Immerse yourself in the allure of Assateague Island, a stunning spot in Virginia that’s known for its cottages. Choose from 727 diverse options to tailor your perfect trip.

Whether you desire luxury or seek affordability, Assateague Island has cottages to suit your needs. Prices start from $60 and can extend up to $1,637. Key amenities include Air conditioner.

Top Features: Air conditioner, Kitchen / Kitchenette, Internet / Wifi, TV and Laundry

Local Highlights: Ocean City Boardwalk, Northside Park, Salisbury Zoological Park, Bethany Beach Boardwalk and Discoversea Shipwreck Museum

Unlock the secrets of Assateague Island by booking your cottages now. Experience the diverse culture and scenery of Virginia.

Top Cottages in Assateague Island

Property view
4.8
Outstanding(260 Reviews)
Cottage
 in Chincoteague Island
Island Breeze Cottage w/ screened porch. Water view! Quiet location!
4 guests · 1 bedroom · 1 bath
Garden · Pool · Kitchen / Kitchenette

Experience vacation in Assateague Island with our Cottage, Island Breeze Cottage w/ screened porch. Water view! Quiet location!. Enjoy amenities such as Air conditioner, Internet / Wifi and Balcony / Patio, and more.

$$$$
vrbo logo
View deal
Property grounds
4.6
Outstanding(225 Reviews)
Cottage
 in Chincoteague
Newly Renovated Cottage On Main Street - Professionally Sanitized
4 guests · 1 bedroom · 1 bath
Garden · Pets allowed · Kitchen / Kitchenette

Nestled in Assateague Island, this Cottage is perfect for your next vacation. Enjoy Newly Renovated Cottage On Main Street - Professionally Sanitized's top-rated amenities, including Air conditioner, Internet / Wifi and Pets allowed, and more.

$$$$
vrbo logo
View deal
Property grounds
4.8
Outstanding(126 Reviews)
Cottage
 in Chincoteague
Cottage w Private Creek, Sunroom, Fire Pit, & WiFi
6 guests · 3 bedrooms · 2 baths
Garden · Pets allowed · Kitchen / Kitchenette

This attractive Cottage in Assateague Island, $653 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
vrbo logo
View deal
Exterior
5.0
Outstanding(93 Reviews)
Cottage
 in Chincoteague
Small cottage for those little getaways
5 guests · 1 bedroom · 1 bath
Kitchen / Kitchenette · Air conditioner · Internet / Wifi

Discover the beauty of Assateague Island with a stay at Small cottage for those little getaways, a top rated Cottage with amenities such as Air conditioner, Internet / Wifi and Kitchen / Kitchenette, and more.

$$$$
vrbo logo
View deal
Beach
5.0
Outstanding(102 Reviews)
Cottage
 in Chincoteague
Cozy island cottage with a Key West flair - CLOSEST TO THE BEACH!!!
4 guests · 2 bedrooms · 1 bath
Garden · Pool · Kitchen / Kitchenette

Experience the best of Assateague Island with this Cottage available for $473. This property is equipped with amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
vrbo logo
View deal
Fridge, microwave, oven, stovetop
5.0
Outstanding(85 Reviews)
Cottage
 in Chincoteague
Newly renovated water view cottage nestled in the pines.
6 guests · 2 bedrooms · 1 bath
Kitchen / Kitchenette · Air conditioner · Internet / Wifi

Looking for a memorable stay in Assateague Island? Our Cottage might just be what you're looking for. Enjoy amenities including Air conditioner, Dishwasher and Internet / Wifi, and more during your stay.

$$$$
vrbo logo
View deal
Beach nearby
5.0
Outstanding(68 Reviews)
Cottage
 in Chincoteague
The Hideaway Cottage
2 guests · 1 bedroom · 1 bath
Kitchen / Kitchenette · Air conditioner · Internet / Wifi

The best choice in Assateague Island for Cottage, for $129 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
vrbo logo
View deal
Property grounds
4.8
Outstanding(57 Reviews)
Cottage
 in Chincoteague Island
Cottage On Famous Chincoteague Island-Famous Wild Ponies
4 guests · 2 bedrooms · 2 baths
Garden · Kitchen / Kitchenette · Air conditioner

