Eastern Shore of Virginia holiday rentals

We found 1,149 holiday rentals — enter your dates for availability

Holiday rentals with weekly discounts – Eastern Shore of Virginia

Showing deals for:1 Jan - 8 Jan

Dinning Area Photo 2
From Living Room lake view
Living Room Photo 1
Bedroom 4 with Queen size bed and bunk bed - Photo 3
Excellent
(8 reviews)

Peaceful Entire 4 BR 2 BA Cabin with AC, WiFi, Pond View, Recreational room

Marion Station

16% off
AU$2,629
for 7 nights, 1 cabin
AU$376 per night
includes taxes & fees
Peaceful Entire 4 BR 2 BA Cabin with AC, WiFi, Pond View, Recreational room
Pool
Beach
Private kitchen
Newly expanded rear deck
Exceptional
(48 reviews)

Family vacation retreat w/ In-ground Pool with private Chesapeake Bay access!

Cape Charles

8% off
AU$8,644
for 7 nights, 1 home
AU$1,235 per night
includes taxes & fees
Family vacation retreat w/ In-ground Pool with private Chesapeake Bay access!
Marina
Pool
Private kitchen
Living area
Exceptional
(23 reviews)

1BR Waterfront cottage with a view of the wild Chincoteague ponies!

Chincoteague

8% off
AU$4,745
for 7 nights, 1 cottage
AU$678 per night
includes taxes & fees
1BR Waterfront cottage with a view of the wild Chincoteague ponies!
Interior
Marina
Property grounds
Pool
Exceptional
(58 reviews)

2BR Waterfront Cottage with the Most Spectacular View of lighthouse!

Chincoteague

8% off
AU$3,308
for 7 nights, 1 cottage
AU$473 per night
includes taxes & fees
2BR Waterfront Cottage with the Most Spectacular View of lighthouse!
Living area
Room
Interior
Exterior
Exceptional
(23 reviews)

A Mermaid Vacation Beach Rental BAY VIEW CAPE CHARLES

Cape Charles

5% off
AU$7,460
for 7 nights, 1 home
AU$1,066 per night
includes taxes & fees
A Mermaid Vacation Beach Rental BAY VIEW CAPE CHARLES
Dining
Exterior
Living area
Property grounds
Exceptional
(9 reviews)

Bayfront Cottage-Private Lane with Ponies in the backyard - Chincoteague

Chincoteague

8% off
AU$3,672
for 7 nights, 1 home
AU$525 per night
includes taxes & fees
Bayfront Cottage-Private Lane with Ponies in the backyard - Chincoteague
Amazing views from the house!
The breathtaking sunset to close the day
Spacious well stocked kitchen
Spacious living area
Exceptional
(5 reviews)

10 Acre 3 BR Waterfront Retreat on Thicket Creek has dock & neighborhood beach

Onancock

8% off
AU$4,148
for 7 nights, 1 home
AU$593 per night
includes taxes & fees
10 Acre 3 BR Waterfront Retreat on Thicket Creek has dock & neighborhood beach
Marina
Private kitchen
Exterior
Entryway
Exceptional
(17 reviews)

First Floor King Suite, Kids Bunk Room ~ Private Beach & Community Pool Access!

Cape Charles

7% off
AU$4,905
for 7 nights, 1 home
AU$701 per night
includes taxes & fees
First Floor King Suite, Kids Bunk Room ~ Private Beach & Community Pool Access!
kitchen area
screen porch view
BEACH VIEW FROM SKY
living room
Exceptional
(27 reviews)

your own Private beach, adjacent nature preserve-Sunset Dunes Cape Charles, VA

Eastville

8% off
AU$6,983
for 7 nights, 1 home
AU$998 per night
includes taxes & fees
your own Private beach, adjacent nature preserve-Sunset Dunes Cape Charles, VA
Living area
Outdoor dining
Private kitchen
Dining
Exceptional
(17 reviews)

Golf cart included! 5 blocks to the beach, and in historic district!

Cape Charles

7% off
AU$3,576
for 7 nights, 1 home
AU$511 per night
includes taxes & fees
Golf cart included! 5 blocks to the beach, and in historic district!
Ottoman filled with board games for the family and lots of children's books
Breakfast nook with TV
Shed packed with all you need! Bikes, floats, chairs, beach toys
Open kitchen and dining space with tons of seating
Exceptional
(69 reviews)

Sweet Victorian Beach Cottage

Cape Charles

8% off
AU$3,983
for 7 nights, 1 home
AU$569 per night
includes taxes & fees
Sweet Victorian Beach Cottage
Bright eat-in kitchen, easy access to screened porch for indoor/outdoor dining.
Soak under the stars in your own private hot tub - quiet & relaxing!
Cozy living room with a fireplace, TV, and plenty of space to unwind together.
Enjoy fresh air and easy conversation on the screened porch. A favorite spot!
Exceptional
(7 reviews)

Mermaid & Mare, Downtown Retreat. Hot Tub, Firepit, fenced yard & Pet Friendly!

