Vacation rentals in Cheshire

Betty’s Brickhouse-ask about shorter stays

This is a very cozy one bedroom (2nd floor)- the bedroom has a 33” TV and fanimation fan/light -comfortable and inviting living room with 50” TV with WiFi. Great new kitchen space with ss appliances including a “knock knock” refrigerator, stove, toaster, microwave, dishwasher, coffee maker, pots and pans and even a washer and dryer. The bath is simply spectacular -all new and sparkling clean with plenty of towels, etc. We also have the convenience of keyless entry. Please note-Must climb stairs

Cozy & Private Studio Suite

Quiet and private in-law suite. Located close to the center of Cheshire, convenient to Route 10, I-691, and Route 15. Near to grocery stores, great restaurants, and shopping centers. 15 minute drive to Toyota Oakdale Theater, 20 minute drive to Lake Compounce Amusement and Water Park, and 30 minute drive to Yale University, Museums, and downtown New Haven. A slightly longer drive will take you to to the beautiful shoreline, Hammonasset Beach State Park, Foxwoods and Mohegan Sun Casinos!

Modern cozy, pet friendly

Kick back and relax in this calm, stylish space. This is a full finished apartment with a private entrance full bathroom full one bedroom full kitchen, second bed-sleeper sofa in the living room. This is a private property we live upstairs. very safe clean neighborhood. Property sits on a 3.5 acres. From parking to the entrance is a short walk thru the grass yard. protect you trip in case of unexpected events that may require cancellation. Travel insurance can be purchased thru Airbnb .

Connecticut Chalet: Winter Nights by the Fire

Escape to a unique & stylish home perfectly tucked away in a picturesque New England town. Indulge in the privacy & serenity of this 5 acre wooded property and peaceful pond while being minutes from an abundance of restaurants, shops & entertainment. Enjoy the natural setting from the comfort of the glass enclosed sunroom with panoramic views of the property. This 3 bed, 2 bath home maintains it’s original 1960’s charm while boasting thoughtful modern touches and intentional functionality.

The Garden Loft - A Charming Choate Stay

Welcome to The Garden Loft! Located in the heart of downtown Wallingford, CT. This traditional and historic New England carriage house has been completely renovated in the summer of 2022 into a peaceful, cozy, bright & airy loft. We are a 3 minute walk from downtown where you will find a variety of restaurants, bars, a brewery & only 1 mile from from Choate Rosemary Hall. A 15 minute drive to Yale University & downtown New Haven. Get ready to relax, get cozy & enjoy The Garden Loft!

Cozy Waterfront Lake House: 5 mins from ski slopes

Relax at this peaceful 1BR lakefront retreat—perfect for couples or small families. Summer: Enjoy kayaking, swimming, grilling, outdoor dining, and fire pit s’mores. Off-season stays offer crisp hikes, lake views, fires, nearby skiing at Mt. Southington (5 mins), and family fun at Lake Compounce. Sleeping arrangements include a queen size bed in a Bedroom, a pullout sofa bed and a queen sized blow up mattress. Self check-in, fresh linens, and a welcoming vibe await.

Cozy Private Guest Suite

Welcome to your perfect home-away-from-home in Southington, CT! This private basement guest suite offers a cozy, quiet escape with everything you need for a comfortable stay. Whether you're visiting for business, or just passing through, you'll enjoy a peaceful space with a private entrance, living area, and essential amenities. Free parking on premises Located in a quiet neighborhood just minutes from local restaurants, walking trails, and easy access to I-84

The Winchester House at Science Park-Yale

Located 2 blocks from Yale University's Franklin and Murray College and Ingall's Ice rink, The Winchester House at Science Park is a newly renovated luxuriously appointed 2 bedroom 2.5 bathroom apartment. The apartment features bespoke amenities, free secure off-street parking, snacks and beverages, stylish furniture, 1000 ct. beddings, ample cooking pantry items and everything you need as a guest. Let us welcome you in relaxed luxury!

Wintergreen Gardens Suite @ William Becroft House

LGBTQ friendly. Our 1915 Arts & Crafts bungalow's spacious in-law suite offers driveway parking, private entrance, sunroom, king bedroom, en-suite bath, kitchenette w/fridge, micro, coffee maker, toaster. Relax in bed with 40" HDTV with Amazon Prime, HBO Max, Netflix, premium cable. Enjoy private gardens to sun, read a book or cup of coffee. Short drive to 4 Vineyards, Theater and the train station. I am not responsible for wifi.

Sweet Sparkling Clean Boho 1 bedroom

One bedroom, 3rd story apartment, completely separate, with its own entrance. Comes with a single off street parking space. Centrally located in downtown Wallingford. Close to shops, restaurants and bars. Also within a couple of miles of the Toyota Oakdale Theatre. If you are looking for a place to come and party for the night, this is not a good space for you. This is a quiet building with the landlord on premise. No pets.

Seasons Hospitality LibraryLuxe 1BR

Welcome to Platform 9 at "The Station" Once an old silver factory now converted into a fully furnished 1-bedroom apartment, where the echoes of the past harmonize with the comforts of the present. This brand new apartment includes all utilities, free off street parking, free washer and dryers and all linens. Located in the center of town and walking distance to shopping, restaurants and all what Wallingford has to offer.

Beautiful Cozy Apt/ Soaking Tub & Serene Vibes

Relax in this peaceful retreat just 10 minutes from downtown New Haven and Yale. Ideal for solo travelers or anyone seeking a quiet escape. Enjoy the deep soaking tub, calming decor, fast Wi-Fi, and a serene space to recharge. No parties—just peace, comfort, and good vibes. This is a calm, intentional space for peaceful stays only. We welcome guests who appreciate good energy and quiet rest.