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

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120 Vacation rentals

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 - $995 / week

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from $110 / 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 - $800 / week

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from $135 / 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
***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: $1190 weekly/$238 per night.Off Season Rates: $965 weekly/$193 per night. Additional amenities include: d …see more

from $193 / night

$965 - $1,190 / week

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from $193 / 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 weekly …see more

from $180 / night

$900 - $1,400 / week

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from $180 / night

16

Vacation home with shared 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
***7134 Silver Sails Landing***Beautiful spacious duplex with all new furnishings. Screened porch overlooking the wetlands. Deck and community pool. Offers wireless internet!! Close to carnival grounds!***Bed Sizes: 2 Queen, 2 Twin.***Prime Season Rates: $1350 weekly/$2 …see more

from $195 / night

$975 - $1,350 / week

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from $195 / 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
***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. Sp …see more

from $210 / night

$1,050 - $1,350 / week

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from $210 / 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

(1) Excellent 

20

Vacation home in Chincoteague Island

Virginia / Chincoteague Island

3 9 7 nights min

  • 3 bedrooms
  • Sleeps 9
  • 7 nights min
  • Child friendly
  • Air conditioning
***6404 Pine Drive-Piney Island***Nature lover’s dream! Tucked away in Piney Island with Assateague just a short bike ride away . You’ll love relaxing in the large screen porch or enjoy the water views from the second level deck. Community boat launch great for kayaker …see more

from $340 / night

$1,700 / week

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from $340 / 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. Within walking distance to Assateague and Water Park.***Also offering Internet c …see more

from $199 / night

$995 - $1,350 / week

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from $199 / night

13

Chincoteague Island Vacation home rental

Virginia / Chincoteague Island

2 7 7 nights min

  • 2 bedrooms
  • Sleeps 7
  • 7 nights min
  • Child friendly
  • Air conditioning
***7514 Beebe Road***Artist styled bungalow is delightful and comfortable.***Bed Sizes: 2 Queen, 3 Twin, 1 Sleep Sofa***Prime Season Rates: $750 weekly/$150 per night.Off Season Rates: $650 weekly/$130 per night.Shoulder Season Rates: $700 weekly/$140 per night. Additi …see more

from $130 / night

$650 - $750 / week

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from $130 / 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) 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 $290 / night

$1,450 - $1,850 / week

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from $290 / night

10

Vacation home in Chincoteague Island

Virginia / Chincoteague Island

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Air conditioning
***6368 Pine Drive-Piney Island***Brand new Piney Island home. Spacious design open and bright with large screened porch and two covered porches offer views of Assateague in the distance. Close to Edie's Folly. Acess to community boat dock.***This Property provides Line …see more

from $220 / night

$1,100 - $1,300 / week

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from $220 / night

(1) Excellent 

12

Chincoteague Island Vacation home rental

Virginia / Chincoteague Island

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
***6347 Jester Street***Unique Pet Friendly Chincoteague home located in town within walking distance to shops and restaurants. Has large fenced in back yard and a private outside rinse area.******New HVAC-Central heating and Air for 2018***Bed Sizes: 1 King, 2 Twins, …see more

from $170 / night

$850 - $1,050 / week

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from $170 / night

11

Chincoteague Island Vacation home rental

Virginia / Chincoteague Island

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
***5348 Oak Drive-Piney Island***Tucked away in Piney Island Just minutes from Assateague's nature trails and beach. Wireless internet and water access for canoe and kayak. Pet Friendly! New bedroom and bathroom added in 2013. All bedrooms on same level.***Bed Sizes: 1 …see more

from $118 / night

$590 - $825 / week

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from $118 / night

15

Vacation home rental

Virginia / Chincoteague Island

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Air conditioning
***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