This Cottage for $209 in Assateague Island, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
vrbo logo
View deal
Pool
4.7
Outstanding(40 Reviews)
Cottage
 in Chincoteague Island
2BR Snug Harbor Waterfront Cottage with the Most Spectacular View of lighthouse
6 guests · 2 bedrooms · 1 bath
Pool · Pets allowed · Kitchen / Kitchenette

Looking to create some memories in Assateague Island? Look no further than our Cottage, 2BR Snug Harbor Waterfront Cottage with the Most Spectacular View of lighthouse. Enjoy top-rated amenities including Air conditioner, Internet / Wifi and Pets allowed, and more.

$$$$
vrbo logo
View deal
1 bedroom, iron/ironing board, free WiFi, bed sheets
5.0
Outstanding(25 Reviews)
Cottage
 in Chincoteague
SeaLaVie!!!
4 guests · 1 bedroom · 1 bath
Pool · Pets allowed · Kitchen / Kitchenette

Enjoy the best of Assateague Island in our Cottage, SeaLaVie!!! . A stunning property with amenities including Air conditioner, Internet / Wifi and Pets allowed, and more.

$$$$
vrbo logo
View deal
Fridge, microwave, coffee/tea maker, toaster
4.8
Outstanding(19 Reviews)
Cottage
 in Chincoteague Island
Shore Bird - 1 BR Studio Cottage with open floor plan. Close to Carnival.
2 guests · 1 bedroom · 1 bath
Kitchen / Kitchenette

Experience vacation in Assateague Island with our Cottage, Shore Bird - 1 BR Studio Cottage with open floor plan. Close to Carnival.. Enjoy amenities such as Kitchen / Kitchenette, and more.

$$$$
vrbo logo
View deal
Property grounds
4.6
Outstanding(21 Reviews)
Cottage
 in Chincoteague
Cozy Little Cottage on chincoteague island va.
2 guests · 1 bedroom · 1 bath
Kitchen / Kitchenette · Air conditioner · Internet / Wifi

Experience the best of Assateague Island with this Cottage available for $121. This property is equipped with amenities including Air conditioner, Internet / Wifi and Smoking allowed, and more.

$$$$
vrbo logo
View deal

Search by amenity

Explore Cottages with the most popular amenities in Assateague Island

Vacation rentals with air conditioning in Assateague Island

TV
5.0
Outstanding(14 Reviews)
Cottage
 in Chincoteague
Chincoteague Island Cottage ~ 2 Mi to Beaches
5 guests · 2 bedrooms · 1 bath
Kitchen / Kitchenette · Air conditioner · Parking

Looking for the perfect place to call home during your trip to Assateague Island? This Cottage offers a comfort and style with top-notch amenities, including Air conditioner, Dishwasher and Balcony / Patio, and more.

$$$$
vrbo logo
View deal
Property grounds
5.0
Outstanding(5 Reviews)
Cottage
 in Chincoteague
CATCHTHEWAVE!! And a discounted rate to get us started!!
10 guests · 3 bedrooms · 2 baths
Pets allowed · Kitchen / Kitchenette · Air conditioner

Discover the beauty of Assateague Island with a stay at CATCHTHEWAVE!! And a discounted rate to get us started!!, a top rated Cottage with amenities such as Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
vrbo logo
View deal
Pool
5.0
Outstanding(4 Reviews)
Cottage
 in Chincoteague
COTTAGE BLUEFISH on Chincoteague Island! A cozy island getaway -NEW REMODEL 2024
4 guests · 2 bedrooms · 1 bath
Garden · Kitchen / Kitchenette · Air conditioner

This inviting Cottage in Assateague Island can fit your needs for many types of vacations, at $390 per night.

$$$$
vrbo logo
View deal
Property grounds
3.5
Average(6 Reviews)
Cottage
 in Chincoteague
Salty Sailor - 2BR cottage close to Memorial Park & launch area Pet friendly
6 guests · 2 bedrooms · 1 bath
Pets allowed · Kitchen / Kitchenette · Air conditioner

Looking to create some memories in Assateague Island? Look no further than our Cottage, Salty Sailor - 2BR cottage close to Memorial Park & launch area Pet friendly. Enjoy top-rated amenities including Air conditioner, Internet / Wifi and Laundry, and more.

