Vacation Rentals in Cheshire, CT

Charming Mountain View Home

No reviews

·
Cheshire
·
4 br
·
Sleeps 9
·
Ski In Ski Out · Oven · Outdoor Space ·
From
$317/night
Check availability
Property
Apartment · 4 Beds · 3 baths
Amenities
Ski In Ski Out
Oven
On Site Laundry
Assigned Parking
Fireplace
Dishwasher
Hardwood Floor
Carpet
Other spaces
Kitchen, Workspace
Charming Mountain View Country House close to hiking trails waterfall

No reviews

·
Cheshire
·
4 br
·
Sleeps 8
·
Kitchen · In Unit Laundry · Air Conditioning ·
From
$257/night
Check availability
Property
House · 4 Beds · 3 baths
Amenities
In Unit Laundry
Air Conditioning
Furnished
Wifi
Other spaces
Kitchen
Holiday Inn - Cheshire - Southington, an IHG Hotel
7.8

Very good

·
Cheshire
·
1 br
·
Sleeps 4
·
Pool · Smoking Allowed · On Site Laundry ·
From
$81/night
Check availability
Property
Hotel · 1 Bed
Amenities
Pool
Smoking Allowed
On Site Laundry
Assigned Parking
Hardwood Floor
Carpet
Free Parking
Air Conditioning
Other spaces
Workspace
Charming Mountain view country home with porch and deck

No reviews

·
Cheshire
·
3 br
·
Sleeps 2
·
Mountains · Outdoor Space · Fireplace ·
From
$285/night
Check availability
Property
House · 3 Beds · 4 baths
Amenities
Mountains
Fireplace
Dishwasher
In Unit Laundry
Air Conditioning
Furnished
Wifi
Garage Parking
Showing 1 - 4 of 4 results
Expand your search criteria to see more vacation rentals near Cheshire.

Explore more stays nearby

NEW! Lakefront Home, Close to Mt Southington!
10

Excellent

·
Wolcott
·
3 br
·
Sleeps 8
·
Ceiling Fan · Lake · Waterfront ·
From
$192/night
Check availability
Property
House · 3 Beds · 2 baths
Amenities
Ceiling Fan
Lake
Waterfront
Oven
On Site Laundry
Fireplace
Dishwasher
In Unit Laundry
Other spaces
Kitchen, Workspace
Exhilarating Emerald & Gold Apt!

No reviews

·
Wallingford
·
2 br
·
Sleeps 5
·
Oven · Dishwasher · Kitchen ·
From
$334/night
Check availability
Property
Apartment · 2 Beds · 1 bath
Amenities
Oven
Dishwasher
In Unit Laundry
Air Conditioning
Furnished
Wifi
Other spaces
Kitchen
The house on the hill

No reviews

·
Hamden
·
4 br
·
Sleeps 8
·
Mountains · Oven · Fireplace ·
From
$347/night
Check availability
Property
House · 4 Beds · 2 baths
Amenities
Mountains
Oven
Fireplace
Dishwasher
In Unit Laundry
Furnished
Wifi
Other spaces
Kitchen
NEW! Lakefront Home, Close to Mt Southington!

No reviews

·
Wolcott
·
3 br
·
Sleeps 8
·
Ceiling Fan · Toiletries · Garden ·
From
$155/night
Check availability
Property
House · 3 Beds · 2 baths
Amenities
Ceiling Fan
Toiletries
Lake
Waterfront
Central Heat
Tv
Microwave
Oven
Other spaces
Garden, Kitchen
#25 *MASSIVE 5 BR APT in Downtown Southington*

No reviews

·
Southington
·
5 br
·
Sleeps 10
·
Oven · Fireplace · Dishwasher ·
From
$135/night
Check availability
Property
Apartment · 5 Beds · 1 bath
Amenities
Oven
Fireplace
Dishwasher
In Unit Laundry
Air Conditioning
Furnished
Wifi
Business Center
Other spaces
Kitchen, Workspace
Clean Private room in Downtown Meriden close to public transportations
2

Poor

·
Meriden
·
1 br
·
Sleeps 1
·
Oven · Kitchen · In Unit Laundry ·
From
$60/night
Check availability
Property
House · 1 Bed · 1 bath
Amenities
Oven
In Unit Laundry
Furnished
Wifi
Other spaces
Kitchen
NEW! Woodsy Hamden Condo Near Sleeping Giant!

