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Results: 762 Rentals

  • Brand New Home -  Water Views and Walk to Carnival Grounds!
    From $383 per night (USD)

    VRBO

    Brand New Home - Water Views and Walk to Carnival Grounds!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    “Travel not to escape Life, but so Life doesn't escape you.” ~ Unknown Welcome to The Feathered Nest - a tranquil retre ...

    From $383 per night (USD)

    VRBO

    Details
  • Oyster Bay Oasis - 5 Min to Assateague!
    From $380 per night (USD)

    Expedia

    Oyster Bay Oasis - 5 Min to Assateague!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Memories made together last a lifetime….. Welcome to Oyster Bay Oasis in ever-popular Oyster Bay I on Chincoteague Isla ...

    From $380 per night (USD)

    Expedia

    Details
  • Rising Tide-Beautiful House w\/ Canal Views & Expansive Decks & Outdoor Space
    From $593 per night (USD)

    VRBO

    Rising Tide-Beautiful House w\/ Canal Views & Expansive Decks & Outdoor Space

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    11

    Beautiful, newly built home located on a quiet lane in the Richard's Landing Community. Great views looking down the can ...

    From $593 per night (USD)

    VRBO

    Details
  • Mulligan Home - Waterfront w\/ boat dock & community pools!
    From $426 per night (USD)

    Expedia

    Mulligan Home - Waterfront w\/ boat dock & community pools!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Nestled in the picturesque Captain's Cove community, this exquisite three-bedroom, two-bathroom waterfront residence rep ...

    From $426 per night (USD)

    Expedia

    Details
  • Casa Mar - Main Street w\/ Screened Porch!
    From $295 per night (USD)

    VRBO

    Casa Mar - Main Street w\/ Screened Porch!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Welcome to your perfect getaway on Chincoteague Island! This newly listed 3-bedroom, 2-bathroom townhouse offers the ide ...

    From $295 per night (USD)

    VRBO

    Details
  • Closest Community to the Beach!
    From $395 per night (USD)

    Expedia

    Closest Community to the Beach!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    “Time has a wonderful way of showing us what really matters…..” ~ Unknown Time flies, as they say - you blink and the k ...

    From $395 per night (USD)

    Expedia

    Details
  • Assateague Inn #209 Cozy Efficiency Suite w\/ Shared Pool, Crabbing Pier &  Wi-Fi
    From $273 per night (USD)

    VRBO

    Assateague Inn #209 Cozy Efficiency Suite w\/ Shared Pool, Crabbing Pier & Wi-Fi

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    New Kitchen, Bathroom, and Flooring for 2025! New photos when completed! Amazing marsh and wetland views. Shared private ...

    From $273 per night (USD)

    VRBO

    Details
  • Misty Mare Townhouse - Gorgeous home on Chincoteague Island
    From $210 per night (USD)

    Expedia

    Misty Mare Townhouse - Gorgeous home on Chincoteague Island

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    4

    Your Chincoteague adventure begins at this 2-bedroom townhome. Step inside and be greeted by the gorgeous decor and soot ...

    From $210 per night (USD)

    Expedia

    Details
  • 11 Mi to Chincoteague: Atlantic Home w\/ Decks!
    From $299 per night (USD)

    VRBO

    11 Mi to Chincoteague: Atlantic Home w\/ Decks!

    Bedrooms:
    2
    Bathrooms:
    5
    Sleeps:
    8

    Waterfront Property | Fire Pit w/ Seating | Outdoor Dining Area Let your troubles drift out to sea when you stay at thi ...

    From $299 per night (USD)

    VRBO

    Details
  • Epiphany-Deep Hole Creek-Chincoteague - Deep Water Dock! 2 King 4 Twin 5 Bath
    From $1070 per night (USD)

    Expedia

    Epiphany-Deep Hole Creek-Chincoteague - Deep Water Dock! 2 King 4 Twin 5 Bath

    Bedrooms:
    5
    Bathrooms:
    4
    Sleeps:
    10

    Tie up your boat at our Deep Water Dock. Swim from the Dock! Escape to this brilliant 4-bedroom Chincoteague retreat o ...

    From $1070 per night (USD)

    Expedia

    Details
  • Bay Pony on Chincoteague - Pool and 5 min. to Beach!
    From $367 per night (USD)

    VRBO

    Bay Pony on Chincoteague - Pool and 5 min. to Beach!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Isn't it time for a new romance.....with Life?! A visit to fabulous Bay Pony is certainly the place to begin. This pheno ...

    From $367 per night (USD)

    VRBO

    Details
  • Robert's Retreat - Brand new home w\/ gorgeous water views!
    From $1477 per night (USD)

    Expedia

    Robert's Retreat - Brand new home w\/ gorgeous water views!

