50 Best Chincoteague Island Vacation rentals on Holiday Lettings - House rentals

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123 Vacation rentals

(1) Excellent 

11

Vacation home rental

Virginia / Chincoteague Island

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
***6166 Ocean Blvd*** Pet Friendly with a fenced back yard, outside shower, Wi-Fi, Central A/C. All bedrooms and baths on the 1st floor. Sunny enclosed front porch. Beautiful renovated home close to everything! Nearby is Sunshine House & Atlantic Delight.*** Bed Siz …see more

from $155 / night

$775 - $925 / week

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from $155 / night

(16) Very Good 

Certificate of Excellence

13

Chincoteague Island Vacation cottage rental

Virginia / Chincoteague Island

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
5203 Wild Pony Court. Oyster Bay II community. 2 story house located on secluded cul-de-sac. 3 bedrooms, 2 1/2 bathrooms, kitchen, laundry, living, and dining rooms, screened porch, wrap around porch, handicapped ramp, master bedroom on main floor. Private back yard and …see more

Certificate of Excellence

from $150 / night

$1,000 - $2,160 / week

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Responds fast!
avg. 2 hours 45 minutes

from $150 / night

(1) Excellent 

9

Vacation condo in Chincoteague Island

Virginia / Chincoteague Island

2 8 Min stay varies

  • 2 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning
New Chincoteague rental with panoramic views of Asseteague Island, ponies and lighthouse. Enjoy sunsets, crab, fish, swim, and kayak from shared dock with optional boat slip. 2 bedrooms (full and 2 twin bunks) (queen) pullout queen couch in living room. One full bathroo …see more

from $115 / night

$900 - $1,250 / week

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Responds fast!
avg. 2 hours 0 minutes

from $115 / night

(11) Very Good 

13

Chincoteague Island Vacation home rental

Virginia / Chincoteague Island

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Child friendly
  • Car not necessary
Totally updated but traditional "home away from home" facing the Chincoteague Channel on Chincoteague Island, minutes from the quaint downtown and the Assateague National Seashore and Wildlife refuge. Relax in this spacious, clean, and beautifully furnished home with w …see more

from $170 / night

$1,200 - $1,480 / week

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from $170 / night

(1) Excellent 

19

Home rental in Chincoteague Island

Virginia / Chincoteague Island

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Nearest beach 2 mi
  • Child friendly
  • Air conditioning
SEA ADVENTURE next to Sea Heart and Soul are 2 miles from Assateague Island and 5 miles from beach front fun. Check-in 4pm/ check-out 12pm. $229.00 per night. This home, right out your front door, has the coolest waterfront park ever!!! Chincoteague Veteran's Memorial …see more

from $229 / night

$1,400 / week

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Responds fast!
avg. 1 hour 49 minutes

from $229 / night

12

Vacation home in Chincoteague Island

Virginia / Chincoteague Island

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Ask about pets
***6402 Teal Lane*** The unobstructed view of Eel Creek and Little Oyster Bay will get your attention at sunrise and sunset! Put your kayak in the water at the shared dock at high tide. Now has WiFi and 42" TV*** This Property accepts Weekly Rentals Only.*** Bed Siz …see more

from $140 / night

$700 - $800 / week

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from $140 / night

(2) Very Good 

26

Vacation home rental

Virginia / Chincoteague Island

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning
Leave all of your worries behind when you stay at this marvelous 3-bedroom, 2-bathroom Chincoteague Island vacation rental house! Boasting space to sleep 8 guests, water views and a secluded canalside location with private pier, this quaint trailer-style property will a …see more

from $95 / night

$665 / week

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Responds fast!
avg. 7 minutes

from $95 / night

(14) Very Good 

Certificate of Excellence

15

Vacation home in Chincoteague Island

Virginia / Chincoteague Island

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 8 mi
  • Child friendly
Come stay and relax at this quiet retreat. This listing is a newly remodeled home which is tastefully decorated. There are three color themed bedroom's; which have two queens and two twin sized beds. There is serenity all around you, come sit on the screened in porch …see more

