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.

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.

Waterside Bungalow Retreat

Experience the magic of autumn in New Haven from this charming riverfront bungalow, where crisp air and golden reflections dance across the water. Enjoy peaceful marina views right from your window and easy access to all the marina’s amenities just across the street. Recently updated with a modern yet inviting design, the home blends warmth and comfort with its breezy coastal character. Whether you’re here for a quiet weekend retreat or an extended stay, this is the perfect place to unwind!

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.

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.

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.

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.