Assateague Island Vacation Rentals, Cabins, Hotels

Choose from 322 vacation rentals located in Assateague Island, Maryland. Top filters in Assateague Island include kitchen / kitchenette, air conditioner, and laundry. Prices range from $44 to $2,331 per night. Our most popular vacation rental types near Assateague Island are houses and hotels.

Top vacation rentals in Assateague Island

Browse all rentals

Hotel

Marina Bay Hotel & Suites, Ascend Hotel Collection

3-Star Hotel · Booking.com

4.3

(538)

$76

Entire house

★Jay’s Waterfront Retreat: Private Dock-Fire-pit-Kayaks & Bikes Inc.-Beach★

6 guests · 3 bedrooms · 2 baths · Vrbo

5.0

(154)

$247

Hotel

Comfort Suites Chincoteague Island Bayfront Resort

3-Star Hotel · Booking.com

4.7

(902)

$84

Hotel

Refuge Inn

3-Star Hotel · Expedia

4.7

(1008)

$109

Entire house

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

6 guests · 3 bedrooms · 3 baths · Vrbo

5.0

(148)

$166

Rental

Anchor Inn

Booking.com

4.2

(388)

$76

Hotel

Best Western Chincoteague Island

3-Star Hotel · Booking.com

4.5

(266)

$76

Entire house

Newly Renovated Cottage On Main Street - Professionally Sanitized

4 guests · 1 bath · Vrbo

4.6

(189)

$77

Bed & breakfast

Channel Bass Inn

Booking.com

4.6

(145)

$86

Hotel

Atlantic Shores Inn and Suites

Booking.com

3.4

(946)

$61

Bed & breakfast

Chanceford Hall Bed & Breakfast

Booking.com

4.8

(13)

$169

Beautifully decorated, comfortable, clean home

Entire house

5 star Waterview Assateague Channel closest community to beach. Fireplace .

6 guests · 3 bedrooms · 3 baths · Vrbo

5.0

(108)

$170

Hotel

Island Resort

Booking.com

4.6

(645)

$79

Hotel

Americas Best Value Inn Chincoteague

3-Star Hotel · Booking.com

3.6

(569)

$44

Hotel

Hampton Inn & Suites Chincoteague-Waterfront, Va

Booking.com

4.8

(398)

$89

Entire house

The Brass Crab- 4 Bedrooms, 2 bathrooms - Flexible stays!

8 guests · 4 bedrooms · 2 baths · Vrbo

5.0

(104)

$175

Hotel

Sea Shell Motel

Booking.com

4.7

(228)

$85

Hotel

Hampton Inn & Suites Chincoteague Waterfront

Expedia

4.8

(461)

$93

Hotel

Chincoteague Inn

Booking.com

3.9

(701)

$60

A delightful Chincoteague coastal cottage that’s perfect for couples, families, or small groups of friends.

Entire house

Creekside Cottage with Sunroom, Fire Pit, & WiFi!

6 guests · 3 bedrooms · 2 baths · Vrbo

4.9

(110)

$76

Rental

Waterside Inn

Booking.com

4.3

(517)

$67

Hotel

Days Inn by Wyndham Chincoteague Island

3-Star Hotel · Booking.com

3.1

(270)

$55

Entire villa

Key West Cottages

Booking.com

4.1

(43)

$85

Chincoteague. Quiet location, beautiful waterfront home facing Oyster Bay

Entire house

Roaming ponies, Peaceful Waterfront

7 guests · 3 bedrooms · 3 baths · Vrbo

4.9

(91)

$313

Hotel

Fairfield Inn & Suites by Marriott Chincoteague Island Waterfront

3-Star Hotel · Booking.com

4.3

(135)

$105

Entire house

Chincoteague Townhome with Pony Views from Deck!

Booking.com

4.3

(9)

$112

Entire house

Chincoteague Charm Escape with Bikes and Yard Games!

Booking.com

$204

Entire house

Tranquil Shores - Relaxation With a Water View!

6 guests · 3 bedrooms · 2 baths · Vrbo

4.9

(94)

$100

Entire house

Quaint Chincoteague Island Hideaway with 2 Porches!

Booking.com

4.8

(3)

$112

Entire house

Chincoteague Island Beach House - The Neigh-Neigh

Booking.com

5.0

(1)

$84

Search by property type

Browse the most popular vacation rental types in Assateague Island

Vacation rentals with a kitchen in Assateague Island

Browse all rentals

Hotel

Chincoteague Inn

Expedia

3.9

(914)

$59

Quaint home-like atmosphere for your vacation. Your home away from home!

Entire house

Duck's Delight - Pet friendly rentals within walking distance to Maddox Blvd!

10 guests · 4 bedrooms · 3 baths · Vrbo

4.7

(95)

$105

Entire apartment

Water Front Property With Boatslip!