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    10

    Discover the ultimate family retreat in this brand new 5-bedroom, 3.5-bathroom home located in the picturesque Captain's ...

    From $1477 per night (USD)

    Expedia

    Details
  • Gray Pearl - Gorgeous Waterfront just a few minutes to the Beach!
    From $524 per night (USD)

    VRBO

    Gray Pearl - Gorgeous Waterfront just a few minutes to the Beach!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    Freedom - it's a State of Mind. The sense of freedom that comes with being on Vacation is like none other. When was the ...

    From $524 per night (USD)

    VRBO

    Details
  • Above The Bay - SFH - WF w\/Views Everywhere.  Brand New Home, Linens included
    From $610 per night (USD)

    Expedia

    Above The Bay - SFH - WF w\/Views Everywhere. Brand New Home, Linens included

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Amenities: Central A/C, WiFi, Microwave, W/D, TV. NO PETS AND NO SMOKING. First Year Special $ 3703 for any remaining we ...

    From $610 per night (USD)

    Expedia

    Details
  • Cantering Sands-  New for 2025 3BR\/2Bath home w\/patio & Sc Porch.
    From $304 per night (USD)

    VRBO

    Cantering Sands- New for 2025 3BR\/2Bath home w\/patio & Sc Porch.

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    New Rental for 2025. Amenities:3BR/2B***(1B Down2T , 2 bedroom (2Q) up) {2T,2Q} Linens and Towels Provided, screen porch ...

    From $304 per night (USD)

    VRBO

    Details
  • Charming Getaway - 4 Bedroom Home, Pool Access
    From $450 per night (USD)

    Expedia

    Charming Getaway - 4 Bedroom Home, Pool Access

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Welcome to your dream waterfront rental, "Charming Getaway," a newly built home perfect for both relaxation and entertai ...

    From $450 per night (USD)

    Expedia

    Details
  • Near Chincoteague & Assateague Island\nCharming 2-bedroom cottage
    From $169 per night (USD)

    VRBO

    Near Chincoteague & Assateague Island\nCharming 2-bedroom cottage

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Located in Saxis, enjoy what this 2-bedroom cottage has to offer. This delightful property features 1 queen bed and 1 fu ...

    From $169 per night (USD)

    VRBO

    Details
  • 2 Mi to Downtown: Tranquil Abode in Chincoteague!
    From $334 per night (USD)

    Expedia

    2 Mi to Downtown: Tranquil Abode in Chincoteague!

    Bedrooms:
    2
    Bathrooms:
    5
    Sleeps:
    8

    Spacious Private Yard | Screened Porch/Game Room | Pets Welcome w/ Fee | WFH Friendly A blissful island escape awaits a ...

    From $334 per night (USD)

    Expedia

    Details
  • Casa del Sol in Captain's Cove Golf & Yacht Club!
    From $579 per night (USD)

    VRBO

    Casa del Sol in Captain's Cove Golf & Yacht Club!

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    10

    Welcome to Casa Del Sol - “Live in the Sunshine, swim the Sea, drink the Wild Air….” When was the last time your Vacati ...

    From $579 per night (USD)

    VRBO

    Details
  • 3 story 2-bedroom house, Large decks, waterview, near beach, Fitness, Game room
    From $295 per night (USD)

    Expedia

    3 story 2-bedroom house, Large decks, waterview, near beach, Fitness, Game room

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Close to the beach! Enjoy this unique and tranquil 2 bedroom home with occupancy for 6. Pack and play crib is also avail ...

    From $295 per night (USD)

    Expedia

    Details
  • Sunset Bay Villa 109 - Spectacular Waterfront on Chincoteague Island!
    From $376 per night (USD)

    VRBO

    Sunset Bay Villa 109 - Spectacular Waterfront on Chincoteague Island!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Welcome to Sunset Bay 109 at fabulous Sunset Bay Villas on the Chincoteague Bay - pure Paradise! These gorgeous Condos s ...

    From $376 per night (USD)

    VRBO

    Details
  • Stunning Views. One-of-a-KInd Design, Renovated 2024 - Wright on the Water!
    From $705 per night (USD)

    Expedia

    Stunning Views. One-of-a-KInd Design, Renovated 2024 - Wright on the Water!

    Bedrooms:
    5
    Bathrooms:
    4
    Sleeps:
    14

    Stunning views throughout the home - over 100ft of direct waterfront. Authentic Eastern Shore experience, within a uniqu ...

