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

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Chincoteague Island

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127 Vacation rentals

(6) Excellent 

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

from $125 / night

$750 - $900 / week

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Responds fast!
avg. 49 minutes

from $125 / night

(7) 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

$1200 - $1480 / week

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from $170 / night

(36) Excellent 

Certificate of Excellence

21

Chincoteague Island Vacation home rental

Virginia / Chincoteague Island

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
This historic Waterman's Cottage , circa 1920, located on Chincoteague Island, has been beautifully restored and is a perfect family vacation spot. We are across the street from the Chincoteague Bay and 1 mile to the center of town. The house has a large eat-in-kitch …see more

Certificate of Excellence

from $135 / night

$900 - $940 / week

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Responds fast!
avg. 1 hour 38 minutes

from $135 / night

37

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 Virginia property will allow …see more

from $96 / night

$665 - $1050 / week

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Responds fast!
avg. 32 minutes

from $96 / night

(2) Excellent 

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

from $85 / night

$875 - $900 / week

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Responds fast!
avg. 20 minutes

from $85 / night

(10) Excellent 

Certificate of Excellence

13

Chincoteague Island Vacation cottage rental

Virginia / Chincoteague Island

3 8 2 nights min

  • 3 bedrooms
  • Sleeps 8
  • 2 nights min
  • 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 $125 / night

$800 - $1500 / week

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Responds fast!
avg. 1 hour 15 minutes

from $125 / night

(42) Excellent 

Certificate of Excellence

21

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

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Responds fast!
avg. 20 minutes

from $85 / 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 $90 / night

$743 / week

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from $90 / night

(1) Excellent 

19

Home rental in Chincoteague Island

Virginia / Chincoteague Island

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 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 $230 / night

$1450 / week

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Responds fast!
avg. 1 hour 52 minutes

from $230 / night

(8) Excellent 

Certificate of Excellence

32

Vacation home in Chincoteague Island

Virginia / Chincoteague Island

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 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 $230 / night

$1450 / week

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Responds fast!
avg. 1 hour 52 minutes

from $230 / night

(1) Excellent 

48

Vacation home in Chincoteague Island

Virginia / Chincoteague Island

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary
The Moorings North is an unique architecturally designed luxury 5 bedroom home in the heart of Chincoteague Island. The house is elegantly decorated and has mesmerizing panoramic views of Chincoteague Bay. It is conveniently located in walking distance to small shops, a …see more

from $551 / night

$2518 - $4645 / week

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from $551 / night

14

Vacation apartment with shared 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 $240 / night

$1200 - $1725 / week

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from $240 / night

12

Vacation home rental

Virginia / Chincoteague Island

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Air conditioning
***7141 Wayne Road***Welcome to Blue Pearl Cottage, a lovely, sunny beach house, just minutes from fabulous beaches, wildlife and the quaint downtown of Chincoteague. This airy cottage nestled beside pine woods has a large wrap-around deck, a screened porch and offers p …see more

from $135 / night

$650 - $875 / week

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from $135 / night

11

Vacation home in Chincoteague Island

Virginia / Chincoteague Island

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Child friendly
  • Air conditioning
****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 bot …see more

from $120 / night

$600 - $750 / week

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from $120 / night

10

Vacation home in Chincoteague Island

Virginia / Chincoteague Island

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
***6201 Ocean Blvd***Bring your four legged friend to this well-appointed home within walking distance to restaurants, shops, and more! This is a great pet friendly house right in the heart of downtown. It offers DSL Wi-Fi and a fax machine in the separate sitting room …see more

from $110 / night

$550 - $995 / week

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from $110 / 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
***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 - $1625 / week

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from $110 / night

(2) Excellent 

9

Home rental in Chincoteague Island

Virginia / Chincoteague Island

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Air conditioning
***3545 Willow Street***Very nice, comfortable 2 BR home will delight you with it's updated kitchen and new appliances. The large screened-in back porch with gas grill. Deck will accommodate outdoor entertaining. Centrally located, it is a short walk to town/shopping …see more

from $110 / night

$550 - $750 / week

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from $110 / night

21

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 $290 / night

$1450 - $1850 / week

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from $290 / 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
***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

