Vacation Rentals & Apartments in Chincoteague Island

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Stunning, Newer Chesapeake Waterfront Estate, Pool - 7 Bedrms 5 Baths

Cambridge house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 18

“Outstanding Vacation Rental” Our extended family (22 people - 13A/9K) had a great week at Saddle Beach. The house was beautiful and in very good condition. The option of being in the pool or the river during the day was wonderful. The house was clean and well furnished. The dining room table and table on the porch provided plenty of seating for meals. There was plenty of hot water for showers and clean-up after meals. The pool was clean and the river was awesome, with a gradual slope that was perfect for kids and adults. We used the crab traps provided and caught 2 dozen crabs that made a great contribution to dinner on Friday. Crabbing was best by the dock. We caught all but 3 crabs there, rather than out closer to the middle of the river. The AC on the ground floor stopped working on Tuesday, but one call to the owner and the repair team was on-site in less than 2 hours. The issue was resolved before noon on Wednesday. We have been renting vacation properties for years and issues crop up from time to time. We appreciated the quick response and resolution. The one recommendation we will make is to bring bug spray (mosquitos and horse flies). We anticipated it being right on the river, but if you haven't had that experience, you need to be prepared.

Match: Private outdoor pool (heated) Swimming pool

All filters match

Price per night from

$1,030

Maren Estate (Mountain Estate 20 min to UVA)

Afton house

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 14

Match: Private outdoor pool (heated) Swimming pool

All filters match

Price per night from

$1,947

Kingsbay Waterside Retreat Compound

Marion Station house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

Match: Private outdoor pool (heated) Swimming pool

All filters match

Price per night from

$1,369

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Greenwood - near Old Rag & White Oak Canyon Trails

Syria cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Private outdoor pool (heated), Swimming pool

1 of 2 filters match

Price per night from

$1,143

Peon Palace Cottage on Rose River by Blue Ridge

Syria cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 12

1 of 2 match: Private outdoor pool (heated), Swimming pool

1 of 2 filters match

Price per night from

$1,143

Pete's House - on Graves Mountain Farm

Syria house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Private outdoor pool (heated), Swimming pool

1 of 2 filters match

Price per night from

$1,143

Old Farmhouse - Itty-bitty cottage - Rose River

Syria cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Private outdoor pool (heated), Swimming pool

1 of 2 filters match

Price per night from

$1,143

Blackwood - Valley of Rose River by the Blue Ridge

Syria cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Private outdoor pool (heated), Swimming pool

1 of 2 filters match

Price per night from

$2,285

Wyndham Kingsgate Vacation Rental

Williamsburg apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

1 of 2 match: Private outdoor pool (heated), Swimming pool

1 of 2 filters match

Price per night from

$315

The Great Adventure

McGaheysville house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

1 of 2 match: Private outdoor pool (heated), Swimming pool

1 of 2 filters match

Price per night from

$492

Wild Wind Cabin - on Rose River Mountain Trout Stream

Syria cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Private outdoor pool (heated), Swimming pool

1 of 2 filters match

Price per night from

$2,285

One week rental - Thanksgiving getaway

Massanutten condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (heated), Swimming pool

1 of 2 filters match

Price per night from

$229

Lovely 2-bedroom condo at Wyndham resort

Williamsburg condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Private outdoor pool (heated), Swimming pool

1 of 2 filters match

Price per night from

$114

Historical Masonry Apt in Shockoe

Richmond apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Responds fast! avg. 1 hour 5 minutes

1 of 2 match: Private outdoor pool (heated), Swimming pool

1 of 2 filters match

Price per night from

$103

Cozy 2 Bedroom Apartment in the Heart of it All!

