Virginia Beach Attractions - Vacation Rentals in Cheswold

3 Mi to Dover Motor Speedway Pet-Friendly Retreat From US $360
         

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10.0 (1 Review)
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  • Parking
  • Pet Friendly
  • Accessibility
Residence Inn Marriott Dover From US $112
         

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9.0 (471 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
JVA LUXURY HOUSING From US $589
         

10.0 (1 Review)
House
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens
Charming bed & breakfast in Smyrna with AC, WiFi. Enjoy From US $486
         

10.0 (1 Review)
Bed & Breakfast
  • Air Conditioner
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  • TV
Harvest of tranquillity From US $250
         

9.6 (11 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Dover Home - 2 Mi to Delaware State University! From US $211
         

9.2 (12 Reviews)
House
  • Air Conditioner
  • Parking
  • TV

Luxury Places to Stay in Cheswold

Over 75+ Luxury Places to Stay in or Near Cheswold
Pet-Friendly Dover Retreat w/Yard & Pool Table! From US $728
         

Good Times and Tan Lines - Private Custom Pool! From US $581
         

Hilton Garden Inn Dover From US $362
         

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9.3 (118 Reviews)
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  • Pet Friendly
Right in the center of everywhere in Dover From US $340
         

8.6 (4 Reviews)
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Home2 Suites Dover From US $339
         

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8.7 (154 Reviews)
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  • Pet Friendly
Red Roof Inn & Suites Dover Downtown From US $300
         

7.1 (435 Reviews)
Hotel
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  • Pet Friendly
Wyndham Garden Dover From US $283
         

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6.5 (287 Reviews)
Hotel
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  • Designated Smoking Area
Comfort Inn & Suites Dover near Speedway From US $272
         

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8.2 (427 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool

Top-Rated Vacation Rentals with a Pool in Cheswold

Over 14+ Top-Rated Vacation Rentals with a Pool in or Near Cheswold
Residence Inn Dover From US $213
         

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9.0 (77 Reviews)
Hotel
  • Air Conditioner
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  • Pet Friendly
Holiday Inn Express Hotel & Suites Dover by IHG From US $124
         

8.9 (315 Reviews)
Hotel
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  • Parking
  • Pet Friendly
Holiday Inn Express Hotel & Suites Dover by IHG From US $101
         

8.8 (1004 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Comfort Inn & Suites Dover near Speedway From US $111
         

8.8 (1003 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Hilton Garden Inn Dover From US $138
         

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8.8 (1002 Reviews)
Hotel
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Home2 Suites by Hilton Dover, DE From US $140
         

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8.8 (706 Reviews)
Hotel
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Hampton Inn Dover From US $99
         

8.6 (1002 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Sleep Inn & Suites Dover University Area From US $104
         

8.4 (1003 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in Cheswold

Over 9+ Pet-Friendly Vacation Rentals in or Near Cheswold
Hampton Inn Dover From US $153
         

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8.2 (109 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Red Roof Inn & Suites Dover Downtown From US $84
         

7.4 (1005 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
3 Mi to Dtwn: Townhome w/Deck in Dover From US $285
         

10.0 (3 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Supreme Luxury Living in Smyrna Delaware From US $330
         

New
House
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  • Pet Friendly
Quiet Peaceful 4 Bedroom 2½ Bath home on a Cul-da-sac From US $313
         

10.0 (13 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Walking Distance To Firefly And Nascar Monster Mile At Dover Downs Speedway From US $400
         

See More Pet-Friendly Vacation Rentals in Cheswold on PetFriendly.io

Large Vacation Homes & Villas in Cheswold

Over 3+ Large Vacation Homes & Villas in or Near Cheswold
Cozy house in Dover, DE From US $400
         

New
House
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  • Bedding/Linens
  • Child Friendly
Remodeled historical townhouse in downtown From US $305
         

New
House
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  • Bedding/Linens
  • Child Friendly

Wheelchair Accessible Vacation Homes in Cheswold

Over 8+ Wheelchair Accessible Vacation Homes in or Near Cheswold
Bally's Dover From US $218
         

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8.3 (1124 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Bally's Dover Casino Resort From US $107
         

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8.8 (3476 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Wheelchair Accessible
Fairfield Inn & Suites by Marriott Dover From US $256
         

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8.2 (93 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Quality Inn Smyrna From US $85
         

7.6 (1004 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Comfort Suites Dover University Area From US $247
         

6.6 (98 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Comfort Suites Dover University Area From US $99
         

7.2 (1002 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Days Inn by Wyndham Dover Downtown From US $78
         

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3.5 (283 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Wheelchair Accessible
Wyndham Garden Dover From US $106
         

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6.4 (1004 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV

Cheswold Vacation Rentals and Airbnb Places to Stay Under $200

Over 29+ Cheswold Vacation Rentals and Airbnb Places to Stay Under $200
THE BLUE ROOM Luxury suite From US $80
         

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8.3 (51 Reviews)
House
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Fairfield Inn & Suites by Marriott Dover From US $90
         

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8.6 (530 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
Camper Apt DE Sleeps 3 From US $126
         

New
Apartment
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  • TV
  • Security/Safety
2-bedroom apartment in Dover From US $84
         

New
Apartment
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Extended stay - 2-bedroom 1.5 bath condo in Dover From US $82
         

New
Condo
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  • Security/Safety
  • Bedding/Linens

Instantly Bookable Vacation Homes in Cheswold

Over 10+ Instantly Bookable Vacation Homes in or Near Cheswold
Home away from home From US $203
         

8.0 (6 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Centric & spacious home with ample parking and king beds in all rooms. From US $300
         

10.0 (1 Review)
House
  • Air Conditioner
  • Security/Safety
  • Sports/Activities
Your Chic Hotspot Away from Home - Latinos Bienvenidos From US $290
         

5.0 (5 Reviews)
House
  • Air Conditioner
  • TV
  • Bedding/Linens
Blue Room in Delaware From US $121
         

5.0 (2 Reviews)
Apartment
  • Parking
  • TV
  • Security/Safety
Suite Deal Comfort for corporate stay From US $74
         

5.0 (1 Review)
House
  • Air Conditioner
  • Bedding/Linens
  • Kitchen

About Cheswold Vacation Rentals

With more than 84 Cheswold vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Virginiabeachattractions and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Cheswold.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Virginiabeachattractions Cheswold, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Cheswold. Places to stay near Cheswold are 524.99 ft² on average, with prices averaging $207 a night.

Virginiabeachattractions makes it easy and safe to find and compare vacation rentals in Cheswold with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Cheswold

Type Count
Vacation Homes 37
Hotels with Suites 35
Holiday Apartments 7
B&B 2
Cabin Rentals 1

Use these Quick Filters to Find a Vacation Rental in Cheswold

Pro Tip: Virginiabeachattractions makes it easy to compare the best listings on Virginiabeachattractions homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Virginiabeachattractions homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Cheswold.

Weather in Cheswold

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

Cheswold Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Cheswold?
How many vacation rentals are available in Cheswold?

Currently, the total number of properties listed in 2026 is over 84 in the Cheswold area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Cheswold.