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  • PET-FRIENDLY! Just Steps To Famous Chincoteague Pony Penning & Carnival Grounds
    From $213 per night (USD)

    VRBO

    PET-FRIENDLY! Just Steps To Famous Chincoteague Pony Penning & Carnival Grounds

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Pet Friendly, Community Pool, Screened Porch/Patio, Grilling Deck & Fishing Dock: --Creek-side, comfortably-decorated du ...

    From $213 per night (USD)

    VRBO

    Details
  •   QUIET, pet-friendly nature retreat with HOT TUB & without getting BIT!\n
    From $258 per night (USD)

    Expedia

    QUIET, pet-friendly nature retreat with HOT TUB & without getting BIT!\n

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Enjoy all the Eastern shore of Virginia has to offer! Welcome to Messongo Lodge! Listen to the owls & woodpeckers whil ...

    From $258 per night (USD)

    Expedia

    Details
  • Discover Your Perfect Getaway on the Chesapeake Bay
    From $371 per night (USD)

    VRBO

    Discover Your Perfect Getaway on the Chesapeake Bay

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Escape to our serene 3-bedroom, 2-bathroom retreat, designed to comfortably accommodate up to 8 guests. Nestled on the s ...

    From $371 per night (USD)

    VRBO

    Details
  • Secluded Home near Chincoteague Island with VB&BB
    From $274 per night (USD)

    Expedia

    Secluded Home near Chincoteague Island with VB&BB

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    11

    ***Private Sand Volleyball and Basketball courts were added this year*** Green Woods is a newly renovated 4 bedroom, two ...

    From $274 per night (USD)

    Expedia

    Details
  • Sunset Views on the Chincoteague Bay
    From $455 per night (USD)

    VRBO

    Sunset Views on the Chincoteague Bay

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    9

    Our family has loved staying on Chincoteague Island for years, and we are excited to be able to share our favorite desti ...

    From $455 per night (USD)

    VRBO

    Details
  • Stately Home on Chincoteague Island - Professionally Sanitized
    From $565 per night (USD)

    Expedia

    Stately Home on Chincoteague Island - Professionally Sanitized

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    12

    5 BDRM, 3 FULL BATH, 2400SF, HOME ON 0.5 ACRE PRIVATE LOT WITH AWESOME WATERFRONT VIEWS FROM ANY FRONT HOUSE VIEW. NICE ...

    From $565 per night (USD)

    Expedia

    Details
  • Waterfront Unit on Assateague Channel View with Floating Dock
    From $280 per night (USD)

    VRBO

    Waterfront Unit on Assateague Channel View with Floating Dock

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Waterfront on the Assateague Channel! The Sea Tag Lodge is loved by all for the views, dock, and ideal location. Perfe ...

    From $280 per night (USD)

    VRBO

    Details
  • Elegant Waterfront Residence, Magnificant Sunsets, Close to Town Ctr, Elevator
    From $696 per night (USD)

    Expedia

    Elegant Waterfront Residence, Magnificant Sunsets, Close to Town Ctr, Elevator

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    10

    Moorings North is an unique architecturally designed five bedroom home in the heart of Chincoteague Island, VA. The hous ...

    From $696 per night (USD)

    Expedia

    Details
  • SUNSHINE & VITAMIN SEA IS CALLING!
    From $331 per night (USD)

    VRBO

    SUNSHINE & VITAMIN SEA IS CALLING!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Grab your copy of ‘Misty’ and head to Chincoteague Island as everyone loves a little Vitamin Sea! This veteran-owned cot ...

    From $331 per night (USD)

    VRBO

    Details
  • Historic Whealton House with full access to Waterside Inn facilites
    From $326 per night (USD)

    Expedia

    Historic Whealton House with full access to Waterside Inn facilites

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Charming condo with water view front deck and back deck with table and chairs. Fully equipped kitchen including microwav ...

    From $326 per night (USD)

    Expedia

    Details
  • Waterfront 5 star:  Ponies!  Discounted rates for Spring 2025!
    From $598 per night (USD)

    VRBO

    Waterfront 5 star: Ponies! Discounted rates for Spring 2025!

    Bedrooms:
    4
    Bathrooms:
    3
    Sleeps:
    7

    Baywatch House is a waterfront home ideally located in a quiet and isolated location, perfect for a Chincoteague Island ...