    From $705 per night (USD)

    Expedia

    Details
  • My Happy Place :  Space for EVERYONE plus a PRIVATE POOL too!
    From $476 per night (USD)

    VRBO

    My Happy Place : Space for EVERYONE plus a PRIVATE POOL too!

    Bedrooms:
    2
    Bathrooms:
    5
    Sleeps:
    15

    If you're looking for a spacious vacation home suitable for ALL of your friends and family members, My Happy Place will ...

    From $476 per night (USD)

    VRBO

    Details
  • Waterfront Estate - Amazing Views And Sunsets - Pet Friendly - New rate for 2025
    From $529 per night (USD)

    Expedia

    Waterfront Estate - Amazing Views And Sunsets - Pet Friendly - New rate for 2025

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Welcome to Sunshine Bay! A beautifully inviting year-round waterfront house maintained to the highest standards. The hom ...

    From $529 per night (USD)

    Expedia

    Details
  • Charming Waterfront Cottage with Boat Ramp and boat docking - Pet Friendly
    From $268 per night (USD)

    VRBO

    Charming Waterfront Cottage with Boat Ramp and boat docking - Pet Friendly

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    You will fall in love with this completely renovated and modern guest house on an 11 acre waterfront estate. The Sunshi ...

    From $268 per night (USD)

    VRBO

    Details
  • Sunset Breeze - Waterfront!
    From $428 per night (USD)

    Expedia

    Sunset Breeze - Waterfront!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Sunset Breeze - if you’re not wearing flip flops, you’re overdressed….. At the Beach, Life is different - Time doesn’t ...

    From $428 per night (USD)

    Expedia

    Details
  • Riptide’s Crossing:  A waterfront getaway w\/deep water dock and incredible views
    From $431 per night (USD)

    VRBO

    Riptide’s Crossing: A waterfront getaway w\/deep water dock and incredible views

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    When you need to check off ALL of the boxes, you'll find everything you’re looking for at "Riptide's Retreat". Named ...

    From $431 per night (USD)

    VRBO

    Details
  • Timeless Elegance with Modern Luxury: Historic 6-BR Home plus attached 1-BR Apt
    From $1244 per night (USD)

    Expedia

    Timeless Elegance with Modern Luxury: Historic 6-BR Home plus attached 1-BR Apt

    Bedrooms:
    6
    Bathrooms:
    7
    Sleeps:
    18

    Historic Victorian Elegance Meets Modern Comfort in Quaint Onancock – 6-BD Main House + 1-BD Attached Apartment Comforta ...

    From $1244 per night (USD)

    Expedia

    Details
  • Sunset in Sunnywood:   A peaceful retreat with a PRIVATE POOL!
    From $613 per night (USD)

    VRBO

    Sunset in Sunnywood: A peaceful retreat with a PRIVATE POOL!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    18

    Nestled away on a serene and private lot in the sought-after Sunnywood neighborhood, this beloved vacation home will mak ...

    From $613 per night (USD)

    VRBO

    Details
  • Misty Manor! Updated Cottage Near Beach! Water Access, Linens Included!
    From $359 per night (USD)

    Expedia

    Misty Manor! Updated Cottage Near Beach! Water Access, Linens Included!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Enjoy your home away from home at Misty Manor on Piney Island, off of Chincoteague Island. It is the second closest stre ...

    From $359 per night (USD)

    Expedia

    Details
  • CoZyQ is a 2-bedroom, 2 full baths cottage in charming Chincoteague Island, VA
    From $279 per night (USD)

    VRBO

    CoZyQ is a 2-bedroom, 2 full baths cottage in charming Chincoteague Island, VA

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Located on the quaint Chincoteague Island, our charming 2 bedroom/2 full bath CoZyQ home is nestled on a quiet road with ...

    From $279 per night (USD)

    VRBO

    Details
  • 3-bedroom house steps from the beach in Saxis,VA with WiFi, AC, & screened porch
    From $203 per night (USD)

    Expedia

    3-bedroom house steps from the beach in Saxis,VA with WiFi, AC, & screened porch

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    5

    Welcome to this adorable house in Saxis. This charming property features 3 bedrooms - 1 full bed and 2 twin beds, perfec ...

    From $203 per night (USD)

    Expedia

    Details
  • Waterfowl Watch Chincoteague Island Great Rates Quiet area, 2 night stays, bikes
    From $206 per night (USD)

    VRBO

    Waterfowl Watch Chincoteague Island Great Rates Quiet area, 2 night stays, bikes

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Small family-friendly two bedroom cottage on Chincoteague Island! In a quiet residential area with a slight view of Lit ...