Certificate of Excellence

from $125 / night

$750 - $1,300 / week

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Responds fast!
avg. 2 hours 19 minutes

from $125 / night

(3) Very Good 

4

Vacation cottage in Chincoteague Island

Virginia / Chincoteague Island

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
Beautiful cottages located in the heart of Downtown Chincoteague with views of the Chincoteague Channel and Bay. The Key West Cottages are equipped with full kitchens, cozy living rooms, Queen bedrooms and large tiled showers. Amenities such as an indoor pool, hot tub …see more

from $149 / night

$1,043 / week

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Responds fast!
avg. 2 hours 55 minutes

from $149 / night

(1) Very Good 

12

Vacation home in Chincoteague Island

Virginia / Chincoteague Island

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Nearest beach 6 mi
  • Child friendly
  • Air conditioning
Cute, colorful 2 bedroom cottage with front and back porches. Walking distance to charming old town Main Street shops and restaurants. Back yard with grill and picnic table. Outside shower. Have coffee on the sunny back porch overlooking private back yard. Lots of w …see more

from $159 / night

$900 / week

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from $159 / night

14

Vacation apartment with swimming pool in Chincoteague Island

Virginia / Chincoteague Island

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
***FEATURED SPECIAL - DON'T MISS OUT ON THIS SPECTACULAR DEAL! BEAUTIFUL WATERFRONT CONDO FOR $2000 A MONTH SEPTEMBER - NOVEMBER - You can't beat this price! If you are looking for a long stay for fun or coming for work, this condo is perfect! Has everything you need …see more

from $230 / night

$1,150 - $1,725 / week

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from $230 / night

(9) Excellent 

Certificate of Excellence

32

Vacation home in Chincoteague Island

Virginia / Chincoteague Island

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Nearest beach 2 mi
  • Child friendly
  • Air conditioning
SEA HEART&SOUL next to SEA ADVENTURE: This home offers open spaces, a cozy, clean and comfortable place to stay along with amazing adventures for everyone to explore. It is furnished with many necessities so you can rest, relax and enjoy, coolers, beach chairs, grill, b …see more

Certificate of Excellence

from $229 / night

$1,400 / week

Book View

Responds fast!
avg. 1 hour 49 minutes

from $229 / night

(2) Excellent 

17

Vacation home in Chincoteague Island

Virginia / Chincoteague Island

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Ask about pets
****5466 Amrien Circle**** You won't believe the outstanding views of Assateague Island with this lovely 3 Bedrooms, 2 Bathrooms, contemporary home. Lovely marsh to the back, this home has location going on. Large, open and bright great room leads out to deck and porch. …see more

from $190 / night

$950 - $2,900 / week

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from $190 / night

9

Home rental in Chincoteague Island

Virginia / Chincoteague Island

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Ask about pets
***6248 Ocean Boulevard*** Walk to restaurants, shopping, etc. from this in town home. Nearby is Atlantic Delight and A Sea Change. WiFi Available. Upstairs offers a master suite with a private bathroom and 2 bedrooms and a full bath. 1/2 bath downstairs.*** Bed Sizes …see more

from $120 / night

$600 - $900 / week

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from $120 / night

9

Home rental in Chincoteague Island

Virginia / Chincoteague Island

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Ask about pets
****6300 Church Street **** Affordable vacation rental in historic downtown Chincoteague. Walk to shops, restaurants, fishing pier, waterfront park and farmers market. First floor bedroom, both bathrooms downstairs. Enjoy the back screened porch after the beach or re …see more

from $110 / night

$550 - $1,500 / week

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from $110 / night

(1) Excellent 

18

Vacation home rental

Virginia / Chincoteague Island

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
***5094 Blake Point Road**** Timeless Traditional home dates back to the turn of the century. Renovations have upgraded this fine 4 bedroom home that is also pet friendly and sleeps 10. Grand views of the Chincoteague Bay with large front screened porch and decks off b …see more

