Cheshire Holiday Rentals

Compare Villas, Resorts, & Rentals in Cheshire, Connecticut, USA

9.6 (8 Reviews)
2 Bedrooms 5 Guests
|
10.0 (1 Review)
3 Bedrooms 8 Guests
From CA $420 per night
10.0 (1 Review)
1 Bedroom 2 Guests
New
2 Bedrooms 14 Guests
From CA $303 per night
|
7.8 (4 Reviews)
2 Bedrooms 5 Guests
|
10.0 (2 Reviews)
1 Bedroom 2 Guests
10.0 (5 Reviews)
4 Bedrooms 11 Guests
From CA $253 per night
|
7.7 (3 Reviews)
2 Bedrooms 6 Guests
|
New
1 Bedroom 2 Guests
From CA $785 per night
10.0 (4 Reviews)
5 Bedrooms 10 Guests
From CA $287 per night
7.0 (4 Reviews)
3 Bedrooms 7 Guests
10.0 (1 Review)
4 Bedrooms 10 Guests
6.9 (145 Reviews)
60 Bedrooms 24 Guests
|
New
3 Bedrooms 6 Guests
From CA $256 per night
9.8 (77 Reviews)
3 Bedrooms 6 Guests
From CA $479 per night
|
8.1 (363 Reviews)
10 Bedrooms 8 Guests
9.8 (20 Reviews)
3 Bedrooms 6 Guests
|
7.8 (297 Reviews)
158 Bedrooms 36 Guests
9.8 (8 Reviews)
3 Bedrooms 6 Guests
From CA $124 per night
6.4 (366 Reviews)
50 Bedrooms 8 Guests
9.8 (6 Reviews)
3 Bedrooms 6 Guests
|
8.0 (1 Review)
4 Bedrooms 3 Guests
From CA $1,019 per night
8.0 (1 Review)
4 Bedrooms 10 Guests
From CA $388 per night
7.4 (3 Reviews)
3 Bedrooms 6 Guests
From CA $526 per night
6.0 (4 Reviews)
3 Bedrooms 8 Guests
10.0 (8 Reviews)
1 Bedroom 2 Guests
10.0 (2 Reviews)
1 Bedroom 2 Guests
10.0 (2 Reviews)
1 Bedroom 2 Guests
10.0 (1 Review)
1 Bedroom 2 Guests
From CA $243 per night
10.0 (1 Review)
1 Bedroom 4 Guests
10.0 (1 Review)
1 Bedroom 2 Guests
From CA $219 per night
10.0 (1 Review)
1 Bedroom 2 Guests
10.0 (1 Review)
1 Bedroom 2 Guests
From CA $180 per night
10.0 (1 Review)
2 Bedrooms 3 Guests
9.8 (10 Reviews)
2 Bedrooms 4 Guests
|
8.4 (1005 Reviews)
1 Bedroom 2 Guests
New
2 Bedrooms 4 Guests
From CA $158 per night
8.4 (712 Reviews)
1 Bedroom 2 Guests
From CA $148 per night
6.8 (1003 Reviews)
1 Bedroom 2 Guests
New Sweet sparkling clean 1 bedroom
New
1 Bedroom 2 Guests
10.0 (4 Reviews)
3 Bedrooms 6 Guests
10.0 (2 Reviews)
2 Bedrooms 4 Guests
10.0 (1 Review)
1 Bedroom 3 Guests
From CA $227 per night
New
1 Bedroom 4 Guests
From CA $143 per night
New
1 Bedroom 2 Guests
New
3 Bedrooms 6 Guests
10.0 (2 Reviews)
3 Bedrooms 3 Guests
10.0 (1 Review)
2 Bedrooms 5 Guests
From CA $188 per night
10.0 (1 Review)
1 Bedroom 2 Guests
5.0 (5 Reviews)
4 Bedrooms 8 Guests
5.0 (2 Reviews)
2 Bedrooms 4 Guests
New
2 Bedrooms 4 Guests
6.6 (527 Reviews)
1 Bedroom 2 Guests
From CA $840 per night
10.0 (3 Reviews)
5 Bedrooms 10 Guests
From CA $83 per night
4.6 (25 Reviews)
1 Bedroom 2 Guests

About Casai's Private Villas and Holiday Rentals in Cheshire

Discover more than 104 vacation rentals available in Cheshire. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Cheshire.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Cheshire, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Cheshire. On average, places to stay near Cheshire offer 600.9 ft², with nightly prices averaging CA $380.

With Casai, finding and comparing holiday rentals in Cheshire is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.

Frequently Asked Questions About Cheshire?

What are the top holiday rentals in Cheshire?

How many Casai.ca holiday rentals are available in Cheshire?

As of 2025, Casai boasts over 104 properties listed in the Cheshire area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Cheshire.

Nearby Neighborhood (1)

Neighborhood Property Count
Milldale Vacation Rentals in New Haven, Connecticut 38