    From $598 per night (USD)

    VRBO

    Details
  • Walking distance of town!
    From $221 per night (USD)

    Expedia

    Walking distance of town!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Homeport is a comfortable, inviting, 2 bedroom, 1 bathroom, centrally air conditioned home located on a quiet street wit ...

    From $221 per night (USD)

    Expedia

    Details
  •  Featured DC magazine 10 BEST\/Waterview CLOSEST community 2 BEACH\nJune discount!
    From $309 per night (USD)

    VRBO

    Featured DC magazine 10 BEST\/Waterview CLOSEST community 2 BEACH\nJune discount!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    This Property is located in a very private location, nestled between Assateague Chanel and Oyster Bay. In the private co ...

    From $309 per night (USD)

    VRBO

    Details
  • Enjoy sandpiperHouse on Chincoteague's Peaceful Piney Island! A virtual office
    From $292 per night (USD)

    Expedia

    Enjoy sandpiperHouse on Chincoteague's Peaceful Piney Island! A virtual office

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Fall pony roundup October 2024 FULL WEEKS ONLY DURING JUNE, JULY and AUGUST Great fall weekends ! Stay in Chincoteague ...

    From $292 per night (USD)

    Expedia

    Details
  • Shore Bird - 1 BR Studio Cottage with open floor plan. NO LINENS PROVIDED
    From $112 per night (USD)

    VRBO

    Shore Bird - 1 BR Studio Cottage with open floor plan. NO LINENS PROVIDED

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Amenities: Window A/C, Microwave, Cable TV (Basic Cable Package), WiFi, Charcoal Grill Charming studio apartment very ...

    From $112 per night (USD)

    VRBO

    Details
  • Lookout on Main - Your Waterfront Wonderland!
    From $775 per night (USD)

    Expedia

    Lookout on Main - Your Waterfront Wonderland!

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    10

    Traveling - it leaves you speechless, then turns you into a storyteller….. And oh, the stories that newly renovated ‘L ...

    From $775 per night (USD)

    Expedia

    Details
  • Sandy Gem- Waterfront Cottage w\/ Sunset Views & Private Dock
    From $248 per night (USD)

    VRBO

    Sandy Gem- Waterfront Cottage w\/ Sunset Views & Private Dock

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    Sandy Gem is a Charming Waterman's Cottage on Chincoteague Bay. Lots of Charm with ALL the modern amenities for your com ...

    From $248 per night (USD)

    VRBO

    Details
  • Piney Island Paradise - Waterfront; Pier & Patio!
    From $427 per night (USD)

    Expedia

    Piney Island Paradise - Waterfront; Pier & Patio!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Welcome to Piney Island Paradise! This well-furnished townhouse is nestled in a secluded cul-de-sac along East Side Driv ...

    From $427 per night (USD)

    Expedia

    Details
  • A Shore Joy - Private Pool - Waterfront with Pier!
    From $756 per night (USD)

    VRBO

    A Shore Joy - Private Pool - Waterfront with Pier!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    “The Ocean stirs the heart, inspires the imagination, and brings eternal Joy to the Soul.” ~ R. Wyland When was the las ...

    From $756 per night (USD)

    VRBO

    Details
  • Stunning  waterfront  panoramic view getaway house
    From $485 per night (USD)

    Expedia

    Stunning waterfront panoramic view getaway house

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    6

    Welcome to this thoughtfully remodeled waterfront property on the beautiful eastern shore of Virginia. Immerse yourself ...

    From $485 per night (USD)

    Expedia

    Details
  • Sunkissed Bliss - 2BR Townhouse - Close to Beach, NO LINENS
    From $192 per night (USD)

    VRBO

    Sunkissed Bliss - 2BR Townhouse - Close to Beach, NO LINENS

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Amenities: Central A/C, Microwave, W/D, Dishwasher, WiFi, Charcoal Grill, Deck Top of the line town home. Very comforta ...

    From $192 per night (USD)

    VRBO

    Details
  • Sea Glass - 3BR Water Front w\/floating dock. LINENS AND TOWELS PROVIDED
    From $323 per night (USD)

    Expedia

    Sea Glass - 3BR Water Front w\/floating dock. LINENS AND TOWELS PROVIDED

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    7

    Amenities: Central A/C, Smart TV with Netflix only, WiFi, Microwave, W/D, Dishwasher, Floating Dock, Outside Shower, Gas ...

    From $323 per night (USD)

    Expedia

    Details
  • Cozy Little Cottage on chincoteague island va.
    From $131 per night (USD)

    VRBO

    Cozy Little Cottage on chincoteague island va.