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

$1,450 - $1,875 / week

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from $290 / 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 Drive***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 Rate …see more

from $115 / night

$575 - $780 / week

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from $115 / 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
***8172 Marsh Point Lane***Charming, traditional island home near town. Walking distance to shops, restaurants, waterfront. Perfect for gathering family/friends. 1 bedroom and 1 bath downstairs/2 bedrooms and 1 bath upstairs.***Bed Sizes: 2 Queen, 1 Queen Sleep Sofa, 2 …see more

from $139 / night

$695 - $995 / week

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from $139 / 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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avg. 53 minutes

from $125 / 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 - $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
***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 Do …see more

from $100 / night

$500 - $650 / week

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from $100 / night

(1) Excellent 

11

Chincoteague Island Vacation home rental

Virginia / Chincoteague Island

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Air conditioning
***7071 Bond Street***Tastefully decorated townhouse with many new appliances, screen porch and convenient in town location. Offers Wi-Fi. 2 bedrooms and 1 bath downstairs/1 bedroom and 1 bath upstairs.***Bed Sizes: 1 King, 1 Double, 2 Twin, 1 Queen Sleep Sofa***Prime S …see more

from $110 / night

$550 - $650 / week

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from $110 / 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

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

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

(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

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 - $1,350 / week

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from $195 / night

12

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
***6321 Captain's Lane Unit #107 Sunset Bay Villas***Beats Campin in a total luxury Waterfront Condo, first floor unit overlooks Marina and Chincoteague Bay. Master Bedroom with jacuzzi tub and large waterfront balcony off the spacious living area. Fully equipped with …see more

from $240 / night

$1,200 - $1,500 / week

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from $240 / night

(1) Excellent 

13

Vacation home rental

Virginia / Chincoteague Island

3 7 7 nights min

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min
  • Child friendly
  • Air conditioning
***5175 Coley's Lane***Totally remodeled traditional island home. Perfect for your vacation getaway! Located on private lane with large back yard. Master suite with sitting area. Two additional bedrooms and loft. Short distance to seafood market and boat launch.*** …see more

from $150 / night

$750 - $975 / week

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from $150 / night

(1) Very Good 

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), half bath downstairs*** Bed Sizes: 1 Queen, 2 Twin, 1 …see more

from $150 / night

$750 - $950 / week

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from $150 / 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 $160 / night

$800 - $850 / week

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from $160 / night

19

Vacation home in Chincoteague Island

Virginia / Chincoteague Island

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
  • Air conditioning
***5505 Warren Street***Lovely spacious3 BR canal home at Northern end of island is top notch for a delightful vacation experience. Wildlife and birdwatching throughout the day with panaramic views throughtout. Open floor plan with large dining area and back screened …see more

from $260 / night

$1,300 - $1,650 / week

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from $260 / night

9

Vacation home rental

Virginia / Chincoteague Island

4 7 7 nights min

  • 4 bedrooms
  • Sleeps 7
  • 7 nights min
  • Child friendly
  • Air conditioning
***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 Rates: $60 …see more

from $120 / night

$600 - $1,550 / week

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from $120 / night

17

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

$1,750 - $1,975 / week

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from $350 / 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

(1) Very Good 

10

Chincoteague Island Vacation home rental

Virginia / Chincoteague Island

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
  • Air conditioning
***4560 Shelley Cove Lane - Smugglers Cove***Private, secluded neighborhood. Very natural wooded setting with water access available. Next door to Pine Cove Place and Serenity Now. Water access is for kayaks and canoes. 2 bedrooms and 1 bath downstairs/2 bedrooms and …see more

from $172 / night

$1,200 / week

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from $172 / night

13

Vacation home in Chincoteague Island

Virginia / Chincoteague Island

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
***3757 Willow Street***Completely renovated traditional home in town with bright cheerful rooms and offers all amenities. Pet friendly! Two bedrooms on second level of home and two walk thru third story bedrooms. Third story loft with 4 twin beds has a typical Traditi …see more

from $140 / night

$700 - $975 / week

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from $140 / 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

$550 - $950 / week

Inquire View

from $110 / 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
***3196 Main Street***Enjoy sunsets from this lovely waterfront home with dock!! Offers wireless internet and great views.***Bed Sizes: 1 Queen, 1 Double, 2 Twin, 1 Queen Sleep Sofa***Prime Season Rates: $1100 weekly/$220 per night.Off Season Rates: $800 weekly/$160 per …see more

from $160 / night

$800 - $1,100 / week

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from $160 / night