    From $206 per night (USD)

    VRBO

    Details
  • The Neigh-Neigh - Location! Location! Location!
    From $395 per night (USD)

    Expedia

    The Neigh-Neigh - Location! Location! Location!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    About this space Named in honor of the ponies that first put Chincoteague on the map, this charming newly renovated fami ...

    From $395 per night (USD)

    Expedia

    Details
  • Ryokan - Water views, Shared Boat Launch!
    From $573 per night (USD)

    VRBO

    Ryokan - Water views, Shared Boat Launch!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    12

    We are pleased to introduce 'Ryokan' as one of the newest additions to the Chincoteague Resort selection of vacation hom ...

    From $573 per night (USD)

    VRBO

    Details
  • Chincoteague House w\/ Enclosed Porch + Deck
    Click For Pricing

    Expedia

    Chincoteague House w\/ Enclosed Porch + Deck

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    5

    Blend nature, fishing, and a relaxing island lifestyle together at this welcoming vacation rental! Ideally located withi ...

    Click For Pricing

    Expedia

    Details
  • Lighthouse Estates 8 - Water views; Shared pool!
    From $298 per night (USD)

    VRBO

    Lighthouse Estates 8 - Water views; Shared pool!

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    6

    Welcome to Lighthouse Estates #8, Formerly known as 'Natalie's Nook'! This 2 bedroom beach retreat is located in the pop ...

    From $298 per night (USD)

    VRBO

    Details
  • Dancing Waters at Sea Tag - Waterfront Condo!
    From $926 per night (USD)

    Expedia

    Dancing Waters at Sea Tag - Waterfront Condo!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Do you love to be on the water? Maybe that means casting a line from your fishing pole, trying your hand at crabbing, or ...

    From $926 per night (USD)

    Expedia

    Details
  • The C-Ray Cottage is a one-of-a-kind Chincoteague Vacation Experience.
    From $285 per night (USD)

    VRBO

    The C-Ray Cottage is a one-of-a-kind Chincoteague Vacation Experience.

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    The C-Ray Cottage - Life is better with a little sand between your toes....... We are big believers that every Home h ...

    From $285 per night (USD)

    VRBO

    Details
  • Escape to Chincoteague, just 7 mins from wildlife refuge
    From $270 per night (USD)

    Expedia

    Escape to Chincoteague, just 7 mins from wildlife refuge

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Charming towns like Chincoteage offer you the chance to enjoy the stunning views of this two-bedroom apartment. Located ...

    From $270 per night (USD)

    Expedia

    Details
  • Windshadow - Waterfront; Pet friendly!
    From $628 per night (USD)

    VRBO

    Windshadow - Waterfront; Pet friendly!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    You will enjoy spectacular sunsets from this lovely waterfront home overlooking the Chincoteague Bay. There is a waterfr ...

    From $628 per night (USD)

    VRBO

    Details
  • Wildflower - Waterfront; Deep water dock!
    From $375 per night (USD)

    Expedia

    Wildflower - Waterfront; Deep water dock!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Beautiful waterfront home with shared pier plus floating dock on deep water!! Ground level is a large screened patio per ...

    From $375 per night (USD)

    Expedia

    Details
  • Return - Waterfront w\/ Boat dock!
    From $716 per night (USD)

    VRBO

    Return - Waterfront w\/ Boat dock!

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    11

    Beautiful waterfront contemporary perched on the edge of Assateague Channel. Enjoy breathtaking vistas of Assateague Isl ...

    From $716 per night (USD)

    VRBO

    Details
  • Almost Heaven - Pet friendly; Waterfront home!
    From $337 per night (USD)

    Expedia

    Almost Heaven - Pet friendly; Waterfront home!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    A lovely 3 bedroom waterfront Victorian home that features a first-floor bedroom with a queen bed and full bathroom with ...

    From $337 per night (USD)

    Expedia

    Details
  • Admiral Benbow - contemporary home with shared boat ramp
    From $376 per night (USD)

    VRBO

    Admiral Benbow - contemporary home with shared boat ramp

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    A very nice contemporary home located in Oyster Bay I community. Located next to the community boat ramp - you have acce ...

    From $376 per night (USD)

    VRBO

    Details
  • Misty's Thicket - Water access; Screened porches!
    From $282 per night (USD)

    Expedia

    Misty's Thicket - Water access; Screened porches!

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    8

    Located on South Ridge Road, this lovely town-home features a private pier, central air conditioning, and galley style k ...

    From $282 per night (USD)

    Expedia

    Details
  • Shady Side - Water access, screened porch!
    From $412 per night (USD)

    VRBO

    Shady Side - Water access, screened porch!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    Shady Side is located in Piney Island, which is among the closest communities to the beach. There is community water acc ...