from $290 / night

$1,450 - $1,850 / week

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from $290 / night

20

Chincoteague Island Vacation home rental

Virginia / Chincoteague Island

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Ask about pets
***6265 Hancock Lane*** This historic island home is immaculate and totally renovated for 2015! Tucked away on a private lane with a large screened porch overlooking a lovely yard. A perfect spot to unwind and enjoy your beach vacation! Remodeled kitchen and bath, ne …see more

from $155 / night

$775 - $975 / week

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from $155 / night

11

Vacation home with swimming pool in Chincoteague Island

Virginia / Chincoteague Island

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
***3241 Lekites Drive*** Lovely, spacious home tucked away off Main Street with large deck and 15 by 30 ft pool. 3 bedrooms and 2 baths upstairs (includes master bed and bath), 1/2 bath downstairs. Has WiFi*** Bed Sizes: 2 Queen, 1 Bunk*** Prime Season Rates: $1400 w …see more

from $180 / night

$900 - $1,400 / week

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from $180 / night

(7) Excellent 

Certificate of Excellence

31

Chincoteague Island Vacation home rental

Virginia / Chincoteague Island

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 4 mi
  • Child friendly
  • Air conditioning
Peaceful 3 bedroom/2 bathroom home located directly on Eel Creek. Appreciate the natural beauty of Chincoteague Island with gorgeous nature views from both the lower level screened in porch as well as the balcony off of the master suite. Enjoy relaxing mornings with t …see more

Certificate of Excellence

from $85 / night

$900 / week

Book View

Responds fast!
avg. 11 minutes

from $85 / night

(1) Excellent 

9

Vacation home in Chincoteague Island

Virginia / Chincoteague Island

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Ask about pets
***6313 Cleveland Street*** Walk to everything including shopping, restaurants and entertainment from this convenient in town location! This house has been completely renovated and is a great house for your vacation! Wireless internet!*** Outside Shower is not enclose …see more

from $185 / night

$925 - $1,175 / week

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from $185 / night

14

Chincoteague Island Vacation home rental

Virginia / Chincoteague Island

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Ask about pets
***7518 Doe Bay Lane*** Beautiful waterview 3 bedroom, 2.5 Bath Duplex with waterside balcony, fully equipped kitchen, comfortably furnished.*** Bed Sizes: 2 Queen, 2 Twin, 1 Queen Sleep Sofa *** Prime Season Rates: $1195 weekly/$239 per night. Off Season Rates: $775 …see more

from $155 / night

$775 - $1,350 / week

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from $155 / night

(4) Excellent 

16

Chincoteague Island Vacation home rental

Virginia / Chincoteague Island

2 15 2 nights min

  • 2 bedrooms
  • Sleeps 15
  • 2 nights min
  • Child friendly
  • Car not necessary
  • Air conditioning
Fresh redo on this spacious and comfortable home, new carpet, flooring, furnishings, mattresses, granite counter tops, tile work and more ! This house has extensive accomadations, two and a half bathrooms and an outdoor shower and foot washing station make as well …see more

from $450 / night

$2,750 - $3,625 / week

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from $450 / night

15

Vacation home rental

Virginia / Chincoteague Island

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Ask about pets
***4274 Pension Street*** Quaint cottage near town. Big surprise when you walk inside! Bright, airy kitchen with a separate dining room and spacious living room. Lovely screened side porch and open back yard. Within walking distance to shops, restaurants and waterfront. …see more

from $130 / night

$650 - $800 / week

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from $130 / night

18

Vacation home in Chincoteague Island

Virginia / Chincoteague Island

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Ask about pets
***5215 Shell Drive*** "Belle of The Bay" is a unique vacation experience. Premier & private location for total waterfront enjoyment on Chincoteague's Oyster Bay and overlooking Assateague Island. Panoramic views, large multi-level decks & screened porch. 3 bedroom …see more