5 guests · 2 bedrooms · 1 bath · Vrbo

4.8

(97)

$157

Entire house

Stately Home on Chincoteague Island - Professionally Sanitized

12 guests · 5 bedrooms · 3 baths · Vrbo

4.6

(114)

$203

Entire house

Cozy island cottage with a Key West flair (w/ convenient EV Recharge Station)

4 guests · 2 bedrooms · 1 bath · Vrbo

5.0

(76)

$255

Entire house

Small cottage for those little getaways

5 guests · 1 bedroom · 1 bath · Vrbo

5.0

(72)

$134

Hotel

Americas Best Value Inn & Suites Chincoteague Island

Expedia

3.5

(491)

$55

Entire house

3 Bedroom Home. Central Air. Pool. Firepit. Closest to the Beach.

8 guests · 3 bedrooms · 3 baths · Vrbo

5.0

(68)

$218

Entire house

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

10 guests · 5 bedrooms · 4 baths · Vrbo

5.0

(68)

$400

Private 21 foot boat slip with deep water.

Entire apartment

A Boaters Dream Waterfront Condo<br>With boat slip

6 guests · 2 bedrooms · 1 bath · Vrbo

4.9

(67)

$159

Entire house

Charming Chincoteague getaway, short walk to the fair grounds and pony penning

10 guests · 3 bedrooms · 2 baths · Vrbo

5.0

(64)

$185

Discover the treasure that is Ariel`s Grotto on Chincoteague Island.

Entire house

Ariel`s Grotto is a gorgeous 3 Bedroom/2.5 Bath Vacation Rentals on incredible C

8 guests · 3 bedrooms · 3 baths · Vrbo

4.8

(60)

$156

Entire house

Newly renovated water view cottage nestled in the pines.

6 guests · 2 bedrooms · 1 bath · Vrbo

5.0

(58)

$210

Entire house

Key West Cottages on the Chincoteague Bay

Expedia

4.6

(57)

$900

Entire apartment

CHINCOTEAGUE ISLAND'S SEABREEZE AT SUNSET BAY>>((((•>THE GOOD LIFE >>(((•>

8 guests · 3 bedrooms · 2 baths · Vrbo

4.9

(53)

$282

Huge, private backyard with putting green!

Entire house

Located Minutes to Assateague Island! Now taking 2023 RESERVATIONS!

14 guests · 4 bedrooms · 4 baths · Vrbo

5.0

(52)

$500

Entire house

Perfect Chincoteague Home for your small family getaway

5 guests · 1 bedroom · 1 bath · Vrbo

4.7

(59)

$139

Corner/End Unit Yellow siding location of Master Bedroom-and corner living area

Entire apartment

Sunset Bay Villas on Chincoteague Island Waterfront Condo

7 guests · 3 bedrooms · 2 baths · Vrbo

4.9

(52)

$214

Stunning, immaculate, contemporary home. Updated amenities. Modern furnishings.

Entire house

Stunning, Immaculate, Contemporary Home Near Beach And Ponies

8 guests · 3 bedrooms · 2 baths · Vrbo

5.0

(46)

$255

Entire apartment

Bayfront Chincoteague Getaway with Fire Pit!

Booking.com

$76

Welcome to Sunset Bay 209 - you`re on Island Time now.....

Entire apartment

A stunning 3 Bedroom Waterfront Dream Condo that even allows your Family Dog!

8 guests · 3 bedrooms · 2 baths · Vrbo

5.0

(51)

$240

Hotel

The Inn On Main

Booking.com

4.3

(110)

$84

Hotel

birchwood inn

Expedia

3.4

(146)

$45

Entire house

Waters Edge - Waterfront Vacation Home on Chincoteague Island Virginia

12 guests · 5 bedrooms · 6 baths · Vrbo

4.8

(51)

$200

Entire house

Chincoteague Island Cottage about 2 Mi to Beaches

Booking.com

4.0

(1)

$84

Entire house

STUNNING WATERFRONT VIEWS!

8 guests · 3 bedrooms · 3 baths · Vrbo

4.9

(43)

$350

Entire house

The Hideaway Cottage

2 guests · 1 bedroom · 1 bath · Vrbo

5.0

(48)

$95

Entire house

Brant Point Waterfront Bungalow with Deck and Views!

Booking.com

$204

Entire apartment

Premium 2nd floor waterfront unit with floating dock. Highly rated.

6 guests · 2 bedrooms · 1 bath · Vrbo

5.0

(44)

$159

Entire house

Creekside Cottage with Sunroom, Fire Pit, & WiFi!

Booking.com

3.4

(4)

$87

Search by amenity

Explore vacation rentals with the most popular amenities in Assateague Island

Kitchen / Kitchenette

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Looking for a vacation rental near a particular attraction, famous landmark, or another point of interest? Use this map of Assateague Island to help guide your rental search.

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Assateague Island travel guide

Let us help you plan your perfect Assateague Island vacation. Our travel guide highlights things to do, places to see, favorite vacation rental amenities in Assateague Island, and more.