    From $412 per night (USD)

    VRBO

    Details
  • Morning Memories - Pet friendly; Shared pool & dock!
    From $257 per night (USD)

    Expedia

    Morning Memories - Pet friendly; Shared pool & dock!

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    6

    A light, bright and airy beach rental with community pool and water access with shared dock. The spacious 2 bedroom, 2.5 ...

    From $257 per night (USD)

    Expedia

    Details
  • Serendipity - Main Street; Screened porch!
    From $269 per night (USD)

    VRBO

    Serendipity - Main Street; Screened porch!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Come stay in this classic Eastern Shore Style home. Located just a few blocks from our famous downtown Main Street area, ...

    From $269 per night (USD)

    VRBO

    Details
  • Stingray - Waterfront; Waterside balcony!
    From $302 per night (USD)

    Expedia

    Stingray - Waterfront; Waterside balcony!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Luxurious 2nd-level waterfront condo with views you won't believe! Tastefully decorated with work of local artisans, fea ...

    From $302 per night (USD)

    Expedia

    Details
  • My Island Escape - North Main; Private dock!
    From $340 per night (USD)

    VRBO

    My Island Escape - North Main; Private dock!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    7

    Tucked away on a quiet lane off of North Main is where you will find My Island Escape. This brand-new home is absolutely ...

    From $340 per night (USD)

    VRBO

    Details
  • Moon Rising - Waterfront; Shared dock!
    From $411 per night (USD)

    Expedia

    Moon Rising - Waterfront; Shared dock!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Very nice waterfront home overlooking Assateague Island and lighthouse. Satellite TV, all amenities. Nice waterside deck ...

    From $411 per night (USD)

    Expedia

    Details
  • Sunshine Daydream - Pet friendly; Waterfront!
    From $342 per night (USD)

    VRBO

    Sunshine Daydream - Pet friendly; Waterfront!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Beautiful 3 bedroom home located in one of Chincoteague Island's private WATERFRONT communities! Formerly known as "Snoo ...

    From $342 per night (USD)

    VRBO

    Details
  • Mermaid Crossing - Pet friendly; Waterfront w\/ Dock!
    From $322 per night (USD)

    Expedia

    Mermaid Crossing - Pet friendly; Waterfront w\/ Dock!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    10

    Comfortable, pet friendly home on large, side-creek lot with fantastic views from both the front and back of house! Exce ...

    From $322 per night (USD)

    Expedia

    Details
  • Sundance at Marsh Island - Waterfront townhome!
    From $266 per night (USD)

    VRBO

    Sundance at Marsh Island - Waterfront townhome!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Nestled on the tip of Marsh Island, this fabulous 2 bedroom townhome features spectacular views of the Chincoteague Bay. ...

    From $266 per night (USD)

    VRBO

    Details
  • Shreiner's Tradition - In Town, Pet friendly!
    From $255 per night (USD)

    Expedia

    Shreiner's Tradition - In Town, Pet friendly!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    As one of our newest vacation rental offerings, we're pleased to be have this downtown charmer! Shreiner's Tradition is ...

    From $255 per night (USD)

    Expedia

    Details
  • Marsh Point - Screened Porch & Shared Dock!
    From $311 per night (USD)

    VRBO

    Marsh Point - Screened Porch & Shared Dock!

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    8

    Located just off of Ridge Road on the southern portion of the island, you'll find Marsh Point. A two bedroom, two and a ...

    From $311 per night (USD)

    VRBO

    Details
  • Southern Exposure - Waterfront; Boat dock!
    From $548 per night (USD)

    Expedia

    Southern Exposure - Waterfront; Boat dock!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    7

    Southern Exposure is nestled along the natural shoreline of the Assateague Channel, offering some of the most beautiful ...

    From $548 per night (USD)

    Expedia

    Details
  • Tall Pines - Pet friendly; Screened porch!
    From $246 per night (USD)

    VRBO

    Tall Pines - Pet friendly; Screened porch!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Located in lovely Piney Island within a short bike ride to the beach. This single story 2 bedroom, 1.5 bathroom house of ...

    From $246 per night (USD)

    VRBO

    Details
  • Sea Charm - Downtown, Screened porch!
    From $356 per night (USD)

    Expedia

    Sea Charm - Downtown, Screened porch!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Charming in-town 3 bedroom home with a day-bed alcove, 2 baths, large fenced yard, carport and screened porch. Located o ...

    From $356 per night (USD)

    Expedia

    Details
  • Poole's Cove - Waterfront; Main Street!
    From $782 per night (USD)

    VRBO

    Poole's Cove - Waterfront; Main Street!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Poole's Cove manages to be tucked away right on Main Street. This home has been decorated with an artists' eye and poet' ...