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    A cozy little cottage for a base to explore the eastern shores chincoteague island and Assateague beaches. Fishing, boat ...

    From $131 per night (USD)

    VRBO

    Details
  • A fabulous Pet-Friendly home that sleeps 10 in 4 Bedrooms, with a Private Pool!
    From $440 per night (USD)

    Expedia

    A fabulous Pet-Friendly home that sleeps 10 in 4 Bedrooms, with a Private Pool!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    Black Skimmer - The Best Days are Beach Days..... Black Skimmers are known for their unique grace as they forage in ...

    From $440 per night (USD)

    Expedia

    Details
  • This delightful Vacation Home sleeps 7 and is in a fabulous downtown location on
    From $362 per night (USD)

    VRBO

    This delightful Vacation Home sleeps 7 and is in a fabulous downtown location on

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    7

    Wind Rose - In the waves of change we find our true direction..... Wanderlust - "a strong desire or urge to wander or ...

    From $362 per night (USD)

    VRBO

    Details
  • Tiki Time - Canal Front! Private Boat Dock
    From $357 per night (USD)

    Expedia

    Tiki Time - Canal Front! Private Boat Dock

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Great Outdoor Living Space at Tiki Time: Private Boat Dock, A Tiki Bar and A Large Screened Porch. The interior of thi ...

    From $357 per night (USD)

    Expedia

    Details
  • Ocean East 1 is a beautifully located Vacation Home and even welcomes your famil
    From $396 per night (USD)

    VRBO

    Ocean East 1 is a beautifully located Vacation Home and even welcomes your famil

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Ocean East 1 - Because not all who wander are lost....... Welcome to Ocean East 1 on the Eastside of Chincoteague Isl ...

    From $396 per night (USD)

    VRBO

    Details
  • Sandy Bottoms on Chincoteague Island!
    From $322 per night (USD)

    Expedia

    Sandy Bottoms on Chincoteague Island!

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    10

    May you always have a shell in your pocket, and sand in your shoes….. Sandy Bottoms - the name alone stirs up fond memo ...

    From $322 per night (USD)

    Expedia

    Details
  • Sea Glass - A Waterfront Treasure on Marsh Island!
    From $402 per night (USD)

    VRBO

    Sea Glass - A Waterfront Treasure on Marsh Island!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Sea Glass - All you need is Sunshine and Saltwater.... Much like finding sea glass as you stroll on the Beach, it’s the ...

    From $402 per night (USD)

    VRBO

    Details
  • NEW FOR '2025 SEASON!!
    From $227 per night (USD)

    Expedia

    NEW FOR '2025 SEASON!!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Adorable cottage in the heart of Chincoteague. Enjoy a serene, tranquil vacation in this centrally-located cabin, walkin ...

    From $227 per night (USD)

    Expedia

    Details
  • Gallops Point - Luxury on the Chincoteague Bay!
    From $602 per night (USD)

    VRBO

    Gallops Point - Luxury on the Chincoteague Bay!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Were you dazzled by your last Vacation? If not, you clearly weren’t staying at absolutely stunning and Brand New ‘Gallop ...

    From $602 per night (USD)

    VRBO

    Details
  • Bays Landing -Dynamic Waterfront Views-Townhouse -LINENS ANDTOWELS PROVIDED
    From $276 per night (USD)

    Expedia

    Bays Landing -Dynamic Waterfront Views-Townhouse -LINENS ANDTOWELS PROVIDED

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    6

    Amenities: Central A/C, Microwave, Dishwasher, W/D, WiFi, Decks LINENS AND TOWELS PROVIDED Waterfront end unit townhou ...

    From $276 per night (USD)

    Expedia

    Details
  • Chincoteague Island Creekside Cottage
    From $313 per night (USD)

    VRBO

    Chincoteague Island Creekside Cottage

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Creekside Cottage delivers all the feels... July 2020 USA Today "Best Coastal Small Town". Private dock off large back y ...

    From $313 per night (USD)

    VRBO

    Details
  • Salty Sailor - 2BR , close to Memorial Park Pet friendly LINENS AND TOWELS
    From $155 per night (USD)

    Expedia

    Salty Sailor - 2BR , close to Memorial Park Pet friendly LINENS AND TOWELS

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    New Rental ! More Photos and information coming soon. Cozy pet friendly cottage, with 2 bedroom and 1 bath. Each bedroom ...

