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Compare 351 Vacation Homes in Cheshire with updated reviews, rates, and availability.

"This is a beautiful property. When we arrived, everything was perfect. It is completely stocked, including games for the family, and an unbelievable view of the lake. Communication with the homeowner was wonderful and we definitely plan to come back. We highly recommend this beautiful, clean and well kept home on the lake!."

"We needed a place for our family of 6 to stay while visiting family in the area. This place was exactly what we needed, as advertised, and the owner was quick with communications. We would definitely stay here again!"

"Great location "

"Beautiful view from the upstairs window. I enjoyed the pellet stove on the cold days."

"The house easily accommodated my friends and family for a weekend of relaxation. The place is very spacious with all modern amenities. We especially loved waking up to the gorgeous view of the lake in the back. The views were breathtaking. Would definitely consider going back. "

AED 3,473 total

includes taxes & fees

6 Apr - 7 Apr

"This is a neat, clean and lovely little place that perfectly suited our needs. It had all the amenities we needed for our short stay. Jose was a gracious host, answering all of my questions promptly - even the one about the mattresses which were incredibly comfortable! "

AED 1,152 total

includes taxes & fees

4 Apr - 5 Apr

"The home was beautiful. Some of the furniture was old and it shouldn’t be sat on plenty of room for family plenty of games to play beautiful electricfireplace,beautiful view! The beds were uncomfortable and a few things needed to be updated."

Beach nearby, sun loungers, beach towels

"This property is beautiful and the house is spacious and well equipped for a wonderful stay. The host was attentive and easy to contact when it was necessary. Such a fantastic choice for a stay in a delightful town. "

"It was a great house to host our family for Thanksgiving dinner! "

"The house was exactly what I needed to be close to my son at Yale for a few days. The house and neighborhood was great for our dog. The host had just about everything we needed for a comfortable stay, and the welcome snacks and extra toilet paper, etc. was welcomed. The only thing I would say is the shower in the bathroom was very small…think RV shower, and there didn’t appear to be a shower head, so the water came out really hard like a water hose. But other than that, nice little house in a...

"Very nice clean house. Felt like coming home after work"

"I had a great stay in West Hartford with my 17 year old daughter. The property is conveniently located in West Hartford and also a quick drive to the University of Hartford, which we visit for an Art School event. The host is fantastic, provides great communication and simple check-in/ check-out process. The parking spot is ample and the home was comfortable and just as described. We will book this place again and highly recommend! "

"We came to the area for a long weekend event at Wesleyan University. I had never booked through VRBO and was not familiar with the process. From my first communication with Gilbert I felt like I was going to visit family. He was amazing to communicate with provided information about the area and the process and was super accommodating when he learned our flight was arriving early. From the moment we stepped through the door we knew our stay would be special. The home is beautiful, beds...

AED 891 total

includes taxes & fees

28 Apr - 29 Apr

"our annual girls (5) trip took us to Branford, CT this year. It was awesome to have a private beach access even though we couldn’t get in the water, but it was great for strolls and shell collecting. Would definitely do better with a second bathroom, but we managed just fine. Overall, it’s a nice little place to stay for a getaway. My only issue is not with the hosts or place, but with one of the fees and the checkout process. However, it does not take away from our stay. "

On the beach, sun loungers, beach towels

"The Arts and Crafts home was more beautiful than the pictures reflected! We loved all of the details in the woodwork, hidden little corners, tons of space to spread out and wonderful places to gather together. Having recently sold our "family home" we were thrilled to find this home in which to have a mini- family reunion. The kitchen was incredibly well-stocked- from serving platters to garlic powder to paper towels...We had everything we needed. The gas fireplace created a beautiful focal...

"Communication was top notchThe property was very well appointed and perfect for a family gathering The most important part was the accessibility of the bathroom and bedroom for my mom who has mobility issues I was worried about the half step from bedroom to bathroom but I put pick lights on floor to remind her to step upLocation was perfect Especially loved visiting pez!"

"The house was great! Beautiful ocean front property with beachy vibes all throughout the neighborhood and interior of the home. The host was extremely clear on directions and provided amazing instructions. Very comfortable stay! "

"My family and I had a wonderful week long stay at this beautiful cozy home. Plenty of amenities in the house to make everyone happy. The convenience of 3 bathroom with a large family was wonderful. The location was great for everything i meeded. The park next door is a great addition to get the kids outside. Thankbyou so much for the great communication and hospitality "

"Considering that area does not have convenient hotels, this location was perfect for the event we attended. It was nice of them to vacate their home so we could stay - though we wish that would have been communicated. There is no extra room with twin beds - at least not functional. The property is nice. Whomever took the pictures did a great job. It worked for us for the short time we were in the area."

