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 · Value · Air conditioning

Historic Haskell House 1700s Get Away!

Four Room Entire Cottage with private entrance. 15 minutes from the casinos, but centuries away! Enjoy the serenity and coziness of your own authentic 1750 New England farmhouse surrounded by beautiful gardens. Antique interiors, granite fireplaces, flickering candlelight, original woodwork create a romantic ambiance. There’s nothing like sleeping in a canopy bed, peering up at a wood-beamed ceiling! Beautiful modern kitchen with generous amenities and large full bath with washer & dryer.

Location · Family · Accuracy

Water Forest Retreat -Octagon

Water Forest retreat is a very private 122ft.² electrified and heated cedar octagon next to a brook on 56 acres of forest with a pond, waterfall, marsh and hiking trails. Cozy up in this quiet comfortable space while listening to Goldmine brook while you sleep. Fire pit, heated outhouse with composting toilet, outdoor dining area, brook, pond and trail head are just steps away. We also have a TREE HOUSE and HIKER’S HAVEN house by the brook. Please click on our profile picture to read more.

Family · Value · View

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 · View · Outdoor spaces

Bunny’s 15-Acre Woodland Retreat

With 15 acres of private wooded land, count on High Speed Wi-Fi throughout Bunny's Retreat if you work from home or just need to catch up on emails! Coffee bar is stocked, have a cup taking in an ideal view of the woods! Television is ready to stream movies with family & friends! Plenty of indoor & outdoor seating for meals as you watch the sunrise or sunset cast pink hues over the woods & sky! As the sky darkens & the stars light up, gaze up in wonder in a very quiet area of New England!

Location · Family · Pets

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 · Check-in

The Carriage House at Chaprae Hall

Welcome to the Carriage House at Chaprae Hall! A cozy, quiet respite from a busy world awaits you. This fully furnished & appointed vintage living space has been updated over the years to be an inviting and welcoming stop for your journey. Whether you’re traveling for business, in town for an event, or looking for a central home base for day trips across southern New England, we've got you covered with your own kitchen, full bath, living space, and bedroom with a queen-sized bed.

Location · Family · Solo travel

Windham Gardens

Our guesthouse is a newly-renovated bespoke cottage located on the grounds of the circa 1750 Windham Gardens estate in the heart of historic colonial Windham Center. The cottage sits in the midst of a private garden, with several intimate outdoor seating areas. The cottage has a bedroom, bathroom, and a orchid filled garden conservatory with a retro kitchenette. The garden cottage is just 15 minutes from UConn and close to numerous restaurants and antique shops.

Family · Location · Sleep quality

Barn suite at Southwood Alpacas

Country living at its best. Renovated guest space on a working alpaca farm. This is a two story unit with a kitchenette, living room and bathroom on the first floor and a studio loft on the second floor. Two decks, one on each level overlook the farm. Recently renovated. Great light floods the unit. Central heat & AC. Enjoy the farm and the bucolic setting in Woodstock. Watch the alpaca from your windows or deck. Cafes for morning breakfast and fine dining await.

Location · Family · Hiking

Lakeside Retreat

Enjoy this newly renovated lakefront, year round cottage, located on crystal clear Alexander’s lake. If you’re looking to unwind, this is the place to be! A tastefully decorated one bedroom home with all of the amenities you could need. Enjoy your morning coffee on the expansive deck looking out over the water. Spend your days sunning yourself on the dock, swimming, fishing, kayaking or canoeing. Spend your evenings enjoying the peaceful surroundings of the lake.

Family · Value · View

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.

Location · Family · Quiet

"The Getaway" at Alexanders Lake

Relax with the whole family at this peaceful, lakefront home. Located on the beautiful, clean Alexanders Lake, this home offers outdoor enjoyment with all the comforts of home. Sleeps 5 guests with 2 bedrooms and sleeper sofa. Full kitchen with all you need for cooking and entertaining. Work space available. Enjoy the views from screened porch. Multi decks for outdoor eating and enjoyment. Dock to water. Private parking.

Location · Family · Pool