Owner Direct Vacation
Rentals in Chester
The Best Owner Direct Vacation Rentals in Chester. Explore thousands of vacation home rentals, large cabins, and villas near Chester
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Explore the Best Chester Vacation Homes
Looking for the perfect place to stay in Chester? Discover a curated collection of vacation rentals offering comfort, convenience, and authentic Chester character. Whether you want a beachfront condo, a cozy family home, or a pet-friendly stay close to downtown, Owner Direct makes it easy to compare verified options for your next trip.
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Why Travelers Love Using
Owner Direct to
Find Chester Vacation Rentals
What makes our vacation homes stand out?
Verified Properties
Every vacation home shown on Owner Direct comes from trusted travel sources and verified hosts, so you can browse with confidence.
Value You Can Trust
Compare a range of properties and find fair, transparent pricing—no hidden fees.
Endless Variety
From oceanfront condos and coastal cottages to luxury villas and family homes, there's a rental to fit every traveler and budget.
More Places to Stay Near Chester
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Popular Neighborhoods for Chester Vacation Rentals
What are the best areas to stay in Chester
Discover the top neighborhoods in Chester and choose a place that suits your stay.
Monday Feb 23
Chester, Chester
Common Vacation Rental Amenities Typical Vacation Rental Amenities
What sort of amenities will be available at your stay?
Our Chester vacation rentals are designed for comfort and convenience, with everything you need for a relaxing stay.
Indoor Amenities
Fully equipped kitchens
Spacious living areas with streaming TVs
Complimentary Wi-Fi
Air conditioning and heating
In-unit washer and dryer
Plush bedding and comfortable furniture
Outdoor Amenities
Balconies or patios with coastal views
Private or shared pools
BBQ grills and outdoor dining areas
On-site parking
Easy access to beaches and attractions
More Vacation Rentals You May Like Near Chester
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How to Reserve Your Chester Vacation Rental
Booking Made Simple
Owner Direct helps travelers find verified vacation rentals from trusted sources. Once you select a property you love, you’ll be guided to our partner’s secure booking platform to complete your reservation.
SEARCH PROPERTIES
Use filters for location, amenities, and budget.
VIEW DETAILS
Check photos, reviews, and features for your top picks.
BOOK SECURELY
Confirm your stay safely through our trusted travel partners.
Chester Vacation Rental FAQs
1. What are the top vacation rentals in Chester?
There are a lot of options in Chester. If you plan on staying in the Chester area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Chester:
- Cooperage Cottage - Peaceful & Family Friendly, Oceanfront
- Ahoy!.Oceanfront Family Cottage with Hot Tub, Near South Shore Attractions
- Custom Built Home On The Scenic Waterfront Facing The Picturesque MarriottsCove
- Seascape,Art Deco cottage
- Seapearl Studio: Cozy Coastal Retreat in the Heart of Chester
- The Chester House. Seaside in the village, with private wharf
- Cozy cottage by the river perfect for nature lovers & pet friendly
- White Cottage, An East Coast Architectural Masterpiece
- Chester Village Charmer
- Charming 3-bedroom exclusive house with WiFi, AC in serene Chester
2. Which vacation homes in Chester are best for families?
If you are looking for a family-friendly vacation home in Chester, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Chester:
3. How many vacation rentals are available in Chester?
Currently, the total number of properties listed in 2026 is over 65 in the Chester area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Chester.