Find Vacation Rentals in Cheshire

We have 15 properties to choose from
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Popular Cheshire Vacation Rentals

Find the perfect Cheshire vacation rental

House Cheshire
from $324 per night
2 guests ∙ 3 bedrooms

House

Cheshire, New Haven County, Connecticut, United States
Details
Motel Cheshire
from $138 per night
Motel ∙ 2 guests ∙ 1 bedroom

23 m² Motel

4.2
Very good(631 ratings)
Cheshire, New Haven County, Connecticut, United States
Details
Motel Cheshire
from $94 per night
Motel ∙ 6 guests ∙ 1 bedroom

Cheshire Welcome Inn

3.9
Good
Cheshire, New Haven County, Connecticut, United States
Details
House Cheshire
from $564 per night
House ∙ 10 guests ∙ 4 bedrooms

316 m² House

4.9
Outstanding(33 ratings)
Cheshire, New Haven County, Connecticut, United States
Details
House Cheshire
from $301 per night
House ∙ 6 guests ∙ 3 bedrooms

167 m² House

5.0
Outstanding(1 rating)
Cheshire, New Haven County, Connecticut, United States
Details
House Cheshire
from $618 per night
11 guests ∙ 4 bedrooms

House

5.0
Outstanding(48 ratings)
Cheshire, New Haven County, Connecticut, United States
Details
Cottage Cheshire
from $153 per night
Cottage ∙ 2 guests ∙ 1 bedroom

74 m² Cottage

4.8
Outstanding(144 ratings)
Cheshire, New Haven County, Connecticut, United States
Details
Cottage Cheshire
from $240 per night
Cottage ∙ 4 guests ∙ 1 bedroom

70 m² Cottage

4.9
Outstanding(15 ratings)
Cheshire, New Haven County, Connecticut, United States
Details
House Cheshire
from $335 per night
House ∙ 8 guests ∙ 3 bedrooms

109 m² House

5.0
Outstanding(5 ratings)
Cheshire, New Haven County, Connecticut, United States
Details
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Pet-Friendly Homes and Apartments

House  Cheshire
from $360 per night
House ∙ 6 guests ∙ 3 bedrooms

139 m² House

4.8
Outstanding(4 ratings)
Cheshire, New Haven County, Connecticut, United States
Pet-friendly
Details
House  Cheshire
from $553 per night
6 guests ∙ 5 bedrooms

House

5.0
Outstanding(2 ratings)
Cheshire, New Haven County, Connecticut, United States
Pet-friendly
Details
House  Cheshire
from $383 per night
House ∙ 10 guests ∙ 3 bedrooms

150 m² House

5.0
Outstanding(46 ratings)
Cheshire, New Haven County, Connecticut, United States
Pet-friendly
Details
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Vacation Homes With Terraces

Cottage  Cheshire
from $165 per night
Cottage ∙ 2 guests ∙ 1 bedroom

65 m² Cottage

4.8
Outstanding(55 ratings)
Cheshire, New Haven County, Connecticut, United States
Balcony/Patio
Details
Apartment  Cheshire
from $160 per night
4 guests ∙ 2 bedrooms

Apartment

3.0
(2 ratings)
Cheshire, New Haven County, Connecticut, United States
Balcony/Patio
Details
House  Cheshire
from $339 per night
House ∙ 6 guests ∙ 3 bedrooms

177 m² House

4.9
Outstanding(114 ratings)
Cheshire, New Haven County, Connecticut, United States
Balcony/Patio
Details
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Vacation rentals with a balcony

House  Cheshire
from $559 per night
House ∙ 10 guests ∙ 4 bedrooms

279 m² House

5.0
Outstanding(1 rating)
Cheshire, New Haven County, Connecticut, United States
Balcony
Details
Apartment  Cheshire
from $91 per night
2 guests ∙ 1 bedroom

Apartment

Cheshire, New Haven County, Connecticut, United States
Balcony
Details
House  Cheshire
from $213 per night
2 guests ∙ 1 bedroom

House

5.0
Outstanding(4 ratings)
Cheshire, New Haven County, Connecticut, United States
Balcony
Details
Show more

Frequently Asked Questions

What is the price of vacation rentals in Cheshire?

Accommodation in Cheshire cost from $88 per night.

Are there any vacation rentals available to book in Cheshire?

Our large collection of vacation homes makes it easy to filter and compare 15 offers in Cheshire.

Finding the perfect vacation home has never been easier. Tripping.com searches the world's top vacation rental sites to find the best properties in 190 countries worldwide. One search lets you filter, compare and sort over 10 million available vacation rentals from trusted partners including HomeAway, VRBO, TripAdvisor, Booking.com and more. When you use Tripping.com to plan your trip and book your vacation rental, you never have to wonder if you're getting the best deal.

Vacation Rentals in Cheshire

Looking for the perfect vacation rental for your Cheshire getaway? Tripping.com’s got you covered. Whether you’re seeking a vacation home, cabin rental or cottage, Cheshire offers 143 affordable vacation home rentals to choose from, with far more amenities, space and comforts than the average hotel room. Select from 83 properties with high-speed WiFi Internet, 30 full with jacuzzi and pool, and homes complete with outdoor patio, great for entertaining with guests. Whatever your needs, find the perfect home rental that best matches your accommodation style and budget. For travelers planning for an extended stay, long-term lodging and corporate rentals only cost an average of $25 a month. Save hundreds with affordable vacation rentals on Tripping.com and, in many cases, book directly online so you’re all set to go. Cheshire has 143 gorgeous homes with 33 pet-friendly rentals to choose from, perfect for your dog or cat. Check out our vacation rental listings now to get the latest deals, and book the right vacation home rental for you and the whole family. Feel at home wherever you are and experience an unforgettable vacation with Tripping.com. Search properties from 6 vacation rental sites in Cheshire where the top providers in that area are HRS Holidays, Booking.com, and Agoda. There are 54 HRS Holidays rentals, 26 Booking.com short term rentals and 25 Agoda vacation rentals.

Popular Day Trips Near Cheshire

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