Henrico apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (heated), Swimming pool

1 of 2 filters match

Price per night from

$151

Enjoy Natural Wildlife Setting on 250 Acres of Land

Williamsburg hotel apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (heated), Swimming pool

1 of 2 filters match

Price per night from

$82

Cozy Charm downtown RVA, near VCU

Richmond apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 5 minutes

1 of 2 match: Private outdoor pool (heated), Swimming pool

1 of 2 filters match

Price per night from

$113

The Wyatt, an H4N Fully Furnished Apartment

Norfolk apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Private outdoor pool (heated), Swimming pool

1 of 2 filters match

Price per night from

$123

The Eddington, an H4N Fully Furnished Apartment

Hampton apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Private outdoor pool (heated), Swimming pool

1 of 2 filters match

Price per night from

$187

Dogwood Cottage by Shenandoah Park

Syria cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

1 of 2 match: Private outdoor pool (heated), Swimming pool

1 of 2 filters match

Price per night from

$2,285

Wyndham Kingsgate Resort

Williamsburg condo

  • 3 bedrooms
  • 1 bathroom
  • sleeps 10

1 of 2 match: Private outdoor pool (heated), Swimming pool

1 of 2 filters match

Price per night from

$457

Grand Illumination in Colonial Williamsburg! At the Historic Powhatan Resort

Williamsburg condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (heated), Swimming pool

1 of 2 filters match

Price per night from

$258

1 of 2 match: Private outdoor pool (heated), Swimming pool

1 of 2 filters match

Price per night from

$57

Pool house

Norfolk house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Responds fast! avg. 2 hours 50 minutes

1 of 2 match: Private outdoor pool (heated), Swimming pool

1 of 2 filters match

Price per night from

$487

Coan River Cottage w/ Fire Pit, Pool, Movie Room

Lottsburg house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 12

1 of 2 match: Private outdoor pool (heated), Swimming pool

1 of 2 filters match

Price per night from

$228

Historic Powhatan Resort Condo 10min from Colonial Williamsburg

Williamsburg condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (heated), Swimming pool

1 of 2 filters match

Price per night from

$238

Redwood 3 Condo Graves Mountain Farmthe Blue Ridge

Syria condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

1 of 2 match: Private outdoor pool (heated), Swimming pool

1 of 2 filters match

Price per night from

$1,143

Valley View Cottage in the Blue Ridge Mountains

Syria cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Private outdoor pool (heated), Swimming pool

1 of 2 filters match

Price per night from

$1,143

Redwood 1 Condo Graves Mountain Farm in Blue Ridge

Syria condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Private outdoor pool (heated), Swimming pool

1 of 2 filters match

Price per night from

$1,143

For a private, stunning vacation home or retreat

Lancaster house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 32

1 of 2 match: Private outdoor pool (heated), Swimming pool

1 of 2 filters match

Price per night from

$829

Charming basement w/ firepit and above ground pool

Stafford apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Private outdoor pool (heated), Swimming pool

1 of 2 filters match

Price per night from

$111

Family-Friendly Massanutten cabin w/ Amazing Mountain views! Lots to do!

Massanutten house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 14

1 of 2 match: Private outdoor pool (heated), Swimming pool

1 of 2 filters match

Price per night from

$628

The Colonies at Williamsburg: 2-BR, 2 Baths, Sleeps 6, Full Kitchen

Williamsburg condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 26 minutes

1 of 2 match: Private outdoor pool (heated), Swimming pool

1 of 2 filters match

Price per night from

$224

Williamsburg Plantation: 4-Bedrooms, 4 Baths, 2 Full Kitchens, Sleep 12

Williamsburg villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

1 of 2 match: Private outdoor pool (heated), Swimming pool

1 of 2 filters match

Price per night from

$401

Beautiful and spacious 1 bedroom in Williamsburg

Williamsburg house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Private outdoor pool (heated), Swimming pool

1 of 2 filters match

Price per night from

$228

3 bedroom cottage in beautiful Williamsburg

Williamsburg house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Private outdoor pool (heated), Swimming pool

1 of 2 filters match

Price per night from

$457

2 Bedroom Cabin Sleeps 6

Gordonsville cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Private outdoor pool (heated), Swimming pool

1 of 2 filters match

Price per night from

$224

2 Bedroom Estate in beautiful Williamsburg

Williamsburg house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (heated), Swimming pool

1 of 2 filters match

Price per night from

$287

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rentals in Chincoteague Island

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