Vacation rentals in Killingly

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Top-rated vacation rentals in Killingly

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Top guest favorite
The exterior of a spacious home is presented, featuring a sloped roof and multiple windows. A well-maintained lawn surrounds the house, which is complemented by neatly trimmed shrubs. The structure's muted tones are highlighted under a partly cloudy sky, creating a serene country setting.
Guest suite in Lebanon
4.96 out of 5 average rating, 139 reviews

Rural Homestead Stay in Your a Private Suite

Relaxing country setting secluded off a long private driveway, on a dead end road, in historic Lebanon, Connecticut. Horses line the driveway, and chickens roam the yard. Sunrises over the backyard amongst the tree covered hills. The private accessory apartment, attached to the main home, includes one bedroom, living area, kitchen, bathroom, & porch. Witness the bustle of the active homestead. Relatively close to landmark casinos (Foxwoods & Mohegan Sun), hiking, the shoreline & historic sites.

Top guest favorite
A spacious deck overlooking Lake Bungee features comfortable seating arrangements, including wicker chairs and a swing. Colorful flower pots add vibrancy, while an umbrella provides shade. The peaceful waterfront setting is enhanced by natural surroundings and clear blue skies.
Apartment in Woodstock
4.93 out of 5 average rating, 432 reviews

“Tranquillity on the Lake ” Woodstock Valley, CT.

NEW WINTER WEEKLY DISCOUNTS Fall is here with crisp air, a treasure of rich colors embrace the trees. Enjoy your own private direct waterfront with 1400 sq ft . Queen bed in Master. Queen sofa in living area,Propane fireplace,full stove, full refrigerator, microwave. Enjoy your own deck, propane fire pit, gaze at the stars.Propane BBQ. Stroll around both lakes,catch bird sightings,nature’s delight . Many local dining & wineries. Each season paints its own stunning beauty Experience Tranquility !

Top guest favorite
The exterior of a rustic wooden house is surrounded by lush greenery and trees. A small fenced area is visible near the entrance, where a welcoming front door can be seen. The building features windows and a gabled roof, set in a tranquil natural environment.
Farm stay in Thompson
5 out of 5 average rating, 216 reviews

Rustic Farmette Studio w/yearround Hot Tub

Relax and rejuvenate at this unique getaway on 20 acres in CT’s Quiet Corner. Just an hour from Boston, Providence, & Hartford, enjoy this private in-law studio with beautiful forest views. Lounge in bath robes & soak in the hot tub, take a walk along the trails, enjoy local vineyards, or explore antiques. Folks from all backgrounds and identities are welcome at The Farmette. Ideal for couples, solo travelers, or a family with a young kid. Please include all individuals (&pets) in your booking.

Guest favorite
A spacious sleeping area features a canopy bed with an orange quilt. Surrounding the room are colorful artworks and wooden sculptures. Natural light enters through windows, highlighting the eclectic decor and greenery from nearby plants.
Home in Scituate
4.95 out of 5 average rating, 192 reviews

Artist studio in the woods

Take it easy at this unique and tranquil getaway. Be a little bohemian, stay in an artist’s studio for two adults, views of woods and stone walls.walk along a 300 stone wall past a 5000 gallon koi pond, and discover a stone sculpture in the woods. Wall of windows, private deck, queen size bed, kitchenette, full bath, dishwasher, Wi-Fi, cable tv, guest robes, iron and board, kuerig, all necessary utensils. Quite, tranquil, relax. As of 1/1/26 booking rate will be $120 per day. Pool $20 seasonal.

Top guest favorite
A brown wooden exterior with a blend of traditional and modern design elements is presented. The home features a two-car garage and a welcoming front porch adorned with potted plants. Large windows allow natural light to illuminate the interior.
Guest suite in Pomfret
4.98 out of 5 average rating, 111 reviews

Brookside Chalet

Not just a place to stay but a place where you will want to stay. - Dedicated parking space - Well-appointed full kitchen - Deck overlooking Mashamoquet Brook (our guests refer to it as the tree house:) The bed will be the highlight of your experience. This high quality queen is accessorized with a pillow top mattress, goose down and memory foam pillows and spa quality sheets and pillow cases. Location: - Five minute drive to Pomfret Prep. - Ten minute drive to main Street in Putnam.

Top guest favorite
The charming lake house features a sun-themed front entrance, flanked by dark shutters. A welcoming path leads to the door, surrounded by lush greenery and flower beds. The serene lake can be glimpsed through the trees in the background, enhancing the tranquil setting.
Home in Eastford
4.91 out of 5 average rating, 115 reviews

Serenity Ashford Lake

Lakefront jacuzzi available for fall and winter! Only 15 minutes from UCONN! Welcome to Serenity Ashford Lake. Serenity is removed from the everyday hustle and bustle of life. Nestled on the shores of beautiful Ashford lake, your stay is bound to lead to lasting memories. Waterfront jacuzzi, central air, stainless steel appliances, cozy linens, washer/dryer, kayaks, firepit, boutique toiletries and a new kitchen space make up this beautiful lake home. Bring your favorite book and enjoy!

