Smoking friendly holiday rentals in Litchfield County

Secluded Hilltop Cabin near Beacon & Cold Spring

3 private acres atop small mountain. Feels like you're way upstate - check out the reviews! Hi-speed WiFi. Next to forest preserve and hiking trails. Furnished deck w grill overlooks Mt. Beacon sunsets. Loft w/queen and twin mattresses + pull out couch & twin-size mattress day bed on the porch. Perfect for 2, comfortable for 3, but 4 is probably max comfort since it's a small space. Please note that the road heading up there is steep. A car with AWD is ideal but a sedan will make it up too!

Steele Brook Manor

Kick back and relax in this calm, stylish space. Come enjoy this peaceful setting located on the second floor with a private entrance. The home is tucked away on a dead-end street. You can escape to this lovely spot where the woods are in your backyard and the beautiful sunrise is out your bedroom window! If it's wineries you love Hawk Ridge Winerery 2miles away. The antique trail begins the next town over. Or maybe skiing is on your list just head north under 20 miles and you can be there.

Spacious Family Home Near Yale University

Experience total comfort in this expansive four bedroom home located just minutes from Yale. Whether you are here for a graduation or a long term relocation, you will enjoy a bright, uncluttered environment in a peaceful neighborhood. Our guests consistently rave about the spotless bathrooms and high quality linens that make every stay feel premium. With easy temperature controls and a modern kitchen, this house is a solid choice for groups seeking a reliable and welcoming home base!

Mountain Creek Getaway

Welcome to Mountain Creek, a tranquil retreat on the NY/ CT border. A private forest setting with the soothing sound of a creek surrounds the farmhouse. Relax on the deck or the couch next to an electric fireplace. The spacious apartment has a queen-size bedroom, 1.5 baths, and a sleeper sofa. There is a separate area with a twin bunk bed and desk. Tons of amenities are provided for all the comforts of home. Close to the Appalachian Trail, Bulls Bridge hiking, and Thunder Ridge Ski.

BIG RED the Bus at Menlo Pond

You'll love this unique and romantic escape. BIG RED with its 100% off grid capabilities, has travelled the country, giving the owner the great opportunity to explore the US. It's now tucked away, parked and here at Menlo Pond waiting for you to experience and enjoy the comfort of all it has to offer: *Queen size bed *Large couch *Full bath *Full stove/oven *Air conditioning *Large sink *concrete countertop *Butcher Block *outside picnic table, Barbque and small fire pit

Berkshire Lakefront Lighthouse Getaway

Escape to your own slice of paradise in our 450 Sq. Ft breathtaking Lighthouse rental on East Otis reservoir! This stunning property boasts a multi-level 800 square foot deck with jaw-dropping views of the shimmering Lake below making it the perfect place to unwind and soak up the natural beauty of Massachusetts. For water enthusiasts, the lighthouse rental also includes a 500 ft shared dock, providing easy access to the lake for swimming, fishing, kayaking and more.

Peaceful wooded site, hot tub, free EV charger

Heron On the Hill Glamping is all the fun of camping with all the convenience of a hotel. You will have your own beautiful canvas tent everything is set up for you on arrival. Relax by the Firepit at your site or wander the property play a game of volleyball if you have a group or try your hand at corn hole We have an 18 hole mini golf free to play. If you like hiking we are directly across from Stone Church with hiking trails, a cave and waterfall

Artist A-Frame at Gatherwild Ranch

Welcome to Gatherwild Ranch, an upscale, design-forward farm stay home to 8 beautiful and unique accommodations spread out on the rolling hills of a former apple orchard. Inspired by life upstate, Gatherwild offers guests everything from a pick-your-own veggie garden to artist-led workshops to luxury amenities – including a new to-this-year sunset deck, bathhouse, cold plunge tubs, and sauna – for a unique glamping experience in the Hudson Valley.

NE Historical Mansion-pets and pet lovers welcome

Enjoy seamless check-in and a private 1,000 sq ft space on the third floor of our historic Victorian home. Includes 2 bedrooms, bathroom, open hallway, and a combined living/dining/kitchenette area (no sink). Pet-friendly, updated, and comfortable year-round. Accessed via the back staircase; only the entry/hallway is shared. 3rd and Top floor is strictly for guests only. Just 5 min to I-91 and Pike, 15 min to Northampton 15 min to Big E.

Wallingford Getaway

ENJOY DAILY CONTINENTAL BREAKFAST INCLUDED WITH minimum two night stay. Experience a cozy stay in our spacious 1300 square foot unit with included breakfast. Choose from muffins, bagels, bars and yogurt. Enjoy a relaxing afternoon with a cup of Java from your own Keurig. This unit features a comfy red electric red reclining couches and a flat screen TV. The kitchen area is equipped with a toaster microwave convection oven and fridge.

Cozy Winter Escape | Hot Tub, Game Room, Fireplace

Escape the cold and unwind at Blue Barn, a cozy and private retreat designed for comfort all winter long. Soak in the year-round hot tub, relax by the electric fireplace, and enjoy the game room—perfect for snowy days and quiet nights in. Ideal for couples, families, or small groups looking for a warm, peaceful Connecticut getaway.

Watch Hill Hideaway - Unit B

Enjoy our peaceful, park-like setting with easy access to entertainment, fine dining, distilleries and brewhouses, CT's antique trail, Quassy Park, state beaches, golfing, and the best hiking in the state. Relax on the deck while overlooking the hills of Connecticut in a private space to enjoy indoors and out.