
Vacation rentals in Cheshire
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Top-rated vacation rentals in Cheshire
Guests agree: these stays are highly rated for location, cleanliness, and more.

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!

Amazing views of the Brass City
East Mountain Views at its finest. This clean, 3-bedroom newly updated ranch is centrally located to highways and shopping centers. Walk out to the back deck and experience some of the best views of Waterbury including Fireworks from the back deck (month of July). Wi-Fi/cable, central AC/hot air, washer/dryer, and grill are included with the stay. Plenty of entertainment (board games, corn hole, foosball, air hockey table) are provided. This house is truly relaxing and will feel like home.

Connecticut Chalet: Experience Fall in New England
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!

Urban Garden Suite
Relax & Recharge in Westville’s Hidden Gem in. We Haven✨ Unwind in this serene, sun-filled, spotless garden apartment tucked inside a historic three-family home in charming Westville. The cozy, open-concept design blends modern upgrades with warm, thoughtful touches, creating the perfect balance of comfort and style.🌿 Enjoy peaceful surroundings, inviting details, and everything you need for a seamless stay. 💫 Your attentive (yet discreet) hostess ensures you’ll feel truly at home.

Retreat in New Haven by Stephanie and Damian
Welcome to your retreat in the heart of Westville. This apartment features a spa-like bathroom and a cozy living room with a super-comfy couch and large flatscreen TV. Relax in this centrally located oasis near Yale’s football stadium, Westville Bowl, local art studios, coffee shops, and top restaurants just steps away. Perfect for extended stays, traveling professionals, visiting faculty, or anyone seeking a convenient home base this winter. Discounts for stays of 30+ days.

Cozy Waterfront Lake House
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

Everything you need! Apartment!
Awesome bright 2nd floor apartment, has everything you need for your stay. Full Kitchen, Laundry and is in an very convenient and safe area. Walking distance to several restaurants and bars. Easy access to highway. Parking is available behind left garage, which may be available. Ask for details. Quiet area, On cul-de-sac. Wi-Fi, Netflix, Prime,Hulu FYI: I host a friendly card game every two weeks in the garage till 11:30 PM.

Spacious Cozy Guest Suite
This unique guest suite located in a newly constructed home offers over 600 sq ft of space. There is a private entrance in a quiet and safe location. Minutes from CCSU, UCONN Med Center, I-84, downtown, restaurants and shopping. West Hartford Center is only 10 minutes away. KITCHEN DOESN’T INCLUDED STOVE , fridge, microwave, fully stocked coffee bar. Smart TV, high speed internet and work space are perfect for remote work.

Square 6ix
Inviting, eclectic, and completely private, this single family stand-alone guest house is an intimate and engaging haven. Stylishly decorated with mid-century modern furniture and adorned with pieces from local artists, this quiet home has a separate entrance, separate porch, high ceilings, and a fully equipped kitchen. The guest house is located a walking-block away from the charms of Westville Village and Edgewood Park.
Popular amenities for Cheshire vacation rentals
Other great vacation rentals in Cheshire

Modern cozy, pet friendly

Gemstone: Family-friendly, Close to Yale/Downtown

In-law Private Studio Apartment

UNIQUE and GORGEOUS historic loft style rental

Private studio.

Cozy 1b/1b beautiful views Hopeville Wtby 2nd Flr

Wake Up on the Water, Ski by Noon

Charming Dog Friendly Suite On Scenic Property
Frequently Asked Questions
Do house rentals in Cheshire have free parking?
Absolutely! We offer over 10 house rentals with free parking in Cheshire. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Cheshire have air conditioning?
Absolutely! We offer over 10 house rentals with air conditioning in Cheshire. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Cheshire?
Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with wifi, over 10 homes with free parking, over 10 homes with air conditioning, over 10 homes with a kitchen, and more. Indulge in the ultimate retreat, tailored to your preferences.
Are there vacation rentals with a dedicated workspace in Cheshire?
Yes! Work meets play with ease at over 10 vacation rentals in Cheshire featuring dedicated workspaces. Stay connected and productive in your home away from home.
How much does it cost to stay in house rentals in Cheshire?
Experience the best of Cheshire with our house rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Cheshire have a kitchen?
Absolutely! We offer over 10 house rentals with a kitchen in Cheshire. Enjoy a tailored experience with all the comforts you desire.
Quick stats about vacation rentals in Cheshire

Total vacation rentals
Explore 20 vacation rentals in Cheshire

Nightly prices starting at
Cheshire vacation rentals start at € 26 per night before taxes and fees

Verified guest reviews
Over 530 verified reviews to help you choose

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
20 of Cheshire vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Cheshire rentals

4.7 Average rating
Cheshire stays receive an average rating of 4.7 out of 5 from guests
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