Chincoteague

8% off
AU$2,943
for 7 nights, 1 home
AU$420 per night
includes taxes & fees
Mermaid & Mare, Downtown Retreat. Hot Tub, Firepit, fenced yard & Pet Friendly!
Room
Property grounds
Dining
Interior
Exceptional
(81 reviews)

SEASIDE PRIVATE RETREAT!! 100-Acre Private WATERFRONT Home Stunning island views

Cape Charles

12% off
AU$3,969
for 7 nights, 1 home
AU$567 per night
includes taxes & fees
SEASIDE PRIVATE RETREAT!! 100-Acre Private WATERFRONT Home Stunning island views
Private kitchen
Terrace/patio
Private kitchen
Room
Exceptional
(8 reviews)

Family Friendly 3 Bedroom Home Near Beach and Downtown with Fenced in Yard

Cape Charles

6% off
AU$3,778
for 7 nights, 1 home
AU$540 per night
includes taxes & fees
Family Friendly 3 Bedroom Home Near Beach and Downtown with Fenced in Yard
Renovated kitchen
Unique custom milled wood step into dining room.
Bedroom #2 has queen bed, twin bed, smart TV, & private bathroom.
Dining table w/ chandelier
Exceptional
(51 reviews)

Sea Salt Cottage: Your Tranquil Getaway 3 min to beach

Cape Charles

8% off
AU$3,524
for 7 nights, 1 home
AU$503 per night
includes taxes & fees
Sea Salt Cottage: Your Tranquil Getaway 3 min to beach
Fire pit patio. You will need to bring your own wood.
Living room from kitchen
Queen room 1 with en-suite bathroom
Dining room and books
Exceptional
(161 reviews)

The Brass Crab - Check in/out any day!

Chincoteague

7% off
AU$2,193
for 7 nights, 1 home
AU$313 per night
includes taxes & fees
The Brass Crab - Check in/out any day!
Living area
Exterior
Property grounds
Private kitchen
Exceptional
(94 reviews)

Fish Tales-FISH/EAT/STAY

Cape Charles

8% off
AU$2,389
for 7 nights, 1 home
AU$341 per night
includes taxes & fees
Fish Tales-FISH/EAT/STAY
Private kitchen
Pool
Exterior
Living area
Exceptional
(8 reviews)

Bay Creek Home~ King Suite & Family Friendly Loft!

Cape Charles

7% off
AU$2,663
for 7 nights, 1 home
AU$380 per night
includes taxes & fees
Bay Creek Home~ King Suite & Family Friendly Loft!
Living area
Living area
Interior
Dining
Exceptional
(21 reviews)

Waterfowl Watch Cottage - Chincoteague Island Quiet area,bikes, Spend Christmas

Chincoteague

7% off
AU$1,912
for 7 nights, 1 cottage
AU$273 per night
includes taxes & fees
Waterfowl Watch Cottage - Chincoteague Island Quiet area,bikes, Spend Christmas
Private kitchen
Living area
Outdoor dining
Interior
Exceptional
(49 reviews)

Apartment in the Seaside Village of Wachapreague

Wachapreague

8% off
AU$1,692
for 7 nights, 1 apartment
AU$242 per night
includes taxes & fees
Apartment in the Seaside Village of Wachapreague
FLOATING PIER
CHINCOTEAGUE BAY
FISHING/CRABBING PIER
CRABBING PIER
Exceptional
(72 reviews)

Hidden Gem! Clean & Cozy and Family Friendly!

Horntown

8% off
AU$2,865
for 7 nights, 1 home
AU$409 per night
includes taxes & fees
Hidden Gem! Clean & Cozy and Family Friendly!
Corner/End Unit Yellow siding location of Master Bedroom-and corner living area
Second table and chairs on the balcony - enjoy the sunset!
View from the living room: Chincoteague channel, marsh island and wildlife.
Master bedroom featuring Tommy Bahama furniture
Exceptional
(133 reviews)

Sunset Bay Villas at Chincoteague Island Virginia - direct water front

Chincoteague

17% off
AU$3,031
for 7 nights, 1 apartment
AU$433 per night
includes taxes & fees
Sunset Bay Villas at Chincoteague Island Virginia - direct water front
Exterior
Terrace/patio
Living area
Room
Exceptional
(10 reviews)

3-bedroom Family Friendly House Near Beach and Downtown with Fenced In Back Yard

Cape Charles

6% off
AU$3,822
for 7 nights, 1 home
AU$546 per night
includes taxes & fees
3-bedroom Family Friendly House Near Beach and Downtown with Fenced In Back Yard
  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Explore the natural setting in Eastern Shore of Virginia

The wildlife and island views create a pretty picture of Eastern Shore of Virginia. This city's seafood restaurants, boating and bird watching draw many visitors. Many of our holiday rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.