    From $155 per night (USD)

    Expedia

    Details
  • Sunset Bay 220 - Vista Costeria - Your Dream Vacation awaits!
    From $319 per night (USD)

    VRBO

    Sunset Bay 220 - Vista Costeria - Your Dream Vacation awaits!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Welcome to beautiful Sunset Bay Villas on the Chincoteague Bay - pure Paradise! These gorgeous condos sit directly on th ...

    From $319 per night (USD)

    VRBO

    Details
  • No Egrets!
    From $280 per night (USD)

    Expedia

    No Egrets!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Enjoy great views of Chincoteague Bay from this spacious three-story townhome. The first floor features living and dini ...

    From $280 per night (USD)

    Expedia

    Details
  • Enjoy all that Chincoteague has to offer! Bbb bbb.
    From $193 per night (USD)

    VRBO

    Enjoy all that Chincoteague has to offer! Bbb bbb.

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Close to everything! Xxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxx ...

    From $193 per night (USD)

    VRBO

    Details
  • Catch of the Day on Chincoteague Island!
    From $293 per night (USD)

    Expedia

    Catch of the Day on Chincoteague Island!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Memories at the Beach last a lifetime….. Hoping to land the big one this year for your Chincoteague Island Vacation? L ...

    From $293 per night (USD)

    Expedia

    Details
  • Breezy Corner in the heart of Chincoeague!
    From $305 per night (USD)

    VRBO

    Breezy Corner in the heart of Chincoeague!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    7

    Welcome to Breezy Corner on our little slice of Heaven, Chincoteague Island. Located at the corner of Willow and Jester, ...

    From $305 per night (USD)

    VRBO

    Details
  • Adorable Coquina Cottage on Chincoteague!
    From $252 per night (USD)

    Expedia

    Adorable Coquina Cottage on Chincoteague!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    When was the last time your Vacation made you happier than a Seagull with a french fry? If you’ve been searching for jus ...

    From $252 per night (USD)

    Expedia

    Details
  • The Coastal Retreat you've been longing for!
    From $533 per night (USD)

    VRBO

    The Coastal Retreat you've been longing for!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Live for the moments you can’t put into words….. When was the last time you took a Vacation that truly took your breat ...

    From $533 per night (USD)

    VRBO

    Details
  • Channel View Charmer - Water Views and Pet Friendly!
    From $306 per night (USD)

    Expedia

    Channel View Charmer - Water Views and Pet Friendly!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Channel View Charmer - Every moment has the potential to be amazing…. **Now Dog Friendly!** Looking for the perfect b ...

    From $306 per night (USD)

    Expedia

    Details
  • Channel View Cottage - Waterfront Wonderland!
    From $374 per night (USD)

    VRBO

    Channel View Cottage - Waterfront Wonderland!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    This lovely Home is the perfect Vacation Destination for your next Beach Getaway. Located on Lewis Creek, you'll enjoy s ...

    From $374 per night (USD)

    VRBO

    Details
  • George's Retreat - Tucked away, yet close to the Beach!
    From $219 per night (USD)

    Expedia

    George's Retreat - Tucked away, yet close to the Beach!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Traveling - it leaves you speechless, then turns you into a Storyteller. Welcome to the Chincoteague Island Retreat you' ...

    From $219 per night (USD)

    Expedia

    Details
  • Island Retreat - Lovely Marsh Views and Pet Friendly!
    From $216 per night (USD)

    VRBO

    Island Retreat - Lovely Marsh Views and Pet Friendly!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    7

    Travel - the only thing you pay for that makes you richer. But, you don't have to break the bank to have the Vacation of ...

    From $216 per night (USD)

    VRBO

    Details
  • Little Red Cottage on Chincoteague Island!
    From $287 per night (USD)

    Expedia

    Little Red Cottage on Chincoteague Island!

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Little Red Cottage - “My heart will always be in a Little Cottage by the Sea….” Life takes you down many paths, but our ...

    From $287 per night (USD)

    Expedia

    Details
  • Only 5 min. from the Beach!
    From $191 per night (USD)

    VRBO

    Only 5 min. from the Beach!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Assateague Inn 213-2R has been TOTALLY updated and is STUNNING! All new bedding, carpet, paint, appliances and more! Sit ...

    From $191 per night (USD)

    VRBO

    Details
  • Lighthouse Overlook - Amazing Views!
    From $382 per night (USD)

    Expedia

    Lighthouse Overlook - Amazing Views!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Lighthouse Overlook - Every day should be a Beach Day….. Life is busy - too busy at times, it seems. When was the last ...

