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

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126 Vacation rentals

(31) Excellent 

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

from $135 / night

$900 - $940 / week

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from $135 / night

(1) 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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from $85 / night

(4) 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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from $125 / night

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 Virginia property will allow …see more

from $95 / night

$665 - $1050 / week

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from $95 / night

(6) 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 $160 / night

$1200 - $1340 / week

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from $160 / night

(9) 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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from $125 / 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

(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

15

Home rental in Chincoteague Island with swimming pool

Virginia / Chincoteague Island

4 11 7 nights min

  • 4 bedrooms
  • Sleeps 11
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
***7111 Horseshoe Lane***Lovely home centrally located on a quiet residential street. Watch the Saltwater Cowboy's saddle up for the pony round ups right from the comfort of the airy screened porch. Too hot at the beach, no problem than enjoy the pool. This home has al …see more

from $250 / night

$1250 - $1750 / week

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from $250 / night

(6) Very Good 

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 $229 / night

$1450 / week

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from $229 / night

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 $525 / night

$2518 - $4510 / week

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from $525 / 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
***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 dec …see more

from $290 / night

$1450 - $1875 / week

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from $290 / night

(41) 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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from $85 / night

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

$550 - $1625 / week

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from $110 / night

20

Vacation home in Chincoteague Island

Virginia / Chincoteague Island

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
  • Air conditioning
***5203 Oak Springs Lane****Very private water front home with view of the Chincoteague Bay. Features a lovely pond in the front yard. Large back deck, screen porch, Wi-Fi, private dock & fenced back yard. Nearby is Refuge.***Bed Sizes: 2 Queen, 2 Sets of Bunks (4 Tw …see more

from $180 / night

$900 - $1200 / week

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from $180 / 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

10

Vacation home in Chincoteague Island

Virginia / Chincoteague Island

4 12 7 nights min

  • 4 bedrooms
  • Sleeps 12
  • 7 nights min
  • Child friendly
  • Air conditioning
***4328 Estella Drive***Room for family and friends! Spacious design with two living areas, and two kitchens! Newly decorated with all new furnishings, large screened porch. Two bedrooms and two baths downstairs and 2 bedrooms one bath upstairs reached by Spiral Stai …see more

from $150 / night

$800 - $1050 / week

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from $150 / 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

(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 $229 / night

$1450 / week

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from $229 / 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 dow …see more

from $139 / night

$695 - $950 / week

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from $139 / night

11

Vacation apartment in Chincoteague Island

Virginia / Chincoteague Island

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Child friendly
  • Air conditioning
***208 WonderView - 7622 East Side Drive***This top floor end unit offers spectacular views over Assteague Channel and lighthouse. The covered deck is a perfect spot after a long day at the beach. Ideal place for kayaking or bird watching. WiFi Available***Bed Sizes: …see more

from $140 / night

$700 - $2000 / week

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from $140 / 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

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

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

12

Vacation home in Chincoteague Island

Virginia / Chincoteague Island

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Air conditioning
***6751 Megan Lane***Spacious updated duplex with Screened Porch, W-iFi and Outside Shower. Within walking distance to Maddox Blvd. with shopping, restaurants and attractions.***Bed Sizes: 2 Queen, 2 Twin***Prime Season Rates: $780 weekly/$156 per night.Off Season Rates …see more

from $115 / night

$575 - $780 / week

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from $115 / 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 - $1450 / week

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from $190 / 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 - $1975 / week

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from $350 / night

(2) 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
  • Pet friendly
***5609 Hibiscus Drive***Lovely home located in private community.***This Property accepts Dogs Only.***Bed Sizes: 1 Queen, 2 Twin, 2 Double.***Prime Season Rates: $1100 weekly/$220 per night.Off Season Rates: $875 weekly/$175 per night. Additional amenities include: a …see more

from $175 / night

$875 - $1100 / week

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from $175 / night

13

Vacation home rental

Virginia / Chincoteague Island

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
***7136 Silver Sails Landing***Spacious duplex overlooking the wetlands. With screen porch, deck, first floor master suite, enjoy the community pool after a long day at the beach! Next door to Bay Pony.***Bed Sizes: 2 King, 2 Twin***Prime Season Rates: $1350 weekly/$27 …see more

from $195 / night

$975 - $1350 / week

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from $195 / 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

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

14

Vacation home in Chincoteague Island

Virginia / Chincoteague Island

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
  • Air conditioning
***6317 Highland Park Drive***Bring your kayaks and kids! This is a bright tastefully decorated rancher! Playset in backyard for small children, located in quiet neighborhood and in walking distance of restaurants and attractions. All bedrooms on the same level.***Bed …see more

from $165 / night

$825 - $1020 / week

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from $165 / 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

(4) Very Good 

6

Vacation home rental

Virginia / Chincoteague Island

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Child friendly
  • Air conditioning
****4150 Grumpy's Lane****Charming cottage located on a quiet, private lane. Close to town. Spacious sunroom addition! Newly added outside shower! Nearby are Smitty's Paradise.***Bed Sizes: 1 Double, 1 Double Sleep Sofa***Prime Season Rates: $550 weekly/$110 per night. …see more

from $80 / night

$400 - $550 / week

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from $80 / night

18

Vacation home in Chincoteague Island

Virginia / Chincoteague Island

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Air conditioning
***7200 Fiddler Bay***Very nice waterfront townhome with remodeled chef's kitchen. Spectacular vistas of Assateague Island. Perfect spot for kayaking. 2 bedrooms and 2 baths upstairs(includes master bed and bath)*** Bed Sizes: 1 Queen, 2 Twin, 1 Futon ***Prime Season …see more

from $150 / night

$750 - $950 / week

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from $150 / 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 Two weeks in late June still available! Pets subject to approval and an additional fee. See DeepHoleCreek site for more info and photos.! Scroll down to email Blair …see more

from $298 / night

$1500 - $3650 / week

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from $298 / 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

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 $120 / night

$600 - $750 / week

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from $120 / 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 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

1