Smoking-friendly holiday rentals in New Haven County

Apartment in Artsy Westville New Haven.

Welcome to your spacious 1500+ sq ft Westville home! This cozy, fun retreat is perfect for families and groups. Enjoy 1 Gig Fiber Internet, a fully stocked kitchen (with dishwasher, washer/dryer, ice-dispensing fridge), and two comfortable bedrooms. The master features a Cal-King bed, crib, and changing station The dining area offers big fun: a table that converts to a pool and ping-pong table! Relax on the front porch with a TV. The yard is pet-friendly, and street parking is ample for guests

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.

Cozy 2 bedroom home located minutes from downtown

Come enjoy this beautiful Cape, centrally located in a quintessential, family-oriented neighborhood in walking distance of restaurants & 12 minutes from downtown New Haven. Upon entering you'll find a spacious living area with large windows, and ample seating. Also on this level is a large master bedroom with king size bed, & 2nd bedroom with a queen size bed, spacious eat in kitchen & dining room which can seat 8 comfortably. The finished lower level features a den, full bathroom & laundry.

Country Guest Cottage/Barn

Enjoy nature in the guest cottage/barn on our property in bucolic Litchfield County. King bed in the sleeping loft and queen bed in the room. Air mattress available. Nestled in the Litchfield Hills three miles from Lake Waramaug and close to the quaint shops, restaurants, galleries and cultural scene in Kent, Bantam, Litchfield, Washington, New Preston and Cornwall, among others. Hike beautiful Kent Falls and explore the many hiking trails and ponds, lakes and rivers. Newly upgraded with Wi-Fi!

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.

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 Beach Home Mid NYC-Bos/Comfy Getaway all year

Midpoint between Boston & NYC, Central Connecticut Coast…easy drive to many attractions. Quaint, Private New England Beach Ass. yet minutes to the best restaurants, Outlets and Charming towns. The cottage is less than a 1/2 block (2m walk) to private beach. An “Oasis, Hidden Gem’ are quotes per Guest reviews. Coastal decor,love of old and new. Welcoming, relaxing home away from home…TV, games, book collection, puzzles, outdoor games and gear…Established 2019.

Penny Corner Airbnb

My place is located up the hill from Good Speed Opera House. The Opera House is on the same side of the river as my place. The folklore is that vacationers used to pay a penny to have their belongings transported by ox and wagon from the port at the river to this corner. A two family home built in 1884. The space is a ground level 1 bedroom apartment with private entrance. There is no TV in the unit, WIFI is available for your devices.

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.

Country getaway - pool, huge yard,

Private rental unit on 2nd and 3rd floors of historic 2-family home (owners live in rest of house) amid forests, lakes, rivers and ponds. Private deck, outdoor shower, & full access to the 4 acre property. Just minutes from swimming, hiking, cycling, boating and more! Enjoy the area’s many tourist destinations, family attractions, restaurants, vineyards & breweries, antique shops, golf courses and entertainment!

Shelter Bay Cove Waterfront Escape

Enjoy spectacular views of Hashamomuck Inlet off Shelter Bay from the living room, kitchen, deck, garden, and private dock of this newly renovated 3-bedroom home. With 90 feet of waterfront and a small sandy beach, it's ideal for kayaking, clamming, and swimming — perfect for families with young children. Relax with sunsets, barbecues, and local North Fork wine. The perfect family getaway!