113+ Private Villas and Holiday Rentals in Cheshire |
Cheshire Holiday Rentals
House
- Connecticut
- ·
- Yalesville
- 8.30 mi to center
10.0Exceptional
(29 Reviews)
3 Bedrooms
2 Baths
8 Guests
1176 ft²
Fireplace/Heating
Balcony/Terrace
Kitchen
Parking
د.إ.1,658/Night
7 Nights - د.إ.11,605
House
- Connecticut
- ·
- Yalesville
- 8.30 mi to center
10.0Exceptional
(1 Review)
3 Bedrooms
2 Baths
8 Guests
1173.27 ft²
- Fireplace/Heating
- Parking
Internet
Child Friendly
د.إ.1,950/Night
7 Nights - د.إ.13,651
Cottage
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
- Fireplace/Heating
Ocean View
View- Kitchen
د.إ.2,189/Night
7 Nights - د.إ.15,322
Apartment
10.0Exceptional
(14 Reviews)
2 Bedrooms
1 Bath
4 Guests
800 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
د.إ.556/Night
7 Nights - د.إ.3,893
House
8.0Excellent
(1 Review)
4 Bedrooms
3 Baths
3 Guests
2400.35 ft²
- Parking
Air Conditioner- Internet
- Child Friendly
د.إ.815/Night
7 Nights - د.إ.5,707
House
- Connecticut
- ·
- Yalesville
- 0.06 mi to center
10.0Exceptional
(10 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
د.إ.590/Night
7 Nights - د.إ.4,132
House
- New Haven
- ·
- Plantsville
- 0.83 mi to center
10.0Exceptional
(4 Reviews)
5 Bedrooms
2 Baths
10 Guests
2002 ft²
- Fireplace/Heating
Pet Friendly- Kitchen
- Parking
د.إ.1,887/Night
7 Nights - د.إ.13,206
House
- New Haven
- ·
- Plantsville
- 1.91 mi to center
10.0Exceptional
(3 Reviews)
3 Bedrooms
2 Baths
6 Guests
1500 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
د.إ.2,031/Night
7 Nights - د.إ.14,216
Apartment
- Connecticut
- ·
- Yalesville
- 0.05 mi to center
10.0Exceptional
(3 Reviews)
1 Bedroom
1 Bath
2 Guests
800 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
د.إ.1,064/Night
7 Nights - د.إ.7,448
Luxury Holiday Rentals in Cheshire
Over 104+ Luxury Holiday Rentals in or Near Cheshire
House
- New Haven
- ·
- Plantsville
- 0.24 mi to center
5 Bedrooms
3 Baths
10 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
د.إ.8,373/Night
7 Nights - د.إ.58,613
House
10.0Exceptional
(11 Reviews)
5 Bedrooms
2 Baths
8 Guests
2500 ft²
Private Pool
Hot Tub- Fireplace/Heating
Pool
د.إ.3,022/Night
7 Nights - د.إ.21,154
Cottage
1 Bedroom
1 Bath
Spa- Fireplace/Heating
- Pet Friendly
- Kitchen
د.إ.2,707/Night
7 Nights - د.إ.18,946
Apartment
8.0Excellent
(1 Review)
4 Bedrooms
2 Baths
10 Guests
2992 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
د.إ.2,436/Night
7 Nights - د.إ.17,055
House
- Hartford
- ·
- Southington
- 2.20 mi to center
9.0Exceptional
(7 Reviews)
1 Bedroom
3 Baths
15 Guests
2034 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
د.إ.2,225/Night
7 Nights - د.إ.15,575
Cabin
8.0Excellent
(1 Review)
3 Bedrooms
2 Baths
6 Guests
1884 ft²
- Pet Friendly
- Kitchen
- Parking
- Air Conditioner
د.إ.2,207/Night
7 Nights - د.إ.15,447
New
Apartment
- New Haven
- ·
- Wallingford Center
- 0.33 mi to center
5 Bedrooms
2 Baths
8 Guests
- Hot Tub
- Fireplace/Heating
- Pet Friendly
- Kitchen
د.إ.2,077/Night
7 Nights - د.إ.14,536
House
9.0Exceptional
(2 Reviews)
4 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
د.إ.1,832/Night
7 Nights - د.إ.12,824
House
- Hartford
- ·
- Southington
- 1.29 mi to center
2 Bedrooms
2 Baths
14 Guests
2347 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
د.إ.1,780/Night
7 Nights - د.إ.12,464
Top-Rated Holiday Rentals with a Pool in Cheshire
Over 6+ The Best Private Villas and Holiday Rentals in Cheshire with a Pool
Hotel
8.4Excellent
(1009 Reviews)
1 Bath
- Pool
Breakfast- Kitchen
- Parking
د.إ.498/Night
7 Nights - د.إ.3,489
Hotel
