Holiday rentals in Cheshire

Bright 1 BR Apt Steps From Yale

Enjoy a bright and cozy 1 bedroom apartment just 2 blocks from the Yale campus and The Shops at Yale. Located in a 3 unit brick building, designated as a property on The National Register of Historic Places, this small renovated 2nd floor apartment maintains the characteristics of the building's original design, while providing all amenities needed for a comfortable stay. Convenient free off street parking provided. Great shops, restaurants, nightlife, and museums can all be accessed by foot.

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!

In-law Private Studio Apartment

Enjoy a stylish experience at this centrally-located studio apartment. Located in the quaint, quiet, and highly desirable Spring Glen neighborhood, it’s short walking distance of city bus line, as well as several local restaurants, cafes, & local entertainment. Centrally located to Yale University & Hospital, Quinnipiac University, SCSU, Albertus Magnus, as well as downtown Hamden & New Haven. The 400 sq ft apartment has a full bed w/ Tempur-Pedic mattress, & couch pulls out into a full bed.

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!

Westville Schoolhouse by Stephanie and Damian

The beautiful "School House" sits in the heart of Westville, New Haven's most artsy and eclectic neighborhood. The "School House" is a 15 minute walk to the Westville Concert bowl, and the Yale Football stadium for an easy commute to a concert or game. Just a one minute walk to the center of Westville you will find Lotta's artist studio, Bella's restaurant, RAWA, Pistachio Coffee and Manjares Tapas & Wine, as well as the famous Camacho Garage restaurant amongst other attractions.

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.

Square6ix Stylish Guesthouse in Westville

Inviting, eclectic, and completely private, this single family stand-alone guest house is an intimate and engaging haven. A serene private guesthouse perfect for couples, creatives, and travelers. Stylishly decorated with modern amenities, this space is a cozy retreat just a short walk to Westville Village and Edgewood Park. Ideal for weekend getaways, local visitors, or professionals seeking a quiet base with fast WiFi and free parking.

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.