Stay If You Dare - Vacation Rentals in Cheriton

Charming Cape Charles Vacation Rental Home! From US $437
         

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10.0 (2 Reviews)
House
  • Parking
  • Accessibility
  • Security/Safety
Cape Charles Tiny Livin From US $260
         

9.2 (9 Reviews)
Hotel
  • Parking
  • Child Friendly
  • Internet
Classically Current - Chesapeake Properties From US $513
         

9.8 (86 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Blue Bay - Chesapeake Properties From US $507
         

10.0 (57 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Family-Friendly Fun Just 1 Block from Downtown Cape Charles From US $517
         

Downtown, Sleeps 9, Dog-friendly, Short Walk to the Beach From US $294
         

9.6 (137 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Luxury Places to Stay in Cheriton

Over 374+ Luxury Places to Stay in or Near Cheriton
The Tazewell House - Chesapeake Properties From US $1,522
         

Life Just Got Better From US $1,253
         

9.8 (27 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Sunset Shores - Chesapeake Properties From US $1,140
         

10.0 (6 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Minchew- 5 Bedrooms, Bay Creek, Beach Access From US $960
         

Top-Rated Vacation Rentals with a Pool in Cheriton

Over 87+ Top-Rated Vacation Rentals with a Pool in or Near Cheriton
Coastal Elegance Meets Small Town Charm From US $702
         

10.0 (37 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Bay Creek Meets Historic Cape Charles! pool access! From US $410
         

Charming Historic 5-Bedroom Home with a Refreshing Pool! From US $706
         

10.0 (28 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Pet-Friendly Vacation Rentals in Cheriton

Over 107+ Pet-Friendly Vacation Rentals in or Near Cheriton
Near Beach and Trails Elegant Home in Cape Charles! From US $656
         

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10.0 (1 Review)
House
  • Parking
  • Pet Friendly
  • Accessibility
Newly renovated home just steps from the beach! From US $460
         

10.0 (59 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Game Barn! Next to Central Park! 2 Blocks 2 Beach/Resturants/Shops From US $406
         

Key Lime Cottage: Your Cape Charles Beachside Retreat From US $361
         

10.0 (51 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Brand new Stylish home for you and your pet! From US $619
         

10.0 (13 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Pet Friendly Tiny Livin 3min from Cape Charles From US $382
         

10.0 (11 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
See More Pet-Friendly Vacation Rentals in Cheriton on PetFriendly.io

Large Vacation Homes & Villas in Cheriton

Over 98+ Large Vacation Homes & Villas in or Near Cheriton
Cape Charles Tiny Livin' From US $338
         

9.4 (12 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Belle is a cute cottage blocks from shops, bay, cafes From US $339
         

10.0 (24 Reviews)
House
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens
Handicap Accesible, with Beach, Pool & Tennis! From US $499
         

10.0 (18 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
HGTV House! 2 Blocks to Beach- 2024 New Bathroom! From US $387
         

Beach Bums Only - Chesapeake Properties From US $734
         

10.0 (12 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool

Wheelchair Accessible Vacation Homes in Cheriton

Over 2+ Wheelchair Accessible Vacation Homes in or Near Cheriton
Cape Haven - Condo 1.5 Blocks from Beach From US $356
         

Above it All - Chesapeake Properties From US $375
         

9.6 (28 Reviews)
Condo
  • Air Conditioner
  • TV
  • View

Cheriton Varoom and Airbnb Places to Stay Under $200

Over 17+ Cheriton Varoom and Airbnb Places to Stay Under $200
Sea Salt Cottage: Your Tranquil Getaway 3 min to beach From US $179
         

9.8 (42 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Pet-Friendly Home with Gazebo Minutes to Beach! From US $165
         

Perfect Cozy Vacation Rental on the Eastern Shore From US $169
         

Beach Days & Dtwn Charm! Cape Charles Cottage From US $164
         

Fish Tales-FISH/EAT/STAY From US $176
         

10.0 (92 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Cute and Cozy Vacation Stay on the Eastern Shore! From US $175
         

Coral Cottage by the Bay - It's Last Season From US $186
         

5.0 (56 Reviews)
Cottage
  • Air Conditioner
  • Pet Friendly
  • Balcony/Terrace

Instantly Bookable Vacation Homes in Cheriton

Over 234+ Instantly Bookable Vacation Homes in or Near Cheriton
Doublemint - Chesapeake Properties From US $366
         

10.0 (44 Reviews)
House
  • Air Conditioner
  • TV
  • View
Peach Perfect - Chesapeake Properties From US $380
         

10.0 (21 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Good Times on the Cape-1st & 2nd flr Master From US $384
         

10.0 (19 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Serene Beach Haven in Cape Charles From US $325
         

10.0 (18 Reviews)
House
  • Air Conditioner
  • Parking
  • TV

About Cheriton Vacation Rentals

With more than 383 Cheriton vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Stayifyoudare 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 Cheriton.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Stayifyoudare Cheriton, 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 Cheriton. Places to stay near Cheriton are 776.18 ft² on average, with prices averaging $434 a night.

Stayifyoudare makes it easy and safe to find and compare vacation rentals in Cheriton 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 Cheriton

Type Count
Vacation Homes 323
Holiday Apartments 12
Cottages 6
Villas 2
B&B 1
Cabin Rentals 1
Hotels with Suites 1

Use these Quick Filters to Find a Vacation Rental in Cheriton

Pro Tip: Stayifyoudare makes it easy to compare the best listings on Stayifyoudare homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Stayifyoudare 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 Cheriton.

Weather in Cheriton

View the weather forecast for Cheriton before booking your Cheriton 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