    From $382 per night (USD)

    Expedia

    Details
  • Chincoteague Pony Penning Hideaway
    Click For Pricing

    VRBO

    Chincoteague Pony Penning Hideaway

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Our unique getaway is perfect for large families or a personal spot just for two. We have a great advantage because we a ...

    Click For Pricing

    VRBO

    Details
  • Lost Pearl
    From $256 per night (USD)

    Expedia

    Lost Pearl

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Comfortable home on a quiet street. Conveniently located close to town and Memorial Park. Great for a family vacation. ...

    From $256 per night (USD)

    Expedia

    Details
  • Charming bungalow on the bay behind Chincoteague
    From $134 per night (USD)

    VRBO

    Charming bungalow on the bay behind Chincoteague

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    5

    This memorable place is anything but ordinary. Small bay bungalow tiny house/ camper on private lot in gated community. ...

    From $134 per night (USD)

    VRBO

    Details
  • Find your 'Sea Treasure' on Chincoteague Island!
    From $234 per night (USD)

    Expedia

    Find your 'Sea Treasure' on Chincoteague Island!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Looking for an incredible Chincoteague Island Vacation Experience? You just found it at Sea Treasure - a beautiful Duple ...

    From $234 per night (USD)

    Expedia

    Details
  • Painted Pony Cottage - Pet Friendly!
    From $240 per night (USD)

    VRBO

    Painted Pony Cottage - Pet Friendly!

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Life takes you down many paths, but our favorite ones always lead to the Beach. It's hard to find the words to describe ...

    From $240 per night (USD)

    VRBO

    Details
  • Saltwater Cottage - Pet Friendly!
    From $290 per night (USD)

    Expedia

    Saltwater Cottage - Pet Friendly!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Welcome to beautiful Saltwater Cottage, in the heart of Chincoteague Island, Virginia. You've heard stories about our li ...

    From $290 per night (USD)

    Expedia

    Details
  • Seaside Serendipity on Chincoteague Island!
    From $374 per night (USD)

    VRBO

    Seaside Serendipity on Chincoteague Island!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Welcome to Seaside Serendipity - where happiness comes in waves.... Looking for the perfect beach getaway for your fam ...

    From $374 per night (USD)

    VRBO

    Details
  • Find your peace at One Peace Cottage
    From $246 per night (USD)

    Expedia

    Find your peace at One Peace Cottage

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Peace. Love. Beach. Have you been yearning for a break from the hectic day to day? An affordable getaway that will brin ...

    From $246 per night (USD)

    Expedia

    Details
  • Oyster Bay Hideaway on Chincoteague Island!
    From $337 per night (USD)

    VRBO

    Oyster Bay Hideaway on Chincoteague Island!

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    5

    Oyster Bay Hideaway - Beach Days are the Best Days….. Just imagine relaxing on the Deck taking in that salty, sweet bay ...

    From $337 per night (USD)

    VRBO

    Details
  • Welcome to Paradise!!
    From $414 per night (USD)

    Expedia

    Welcome to Paradise!!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Of all the paths you take in life, make sure a few of them are sandy….. Welcome to ‘Paradise’ on dreamy Chincoteague Is ...

    From $414 per night (USD)

    Expedia

    Details
  • Serendipity on Chincoteague - The perfect getaway!
    From $265 per night (USD)

    VRBO

    Serendipity on Chincoteague - The perfect getaway!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Just give me the Sea, and a little Cottage just to be….. Work, meetings, school, traffic, homework, repeat - right?! It ...

    From $265 per night (USD)

    VRBO

    Details
  • Sugar Shores - A sweet Vacation awaits you!
    From $278 per night (USD)

    Expedia

    Sugar Shores - A sweet Vacation awaits you!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Sugar Shores - Your next Vacation can be both Salty and Sweet! When was the last time you had a Vacation that took your ...

    From $278 per night (USD)

    Expedia

    Details
  • Sunny Shack on Chincoteague Island!
    From $332 per night (USD)

    VRBO

    Sunny Shack on Chincoteague Island!

    Bedrooms:
    2
    Bathrooms:
    5
    Sleeps:
    10

    Sunny Shack - The Best Days are Beach Days..….. Welcome to Sunny Shack on wild and wonderful Chincoteague Island! This ...