    From $782 per night (USD)

    VRBO

    Details
  • Langtree - Pet friendly; Waterfront w\/ boat dock!
    From $463 per night (USD)

    Expedia

    Langtree - Pet friendly; Waterfront w\/ boat dock!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    Your home away from home... enjoy the water views, bring your boat and use your own dock, or just relax and listen to th ...

    From $463 per night (USD)

    Expedia

    Details
  • Island Estate - Pet friendly; Private pool & dock!
    From $777 per night (USD)

    VRBO

    Island Estate - Pet friendly; Private pool & dock!

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    14

    Fabulous, fabulous, fabulous! If you're looking for a large space to have a family vacation or reunion, this is it. This ...

    From $777 per night (USD)

    VRBO

    Details
  • Dockside - Waterfront Condo w\/ Boat Dock!
    From $448 per night (USD)

    Expedia

    Dockside - Waterfront Condo w\/ Boat Dock!

    Bedrooms:
    4
    Bathrooms:
    3
    Sleeps:
    8

    Located on the Assateague Channel, this is your chance to watch the ponies from your own deck. A wonderful panoramic vie ...

    From $448 per night (USD)

    Expedia

    Details
  • Blue Sea Star - Beautiful Pet Friendly Home!
    From $408 per night (USD)

    VRBO

    Blue Sea Star - Beautiful Pet Friendly Home!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    12

    Welcome to Blue Sea Star! You'll fall in love with this fabulous 3 bedroom home from the moment you walk in the door. Br ...

    From $408 per night (USD)

    VRBO

    Details
  • Channel Watch - Waterfront home w\/ Private Pier!
    From $484 per night (USD)

    Expedia

    Channel Watch - Waterfront home w\/ Private Pier!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    7

    Located down a gravel road that runs parallel to Assateague Channel, you'll find Channel Watch nestled in between the pi ...

    From $484 per night (USD)

    Expedia

    Details
  • Island Thyme - Hot tub; Carnival location!
    From $321 per night (USD)

    VRBO

    Island Thyme - Hot tub; Carnival location!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    There's plenty of room for everyone here at Island Thyme! This spacious home features a living room and den, large eat-i ...

    From $321 per night (USD)

    VRBO

    Details
  • Conch Shell - Waterfront villa w\/ wrap around deck!
    From $402 per night (USD)

    Expedia

    Conch Shell - Waterfront villa w\/ wrap around deck!

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    The house is located on Pine Drive in Piney Island - the closest neighborhood to the beach - convenient for shopping and ...

    From $402 per night (USD)

    Expedia

    Details
  • Joint Venture - Pet friendly; Water views!
    From $256 per night (USD)

    VRBO

    Joint Venture - Pet friendly; Water views!

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    6

    Joint Venture is the perfect townhouse for an affordable vacation! Take a short stroll to Maddox Blvd (Beach Road) and e ...

    From $256 per night (USD)

    VRBO

    Details
  • Island Sunrise - Pet friendly; waterfront duplex!
    From $440 per night (USD)

    Expedia

    Island Sunrise - Pet friendly; waterfront duplex!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Island Sunrise is gorgeous 3 bedroom, 2.5 bathroom duplex home located in desirable Piney Island. Not only is this house ...

    From $440 per night (USD)

    Expedia

    Details
  • Changing Tide - Downtown location w\/ large deck!
    From $359 per night (USD)

    VRBO

    Changing Tide - Downtown location w\/ large deck!

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    7

    Book your stay at this quaint home, in a convenient downtown location. The updated coastal decor will bring on the beach ...

    From $359 per night (USD)

    VRBO

    Details
  • Blue Moon - Pet friendly; Great location!
    From $332 per night (USD)

    Expedia

    Blue Moon - Pet friendly; Great location!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Come and enjoy a nice, relaxing vacation at this charming island home. "Blue Moon" is centrally located on Chincoteague ...

    From $332 per night (USD)

    Expedia

    Details
  • Cockleshell Cottage - Pet friendly & Handicap Accessible!
    From $441 per night (USD)

    VRBO

    Cockleshell Cottage - Pet friendly & Handicap Accessible!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    10

    Nestled on a quiet cul-de-sac in a private community just off North Main Street (Oyster Bay II) is where you'll find the ...

    From $441 per night (USD)

    VRBO

    Details
  • Blue Chair Bay - Waterfront townhome w\/ Fishing pier!
    From $341 per night (USD)

    Expedia

    Blue Chair Bay - Waterfront townhome w\/ Fishing pier!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    If you're looking for a little slice of paradise at the beach, look no further! This delightful townhome is adorned with ...

