Chester vacation rentals

KAYAK searches hundreds of travel sites at once for vacation home deals in Chester

Here is why travelers choose KAYAK

Free to useThere are no hidden charges or fees.

Filter your dealsFilter by free cancellation, free breakfast and more.

Millions of reviewsCheck ratings based on millions of real guest reviews.

Recommended by KAYAK
Useful Info
Recommended by KAYAK

Best Chester vacation rentals

Go to map

Search by review score

6+ Okay7+ Good8+ Great9+ Excellent

Search by price

$0 - $652$652 - $1,303$1,303 - $1,955$1,955 - $2,606$2,606+ per night

Property Types

ApartmentChaletCondoCottageHomestayHouse

Search by freebies

Free cancellationFree breakfastFree parkingFree internet

Most recommended vacation rentals in Chester

Show all
Base Serviced Apartments - City Road - Chester - Bedroom
Base Serviced Apartments - City Road
Chester, ENG, United Kingdom
7.6Good(1030)
Free Wi-Fi
$97+
Check availability
Oakwood Farm Mews Chester - Chester - Bedroom
Oakwood Farm Mews Chester
Chester, ENG, United Kingdom
8.5Very good(591)
Parking
Free Wi-Fi
Pet friendly
$124+
Check availability
Royal House Luxury Apartments - Chester - Chester - Living room
Royal House Luxury Apartments - Chester
Chester, ENG, United Kingdom
7.6Good(757)
Free Wi-Fi
$166+
Check availability
14-16 Grosvenor Street Stylish Apartments - Chester - Chester - Building
14-16 Grosvenor Street Stylish Apartments - Chester
Chester, ENG, United Kingdom
7.2Good(948)
Free Wi-Fi
$158+
Check availability
Concorde House Luxury Apartments Chester - Chester - Bedroom
Concorde House Luxury Apartments Chester
Chester, ENG, United Kingdom
7.7Good(864)
Free Wi-Fi
$143+
Check availability
City Suites - Chester - Dining room
City Suites
Chester, ENG, United Kingdom
8.2Very good(292)
Free Wi-Fi
$133+
Check availability
Modern 2br Chester Flat - Chester - Bedroom
Modern 2br Chester Flat
Chester, ENG, United Kingdom
7.5Good(9)
Parking
Free Wi-Fi
Pet friendly
$261+
Check availability
The Chapel Chester - Boutique Apartments - Chester - Living room
The Chapel Chester - Boutique Apartments
Chester, ENG, United Kingdom
9.6Wonderful(474)
Free Wi-Fi
Pet friendly
$206+
Check availability
Chester Apartments - Chester - Bedroom
Chester Apartments
Chester, ENG, United Kingdom
9.1Wonderful(189)
Parking
Free Wi-Fi
Pet friendly
$362+
Check availability
The garden room, pets, fridge Tv - Chester
The garden room, pets, fridge Tv
Chester, ENG, United Kingdom
5.7Fair(153)
Parking
Free Wi-Fi
Pet friendly
$85+
Check availability
Le studio Attic , fridge tv microwave, - Chester
Le studio Attic , fridge tv microwave,
Chester, ENG, United Kingdom
5.9Fair(104)
Parking
Free Wi-Fi
$74+
Check availability
Chester Heights by Guestz - Chester
Chester Heights by Guestz
Chester, ENG, United Kingdom
7.6Good(13)
Free Wi-Fi
$131+
Check availability
Comfy Cosy Little Room Tv fridge microwave - Chester
Comfy Cosy Little Room Tv fridge microwave
Chester, ENG, United Kingdom
6.4Okay(30)
Parking
Free Wi-Fi
Pet friendly
$49+
Check availability
Bridge Street Views - Chester
Bridge Street Views
Chester, ENG, United Kingdom
9.0Wonderful(229)
Free Wi-Fi
Pet friendly
$151+
Check availability
Hope House Apartments - Chester
Hope House Apartments
Chester, ENG, United Kingdom
8.7Very good(266)
Parking
Free Wi-Fi
$164+
Check availability
The Stables, Chester - Luxury Apartments by PolkaStays - Chester
The Stables, Chester - Luxury Apartments by PolkaStays
Chester, ENG, United Kingdom
8.2Very good(99)
Parking
Free Wi-Fi
$241+
Check availability
Useful Info

KAYAK’s insights for vacation rentals in Chester

Discover seasonal trends, ideal booking windows, and other data-driven tips to plan your stay in Chester with confidence.

Which month has the cheapest vacation rental rates in Chester?

Vacation rentals are cheapest in Chester in January, with average rates of $66. In comparison, April is the most expensive month, with prices at $279.

What is the cheapest day of the week to book a vacation rental in Chester?

Sunday offers the lowest rates in Chester, with an average nightly price of $93. The highest prices are found on Wednesday, with average rates at $153.

How early should you book a vacation rental in Chester?

Book at least 70 days before your stay begins to get the best price for your Chester vacation rental.
Find deals

Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

February
May
$97
$135
Cheapest month to stay with an average 52% drop in price.
Most expensive month to stay with an average 20% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

KAYAK's top tips for finding Chester vacation rental deals

  • Hot tub, parking, pet friendly, and pool are the most popular vacation rental property amenities in Chester
  • Vacation rentals in Chester are around 57% more expensive than hotels on average. Search here to compare prices for all accommodation types in Chester.
  • The best vacation rental properties in Chester are Honeypot Hideaways Luxury Glamping - Exclusively for Adults (9.8, 90 reviews), Willow Farm Glamping (9.6, 100), and The Chapel Chester - Boutique Apartments (9.6, 474), based on ratings and reviews from real travelers.
  • If you’re looking for a cheap vacation rental in Chester, you should consider visiting during the low season. The cheapest vacation homes in Chester can be found in February and April.
  • The cheapest night for renting a vacation home in Chester is Tuesday. In contrast, the most expensive is Saturday.
  • Vacation rentals are a popular choice for both long and short-term stays. KAYAK users usually book their vacation rental in Chester for 4 days.

FAQs when booking a vacation home in Chester

  • What types of vacation rentals are available in Chester?

    There are loads of different property types that you can make your vacation home in Chester. You’ll find apartments, campgrounds, chalets, condos, cottages, farm stays, houses, holiday parks, homestays, lodges and luxury tents.

  • Are there any pet-friendly vacation rentals in Chester?

    There are a number of dog and pet-friendly Chester vacation rentals, with around 17% allowing you to bring your pet along with you.

  • How can I find vacation rentals near me in Chester?

    Take a look at our vacation rentals map to find the best vacation rental homes near you.

Where to stay in Chester?

Our map will help you find the perfect place to stay in Chester by showing you the exact location of each vacation rental.

Everything you need to know for your stay in Chester

Chester vacation rental deals. Search for vacation homes, apartments, condos, cabins, cottages, villas and more in Chester. Find cheap vacation homes to rent in Chester. KAYAK searches hundreds of travel sites to help you find and book a vacation rental in Chester that suits you best.

Not what you’re looking for? Find thousands of other hotels, flight deals, car rentals and package deals with KAYAK.