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

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Chincoteague Island

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120 Vacation rentals

(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 53 minutes

from $229 / night

20

Vacation home in Chincoteague Island

Virginia / Chincoteague Island

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
  • 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 $130 / night

$650 - $995 / week

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from $130 / night

(10) 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 $150 / night

$1,200 - $1,480 / week

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from $150 / 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 $568 / night

$2,594 - $4,645 / week

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from $568 / night

(12) 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 - $1,500 / week

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Responds fast!
avg. 1 hour 13 minutes

from $125 / 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
***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

(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

(2) 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. 59 minutes

from $149 / night

(15) 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. 3 hours 24 minutes

from $150 / night

12

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
***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 …see more

from $145 / night

$660 - $895 / week

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from $145 / 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

(45) 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

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Responds fast!
avg. 12 minutes

from $85 / 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

13

Vacation home in Chincoteague Island

Virginia / Chincoteague Island

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Ask about pets
***6242 Church Street*** Proud 3 story Traditional home located at the edge of town is rich in detail and history of the island. Beautiful renovations make this home just right for the whole gang. Just a few steps and walk to shopping and waterfront downtown plaza. S …see more

from $210 / night

$1,050 - $1,350 / week

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from $210 / 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
***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 Only: $725 week …see more

from $145 / night

$725 / week

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from $145 / night

8

Vacation home in Chincoteague Island

Virginia / Chincoteague Island

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Air conditioning
***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*** This Property accepts Weekly Rentals Only.***Bed Sizes: 2 Queen, 1 …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 - $1,050 / week

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Responds fast!
avg. 1 hour 58 minutes

from $95 / night

(1) Very Good 

8

Home rental in Chincoteague Island

Virginia / Chincoteague Island

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
***7203 Bunting Road***Bright and open townhouse with private patio area and gas grill!! Offers nice wetland views. Close by is Island Escape and in walking distance to Firemans Carnival.***Bed Sizes: 1 Queen, 1 Double, 1 Bunk (2 Twins), 1 Queen Sleep Sofa.***Prime Seas …see more

from $90 / night

$450 - $625 / week

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from $90 / 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
****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: 1 Queen, 1 D …see more

from $150 / night

$750 - $950 / week

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from $150 / night

(3) Excellent 

9

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
***6096 Taylor Street*** Perfect retreat for the traveler on a budget! Tastefully decorated cottage with 36 inch television and within walking distance of shops and restaurants. Has outside screend gazibo! All bedrooms on same level.*** Bed Sizes: 1 Queen, 2 Twin, 1 Q …see more

from $104 / night

$520 - $650 / week

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from $104 / night

9

Vacation home rental

Virginia / Chincoteague Island

4 7 Min stay varies

  • 4 bedrooms
  • Sleeps 7
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Ask about pets
***4312 Main Street*** Enjoy the water view from this immaculate home offering spacious rooms and a quiet location off Main Street. All bedroom on the same level.*** Bed Sizes: 3 Queen, 1 Double Futon*** Prime Season Rates: $775 weekly/$155 per night. Off Season Rate …see more

from $120 / night

$600 - $1,550 / week

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from $120 / 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
  • Ask about pets
***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 $75 / night

$375 - $535 / week

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from $75 / 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
  • Ask about pets
***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 Reed …see more

from $140 / night

$700 - $850 / week

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from $140 / 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 added in 2015, George Foreman Outdoor Electric Grill.***Bed Sizes: 1 Queen, 1 …see more

from $130 / night

$650 - $850 / week

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from $130 / 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

$1,200 / week

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Responds fast!
avg. 1 hour 53 minutes

from $179 / night

10

Home accommodation in Chincoteague Island with swimming pool

Virginia / Chincoteague Island

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
***7150 Silver Sails Landing***Exquisite duplex offers top level comfort with screened porch and open deck over looking the creek. Tropical accents with lovely furnishings, living room fireplace, gas grill, and community pool. Also has WiFi.***Bed Sizes: 2 Queen, 2 Twin …see more

from $195 / night

$975 - $1,300 / week

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from $195 / night

13

Chincoteague Island Vacation home rental

Virginia / Chincoteague Island

4 6 7 nights min

  • 4 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Ask about pets
***5392 Sunrise Drive-Oyster Bay I*** Newly remodeled in 2014 now with an open floor plan and expanded rooms! The renovated kitchen in this Oyster Bay waterfront home will inspire cooks and the new dining room is terrific for family gatherings. There is lots of new de …see more

from $290 / night

$1,450 - $1,875 / week

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from $290 / night

9

Chincoteague Island Vacation home rental

Virginia / Chincoteague Island

4 7 7 nights min

  • 4 bedrooms
  • Sleeps 7
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Ask about pets
***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 sa …see more

from $110 / night

$550 - $995 / week

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from $110 / 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
****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 rel …see more

from $110 / night

$550 - $1,500 / week

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from $110 / 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 53 minutes

from $229 / 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

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

(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

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Responds fast!
avg. 12 minutes

from $85 / 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 $375 / night

$2,250 / week

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Responds fast!
avg. 3 hours 34 minutes

from $375 / 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
***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 t …see more

from $240 / night

$1,200 - $1,400 / week

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from $240 / 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
****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

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 f …see more

from $160 / night

$800 - $850 / week

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from $160 / night

(1)  

8

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
***7065 Wayne Road***Spacious rancher is pet friendly with large deck, fenced yard and internet.***Bed Sizes: 1 Queen, 1 Double, 1 Twin, 1 Double Sleep Sofa***Prime Season Rates: $800 weekly/$160 per night.Off Season Rates: $650 weekly/$130 per night.Shoulder Season Rat …see more

from $130 / night

$650 - $800 / week

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from $130 / 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

11

Vacation home in Chincoteague Island

Virginia / Chincoteague Island

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Air conditioning
***6314 Cropper Street***Lovely renovated 3 story Victorian combines classic charm with affordable luxury located in the heart of downtown Chincoteague.***Bed Sizes: 2 Queen, 2 Twin***Prime Season Rates: $1000 weekly/$200 per night.Off Season Rates: $800 weekly/$160 per …see more

from $160 / night

$800 - $1,000 / week

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from $160 / night