    From $341 per night (USD)

    Expedia

    Details
  • Blue Point - Pet friendly w\/ Outdoor shower!
    From $288 per night (USD)

    VRBO

    Blue Point - Pet friendly w\/ Outdoor shower!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Come for an old fashioned family vacation. This wonderfully maintained classic Chincoteague-style home features a large ...

    From $288 per night (USD)

    VRBO

    Details
  • Avalon - waterfront home with fireplace and screened porch
    From $398 per night (USD)

    Expedia

    Avalon - waterfront home with fireplace and screened porch

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    Avalon is a charming 4 bedroom, 2.5 bathroom home situated on a bulkheaded waterfront lot on Oyster Bay! There is a larg ...

    From $398 per night (USD)

    Expedia

    Details
  • Mainstay - Outdoor shower; Multiple balconies!
    From $377 per night (USD)

    VRBO

    Mainstay - Outdoor shower; Multiple balconies!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    10

    We are pleased to be able to offer this rental to you! Mainstay is a wonderful vacation rental home with so many luxurie ...

    From $377 per night (USD)

    VRBO

    Details
  • Homestead - Located on Main St. w\/ outdoor shower!
    From $332 per night (USD)

    Expedia

    Homestead - Located on Main St. w\/ outdoor shower!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    5

    Set back across the street from Chincoteague Bay, Homestead sits on 30 acres of basically pristine land. A cozy cottage, ...

    From $332 per night (USD)

    Expedia

    Details
  • June's Retreat - Waterfront; Boat dock!
    From $1040 per night (USD)

    VRBO

    June's Retreat - Waterfront; Boat dock!

    Bedrooms:
    5
    Bathrooms:
    4
    Sleeps:
    10

    June's Retreat is Chincoteague Island's premier luxury vacation rental home, nestled on serene waterfront marshlands jus ...

    From $1040 per night (USD)

    VRBO

    Details
  • Lottie's Lookout - In town; Pet friendly; Fire pit!
    From $231 per night (USD)

    Expedia

    Lottie's Lookout - In town; Pet friendly; Fire pit!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Come stay at this Chincoteague Island Charmer, better known as Lottie's Lookout! This large spacious home features 3 lev ...

    From $231 per night (USD)

    Expedia

    Details
  • Heron Landing - In town; Coastal Cottage!
    From $236 per night (USD)

    VRBO

    Heron Landing - In town; Coastal Cottage!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Three words : Charming. Coastal. Cottage. Located just off of Ridge Road, in the center of the island, you'll find this ...

    From $236 per night (USD)

    VRBO

    Details
  • Horseshoe Hideaway - Cozy home w\/ screened porches!
    From $319 per night (USD)

    Expedia

    Horseshoe Hideaway - Cozy home w\/ screened porches!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Located in a secluded neighborhood, in the middle of town, 'Horseshoe Hideaway' is comfortably situated back off of a ba ...

    From $319 per night (USD)

    Expedia

    Details
  • Endless Summer - Pet friendly w\/ Screened porch!
    From $387 per night (USD)

    VRBO

    Endless Summer - Pet friendly w\/ Screened porch!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    9

    Come enjoy your stay at one of the most sought out locations on the Island. Easy, convenient access to the beach- With t ...

    From $387 per night (USD)

    VRBO

    Details
  • Hill House - Pet friendly; In town w\/ water views!
    From $494 per night (USD)

    Expedia

    Hill House - Pet friendly; In town w\/ water views!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    9

    Welcome to Hill House! Wonderful traditional island home with fantastic new upgrades! The kitchen has been renovated, al ...

    From $494 per night (USD)

    Expedia

    Details
  • Herbie's Hideaway - Water views & Screened porch!
    From $389 per night (USD)

    VRBO

    Herbie's Hideaway - Water views & Screened porch!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Luxury water view vacation rental home with dock access. This home boasts a full ensemble of amenities and the most beau ...

    From $389 per night (USD)

    VRBO

    Details
  • Lighthouse View - Water views; Shared pool!
    From $355 per night (USD)

    Expedia

    Lighthouse View - Water views; Shared pool!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Lighthouse View is located on the east side of our island and includes a private community pool for your enjoyment. The ...

    From $355 per night (USD)

    Expedia

    Details
  • Dragonfly Point - Waterfront home w boat dock & deck!
    From $690 per night (USD)

    VRBO

    Dragonfly Point - Waterfront home w boat dock & deck!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    "DRAGONFLY POINT" is a magnificent waterfront property on Oyster Bay & canal. Surrounded by water on three sides of the ...