Sightseeing in and around Eastern Shore of Virginia

Do you want to discover top things to see and do during your stay? Travellers enjoy Eastern Shore of Virginia for its boating, bird watching and horse riding. Venture out of your holiday home and experience everything that makes Eastern Shore of Virginia a one-of-a-kind holiday spot. Here are some of the major attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Bay Creek Golf Club (28.1 mi / 45.2 km)
  • North Street Market (9.9 mi / 15.9 km)
  • Chatham Vineyards (15.1 mi / 24.4 km)
  • Eastern Shore Yacht and Country Club Golf Course (8.5 mi / 13.7 km)
  • SouthEast Expeditions (9.9 mi / 16 km)
  • Bloxom Winery (17.5 mi / 28.1 km)

Exploring the beaches and other natural features in Eastern Shore of Virginia

Travellers enjoy Eastern Shore of Virginia for its wildlife and island views. Whether you're looking for fun outdoor activities or just want to spend some time taking in the scenery, Eastern Shore of Virginia is a great spot to appreciate mother nature. These are a few of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city centre:

  • Chesapeake Bay (22.4 mi / 36 km)
  • Cape Charles Beach (27.5 mi / 44.2 km)
  • Cape Charles Harbor (27.8 mi / 44.7 km)
  • Assateague Point (28.2 mi / 45.3 km)
  • Honeymoon Island (19.9 mi / 32 km)
  • Tangier Island Beach (22.7 mi / 36.5 km)

Frequently asked questions

What is the best area to stay in Eastern Shore of Virginia when booking a holiday home?
Among the most in-demand areas for an Eastern Shore of Virginia holiday home is Greenbackville. When you book your holiday property with Stayz, you can look forward to having the whole place to yourselves. That means you won't have to share it with anybody except for your group.
What is the most popular type of holiday home accommodation in Eastern Shore of Virginia?
According to our research, houses are considered the most popular type of holiday home in Eastern Shore of Virginia. But as you know, everyone's idea of an awesome stay isn't the same. Stayz has holiday homes of all sizes, shapes and budgets, and we'll help you find the best fit for your needs.
How much does it cost to rent a holiday home in Eastern Shore of Virginia?
Different things determine how much you pay for a holiday home in Eastern Shore of Virginia, such as the type of property, season and length of stay. But, all of our holiday homes have something in common — amazing value. Simply add your travel dates to find your ideal match.
How much does it cost to rent a beach house in Eastern Shore of Virginia?
When you travel and the style and size of the property will influence the cost of your beachside escape. Enter your Eastern Shore of Virginia travel dates to view your available options on Stayz. Looking for basics like WiFi, or perks like a private pool? Use our filters to choose the features and amenities you want.
What are popular home amenities in Eastern Shore of Virginia?
Some of the most popular home amenities people search for in Eastern Shore of Virginia are a microwave oven, a dryer and a washing machine. Whether you're holidaying with family, your besties or even pets, Stayz holiday homes include the best amenities for ultimate relaxation with the people you love.
Are there large group holiday homes in Eastern Shore of Virginia?
Eastern Shore of Virginia has 128 holiday homes that can host 10 or more people. These stays come with enough space to enjoy good times with your favourite people.
What are the top attractions for families in Eastern Shore of Virginia?
Keep your kids busy at these fabulous family-friendly attractions in Eastern Shore of Virginia:
  • Chincoteague National Wildlife Refuge
  • Chesapeake Bay Bridge-Tunnel
  • Cape Charles Beach
Can I find two-bedroom holiday homes in Eastern Shore of Virginia?
Gather your loved ones and relax in total privacy and comfort in one of the 150 two-bedroom holiday properties Eastern Shore of Virginia has to offer.
Are there holiday homes with WiFi in Eastern Shore of Virginia?
You can pick from 251 holiday homes with WiFi in Eastern Shore of Virginia. If you want to disconnect from daily life during your trip, but still need to be connected to the web, these getaways have just what you need. Narrow your search by applying the WiFi filter on Stayz.
How old do you have to be to rent a holiday home in Eastern Shore of Virginia?
We recommend you check with the Eastern Shore of Virginia holiday property you'd like on Stayz as age restrictions differ. However, it's generally 16, 18 or 21.
How long can I rent a holiday home in Eastern Shore of Virginia for?
It's down to the Eastern Shore of Virginia property. To see a list of options offering extended stays, just enter your travel dates and guest number into the Stayz search page. Look forward to having the entire place to yourself, along with the comforts of home like air conditioning, a fully-equipped kitchen and a backyard where your little ones can play. Keep your eyes open for any long-term stays that offer discounted weekly or monthly prices.