    From $332 per night (USD)

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  • Shore Beats Work - Affordable and Great Location!
    From $206 per night (USD)

    Expedia

    Shore Beats Work - Affordable and Great Location!

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    6

    Ready to kick back and enjoy a little “island time”? ‘Shore Beats Work’! If you’re looking for the perfect Home Base f ...

    From $206 per night (USD)

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  • Sunrise Serenade - AMAZING Views!
    From $152 per night (USD)

    VRBO

    Sunrise Serenade - AMAZING Views!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Have you always wanted to Vacation on Chincoteague Island, but couldn't bear the thought of 4 of you in a hotel room? Lo ...

    From $152 per night (USD)

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  • starbright Cottage - Perfect Location and Pet Friendly!
    From $292 per night (USD)

    Expedia

    starbright Cottage - Perfect Location and Pet Friendly!

    Bedrooms:
    2
    Bathrooms:
    5
    Sleeps:
    9

    Reach for the Stars on your next Chincoteague Island Vacation….. Welcome to whimsical Starbright Cottage on beautiful C ...

    From $292 per night (USD)

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  • Have a \Shell of a Time\ on Chincoteague Island!
    From $235 per night (USD)

    VRBO

    Have a \"Shell of a Time\" on Chincoteague Island!

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Ready to have a ‘Shell of a Time’ on your next trip to our Little Island by the Sea?! You will absolutely fall in love w ...

    From $235 per night (USD)

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  • Wonderview 208 - Breathtaking Channel Views!
    From $344 per night (USD)

    Expedia

    Wonderview 208 - Breathtaking Channel Views!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Wonderview 208 ~ Take the Journey to enjoy the View….. Life gets busy - work, kids, appointments, pets - it never seems ...

    From $344 per night (USD)

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  • The Mane Escape - Pet Friendly on Chincoteague!
    From $462 per night (USD)

    VRBO

    The Mane Escape - Pet Friendly on Chincoteague!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    We travel not to escape Life, but for Life not to escape us….. When was the last time you slowed down - took time to wa ...

    From $462 per night (USD)

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  • The Pearl at Grand Bay on Chincoteague Island!
    From $308 per night (USD)

    Expedia

    The Pearl at Grand Bay on Chincoteague Island!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Salty air breezes and the sweet serenity of pond-front living await you at The Pearl at Grand Bay. This Newly Remodeled ...

    From $308 per night (USD)

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  • The Robinson Family Beach House on Chincoteague!
    From $389 per night (USD)

    VRBO

    The Robinson Family Beach House on Chincoteague!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    There is no time to be bored in a world as beautiful as this…. Welcome to The Robinson Family Beach House on our little ...

    From $389 per night (USD)

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  • K and S Paradise on Chincoteague Island!
    From $442 per night (USD)

    Expedia

    K and S Paradise on Chincoteague Island!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Life’s a Beach - If you’re not barefoot, you’re overdressed…. When was the last time your Vacation made you happier tha ...

    From $442 per night (USD)

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    Details
  • Whelks on Willow - Private Pool!
    From $321 per night (USD)

    VRBO

    Whelks on Willow - Private Pool!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Whelks on Willow - Live in the Sunshine, Swim the Sea, drink the Wild Air..... Welcome to Whelks on Willow - a lovely ...

    From $321 per night (USD)

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  • PonyTime - 4BR WATERFRONT home in Oyster Bay. Dock,decks,Hot Tub,NO LINENS
    From $392 per night (USD)

    Expedia

    PonyTime - 4BR WATERFRONT home in Oyster Bay. Dock,decks,Hot Tub,NO LINENS

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    9

    4BR/2.5B***(Single Level Home) {2Q,2T, Bunk Q/T} Amenities: Central A/C, WiFi, Microwave, W/D, Dishwasher, hot tub, fir ...

    From $392 per night (USD)

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  • Beachin' at the Cove - Golf course, Shared pool & more!
    From $1163 per night (USD)

    VRBO

    Beachin' at the Cove - Golf course, Shared pool & more!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Come and enjoy a private place to call home during your much needed vacation! Beachin' at the Cove has everything you ne ...

    From $1163 per night (USD)

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  • Creek House - Waterfront Oasis on Holden's Creek
    From $542 per night (USD)

    Expedia

    Creek House - Waterfront Oasis on Holden's Creek

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    14

    Creek House, Privately located in an imaginative setting; nature and history are perfectly coupled with luxurious accomm ...

