenity and privacy. The wildflower meadow and plantings attract butterflies, dragonflies and hummingbirds. Trail Wood (Teale Sanctuary), Goodwin Forest and the Airline Trail are nearby.

Family · Location · Outdoor spaces

Secluded 2 Acre Lake Front Home!

Escape to this breathtaking retreat on Lake Chamberlain, tucked away in Connecticut's serene "Quiet Corner". This spacious 2-acre home offers total privacy and stunning natural beauty. In the summer, dive into swimming, fishing, and kayaking 🛶🏊‍♀️. When winter arrives, experience ice skating ⛸️ right on the lake! Whether you're here for relaxation or adventure, this peaceful getaway will steal your heart. Once you arrive, you may never want to leave! 🏡💖

Family · Location · Accuracy

Affordable In-Law Apartment in Brooklyn, CT

This is a great in-law style apartment which was fully renovated in 2020. It can be booked for short stays or more lengthy visits to Northeast CT. The apartment is one minute from Scenic route 169 and Route 6. It is 30 minutes to UCONN and ECSU. We are close toThe Pomfret School/Rectory School. It is 35 mins to Mohegan Sun and Foxwoods. My place is rural and peaceful. It is good for couples, solo adventurers, business travelers, and families.

Family · Location · Breakfast

Connecticut Country Escape

Forget your worries in this spacious and serene space. Quiet country setting in Hampton, CT. set on almost 5 acres of land. Private walking trails and fishing pond (bring your own fishing gear). Feel one with nature but not far from the local attractions. Less than 3 miles to Wrights Mill and Stonehurst wedding venues. 25 minutes from UCONN and 30 minutes from the casinos. Close to the airline trail for off road biking, hiking and jogging.

Family · Location · Cleanliness

The McClellan Mansion

Resting on a sprawling estate in picturesque Woodstock, CT, this fully restored historic home blends timeless architecture with modern luxury, it offers grand spaces, cozy corners, a chef’s kitchen, spa baths, and manicured grounds. Pair with our poolside cottage for extra space and pool access. This Woodstock estate is more than a stay—it’s a destination. Pool is only included by booking the additional listing “Poolside Cottage”.

Family · Location · Check-in