$725 - $1625 / week

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from $110 / night

(1) 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
***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 bedroo …see more

from $300 / night

$1500 - $1875 / week

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from $300 / night

9

Vacation home in Chincoteague Island

Virginia / Chincoteague Island

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
***5323 Hibiscus Drive-Oyster Bay I*** This spacious pet friendly home is located in the private community of Oyster Bay II. Enjoy your morning coffee from the large deck or screened porch. Wildlife abounds with deer, rabbits, ducks, geese, and lots of songbirds in t …see more

from $130 / night

$650 - $850 / 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
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 home s …see more

from $381 / night

$1900 - $4300 / week

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from $381 / night

(44) Excellent 

31

Chincoteague Island Vacation home rental

Virginia / Chincoteague Island

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Child friendly
Epiphany on Deep Hole Creek. Deep Hole Creek Vacation Rentals Member, Chincoteague Chamber of Commerce Late August available! Pets subject to approval and an additional fee. See Deep Hole Creek site for more info and photos.! Scroll down to email Blair & Martha (owne …see more

from $298 / night

$1500 - $3650 / week

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Responds fast!
avg. 2 hours 23 minutes

from $298 / night

14

Chincoteague Island Vacation home rental

Virginia / Chincoteague Island

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 5 mi
  • Child friendly
Enjoy what nature has to offer in this quiet but active resort island on Virginia's Eastern Shore. The atmosphere is a relaxed one yet there is an extensive amount of activities for vacationers. From surf, bay or offshore fishing to kayaking, sunbathing, bird watching, …see more

from $275 / night

$1600 - $2600 / week

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from $275 / night

11

Vacation home in Chincoteague Island

Virginia / Chincoteague Island

3 7 7 nights min

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
***3584 Willow Street***Pet Friendly.Charming restored island home will make you smile! Relax in the screened porch after a day at the beach. Close to everything! A Short walk to the carnival and historic downtown with shops and restarurants. Large yard, perfect for …see more

from $150 / night

$750 - $800 / week

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from $150 / night

(1) Very Good 

8

Vacation home in Chincoteague Island

Virginia / Chincoteague Island

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
  • Air conditioning
***7503 Pony Cove Lane***This pet friendly, affordble duplex is off the beaten path and has room for the whole family! With four bedrooms and two baths! And Wireless Internet.***This Property accepts Dogs Only.***Bed Sizes: 2 Queen, 4 Twin***Prime Season Rates: $825 we …see more

from $125 / night

$625 - $826 / week

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from $125 / night

9

Vacation apartment in Chincoteague Island

Virginia / Chincoteague Island

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Child friendly
  • Air conditioning
****6206 Marsh Island Drive Unit #1***Wonderful effiencency condo unit located on Marsh Island. Enjoy some of the best water views and sunsets on Chincoteague. Fully equipped effiencincy kichen and laundry area. Shared pier and waterside picnic area. Comfortable and …see more

from $85 / night

$425 - $535 / week

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from $85 / night

24

Chincoteague Island Vacation home rental

Virginia / Chincoteague Island

3 8 3 nights min

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min
  • Nearest beach 1 mi
  • Child friendly
  • Air conditioning
SEA HARBOR: 1 mile from Assateague Island and 5 miles from beach front fun. Check-In 4pm Check-Out 12pm. This home offers large open spaces, a cozy, clean and comfortable place to stay along with amazing adventures for everyone to explore. It is furnished with many nece …see more

from $179 / night

$1253 / week

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Responds fast!
avg. 1 hour 52 minutes

from $179 / 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 bo …see more

from $280 / night

$1400 - $1800 / week

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from $280 / 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
***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.***Bed Sizes: 1 King, 1 Queen, 4 Twin***Prime Season Rates: $1350 weekly/$270 per …see more

from $199 / night

$995 - $1350 / week

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from $199 / night

6

Vacation home in Chincoteague Island

Virginia / Chincoteague Island

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
****6204 Poplar Street****Island Cottage has a great in town location! Easy walk to historic downtown's shops and retaurants. Perfect for a budget frienldy vacation. Has WiFi.***This Property accepts Dogs 35lbs and Under Only.***Bed Sizes: 1 Queen, 1 Double, 1 Twin. …see more

