73+ Vacation Rentals & Holiday Homes in Cheswold |
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Cheswold Accommodations - Hotels & Rentals

About Cheswold Vacation Rentals

Discover More than 73 Incredible Getaway Rentals Available in Cheswold. Choose from a Wide Selection of Villas, Hotels, and Other Rental Options. Explore Luxury Amenities at Affordable Prices, Creating the Ideal Base for Your Next Vacation. Plan Your Perfect Escape with Online Reservations and Uncover Fantastic Stays in Cheswold.

Online Reservations Offers Numerous Last-Minute Deals on Villas, Hotels, and Rentals, Both Near You and Across the Globe. Whether You Need Accommodation for a Group or an Event, Be it a Hotel or Vacation Rental (Including Cabins and Private Luxury Villas), We're Here to Assist. With Online Reservations in Cheswold, You Can Easily Compare Options from Multiple Suppliers with a Single Click to Find the Perfect Price Point, Amenities, and Style of Stay That Suit Your Needs. Looking for Group Deals, Properties with Private Pools, Hot Tubs, Pet-Friendly Options, or Spacious Master Suite Bedrooms with Open-Air Showers? You Can Find It All in the Online Reservations Vacation Rentals, Resorts, and Airbnb-Style Properties in Cheswold. The Average Size of Places to Stay Near Cheswold is 556.09 ft², with Prices Averaging US $190 per Night.

Let Online Reservations Help You Discover the Ideal Holiday Rental to Create Lifelong Travel Memories in Cheswold. Our Listed Prices Are Often Discounted Compared to Rack Rates. Simply Search for Your Destination and Secure the Perfect Place to Stay Today.

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Top Hotels & Vacation Rentals in Cheswold

Type Count
Vacation Homes 31
Holiday Apartments 5

Use these Quick Filters to Find a Vacation Rental in Cheswold

★ Pro Tip: Online Reservations is a vacation rental website specializing in cottages, lake houses, and exclusive summer home rentals. We curate a vast selection of incredible properties from trusted suppliers, allowing you to compare prices and locations to find the perfect fit for your getaway. Create lasting memories in Cheswold with Online Reservations.

Weather in Cheswold, DE

View the weather forecast for Cheswold before booking your Cheswold Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Activities CheswoldGuest Reviews Local Attractions

A Large Selection of Hotels and Vacation Rentals from Around the World CheswoldGuest Reviews Discover Exciting Activities and Must-Visit Destinations for Your Upcoming Journey


Dover International Speedway
Dover Downs Casino
Delaware State University
Dover Mall
Firefly Music Festival
Woodland Beach
Killens Pond State Park
Delaware State Visitor Center
Delaware Agricultural Museum and Village
Wheel of Fortune
Delaware State Capitol
Silver Lake Park
Blue Hen Mall
Eden Hill
North Dover Shopping Center
Little Creek Wildlife Area
Appoquinimink Friends Meeting House
Historic Houses of Odessa
Spence's Bazaar
Frog Hollow Golf Club

Frequently Asked Questions About Cheswold?

What are the top hotels, lake houses & vacation rentals in Cheswold?

We provide an array of great vacation destinations in Cheswold. If you are looking to stay in or around the Cheswold area, make sure to browse our options to find a premium rental location in a top vacation destination. Whether it is a few nights, a week, or more, we've got the luxury stays that rank among the Top Vacation Rentals in Cheswold:

Which hotel, lake house, or vacation rental in Cheswold is best for families?

Searching for a family-friendly getaway in Cheswold? We've got you covered. Check out one of these luxurious getaways that are highly-rated and perfect fits for families of all sizes.

How many hotels, resorts, or rentals are available in Cheswold?

Online Reservations™ offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by Online Reservations™ in 2025 is over 73 in the Cheswold area, and that number rises every day. By combining listings from multiple websites and travel providers, Online Reservations™ can provide you with a diverse amount of choices of the best luxury stays in Cheswold.


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