8.0Excellent
(313 Reviews)
3 Baths
322.92 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Breakfast
د.إ.579/Night
7 Nights - د.إ.4,054
Apartment
5.0Average
(2 Reviews)
2 Bedrooms
1 Bath
4 Guests
900 ft²
- Fireplace/Heating
- Pool
- Kitchen
- Parking
د.إ.546/Night
7 Nights - د.إ.3,823
House
2.0Average
(1 Review)
3 Bedrooms
2 Baths
4 Guests
- Fireplace/Heating
- Pool
- Kitchen
- Parking
د.إ.1,338/Night
7 Nights - د.إ.9,365
House
- Connecticut
- ·
- Yalesville
- 2.06 mi to center
5 Bedrooms
3 Baths
16 Guests
2448 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
د.إ.2,638/Night
7 Nights - د.إ.18,469
Apartment
3 Bedrooms
2 Baths
6 Guests
1500 ft²
- Fireplace/Heating
- Pool
- Pet Friendly
- Kitchen
د.إ.1,107/Night
7 Nights - د.إ.7,745
Pet-Friendly Holiday Rentals in Cheshire
Over 26+ Pet-Friendly Holiday Rentals in or Near Cheshire
Apartment
10.0Exceptional
(1 Review)
4 Bedrooms
1 Bath
10 Guests
1991 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
د.إ.1,408/Night
7 Nights - د.إ.9,857
Apartment
7.8Very Good
(4 Reviews)
2 Bedrooms
1 Bath
5 Guests
1302.43 ft²
- Balcony/Terrace
- Pet Friendly
- Parking
- Air Conditioner
د.إ.802/Night
7 Nights - د.إ.5,612
House
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Air Conditioner
د.إ.1,110/Night
7 Nights - د.إ.7,771
House
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Air Conditioner
د.إ.570/Night
7 Nights - د.إ.3,988
Apartment
7.0Very Good
(4 Reviews)
3 Bedrooms
1 Bath
7 Guests
1399.31 ft²
- Pet Friendly
- Parking
- Air Conditioner
- Internet
د.إ.757/Night
7 Nights - د.إ.5,303
Apartment
- Hartford
- ·
- Southington
- 1.55 mi to center
9.8Exceptional
(9 Reviews)
3 Bedrooms
2 Baths
6 Guests
1206 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
د.إ.1,410/Night
7 Nights - د.إ.9,872
House
9.6Exceptional
(4 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
د.إ.1,456/Night
7 Nights - د.إ.10,195
House
9.2Exceptional
(12 Reviews)
3 Bedrooms
1 Bath
6 Guests
1500 ft²
- Hot Tub
- Spa
- Fireplace/Heating
- Balcony/Terrace
د.إ.1,286/Night
7 Nights - د.إ.9,001
House
- New Haven
- ·
- Plantsville
- 1.37 mi to center
6.8Good
(5 Reviews)
3 Bedrooms
2 Baths
8 Guests
2271 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
د.إ.1,652/Night
7 Nights - د.إ.11,565
Large Holiday Rentals and Private Villas in Cheshire
Over 4+ Large Holiday Rentals and Private Villas in or Near Cheshire
House
- New Haven
- ·
- Plantsville
- 1.08 mi to center
6 Bedrooms
3 Baths
15 Guests
- Pet Friendly
- Kitchen
- Air Conditioner
- Child Friendly
د.إ.1,183/Night
7 Nights - د.إ.8,278
Cabin
6.6Good
(141 Reviews)
60 Bedrooms
10 Baths
24 Guests
274.48 ft²
- Pet Friendly
- Parking
- Air Conditioner
- Internet
د.إ.276/Night
7 Nights - د.إ.1,932
House
- New Haven
- ·
- Plantsville
- 0.83 mi to center
10.0Exceptional
(3 Reviews)
5 Bedrooms
2 Baths
10 Guests
2002 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
د.إ.2,219/Night
7 Nights - د.إ.15,531
House
- Hartford
- ·
- Southington
- 2.20 mi to center
4 Bedrooms
3 Baths
11 Guests
2034.38 ft²
- Fireplace/Heating
- View
- Air Conditioner
- Internet
د.إ.1,141/Night
7 Nights - د.إ.7,991
Wheelchair Accessible Holiday Homes in Cheshire
Over 9+ Wheelchair Accessible Holiday Homes in or Near Cheshire
Apartment
- New Haven
- ·
- Wallingford Center
- 0.30 mi to center
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
2 Guests
500 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
د.إ.1,071/Night
7 Nights - د.إ.7,499
Apartment
- New Haven
- ·
- Wallingford Center
- 0.86 mi to center
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