    From $690 per night (USD)

    VRBO

    Details
  • Lazy Days - Pet friendly; Screened gazebo!
    From $273 per night (USD)

    Expedia

    Lazy Days - Pet friendly; Screened gazebo!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    7

    Located on Main Street just north of town, "Lazy Days" may be just the perfect spot for your vacation! Cute and comforta ...

    From $273 per night (USD)

    Expedia

    Details
  • Sunset Bay Villa 206 - Waterfront; Shared pool!
    From $395 per night (USD)

    VRBO

    Sunset Bay Villa 206 - Waterfront; Shared pool!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Villa 206 is a new unit that has been professionally decorated and offers five-star luxury. Spacious and accommodating, ...

    From $395 per night (USD)

    VRBO

    Details
  • Beautiful, Waterfront, Luxury
    From $247 per night (USD)

    Expedia

    Beautiful, Waterfront, Luxury

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    There is a fanciful quality to this secluded property where nature's beauty and luxurious accommodations coexist in quie ...

    From $247 per night (USD)

    Expedia

    Details
  • Sunset Bay Villa 119 - Waterfront; Shared pool!
    From $356 per night (USD)

    VRBO

    Sunset Bay Villa 119 - Waterfront; Shared pool!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Immerse yourself in luxury for days at this pristine waterfront villa! This condo unit provides the most spectacular vie ...

    From $356 per night (USD)

    VRBO

    Details
  • The Quarter Deck\/\/ Spacious Home with Water views!
    From $463 per night (USD)

    Expedia

    The Quarter Deck\/\/ Spacious Home with Water views!

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    16

    Welcome to beautiful East Point! Take in spectacular sunsets from the wrap-around porches or from the community's privat ...

    From $463 per night (USD)

    Expedia

    Details
  • Newly Renovated Cottage On Main Street - Professionally Sanitized
    From $149 per night (USD)

    VRBO

    Newly Renovated Cottage On Main Street - Professionally Sanitized

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Enjoy this newly renovated cottage on main street in chincoteague va. In the center of downtown coffee shops, restaurant ...

    From $149 per night (USD)

    VRBO

    Details
  • Lighthouse View - Waterfront, Boat Docking
    From $250 per night (USD)

    Expedia

    Lighthouse View - Waterfront, Boat Docking

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    6

    Fabulous townhome overlooking Assateague Channel and Lighthouse. Lighthouse View has exceptional decor and is superbly ...

    From $250 per night (USD)

    Expedia

    Details
  • Assateague Lookout - Water Front townhome W\/view. - Shared Pier, No Linens
    From $166 per night (USD)

    VRBO

    Assateague Lookout - Water Front townhome W\/view. - Shared Pier, No Linens

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Amenities: Central A/C, W/D, WiFi, Microwave, TV, DVD, STREAMING TV ONLY , Fireplace, Screen Porch, Dishwasher, Deck, Ga ...

    From $166 per night (USD)

    VRBO

    Details
  • Sunset Bay Villa 315-WATERFRONT! Pool and Fishing Dock
    From $432 per night (USD)

    Expedia

    Sunset Bay Villa 315-WATERFRONT! Pool and Fishing Dock

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    7

    Stylish comfort, sunset views, pool and fitness room. Great location, short walk to shops and restaurants. 3rd Floor ( ...

    From $432 per night (USD)

    Expedia

    Details
  • Sunsinger at Chincoteague
    From $450 per night (USD)

    VRBO

    Sunsinger at Chincoteague

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    10

    Wonderful custom home with panoramic views of the island's natural splendor. Fabulous Sunsets over the Chincoteague Bay ...

    From $450 per night (USD)

    VRBO

    Details
  • Moon Dreams Cottage-Restored Cottage Downtown Chincoteague
    From $253 per night (USD)

    Expedia

    Moon Dreams Cottage-Restored Cottage Downtown Chincoteague

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Bricks and Beams throughout this charmingly renovated/restored Chincoteague Cottage. Located in the heart of downtown. T ...

    From $253 per night (USD)

    Expedia

    Details
  • Myrtle on Mumford-Adorable Downtown Cottage w\/Screened Porch
    From $265 per night (USD)

    VRBO

    Myrtle on Mumford-Adorable Downtown Cottage w\/Screened Porch

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Myrtle on Mumford is a newly constructed replica of a typical 1920's single-story Chincoteague home. A stunning blend of ...

    From $265 per night (USD)

    VRBO

    Details
  • Nature's Retreat - Marsh & Wetland Views
    From $189 per night (USD)

    Expedia

    Nature's Retreat - Marsh & Wetland Views

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    6

    Well cared for Townhome with shared private pier on inland creek. Wetland setting is great for birding. All new floorin ...

    From $189 per night (USD)

    Expedia

    Details