Top guest favorite
The exterior of the cottage is visible, featuring a blue door with a sign that reads 'THE COTTAGE.' A small deck offers a table and chairs, surrounded by colorful planters. A blue umbrella provides shade, with a scenic view of the lake and trees in the background.
Tiny home in Smithfield
4.97 out of 5 average rating, 750 reviews

Tiny Home Eco-Cottage w/ Lake View + Pet Friendly

Good things definitely come in pet friendly, environmentally conscious, small packages. Solar upgrade makes this lake front cottage 100% energy efficient. Built with an open, thoughtful design offering private bath, washer/dryer, full kitchen, Hotel Suite Luxury bedding and Tempur-Pedic mattress, blazing fast wifi, 46"HDTV (w/ Netflix, Sling, Prime and Plex), private deck with nice lake view. Cozy, charming and stocked with everything you could want for a perfect vacation or staycation.

Top guest favorite
A spacious living area showcases large windows that invite natural light and views of the surrounding landscape. Comfortable seating includes a couch and armchair, complemented by a decorative fish tank. A dining table is visible in the background, enhancing the open and airy atmosphere.
Guest suite in Uxbridge
5 out of 5 average rating, 280 reviews

Zen Inspired Retreat with Private Forest Trails

Zig-Zag Trails blends modern comfort with the charm of rural living. Set on 65+ acres of private meadows and forests, our master guest suite is the perfect retreat to relax and recharge. Explore scenic zig-zagging trails, perfect for hiking, mountain and E-biking, and unwinding in nature—a haven for outdoor enthusiasts and homebodies alike. 📍 1 hour from Boston 📍 35 minutes from Providence 📍 25 minutes from Worcester Escape to Zig-Zag Trails—where tranquility meets adventure.

Superhost
A rustic cabin with a stone chimney is set against a backdrop of lush trees and a warm sunset. The wraparound porch features wooden railings and is complemented by neatly landscaped areas. A stone wall borders the driveway, leading to the cabin's entrance.
Cabin in Glocester
4.89 out of 5 average rating, 111 reviews

Get comfy in the country!

This special place is close to everything, making it easy to plan your visit. Just 10 minutes away from town. Secluded cabin on a 57-acre farm outlooking a large paddock with 4 highland cows. This beautiful property has a neighboring golf course and trails connecting to Heritage Park. Pool. Fireplace. Amazing sunsets! Who wouldn’t want to live like Yellowstone for a little? Home of Welcome Pastures, a Nonprofit 501(c)3 organization. Portion of proceeds go towards the foundation.

Guest favorite
A feature wall is adorned with various steampunk elements, including gears, clocks, and unique decorative items. An intricately designed aircraft model is suspended from the ceiling, while a small table with a glass sits nearby, adding to the eclectic ambiance.
Farm stay in Thompson
4.95 out of 5 average rating, 223 reviews

SteamPunk Bunk House and Intergalactic Way Station

A farm stay like no other! The future is the past and the past is the future with STEAMPUNK details that delight at every turn. Feed the goats, walk the trails, meet an alien. A complete apartment great for longer stays. Enjoy the imagined history of this 1825 farm house. Enjoy New England without spending days driving. Come visit a simpler time where nature is just outside your door and ET is sharing the kitchen. Cook s'mores fireside or say hi to "blue" our resident heron.

Guest favorite
A living room is displayed with hardwood flooring and a circular braided rug. Furnishings include a sofa and two high-backed chairs near a large window that offers views of greenery. A coffee table is positioned centrally, with a faux fireplace and a television visible in the background.
Home in Putnam
4.77 out of 5 average rating, 252 reviews

Calm & Cozy House in a Quiet Corner

The perfect place to get away to enjoy a Best Kept Secret of New England. You will have access to the whole house during your stay. All on one level (ground floor). Enjoy the relaxing view of the field, red barn and Quinnebaug River while snuggling up with read a book. The country kitchen is complete with refrigerator, toaster, oven, microwave, and coffee maker. The best of Putnam Antique District, Entertainment, Dining, Nightlife and shopping a 4 minute drive away.

Top guest favorite
The exterior of a red, two-story building is surrounded by a well-maintained lawn featuring trees and landscaped flower beds. A large window above the entrance and additional windows enhance the farmhouse aesthetic. Cloudy skies and natural light create a serene atmosphere.
Farm stay in Woodstock
4.99 out of 5 average rating, 214 reviews

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.

Popular amenities for Killingly vacation rentals