    From $542 per night (USD)

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    Details
  • Seahorse Cove - Screened porch, Shared pools!
    From $297 per night (USD)

    VRBO

    Seahorse Cove - Screened porch, Shared pools!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Welcome to Seahorse Cove! This is an adorable 3 bedroom, 2 bathroom home that has been completely renovated. You will no ...

    From $297 per night (USD)

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  • Bliss on the Bay - Perfect Beach Getaway
    From $226 per night (USD)

    Expedia

    Bliss on the Bay - Perfect Beach Getaway

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Welcome to Bliss on the Bay - leave your troubles at the door, you won't be needing them here! This super charming 1 Bed ...

    From $226 per night (USD)

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    Details
  • House on the Dune - Pure Paradise!
    From $599 per night (USD)

    VRBO

    House on the Dune - Pure Paradise!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Travel - It leaves you speechless, then turns you into a Storyteller….. When was the last time you took a Vacation that ...

    From $599 per night (USD)

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  • Historic Family Vacation Home with Golf Cart
    From $387 per night (USD)

    Expedia

    Historic Family Vacation Home with Golf Cart

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Built in 1905 as a grocery store, this historic home was a gathering place for islanders seeking refuge during the 1962 ...

    From $387 per night (USD)

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  • A Little Serenity- A Cozy One Bedroom Escape in Quant Onancock,Mid-Eastern Shore
    From $263 per night (USD)

    VRBO

    A Little Serenity- A Cozy One Bedroom Escape in Quant Onancock,Mid-Eastern Shore

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

    Comfy and Quiet. An Intimate bedroom with blackout curtains adjoins a simple but clean and upgraded bathroom and shower ...

    From $263 per night (USD)

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  • EVENTIDE on Chincoteague Island!
    From $413 per night (USD)

    Expedia

    EVENTIDE on Chincoteague Island!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    10

    “Travel is the only thing that leaves you speechless, then turns you into a storyteller.” ~ Ibn Battuta Have you been l ...

    From $413 per night (USD)

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    Details
  • Happy Ours- Firepit, Close to Beach!
    From $307 per night (USD)

    VRBO

    Happy Ours- Firepit, Close to Beach!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Escape to the charming coastal town of Chincoteague and experience the perfect vacation at our 3-bedroom vacation home. ...

    From $307 per night (USD)

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    Details
  • Driftwood-  Close to Beach!!
    From $355 per night (USD)

    Expedia

    Driftwood- Close to Beach!!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Wonderful location - quiet street and close to the beach. Great one-level floor plan features: Updated fully equipped ki ...

    From $355 per night (USD)

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    Details
  • Bay View-WATERFRONT, DOCK, SUNSETS!
    From $655 per night (USD)

    VRBO

    Bay View-WATERFRONT, DOCK, SUNSETS!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    9

    Brand New Luxury Vacation Rental Home. Located in the Prestigious Wildcat Community. Enjoy Unobstructed Views of Chinc ...

    From $655 per night (USD)

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  • The Good Life on Ocean
    From $318 per night (USD)

    Expedia

    The Good Life on Ocean

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    10

    The Ocean stirs the heart, inspires imagination, and brings joy to the soul…. Welcome to The Good Life on Ocean - the p ...

    From $318 per night (USD)

    Expedia

    Details
  • Oyster Catcher - Pet friendly; Deep water access!
    From $537 per night (USD)

    VRBO

    Oyster Catcher - Pet friendly; Deep water access!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    Welcome to Oyster Catcher! This home offers a prime location, beautiful views and a deep water dock (6 feet at low tide) ...

    From $537 per night (USD)

    VRBO

    Details
  • Family Friendly Waterfront Escape w\/pier, gameroom, and fire pit!
    From $288 per night (USD)

    Expedia

    Family Friendly Waterfront Escape w\/pier, gameroom, and fire pit!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    12

    Escape the hustle and bustle and get a way from it all at the Oyster Bay Getaway! Enjoy the still of the morning or list ...

    From $288 per night (USD)

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    Details
  • Ocean Pearl Cottage - New Listing and SO adorable!
    From $288 per night (USD)

    VRBO

    Ocean Pearl Cottage - New Listing and SO adorable!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Life takes you down many paths, but our favorite ones always lead to the Beach. It's hard to find the words to describe ...