No reviews

·
Hamden
·
2 br
·
Sleeps 4
·
Ceiling Fan · Balcony · Oven ·
From
$148/night
Check availability
Property
Condo · 2 Beds · 2 baths
Amenities
Ceiling Fan
Oven
On Site Laundry
Dishwasher
In Unit Laundry
Air Conditioning
Furnished
Wifi
Other spaces
Balcony, Kitchen
Eclectic newly renovated 2Br apartment
10

Excellent

·
Meriden
·
2 br
·
Sleeps 3
·
Oven · Kitchen · In Unit Laundry ·
From
$99/night
Check availability
Property
Apartment · 2 Beds · 1 bath
Amenities
Oven
In Unit Laundry
Air Conditioning
Furnished
Wifi
Business Center
Other spaces
Kitchen

The best of Zumper, delivered

Be the first to hear about new listings matching your search.

Email
By clicking submit, I accept Zumper's Terms and Conditions, Privacy Policy, and Community Values.
Super Clean Beautifully Decorated House 10 mins from Yale

No reviews

·
North Haven
·
4 br
·
Sleeps 9
·
Oven · Dishwasher · Kitchen ·
From
$205/night
Check availability
Property
House · 4 Beds · 2 baths
Amenities
Oven
Dishwasher
In Unit Laundry
Air Conditioning
Furnished
Wifi
Garage Parking
Other spaces
Kitchen, Workspace
Beautiful place beautiful area

No reviews

·
North Haven
·
3 br
·
Sleeps 4
·
Pool · In Unit Laundry · Furnished ·
From
$299/night
Check availability
Property
House · 3 Beds · 2 baths
Amenities
Pool
In Unit Laundry
Furnished
Wifi
Swimming Pool
Artistic Quiet Retreat Ideal For Longer Stays
10

Excellent

·
Meriden
·
1 br
·
Sleeps 3
·
Oven · On Site Laundry · Kitchen ·
From
$110/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Oven
On Site Laundry
In Unit Laundry
Air Conditioning
Furnished
Wifi
Business Center
Other spaces
Kitchen
Charming Newly Remodeled 1 Bdr

No reviews

·
Meriden
·
1 br
·
Sleeps 2
·
Fitness Center · Kitchen · In Unit Laundry ·
From
$89/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Fitness Center
In Unit Laundry
Air Conditioning
Furnished
Wifi
Business Center
Other spaces
Kitchen
Deluxe Master Stay. Office Space. Close To All Essentials & Highways.

No reviews

·
Waterbury
·
2 br
·
Sleeps 6
·
In Unit Laundry · Air Conditioning · Furnished ·
From
$119/night
Check availability
Property
Apartment · 2 Beds · 1 bath
Amenities
In Unit Laundry
Air Conditioning
Furnished
Wifi
Once the old Schools house now a newly furnished Apartment
9

Excellent

·
Wallingford
·
1 br
·
Sleeps 2
·
Oven · Kitchen · In Unit Laundry ·
From
$96/night
Check availability
Property
House · 1 Bed · 1 bath
Amenities
Oven
In Unit Laundry
Air Conditioning
Furnished
Wifi
Other spaces
Kitchen
Eclectic & Whimsical themed Apt w/ Free Parking & Pet-Friendly

No reviews

·
Wallingford
·
2 br
·
Sleeps 4
·
High Ceilings · Oven · Kitchen ·
From
$195/night
Check availability
Property
Apartment · 2 Beds · 1 bath
Amenities
High Ceilings
Oven
Free Parking
In Unit Laundry
Air Conditioning
Furnished
Wifi
Other spaces
Kitchen, Workspace
NEW! Upscale Waterbury Retreat w/ Indoor Hot Tub!
10

Excellent

·
Waterbury
·
3 br
·
Sleeps 6
·
Balcony · Oven · Fireplace ·
From
$387/night
Check availability
Property
House · 3 Beds · 2 baths
Amenities
Oven
Fireplace
Dishwasher
In Unit Laundry
Air Conditioning
Furnished
Wifi
Residents Lounge
Other spaces
Balcony, Kitchen, Workspace
Getaway Suite - Near QU, Yale and New Haven