2 Guests
600 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
د.إ.1,071/Night
7 Nights - د.إ.7,499
Apartment
- New Haven
- ·
- Wallingford Center
- 0.86 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
2 Guests
850 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
د.إ.1,071/Night
7 Nights - د.إ.7,499
Apartment
- New Haven
- ·
- Wallingford Center
- 0.51 mi to center
9.8Exceptional
(8 Reviews)
1 Bedroom
1 Bath
2 Guests
500 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
د.إ.1,064/Night
7 Nights - د.إ.7,448
Apartment
- New Haven
- ·
- Wallingford Center
- 0.34 mi to center
9.8Exceptional
(8 Reviews)
1 Bedroom
1 Bath
2 Guests
480 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
د.إ.613/Night
7 Nights - د.إ.4,293
Apartment
- New Haven
- ·
- Wallingford Center
- 0.57 mi to center
9.6Exceptional
(4 Reviews)
1 Bedroom
1 Bath
2 Guests
750 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
د.إ.613/Night
7 Nights - د.إ.4,293
Apartment
- New Haven
- ·
- Wallingford Center
- 0.86 mi to center
6.0Good
(1 Review)
1 Bedroom
1 Bath
2 Guests
860 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
د.إ.1,064/Night
7 Nights - د.إ.7,448
Apartment
- New Haven
- ·
- Wallingford Center
- 0.58 mi to center
1 Bedroom
1 Bath
2 Guests
750 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
د.إ.1,071/Night
7 Nights - د.إ.7,499
Apartment
- New Haven
- ·
- Wallingford Center
- 0.86 mi to center
1 Bedroom
1 Bath
2 Guests
670 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
د.إ.1,064/Night
7 Nights - د.إ.7,448
Cheshire Private Villas and Holiday Homes Under $200
Over 37+ Cheshire Private Villas and Holiday Homes Under $200
Apartment
- Hartford
- ·
- Southington
- 1.19 mi to center
9.8Exceptional
(81 Reviews)
3 Bedrooms
1 Bath
6 Guests
1000 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
د.إ.727/Night
7 Nights - د.إ.5,086
Apartment
6.2Good
(6 Reviews)
2 Bedrooms
1 Bath
6 Guests
1097.92 ft²
- Fireplace/Heating
- Balcony/Terrace
- View
- Pet Friendly
د.إ.731/Night
7 Nights - د.إ.5,119
Hotel
8.4Excellent
(809 Reviews)
1 Bath
- Parking
- Air Conditioner
- Internet
- Child Friendly
د.إ.418/Night
7 Nights - د.إ.2,927
Apartment
9.4Exceptional
(18 Reviews)
2 Bedrooms
1 Bath
4 Guests
950 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
د.إ.688/Night
7 Nights - د.إ.4,818
Apartment
3 Bedrooms
2 Baths
6 Guests
1496.18 ft²
- Fireplace/Heating
- Pet Friendly
- Parking
- Internet
د.إ.477/Night
7 Nights - د.إ.3,342
House
6.0Good
(1 Review)
2 Bedrooms
1 Bath
7 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
د.إ.728/Night
7 Nights - د.إ.5,097
Apartment
6.0Good
(1 Review)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
د.إ.690/Night
7 Nights - د.إ.4,833
Apartment
1 Bedroom
1 Bath
5 Guests
925 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
د.إ.334/Night
7 Nights - د.إ.2,339
Apartment
- Hartford
- ·
- Southington
- 1.01 mi to center
9.6Exceptional
(8 Reviews)
2 Bedrooms
1 Bath
5 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
د.إ.676/Night
7 Nights - د.إ.4,730
Instantly Bookable Holiday Homes in Cheshire
Over 28+ Instantly Bookable Holiday Homes in or Near Cheshire
Apartment
- Connecticut
- ·
- Yalesville
- 0.05 mi to center
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
2 Guests
600 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
د.إ.1,071/Night
7 Nights - د.إ.7,499
House
6.0Good
(2 Reviews)
1 Bedroom
1 Bath
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
د.إ.296/Night
7 Nights - د.إ.2,071
House
9.8Exceptional
(13 Reviews)
3 Bedrooms
