Eastern Shore of Virginia holiday rentals

We found 1,159 holiday rentals — enter your dates for availability

Holiday rentals with weekly discounts – Eastern Shore of Virginia

Showing deals for:13 Nov - 20 Nov

Pool
Beach
Newly expanded rear deck
Front left corner of home.
Exceptional
(45 reviews)

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

Cape Charles

8% off
AU$8,390
for 7 nights, 1 home
AU$1,199 per night
includes taxes & fees
Family vacation retreat w/ In-ground Pool with private Chesapeake Bay access!
Someone has to wash dishes, even on vacation. With this view, who minds?
Guest Suite Living Room - there is more furniture there now. What a view!
party decorations
Main house on right, Guest house on left. A floating dock, water toys.. Wow!
Exceptional
(29 reviews)

Eureka! on Deep Hole Creek - Waterfront! Sleeps 16

Chincoteague

36% off
AU$9,959
for 7 nights, 1 home
AU$1,423 per night
includes taxes & fees
Eureka! on Deep Hole Creek - Waterfront! Sleeps 16
Interior
Room
Private kitchen
Living area
Exceptional
(23 reviews)

A Mermaid Vacation Beach Rental BAY VIEW CAPE CHARLES

Cape Charles

6% off
AU$8,341
for 7 nights, 1 home
AU$1,192 per night
includes taxes & fees
A Mermaid Vacation Beach Rental BAY VIEW CAPE CHARLES
Interior
Lunch on the screen porch, watching the egrets.
The back porch, seen from near water's edge
Interior
Exceptional
(93 reviews)

Feed Your Soul at Silver Beach Cove

Exmore

8% off
AU$4,394
for 7 nights, 1 cottage
AU$628 per night
includes taxes & fees
Feed Your Soul at Silver Beach Cove
Master bedroom includes a king sized bed and plenty of room for as portable crib
A full service marina with slips for guests is a short walk from the house.
Grand entrance to home that accommodates up to 14 guests.
Living area
Wonderful
(14 reviews)

Spacious Beach House: Oystermen's Pearl: Golf Cart Included

Cape Charles

6% off
AU$3,723
for 7 nights, 1 home
AU$532 per night
includes taxes & fees
Spacious Beach House: Oystermen's Pearl: Golf Cart Included
Kitchen with water views. Beautiful every meal!
Upstairs Balcony Sliding Glass Doors.
Stunning views no matter where you look!
Living room view from kitchen sink. High ceilings!
Exceptional
(139 reviews)

As close as you can get to the ocean south of Chincoteague

Parksley

8% off
AU$3,823
for 7 nights, 1 home
AU$546 per night
includes taxes & fees
As close as you can get to the ocean south of Chincoteague
Front of House
Entryway
Laundry room, side entrance off the kitchen
Dining room -- the downstairs bathroom is behind the barn door
Exceptional
(144 reviews)

Downtown, Three Bedroom, Dog-friendly, Short Walk to the Beach

Cape Charles

7% off
AU$2,703
for 7 nights, 1 home
AU$386 per night
includes taxes & fees
Downtown, Three Bedroom, Dog-friendly, Short Walk to the Beach
Entryway
Private kitchen
Living area
Marina
Exceptional
(15 reviews)

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

Cape Charles

7% off
AU$4,168
for 7 nights, 1 home
AU$595 per night
includes taxes & fees
First Floor King Suite, Kids Bunk Room ~ Private Beach & Community Pool Access!
Private kitchen
Outdoor dining
Living area
Outdoor shower and Patio
Exceptional
(16 reviews)

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

Cape Charles

7% off
AU$2,850
for 7 nights, 1 home
AU$407 per night
includes taxes & fees
Golf cart included! 5 blocks to the beach, and in historic district!
Dining
Exterior
Property grounds
Exterior
Exceptional
(10 reviews)

Everyday Your Beachside Escape!

Cape Charles

6% off
AU$3,510
for 7 nights, 1 home
AU$501 per night
includes taxes & fees
Everyday Your Beachside Escape!
Exterior detail
Interior
Exterior detail
Living area
Exceptional
(5 reviews)

Bring the whole family to the Summer House. 6 bedroom, 2 bath sleeps 12.