"Clean house in a convenient and quiet location. Close to many store and restaurants. House was well equipped. Sauna was a nice extra. Only complaints are that the bed in the third bedroom is not for adults and the towels need to be replaced. We would definitely rent the house again when in the area. "

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Fridge, microwave, coffee/tea maker, cookware/dishes/utensils

"Good stay. "

AED 384 total

includes taxes & fees

14 Apr - 15 Apr

"having previously rented VRBO properties in Palm Springs, West Palm Beach & Ft. Lauderdale I can confirm this property is exceptional. The studio has 1st tier amenities, waterfront location & in addition the hosts provided most welcoming foods and snacks, an overall wonderful experienceJimBrooklyn, NY"

Honeymoon Apartment, 3 Bedrooms, Kitchen | In-room dining

"I was completely satisfied with my stay. Apartment had wonderful amenities and an amazing view. Great location near downtown restaurants too."

Recent reviews of Cheshire hotels

Best Western Executive Hotel Of New Haven - West Haven

5/5 Excellent

"Good value"

A verified traveler stayed at Best Western Executive Hotel Of New Haven - West Haven

Posted 1 day ago

5/5 Excellent

"This is absolutely the best hotel I’ve stayed at in my entire 67 years. The room was exceptionally clean, and there was absolutely none of the “hotel room smell” we all know about. I was astounded by the cleanliness and freshness of the room. The bedding was clean and fresh. The staff was very nice and accommodating. The towels were quite rough on the skin I mean REALLY rough. I found myself wishing I had brought my own. Parking wasn’t bad. There’s a pedestrian walkway going from the parking lot (across the street) to the hotel. I would absolutely recommend this hotel to anybody. These people are doing it right. It was a pleasure to stay here."

A verified traveler from Danbury stayed at New Haven Hotel

Posted 2 days ago

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Search Vacation Homes in Cheshire

Plan, book, stay with confidence

Check prices for these dates

Compare 351 Vacation Homes in Cheshire with updated reviews, rates, and availability.

Lakeside luxury: beautiful, relaxing 4 bedroom home

Lakeside luxury: beautiful, relaxing 4 bedroom home

Stylish & Luxurious 3 BDR Home with Play Station

Stylish & Luxurious 3 BDR Home with Play Station

New Madison beach house - Ocean front- Great views- booking Summer 2025

New Madison beach house - Ocean front- Great views- booking Summer 2025

Lakefront Getaway w Hot Tub, Game Room & Views - Pet-Friendly

Lakefront Getaway w Hot Tub, Game Room & Views - Pet-Friendly

Luxe Lake House in Connecticut

Luxe Lake House in Connecticut

Tranquil Litchfield Connecticut Retreat".

Tranquil Litchfield Connecticut Retreat".

Grammy's Lake House w/ Private Waterfront Access

Grammy's Lake House w/ Private Waterfront Access

Steps to beach! Custom-built house with panoramic ocean views, wrap-around deck.

Steps to beach! Custom-built house with panoramic ocean views, wrap-around deck.

Home away from home Hot Tub and Pool in Middletown home of Wesleyan university

Home away from home Hot Tub and Pool in Middletown home of Wesleyan university

7Mins to Yale I ENTIRE HOUSE I Large fenced yard I King bed I 3BR I Group Gather

7Mins to Yale I ENTIRE HOUSE I Large fenced yard I King bed I 3BR I Group Gather

Charming 3BR Hilltop House, Newly Remodeled with Arcade

Charming 3BR Hilltop House, Newly Remodeled with Arcade

WeHa Oak Haven

WeHa Oak Haven

Family Stays: Middletown, CT

Family Stays: Middletown, CT

Beautiful 4BR Beach House with Private Beach Access.

Beautiful 4BR Beach House with Private Beach Access.

Beach Front Arts & Crafts House With Gorgeous Views Of The Sound

Beach Front Arts & Crafts House With Gorgeous Views Of The Sound

Ocean Front Beach House with Private Beach Access - Newly Renovated!

Ocean Front Beach House with Private Beach Access - Newly Renovated!

Direct Waterfront Private Beach Escape

Direct Waterfront Private Beach Escape

Cozy dog friendly updated house in quiet village adjacent to park

Cozy dog friendly updated house in quiet village adjacent to park

Litchfield County Four Season Country Paradise

Litchfield County Four Season Country Paradise

Charming West Haven Home - Walk to Beach!

Charming West Haven Home - Walk to Beach!

Other property types in Cheshire

New Haven Village Suites

New Haven Village Suites

Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub

Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub

Luxury Furnished Apartments by Hyatus Downtown at Yale

Luxury Furnished Apartments by Hyatus Downtown at Yale

Recent reviews of Cheshire hotels

Recent reviews of Cheshire hotels

Best Western Executive Hotel Of New Haven - West Haven

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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