Smoking friendly holiday rentals in Litchfield County

Romantic Botanical Glamping

A spiritual respite for relaxation and mental wellbeing. The perfect relaxing Romantic Botanical Glamping Spiritual Garden Retreat Getaway, off the beaten track but close to civilization with a rustic romantic flair. Pool, gardens, seasonal vegetables & fruit & Fall Colors. Local activities within minutes. Recline by the pool, gardens, explore the areas Antique trail, winery, breweries. distilleries, hiking areas. We provide more amenities than most hotels - bathrobes, slippers, games, etc.

1880s balconied luxury pad, best downtown location

Bright, newly renovated, luxuriously furnished, tree-lined flat a few steps from Northampton's vibrant downtown. Sliding glass doors open to a lovely balcony overlooking trees and roofs. Open floor plan, eat-in butcher-block kitchen, dishwasher, living room with movie projector, home theater system, queen pullout sofa. Spacious queen bedroom with 42" HDTV, private study nook. Access to yard areas with outdoor dining table, heated 36-ft pool, play gym. Basement washer/dryer. Off-street parking.

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.

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.

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.

Firefly Upstate Glamping 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.

Hot Tub Getaway | Game Room + Fireplace

Escape to Blue Barn — your private hot tub + game room getaway, perfect for a fun and relaxing spring stay. Unwind in the year-round hot tub, challenge your group to games, or cozy up by the fireplace after a day out. Whether you’re planning a girls’ weekend, family trip, or low-key celebration, this space is designed for both relaxation and entertainment. ✨ Close enough to everything, yet private enough to truly disconnect.

Harmony Valley Home, bright & inviting studio

You and your guests will be close to it all when you stay at our centrally-located home. The space is nestled perfectly between the Berkshire and Catskill Mountains, which provides countless opportunities for adventure! Whether a romantic getaway or a family vacation- you are an idea away from an unforgetable experience! Wineries & breweries Museums & art Hiking trails Empire State Rail Trail Conservation Areas Shopping

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.

Remodeled Historic Forestville Home w/fire pit

Located near the center of Forestville, a renowned section of Bristol, CT. Bristol is home to ESPN and Lake Compounce theme park. You will find the craftsmanship and wood work in this home quite exceptional. Quiet Neighborhood and centrally located.