    From $288 per night (USD)

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  • Waterfront Sunsets on Marsh Island!
    From $202 per night (USD)

    Expedia

    Waterfront Sunsets on Marsh Island!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    3

    Welcome to Waterfront Sunsets - Sunsets are proof that no matter what happens, every day can end beautifully….. This ad ...

    From $202 per night (USD)

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    Details
  • Misty Sunrise-Waterfront Views-Relax & Unwind-Modern Decor
    From $268 per night (USD)

    VRBO

    Misty Sunrise-Waterfront Views-Relax & Unwind-Modern Decor

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    6

    Just completely Updated! Interior Photos Coming Soon, It is worth the wait! This beautiful unit offers spectacular view ...

    From $268 per night (USD)

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  • Mermaid Manor-Water Lovers Paradise
    From $631 per night (USD)

    Expedia

    Mermaid Manor-Water Lovers Paradise

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    Just Listed! More Photos Coming Soon! This gorgeous home is located directly on the Assateague Channel and affords brea ...

    From $631 per night (USD)

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    Details
  • The Salty Pinecone-Waterfront-Peaceful
    From $398 per night (USD)

    VRBO

    The Salty Pinecone-Waterfront-Peaceful

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Fully Updated townhome with stunning views of Assateague Island & the Lighthouse. Located on deep water with Private B ...

    From $398 per night (USD)

    VRBO

    Details
  • Amistad - Beautiful Historic Home on Chincoteague Island
    From $351 per night (USD)

    Expedia

    Amistad - Beautiful Historic Home on Chincoteague Island

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    10

    The very definition of ‘Amistad’ is friendship - and that suits this beautiful home so well, as you’ll feel like you’re ...

    From $351 per night (USD)

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    Details
  • Beechnut Villa-Waterfront-Cozy
    From $361 per night (USD)

    VRBO

    Beechnut Villa-Waterfront-Cozy

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Waterfront duplex offers some of the best views of Assateague Island and the Lighthouse. Enjoy amazing views from the s ...

    From $361 per night (USD)

    VRBO

    Details
  • Summer Creek - Waterview - Shared Dock, LINENS & TOWELS
    From $162 per night (USD)

    Expedia

    Summer Creek - Waterview - Shared Dock, LINENS & TOWELS

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Amenities: Central A/C, Dishwasher, WIFI, DVD, WiFi, Smart TV Streaming Only, W/D, Microwave, Deck, Shared Dock. The ...

    From $162 per night (USD)

    Expedia

    Details
  • Tangier Island three bedroom house near the beach.
    From $205 per night (USD)

    VRBO

    Tangier Island three bedroom house near the beach.

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    7

    We have a quiet location on southern West Ridge Road, paralleling the runway near the mile-long TI beach and within 10 m ...

    From $205 per night (USD)

    VRBO

    Details
  • Cozy RV with all comforts of home in Horn town VA
    From $171 per night (USD)

    Expedia

    Cozy RV with all comforts of home in Horn town VA

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    6

    Consider this recreational vehicle your home away from home while you visit Horntown. This delightful property features ...

    From $171 per night (USD)

    Expedia

    Details
  • Bayside Haven - Dog Friendly!
    From $335 per night (USD)

    VRBO

    Bayside Haven - Dog Friendly!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    7

    “To travel in the company of those we love is Home in motion.” ~ Unknown When was the last time you stepped away from t ...

    From $335 per night (USD)

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  • Paradise View - AMAZING VIEWS and GAME ROOM!
    From $629 per night (USD)

    Expedia

    Paradise View - AMAZING VIEWS and GAME ROOM!

    Bedrooms:
    6
    Bathrooms:
    5
    Sleeps:
    10

    Were you dazzled by your last Vacation? If not, you clearly were not staying at breathtaking Paradise View in Richardson ...

    From $629 per night (USD)

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  • Mermaid & Mare, A Downtown Retreat with Hot Tub, Firepit, Decks, & Pet Friendly!
    From $367 per night (USD)

    VRBO

    Mermaid & Mare, A Downtown Retreat with Hot Tub, Firepit, Decks, & Pet Friendly!

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    6

    Escape to Mermaid & Mare, a deluxe downtown island retreat designed for relaxation and adventure. This charming getaway ...

    From $367 per night (USD)

    VRBO

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  • Gorgeous Channel Views!
    From $275 per night (USD)

    Expedia

    Gorgeous Channel Views!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Welcome to Ducks, Docks, and Flip Flops - what more could you want, right? This recently renovated and beyond adorable W ...

    From $275 per night (USD)

    Expedia

    Details