Smoking-friendly holiday rentals in Fairfield 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.

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.

Uncle Scott's Family Retreat-Private Mountainside

Private Mountainside Glamping Getaway! Enjoy your own 43' two bedroom glamper nestled upon a mountainside in beautiful upstateNY on your own private campsite with breathtaking panoramic views of Mount Beacon.Only 90 minutes outside NYC.Combine the comforts of a hotel with the beauty of the outdoors.Picturesque mountain sunsets,hike the blue trail,visit local breweries,walks in the woods,evening campfires,morning coffee and fresh air.Get ready to experience everything Upstate NY has to offer.

Gorgeous Suite w/ Private Entrance

Welcome to your private upstairs retreat with its own private entrance and bathroom. This charming efficiency offers a queen bed for restful nights, plus a loveseat sleeper sofa perfect for an adult or two small children. Enjoy the convenience of a mini fridge, coffee maker, and microwave. Step outside your door to our porch sitting area with a grill. Thoughtfully set up to feel both private and inviting, it’s a peaceful space to relax, recharge, and feel right at home during your stay.

Hudson River Peaceful Getaway, Explore from here

Self Check-In/Private Entrance. House trained Dogs and declawed Cats are Welcome (No additional pet fee). Driveway Parking for two cars. Peaceful, private flat on the Hudson River. Train to NYC (Scarborough Station) 10 min walk through historic neighborhood. Arcadian Mall (Grocery Store, Starbucks, etc) 7 min walk. Lots to explore in the area. Panoramic Rivers views from inside and out. Two televisions. Coffee/Condiments/Cooking Essentials provided. $19 cleaning with or without pets.

The Design Studio Suite | 2 Beds | Spacious | Luxe

Private one bedroom apartment with modern decor offers everything you need for a short or long term stay. Space includes a full kitchen separate from studio area, & washer + dryer. Studio offers a Queen Sized bed, pull-out bed, workspace, 70 inch Roku Smart TV & hand painted artwork. The Location Less than two miles from Merritt Parkway, near I-95 & East Norwalk train station. One mile away from large shopping center and less than half a mile away from local convenience center.

Cozy tiny log cabin on 13 acres

Tiny rustic cabin located in the woods. Large screen TV and Wi-Fi. No stove but will provide cooktop and toaster. Full bathroom with shower. People love the back deck to enjoy their morning coffee and to watch for wildlife. One bedroom with comfy queen bed and fan. All linens and towels supplied. Please be aware this is a rustic beautiful site. Trails in the back and very close to rail trail. Mini splits will keep you toasty warm in the winter and ice cold in the summer.

Secluded Hilltop Cabin near Beacon & Cold Spring

3 private acres atop small mountain. Feels like you're way upstate - check out reviews! Hi-speed WiFi. Next to forest 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 is steep. A car with AWD is ideal but a sedan will make it up too!

Rare, glamping, hot tub, EV charger, hot shower

Heron in 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 that is free to play. If you like hiking we are directly across from Stone Church with hiking trails, a cave and a waterfall.

The Hudson Valley Hideaway

Escape to this cozy Hudson Valley hideaway in Poughkeepsie…your perfect home away from home! Whether you’re visiting for a weekend getaway, college event, business trip, or long stay, you’ll enjoy comfort, privacy, and peace. The space is fully private with your own entrance and parking space. My husband and I live on-site but give guests complete space to relax. The pool will reopen in summer…until then, kick back and make yourself at home!

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.