from $380 / night

$1,900 - $2,200 / week

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from $380 / night

8

Chincoteague Island Vacation home rental

Virginia / Chincoteague Island

2 7 7 nights min

  • 2 bedrooms
  • Sleeps 7
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
***6382 Teal Lane*** The unobstructed view of Eel Creek and Little Oyster Bay will get your attention at sunrise and sunset! Put your kayak in the water at the shared dock at high tide. Wi-Fi available. George Foreman Outdoor Electric Grill.*** New laminate flooring in …see more

from $130 / night

$650 - $850 / week

Inquire View

from $130 / night

11

Chincoteague Island Vacation home rental

Virginia / Chincoteague Island

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Ask about pets
***3402 Ridge Road*** Lovely 2 Bedrooms, 1.5 Baths duplex with water views. This duplex overlooks Assateague Island with great views for the Pony Swim. This is the Best way to watch the Pony Swim and not move from your porch! Sit and enjoy the views from 2 porches. The …see more

from $110 / night

$550 - $950 / week

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from $110 / night

10

Home rental in Chincoteague Island

Virginia / Chincoteague Island

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Ask about pets
***3189 Ridge Road**** Lovely island home in great condition. Nice large back yard for the kids. Charcoal barbeque grill and close to Memorial Park and boat launch. 1 bedroom 1st floor/1 bedroom 2nd floor.*** Bed Sizes: 1 Queen, 1 Bunk Bed (1 Twin & 1 Double Futon). 1 …see more

from $100 / night

$500 - $650 / week

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from $100 / night

(5) Very Good 

12

Home rental in Chincoteague Island

Virginia / Chincoteague Island

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Ask about pets
***5052 Main Street*** Enjoy the sunsets from this new wateview home, tucked away off North Main Street. Private setting.***WIFI Available. Bed Sizes: 1 Queen, 2 Twins*** Prime Season Rates: $900 weekly/$180 per night. Off Season Rates: $750 weekly/$150 per night. Ad …see more

from $150 / night

$750 - $900 / week

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from $150 / night

18

Chincoteague Island Vacation home rental

Virginia / Chincoteague Island

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Ask about pets
***5433 Pearl Drive-Oyster Bay I*** Lovely & comfortable 3 bedroom home, newly renovated has sweeping views throughout. Large waterfront screened porch to the back overlooks canal and boat dock. Nicely furnished, wifi, & fully equipped kitchen with granite counter …see more

from $240 / night

$1,200 - $1,400 / week

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from $240 / night

(1) Excellent 

11

Vacation home in Chincoteague Island

Virginia / Chincoteague Island

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Ask about pets
***8172 Marsh Point Lane*** Lovely beachy duplex. Walking distance to Marina's. 1 bedroom and 1 bath downstairs - 2 bedrooms and 1 bath upstairs.*** Bed Sizes: 2 Queen, 1 Queen Sleep Sofa, 2 Twin*** Prime Season Rates: $995 weekly/$199 per night. Off Season Rates: $69 …see more

from $139 / night

$695 - $995 / week

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from $139 / night

(46) Excellent 

Certificate of Excellence

19

Vacation home accommodation

Virginia / Chincoteague Island

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
Duck's Delight is our home in America's Happiest Seaside Town (2014 Coastal Living)! Entire home updated/renovated for the 2015 booking season! 4 bedroom (3 queen sized beds and 2 sets of bunkbeds), 2 bath Cape Cod in Chincoteague, VA., home of the Assateague ponies. …see more