$$$$
vrbo logo
View deal
Interior
4.4
Excellent(4 Reviews)
Cottage
 in Chincoteague Island
Safe Harbor on Chincoteague Island!
6 guests · 2 bedrooms · 1 bath
Garden · Pool · Pets allowed

Nestled in Assateague Island, this Cottage is perfect for your next vacation. Enjoy Safe Harbor on Chincoteague Island!'s top-rated amenities, including Air conditioner, Internet / Wifi and Laundry, and more.

$$$$
vrbo logo
View deal
Terrace/patio
5.0
Outstanding(3 Reviews)
Cottage
 in Chincoteague Island
Shackeau East - Magnificent Views!
4 guests · 1 bedroom · 1 bath
Pool · Kitchen / Kitchenette · Air conditioner

Discover the beauty of Assateague Island with a stay at Shackeau East - Magnificent Views!, a top rated Cottage with amenities such as Air conditioner, Fireplace and Internet / Wifi, and more.

$$$$
vrbo logo
View deal
Fridge, microwave, stovetop, dishwasher
5.0
Outstanding(3 Reviews)
Cottage
 in Snow Hill
‘Christy's Cottage’ w/ Hot Tub - 2 Mi to Beach!
7 guests · 3 bedrooms · 3 baths
Kitchen / Kitchenette · Air conditioner · Internet / Wifi

When traveling to Assateague Island, if you are looking for (business stays, family stays, couples stay, getaway vacation, etc.) this is the perfect place at $340 per night.

$$$$
vrbo logo
View deal
Property grounds
4.4
Excellent(3 Reviews)
Cottage
 in Chincoteague
1BR Snug Harbor Waterfront cottage with a lighthouse view!
4 guests · 1 bedroom · 1 bath
Pets allowed · Kitchen / Kitchenette · Air conditioner

Business stays, family stays, couples stay, getaway vacation, and rental in Assateague Island at 1BR Snug Harbor Waterfront cottage with a lighthouse view! for $332 for your next trip.

$$$$
vrbo logo
View deal
Lake
3.7
Good(3 Reviews)
Cottage
 in Chincoteague
Sandy Gem- Waterfront Cottage w/ Sunset Views & Private Dock
5 guests · 2 bedrooms · 2 baths
Pool · Kitchen / Kitchenette · Air conditioner

Experience the best of Assateague Island with this Cottage available for $243. This property is equipped with amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
vrbo logo
View deal
Fridge, microwave, oven, stovetop
5.0
Outstanding(2 Reviews)
Cottage
 in Chincoteague
Coastal Daze Cottage on Famous Chincoteague Island! Come see the wild ponies!
4 guests · 2 bedrooms · 2 baths
Kitchen / Kitchenette · Air conditioner · Internet / Wifi

Enjoy the best of Assateague Island in our Cottage, Coastal Daze Cottage on Famous Chincoteague Island! Come see the wild ponies! . A stunning property with amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
vrbo logo
View deal
Smart TV, books
5.0
Outstanding(2 Reviews)
Cottage
 in Chincoteague
Waterfowl Watch new listing! Quiet area, great pricing! 5 star host
6 guests · 2 bedrooms · 1 bath
Garden · Kitchen / Kitchenette · Air conditioner

This Cottage for $177 in Assateague Island, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
vrbo logo
View deal
Property grounds
5.0
Outstanding(2 Reviews)
Cottage
 in Chincoteague
Deer Track-Close to town-Firepit!
4 guests · 2 bedrooms · 1 bath
Garden · Kitchen / Kitchenette · Air conditioner

Business stays, family stays, couples stay, getaway vacation, and rental in Assateague Island at Deer Track-Close to town-Firepit! for $143 for your next trip.

$$$$
vrbo logo
View deal
Fridge, microwave, oven, stovetop
5.0
Outstanding(2 Reviews)
Cottage
 in Chincoteague
Cottage on Cleveland- In Town, Close to Everything
6 guests · 2 bedrooms · 2 baths
Garden · Kitchen / Kitchenette · Air conditioner

Nestled in Assateague Island, this Cottage is perfect for your next vacation. Enjoy Cottage on Cleveland- In Town, Close to Everything's top-rated amenities, including Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
vrbo logo
View deal

Find Cottages deals in popular places

Travel inspiration

Keep exploring