No reviews

·
Hamden
·
2 br
·
Sleeps 6
·
Furnished ·
From
$69/night
Check availability
Property
Apartment · 2 Beds · 1 bath
Amenities
Furnished
Cozy New England home near Quinnipiac Yale

No reviews

·
Hamden
·
4 br
·
Sleeps 8
·
Oven · Kitchen · Workspace ·
From
$206/night
Check availability
Property
House · 4 Beds · 2 baths
Amenities
Oven
In Unit Laundry
Air Conditioning
Furnished
Wifi
Other spaces
Kitchen, Workspace
Luxury Colonial near Hiking Trail
10

Excellent

·
Meriden
·
4 br
·
Sleeps 8
·
Oven · Kitchen · In Unit Laundry ·
From
$230/night
Check availability
Property
House · 4 Beds · 3 baths
Amenities
Oven
In Unit Laundry
Air Conditioning
Furnished
Wifi
Other spaces
Kitchen
Luxurious, Spacious Apartment. Free Parking, Close By to Highways and Essentials
9.3

Excellent

·
Waterbury
·
2 br
·
Sleeps 5
·
Oven · Kitchen · Workspace ·
From
$82/night
Check availability
Property
Apartment · 2 Beds · 1 bath
Amenities
Oven
In Unit Laundry
Air Conditioning
Furnished
Wifi
Storage
Other spaces
Kitchen, Workspace
Home > Connecticut Vacation Rentals > Cheshire Vacation Rentals
Updated: March 21, 2023

Learn about vacation rentals in

Cheshire

Explore 5 vacation rentals near Cheshire, Connecticut. Whether you’re a tourist or on a staycation, there’s plenty of things to do and restaurants to try around the city. If you’re looking to take a trip to Cheshire, you can see photos of Cheshire vacation rentals, view amenities and features, browse by specific property types, and more. Use our interactive map to find Cheshire vacation rentals in specific areas. Whether you’re looking for a Cheshire staycation, weekend getaway, or a long vacation, we’ve got you covered. Use the date filters at the top to select your travel dates and view availability. The lowest vacation rental price in Cheshire is $81 per night and the highest price is $317 per night.
4 of the vacation rentals near Cheshire are houses. The average bathroom count for a vacation house near Cheshire is 3. The average price for vacation houses near Cheshire is $286 per night. There are 3 vacation homes under this price. The most common amenities for vacation rentals near Cheshire are: furnished, wifi, and air conditioning. To find vacation properties that might be a good option for large groups or families, use our filters for bedroom count, bathroom count and more.

1 bed rentals

1 available

3 bed rentals

2 available

4+ bed rentals

2 available

Getting around Cheshire

Walking

4/10
Fewer daily needs are within walking distance (unless you’re up for a challenge).

Car

9/10
Commuting is easy with multiple accessible routes and plenty of parking.

Transit

2/10
FYI, there are little to no public transit options within walking distance.

Points of interest in Cheshire

Groceries

4/10
At least one grocery store within a 30-minute walk

Shopping

4/10
Some shops within walking distance

Cafes

3/10
Few or no cafés within walking distance

Restaurants

4/10
Some restaurants within walking distance

Nightlife

2/10
Few or no bars within walking distance

Vacation Rentals in Cheshire, CT FAQ

How many vacation rentals in Cheshire are available?

There are currently 5 vacation rentals in Cheshire available. Our vacation rentals in Cheshire include nightly rentals, weekend rentals, weekly rentals, and monthly rentals.

Are there any pet friendly vacation rentals in Cheshire?

Yes, right now there are 1 pet friendly vacation rentals in Cheshire. A pet friendly vacation rental in Cheshire means a rental home that is dog friendly or cat friendly. Some pet friendly homes may accommodate other types of pets, as well. Contact the listing agent for any pet related inquiries.

Are there any vacation rentals in Cheshire with a pool?

Yes there are vacation rentals with a pool available in Cheshire, CT. View more detailed vacation spots on Vacations by Zumper.

Are there any vacation rentals in Cheshire with internet access?

As of March 21, 2023, there are vacation rentals with internet access available in Cheshire, Connecticut. Check out more enjoyable destinations on Vacations by Zumper.

City Vacation Rentals In Connecticut

Vacation Rentals Woodbridge, CT