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Cheshire, CT Holiday Rentals
Holiday Rentals
USA
Connecticut (CT)
Cheshire, CT Holiday Rentals
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Cheshire
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Internet or Wifi (44)
Air Conditioning (42)
Washer/Dryer (31)
Other outdoor space (16)
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Kid friendly (37)
Pet friendly (11)
Elder access (1)
Wheelchair access (0)
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Holiday Rental House (24)
Condominium/Apartment (21)
Cabin Holiday Rental (0)
Private Room (0)
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Distinctive Features
Waterfront (2)
Private Chef (0)
Private Beach (0)
Ski In/Ski Out (0)
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Distance from
5 km
Barker Character Comic and Cartoon Museum
Drazen Orchards
Roaring Brook Park
Cheshire Hollow Farm
Bartlem Park
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45 rentals
in Cheshire.
Charming Mountain view country home with porch and deck
Holiday Rental House
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3 bedrooms
4 bathrooms
Sleeps 2
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The following properties within 32 kms of Cheshire match all your filters:
Fun Downtown Location
Condo/Apartment
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3 bedrooms
1 bathroom
Sleeps 6
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Amazing Lakefront Property
4 reviews
Holiday Rental House
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4 bedrooms
4 bathrooms
Sleeps 10
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Sleeps
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Peaceful farm area, on the reservoir, near vineyards
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 2
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Once the old Schools house now a newly furnished Apartment
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 2
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#19 *CozySpace* A tiny place to call home*
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 2
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Charming 3-bedroom house
Condo/Apartment
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0 bedrooms
0 bathrooms
Sleeps 7
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Newly Remodeled 1-BR Close to Everything yet Very Private
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 2
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#4 *BRAND NEW*INCREDIBLE LOCATION *SUPERHOST*
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 5
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Newly Remodeled with deck. Close to town center
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 2
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Fully Furnished 1BR Apartment
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 2
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All New Private and Cozy in great location
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 2
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Artistic Quiet Retreat Ideal For Longer Stays
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 3
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Cozy One Bedroom in Residential Home
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 2
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Remodeled Luxury Stay in the Heart of Waterbury
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 4
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Charming Newly Remodeled 1 Bdr
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 2
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Cozy and stylish apartment in central meriden
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 4
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Oh La La!: Home away from home
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 2
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A Peaceful Atmosphere
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 2
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Exhilarating Emerald & Gold Apt! No cleaning fee
Condo/Apartment
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2 bedrooms
1 bathroom
Sleeps 5
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Beautiful place beautiful area
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 4
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Deluxe Master Stay. Office Space. Close To All Essentials & Highways.
Condo/Apartment
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3 bedrooms
1 bathroom
Sleeps 6
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Trendy & Timeless: Home away from home
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 2
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Eclectic & Whimsical themed Apt w/ Free Parking & Pet-Friendly
Condo/Apartment
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2 bedrooms
1 bathroom
Sleeps 4
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As seen on
The Braswell
Condo/Apartment
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2 bedrooms
1 bathroom
Sleeps 6
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As seen on
#12 *RELAX* *SINGLE FAMILY HOME*GREAT LOCATION*
Holiday Rental House
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3 bedrooms
1 bathroom
Sleeps 8
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Short stay gem near Quinnipiac University
Holiday Rental House
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3 bedrooms
1 bathroom
Sleeps 6
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Luxurious, Spacious Apartment. Free Parking, Close By to Highways and Essentials
Condo/Apartment
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3 bedrooms
1 bathroom
Sleeps 6
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#9 - *STUNNING*RENOVATED* *4BR HOUSE*
Holiday Rental House
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4 bedrooms
1 bathroom
Sleeps 10
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Luxury King Suite in Waterbury. 3 Bedroom. Essentials Close-By,
Condo/Apartment
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3 bedrooms
1 bathroom
Sleeps 5
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Majestic Luxury! Stunning Home Away From Home, Deck & Grill #1
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
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Family, pet friendly downtown New England charmer. Mins from Yale, Choate, QU.
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
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Luxury Meets Tranquility! New Stunning Home Away From Home, Patio & Grill - #2
Holiday Rental House
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3 bedrooms
1 bathroom
Sleeps 6
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Central & Chic Apt Sleeps 7 (2 kings, 2 full beds) no cleaning fee
Condo/Apartment
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3 bedrooms
1 bathroom
Sleeps 7
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#23 *COMFORT & LUXURY* 3 BR/2 BA House
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
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The Connecticut Chalet - On 5 Acres!
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
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Cozy New England home near Quinnipiac Yale
Holiday Rental House
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4 bedrooms
2 bathrooms
Sleeps 9
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Lakefront Home, Close to Mt Southington!
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 8
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Upscale Waterbury Retreat w/ Indoor Hot Tub!
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
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Connecticut Vacation Home Rental w/ Private Pool!
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 5
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#16 *A COZY GETAWAY* 4BED/3BATH HOME W/ FIRE PIT
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 11
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Elegant Middlefield Getaway w/ Game Room!
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 8
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Luxury Colonial near Hiking Trail
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 8
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Sleeping Giant Getaway w/ Swim Spa/Tonal/Peloton
Holiday Rental House
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5 bedrooms
2 bathrooms
Sleeps 9
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7 bedroom mansion with Elevator
Holiday Rental House
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7 bedrooms
6 bathrooms
Sleeps 12
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1
Showing results 1-45 of 45
Frequently Asked Questions about Cheshire
Do any holiday rentals in Cheshire have a pool?
Yes, here are some popular holiday rentals in Cheshire that have a pool:
Charming Mountain view country home with porch and deck
Fun Downtown Location
Amazing Lakefront Property
See all holiday rentals with a pool in Cheshire on Tripadvisor
Do any holiday rentals in Cheshire have internet access?
Yes, here are some popular holiday rentals in Cheshire that have internet access:
Charming Mountain view country home with porch and deck
Fun Downtown Location
Amazing Lakefront Property
See all holiday rentals in Cheshire on Tripadvisor
What are the best pet friendly rentals in Cheshire?
The best pet friendly rentals in Cheshire are:
Charming Mountain view country home with porch and deck
#19 *CozySpace* A tiny place to call home*
#4 *BRAND NEW*INCREDIBLE LOCATION *SUPERHOST*
See all pet friendly holiday rentals in Cheshire on Tripadvisor
What are some great rentals in Cheshire that are kid friendly?
Some of the most popular kid friendly rentals in Cheshire are:
Charming Mountain view country home with porch and deck
Fun Downtown Location
Amazing Lakefront Property
See all kid friendly holiday rentals in Cheshire on Tripadvisor
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