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

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.

Her tiny Parisian boat house

SOLO vacation? Reconnect with nature at this unforgettable escape. Perfect work space while lounging by the pool…(in SEASON) this tiny house (on land) has access to SHARED outdoor shower and outdoor soaking tub. Wanna relax? Come Meditate under the giant willow, swing in the hammock or practice yoga. Bathroom (NOT IN THE TINY HOUSE!) is shared and just steps inside the main house with shower and toilet. Great WiFi, front porch to enjoy meals. Bed is a comfytwin with lots of pillows.

Expansive New Haven 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!

Pet Friendly One Bedroom House

Great pet friendly house located close to the water, downtown, beaches, train service and I-95. Off street parking, laundry facilities, great fully fenced in back yard. Large, one bedroom and one bath with a pull out queen size sleeper couch in the main room. Wi-Fi, Roku TV, boards games, and DVDs available. Property is located close to restaurants and many outdoor activities including the town beach and docks. There is a pass available to bring a car to the Clinton town beach.

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.

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!

Clean, quiet 3-bedroom raised ranch (entire house)

Clean, quiet 3-bedroom raised ranch. This property boasts a newly updated kitchen and main-level bathroom. The business center is located in the lower-level for individuals who would like a space to work from "home". All three bedrooms have flat-screen, smart TVs and black out curtains. There is a deck and patio for quiet evenings outside, perfect for grilling.

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.