34 Chesterfield Holiday Rentals

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Compare Chesterfield holiday rentals from 8 rental sites including Booking.com, TripAdvisor, HomeAway and more, ranging from $25 to $1228 a night.
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Information about Chesterfield

Vacation Rentals in Chesterfield

Find the best Chesterfield vacation rentals with Tripping.com. Choose from 901 rentals, from studio apartments to luxurious condos to entire cabin homes. Book in advance or book instantly with properties marked as “Instabook,” with prices ranging from $25 a night to $1228 a night.

Our Tripping.com vacation rentals will save you hundreds, offering more amenities than the average hotel room. Going on a business trip? 369 of homes in Chesterfield offer high-speed wifi internet so you won’t miss a beat. Travelling with kids? Have them splash around in any of the 16 rentals with pool or jacuzzi, or relax with the family in one of the 339 homes with cable TV.

For all those dog lovers and cat lovers, Chesterfield offers 155 pet-friendly vacation rentals at an affordable price. Book the perfect vacation home that best matches your budget and accommodation style. For the ultimate stay, check out our listings now to grab the latest deals.

Search properties from 8 rental sites in Chesterfield where the top providers in that area are Booking.com, TripAdvisor, and HomeAway. There are 435 Booking.com rentals, 184 TripAdvisor short term rentals and 170 HomeAway vacation rentals.