Cape Charles

7% off
AU$7,378
for 7 nights, 1 home
AU$1,054 per night
includes taxes & fees
Bring the whole family to the Summer House. 6 bedroom, 2 bath sleeps 12.
Shed packed with all you need! Bikes, floats, chairs, beach toys
Breakfast nook with TV
Ottoman filled with board games for the family and lots of children's books
Gourmet kitchen has everything you could need including spices, coffee, tea
Exceptional
(64 reviews)

Sweet Victorian Beach Cottage

Cape Charles

7% off
AU$3,054
for 7 nights, 1 home
AU$436 per night
includes taxes & fees
Sweet Victorian Beach Cottage
Property grounds
Property grounds
Interior
Room
Exceptional
(8 reviews)

Harbor Master-Waterfront 3 bedroom home with endless pool pickleball fenced yard

Onancock

8% off
AU$4,739
for 7 nights, 1 home
AU$677 per night
includes taxes & fees
Harbor Master-Waterfront 3 bedroom home with endless pool pickleball fenced yard
Property grounds
Exterior
Dining
Living area
Exceptional
(7 reviews)

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

Chincoteague

8% off
AU$3,554
for 7 nights, 1 home
AU$508 per night
includes taxes & fees
Bayfront Cottage-Private Lane with Ponies in the backyard - Chincoteague
Stunning View of the Chincoteague Bay from the Sunset Deck
View of the house from the kayak!
Walk in the Front Door and enjoy water views from every window and door
Third Floor Sitting Area with Panoramic Water Views
Wonderful
(13 reviews)

Beautiful Sunsets Over The Chincoteague Bay* Panoramic Water Views* Private Dock

Chincoteague

8% off
AU$5,990
for 7 nights, 1 home
AU$856 per night
includes taxes & fees
Beautiful Sunsets Over The Chincoteague Bay* Panoramic Water Views* Private Dock
Exterior detail
Private kitchen
Exterior detail
Living area
Exceptional
(17 reviews)

Lil' Ms. Clementine 2-bedroom home in Historic District with Golfcart option

Cape Charles

7% off
AU$3,062
for 7 nights, 1 home
AU$437 per night
includes taxes & fees
Lil' Ms. Clementine 2-bedroom home in Historic District with Golfcart option
Spacious living area
The breathtaking sunset to close the day
Rear path to secret garden
Spacious well stocked kitchen
Exceptional
(5 reviews)

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

Onancock

8% off
AU$4,067
for 7 nights, 1 home
AU$581 per night
includes taxes & fees
10 Acre 3 BR Waterfront Retreat on Thicket Creek has dock & neighborhood beach
kitchen area
screen porch view
BEACH VIEW FROM SKY
view from garage apartment available separately.
Exceptional
(25 reviews)

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

Eastville

8% off
AU$7,807
for 7 nights, 1 home
AU$1,115 per night
includes taxes & fees
your own Private beach, adjacent nature preserve-Sunset Dunes Cape Charles, VA
Private kitchen
Terrace/patio
Fitness facility
Property grounds
Exceptional
(5 reviews)

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

Chincoteague

8% off
AU$2,374
for 7 nights, 1 home
AU$339 per night
includes taxes & fees
3 story 2-bedroom house, Large decks, waterview, near beach, Fitness, Game room
Living area
Exterior
House sits faraway from street.
Exterior detail
Exceptional
(20 reviews)

Custom 4-bedroom home, boat slip, fenced backyard, pool & paved bike path.

Cape Charles

8% off
AU$4,189
for 7 nights, 1 home
AU$598 per night
includes taxes & fees
Custom 4-bedroom home, boat slip, fenced backyard, pool & paved bike path.
Dining
Private kitchen
Welcome to Kiptopeke Condominiums!
Cape Charles Harbor
Exceptional
(76 reviews)

All the comforts of home!

Cape Charles

7% off
AU$2,411
for 7 nights, 1 home
AU$344 per night
includes taxes & fees
All the comforts of home!
Fire pit patio. You will need to bring your own wood.
Living room from kitchen
Dining room and books
Queen room 1 with en-suite bathroom
Exceptional
(159 reviews)

The Brass Crab - Check in/out any day!

Chincoteague

7% off
AU$2,150
for 7 nights, 1 home
AU$307 per night
includes taxes & fees
The Brass Crab - Check in/out any day!
Exterior
Living area
Dining
Private kitchen
Exceptional
(9 reviews)

CC Cottage is a charming home on a large lot close to Town, away from crowds

Cape Charles

7% off
AU$3,275
for 7 nights, 1 home
AU$468 per night
includes taxes & fees
CC Cottage is a charming home on a large lot close to Town, away from crowds
Interior
The durable stools allow for additional seating.
The main entrance welcomes you to relaxing times.
Living area
Exceptional
(13 reviews)

Wave Haven @ Cape Charles, a new house near a private beach & nature preserve.

Cape Charles

7% off
AU$3,909
for 7 nights, 1 home
AU$558 per night
includes taxes & fees
Wave Haven @ Cape Charles, a new house near a private beach & nature preserve.

  • 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:

  • Chatham Vineyards (15.1 mi / 24.4 km)
  • Bay Creek Golf Club (28.1 mi / 45.2 km)
  • North Street Market (9.9 mi / 15.9 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)
  • Central Park (27.2 mi / 43.8 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)
  • Parramore Beach (4.9 mi / 7.9 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.