2 Baths
6 Guests
1800 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
د.إ.1,568/Night
7 Nights - د.إ.10,981
House
- Hartford
- ·
- Southington
- 1.13 mi to center
9.6Exceptional
(29 Reviews)
3 Bedrooms
1 Bath
6 Guests
1000 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
د.إ.804/Night
7 Nights - د.إ.5,626
House
9.6Exceptional
(8 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
د.إ.1,592/Night
7 Nights - د.إ.11,146
Apartment
- New Haven
- ·
- Wallingford Center
- 0.60 mi to center
9.4Exceptional
(3 Reviews)
1 Bedroom
1 Bath
2 Guests
890 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
د.إ.957/Night
7 Nights - د.إ.6,702
House
- New Haven
- ·
- Wallingford Center
- 0.60 mi to center
9.0Exceptional
(13 Reviews)
1 Bedroom
1 Bath
2 Guests
650 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
د.إ.1,071/Night
7 Nights - د.إ.7,499
Apartment
- Connecticut
- ·
- Yalesville
- 0.05 mi to center
8.8Fabulous
(6 Reviews)
1 Bedroom
1 Bath
2 Guests
702 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
د.إ.1,071/Night
7 Nights - د.إ.7,499
House
- Connecticut
- ·
- Yalesville
- 2.55 mi to center
10.0Exceptional
(2 Reviews)
4 Bedrooms
3 Baths
8 Guests
Skiing- Fireplace/Heating
- Balcony/Terrace
- Kitchen
د.إ.994/Night
7 Nights - د.إ.6,956
Book a Last Minute Place to Stay in Cheshire
About Casai's Private Villas and Holiday Rentals in Cheshire
Discover more than 113 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 674.94 ft², with nightly prices averaging د.إ.1,098.
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.
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Top Accommodation Types in Cheshire
| Type | Count |
|---|---|
| Vacation Homes | 51 |
| Holiday Apartments | 47 |
| Cottages | 2 |
Use these Quick Filters to Find a Holiday Rental in Cheshire
★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Cheshire.
Weather in Cheshire, CT
View the weather forecast for Cheshire before booking your Cheshire Vacation Rentals to confirm your best time to go.
December - February
High 60°F Low 26°F
March - May
High 77°F Low 40°F
June - August
High 91°F Low 64°F
September - November
High 84°F Low 38°F
Top Attractions Around Cheshire, CT
Casai offers a large selection of top attractions around Cheshire . Research things to do on your vacation before you visit Cheshire.
Other Places to Stay in Cheshire, CT
Frequently Asked Questions About Cheshire?
What are the top holiday rentals in Cheshire?
With numerous options available in Cheshire, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Cheshire:
- Lakefront Home, Close to Mt Southington!
- Cozy quite private location that makes you feel like home
- Sleeping Giant Getaway w/Swim Spa/Tonal/Peloton
- Newly Remodeled 1-BR Close to Everything yet Very Private
- #27- Luxury Collection
- Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington
- Fully Furnished 1BR Apartment
- Lakefront Home, Close to Mt Southington!
- Newly Remodeled with deck. Close to town center
- New Railside Residents
Which holiday homes in Cheshire are best for families?
If you're searching for a family-friendly holiday home in Cheshire, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Cheshire:
- Cozy One Bedroom in Residential Home
- Upscale Waterbury Retreat w/Indoor Hot Tub!
- Quality Inn Waterbury East
How many Casai.ae holiday rentals are available in Cheshire?
As of 2026, Casai boasts over 113 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 |
People Also Ask
Finding the best prices in Cheshire
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