Certificate of Excellence

from $85 / night

$595 - $925 / week

Book View

Responds fast!
avg. 11 minutes

from $85 / night

(2) Excellent 

14

Home rental in Chincoteague Island

Virginia / Chincoteague Island

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Ask about pets
***7142 Pine Drive-Piney Island*** Lovely home in Piney Island offers views of Assateague Island and water access. Perfect for a large family. Community boat launch area great for kayakers. Within walking distance to Assateague and Water Park.*** Also offering Interne …see more

from $199 / night

$995 - $1,350 / week

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from $199 / night

17

Vacation home in Chincoteague Island

Virginia / Chincoteague Island

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Ask about pets
***5203 Oak Springs Lane*** Very private water front home with acess to the Chincoteague Bay. Private dock for canoes, kayaks and flat bottom boats. Features a lovely pond in the front yard. Large back deck, screen porch, Wi-Fi, private dock & fenced back yard. Nearby …see more

from $180 / night

$900 - $1,250 / week

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from $180 / night

17

Vacation home in Chincoteague Island

Virginia / Chincoteague Island

3 9 7 nights min

  • 3 bedrooms
  • Sleeps 9
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
***6582 Church Street*** Lovely spacious home with 2 enclosed sunporches. Large kitchen for those looking to cook. Nice back deck and 1st level bedrooms. 3rd bedroom is loft area. Close to town & shopping but very quiet and private setting. 2 bedrooms and 2 baths do …see more

from $139 / night

$695 - $950 / week

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from $139 / night

12

Vacation home in Chincoteague Island

Virginia / Chincoteague Island

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Ask about pets
***4379 Ridge Road*** Lovely 2 bedroom home conveniently located on Ridge Road, not far from Maddox Blvd, with many great island attractions. Perfect house for a family of 4! This house offers extra space in the large sunroom. Bright and airy, the sunroom works for both …see more

from $120 / night

$600 - $750 / week

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from $120 / night

16

Vacation apartment in Chincoteague Island

Virginia / Chincoteague Island

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
***6321 Captain's Lane Unit #320 Sunset Bay Villas*** Luxury Waterfront Condo will delight you with it's vast waterfront views and stylish décor. Overlooking the channel and also offering expansive views of the quaint town of Chincoteague Island. Lovely 3rd floor unit …see more

from $275 / night

$1,275 - $1,725 / week

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from $275 / night

11

Chincoteague Island Vacation home rental

Virginia / Chincoteague Island

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Ask about pets
****5303 Meadow Drive**** Well appointed rancher in Piney Island, with large screened porch and private den with sleep sofa. Offers and water access!! Recently added all new appliances and floors for 2015 season. Very close to Assteague Island.*** Bed Sizes: 2 Queen, …see more

from $150 / night

$750 - $950 / week

Inquire View

from $150 / night

(1) Very Good 

12

Home rental in Chincoteague Island

Virginia / Chincoteague Island

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Ask about pets
***3400 Ridge Road*** Lovely 2 Bedrooms, 1.5 Baths duplex with water views. This duplex overlooks Assateague Island with great views for the Pony Swim. This is the Best way to watch the Pony Swim and not move from your porch! Sit and enjoy the views from 2 porches. The …see more

from $110 / night

$550 - $950 / week

Inquire View

from $110 / night

18

Home accommodation in Chincoteague Island

Virginia / Chincoteague Island

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
***5082 Twilley Drive*** Contemporary 4 bedroom 3 bath Waterfront home. Pet friendly, located in a private area off North Main Street. Offers 2 master suites with waterfront balconies. This home does not disappoint with its vaulted ceilings and gas fireplace. Offers …see more

from $370 / night

$1,850 / week

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from $370 / night

(2) Excellent 

12

Vacation home in Chincoteague Island

Virginia / Chincoteague Island

4 6 7 nights min

  • 4 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Ask about pets
***5187 Oak Spring Lane*** Refuge is no exaggeration with this luxury top of the line four bedroom waterfront home. Two luxury master bedrooms lead out to waterfront decks. Grand views of the Chincoteague Bay and access for kayaks and canoes, jacuzzi tub in master bedro …see more

from $300 / night

$1,500 - $1,875 / week

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from $300 / night