from $85 / night

$425 - $575 / week

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from $85 / night

15

Vacation home in Chincoteague Island

Virginia / Chincoteague Island

4 7 7 nights min

  • 4 bedrooms
  • Sleeps 7
  • 7 nights min
  • Child friendly
  • Air conditioning
***6422 Church Street*** Enjoy all that downtown has to offer in this cozy island home within walking distance to shops and restaurants. There is plenty of privacy in this petite home! First floor bedroom features a table and Tv, great for hanging out playing games or w …see more

from $135 / night

$675 - $750 / week

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from $135 / 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
***3241 Mulberry Lane***Immaculate waterview home with super large screen porch. It has a great kitchen for cooking large meals. This home is in a nice, quiet location that sits at the end of a cul-de-sac and is in walking distance to carnival grounds. All bedrooms on …see more

from $130 / night

$650 - $900 / week

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from $130 / night

12

Vacation home in Chincoteague Island

Virginia / Chincoteague Island

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
  • Air conditioning
***3702 Main Street****Lovely victorian home with new open front porch and large well-appointed rooms. Newly renovated 2 full bathrooms for the 2016 rental season. Newly installed hardwood floors. Also offering wireless internet! Walking distance to town and carnival …see more

from $160 / night

$800 - $1100 / week

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from $160 / night

10

Vacation home in Chincoteague Island

Virginia / Chincoteague Island

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Child friendly
  • Air conditioning
***6153 Marsh Island Drive-Marsh Island*** The owners of this new vacation rental have taken special care to provide their guests with many extras, including 1 person kayaks, beach items and a crab pot for your use. The view looking across Chincoteague Channel to …see more

from $140 / night

$700 - $850 / week

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from $140 / night

8

Chincoteague Island Vacation home rental

Virginia / Chincoteague Island

4 7 7 nights min

  • 4 bedrooms
  • Sleeps 7
  • 7 nights min
  • Child friendly
  • Air conditioning
***5454 Amrien Circle***Enjoy marsh and bay views from the wrap around deck and screened porch. This bright and cheerful single story home was newly furnished in 2005. Tucked away in a private subdivision off North Main Street. Wi-Fi available. All bedrooms on the sam …see more

from $110 / night

$550 - $1945 / week

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from $110 / night

7

Vacation home rental

Virginia / Chincoteague Island

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Air conditioning
***6703 Megan Lane***Bright and spacious duplex located on private lane. In walking distance of many island attractions. Offers second floor master bedroom suite. 1 bedroom and 1 bath downstairs/1 bedroom and 1 bath upstairs. Nearby is Georges Retreat.***Offering WiFi …see more

from $110 / night

$550 - $750 / 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
***7175 Bunting Road***Totally upgraded townhome with large back enclosed sun porch. Nice wetland view! 2 Bedrooms and 2 baths upstairs. Has Wi-Fi.***Bed Sizes: 1 King, 1 Queen, 1 Queen Sleep Sofa, 1 Twin Rollaway, 1 Twin Sleep Sofa.***Prime Season Rates: $725 weekly/$ …see more

from $105 / night

$525 - $725 / week

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from $105 / night

10

Chincoteague Island Vacation home rental

Virginia / Chincoteague Island

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
  • Air conditioning
***7469 Goose Lane***Very private and spacious waterfront home overlooking Assateague Island with pier and deep water dock. It offers over 1100 square feet of outside decking and large screen porch and over one acre prime waterfront setting overlooking marsh and beauti …see more

from $250 / night

$1150 - $3500 / week

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from $250 / night

13

Chincoteague Island Vacation home rental

Virginia / Chincoteague Island

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
***5169 Winder Lane***This waterfront 4 bedroom, pet friendly home is tucked away off North Main Street. Watch the sunset from the large screened porch. Offers fenced yard, well stocked kitchen, dinign room and a spacious living room. Upstairs has master suite with p …see more

from $350 / night

$1750 - $1976 / week

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from $350 / night