Top 50 Eastern Shore of Virginia Vacation Rentals

Houses (205)
Cottages (36)
Condos (15)
Golf rental (205)
Beachfront (99)
Beach view (74)

Explore a selection of Eastern Shore of Virginia vacation rentals

Fall Rates Starting @ $50/Ngt. Charming Chincoteague Cottage...
Guests6
Bedrooms3
Bathrooms2
Wonderful 4.9 / 5
$72 avg/night
3 beds
2 Bathrooms
Guests 6
29 reviews
Bargain Rates Starting@ $50/Ngt.-Fall is Spectacular in Oyster...
Guests6
Bedrooms3
Bathroom1
Wonderful 5 / 5
$83 avg/night
3 beds
1 Bathroom
Guests 6
24 reviews
AT LAST Cottage-PET FRIENDLY-Sleeps 6, Two Blocks To Beach, 1...
Guests6
Bedrooms3
Bathrooms2
Wonderful 4.3 / 5
$120 avg/night
3 beds
2 Bathrooms
Guests 6
12 reviews
Chincoteague Island Bungalow W/ 2 Bedrooms And Guest House
Guests6
Bedrooms3
Bathroom1
Wonderful 4.8 / 5
$150 avg/night
3 beds
1 Bathroom
Guests 6
25 reviews
Newly Renovated Cottage On Main Street
Guests4
Studio
Bathroom1
Wonderful 4.5 / 5
$61 avg/night
Studio
1 Bathroom
Guests 4
33 reviews
Charming Accommodations Backing Misty's Pasture
Guests6
Bedrooms2
Bathrooms2
Wonderful 4.9 / 5
$150 avg/night
2 beds
2 Bathrooms
Guests 6
24 reviews
Dog-Friendly Tranquil Retreat
Guests5
Bedrooms2
Bathroom1
Wonderful 4.8 / 5
$120 avg/night
2 beds
1 Bathroom
Guests 5
40 reviews
The Fishing Cottage located on a Scenic Eastern Shore farm
Guests12
Bedrooms6
Bathrooms2
Wonderful 4.5 / 5
$200 avg/night
6 beds
2 Bathrooms
Guests 12
32 reviews
Grand Escape - Featured on HGTV's Beachfront Bargain Hunt
Guests18
Bedrooms5
Bathrooms6
Wonderful 4.9 / 5
$371 avg/night
5 beds
6 Bathrooms
Guests 18
17 reviews
Breezy Pines- Relax on the Dock of the Bay!
Guests9
Bedrooms3
Bathrooms2
Wonderful 4.8 / 5
$125 avg/night
3 beds
2 Bathrooms
Guests 9
16 reviews
Smith Beach Waterfront Cottage
Guests6
Studio
Bathroom1
Wonderful 4.3 / 5
$149 avg/night
Studio
1 Bathroom
Guests 6
18 reviews
Sisters 3 by the Sea, 400 Feet To The Beach
Guests8
Bedrooms4
Bathrooms2
Wonderful 4.6 / 5
$141 avg/night
4 beds
2 Bathrooms
Guests 8
38 reviews
The Only Thing We Overlook Is The Bay
Guests8
Bedrooms3
Bathrooms3
Wonderful 4.8 / 5
$217 avg/night
3 beds
3 Bathrooms
Guests 8
6 reviews
Stately Home on Chincoteague Island
Guests12
Bedrooms5
Bathrooms3
Wonderful 4.6 / 5
$191 avg/night
5 beds
3 Bathrooms
Guests 12
32 reviews
ROMANTIC GETAWAY 1 BLOCK TO BEACH, BAY & SUNSETS- KAYAK INCLUDED...
Guests5
Bedrooms3
Bathroom1
Wonderful 4.3 / 5
$115 avg/night
3 beds
1 Bathroom
Guests 5
10 reviews
Chesapeake Bay Memories of a Lifetime-GREAT 5 STAR REVIEWS!
Guests8
Bedrooms4
Bathroom1
Wonderful 4.8 / 5
$150 avg/night
4 beds
1 Bathroom
Guests 8
63 reviews
'Gone to the Beach' Cape Charles, VA. Stunning Sunsets, Fishing...
Guests12
Bedrooms4
Bathrooms3
Wonderful 4.8 / 5
$171 avg/night
4 beds
3 Bathrooms
Guests 12
30 reviews
Pink Pearl-Comfortable and Affordable
Guests6
Bedrooms3
Bathrooms2
Wonderful 3.8 / 5
$100 avg/night
3 beds
2 Bathrooms
Guests 6
8 reviews
The Quarter Master has been sold. New name and new listing 4547183
Guests16
Bedrooms4
Bathrooms4
Wonderful 4.2 / 5
$293 avg/night
4 beds
4 Bathrooms
Guests 16
17 reviews
Serene Bayfront Cottage on Private Beach - Waterfront Beach House
Guests6
Bedrooms2
Bathrooms2
Wonderful 4.8 / 5
$212 avg/night
2 beds
2 Bathrooms
Guests 6
32 reviews
Historic Home on Onancock Creek
Guests8
Bedrooms3
Bathrooms3
Wonderful 5 / 5
$171 avg/night
3 beds
3 Bathrooms
Guests 8
42 reviews
THE LIGHTHOUSE INN..Imagine Walking 2 Blocks And Having Your Feet...
Guests14
Bedrooms4
Bathrooms4
Wonderful 4.9 / 5
$271 avg/night
4 beds
4 Bathrooms
Guests 14
46 reviews
Onancock Creek Waterfront Cottage-Premier Location
Guests6
Bedrooms3
Bathrooms3
Wonderful 4.7 / 5
$200 avg/night
3 beds
3 Bathrooms
Guests 6
22 reviews
Up to 25% Off - 4BR Golf Course Front Home at Bay Creek Resort!
Guests10
Bedrooms4
Bathrooms3
Wonderful 5 / 5
$159 avg/night
4 beds
3 Bathrooms
Guests 10
107 reviews
Paradise on the Chesapeake Bay,sunsets over the Bay & steps away...
Guests14
Bedrooms5
Bathrooms3
Wonderful 4.8 / 5
$521 avg/night
5 beds
3 Bathrooms
Guests 14
8 reviews
WOW- FALL VACATION WITH SUMMER WEATHER AND GREAT RATES
Guests12
Bedrooms5
Bathrooms4
Wonderful 5 / 5
$343 avg/night
5 beds
4 Bathrooms
Guests 12
8 reviews
Beautiful Sunsets Over The Chincoteague Bay* Panoramic Water...
Guests10
Bedrooms3
Bathrooms2
Wonderful 4.8 / 5
$233 avg/night
3 beds
2 Bathrooms
Guests 10
8 reviews
Bay Dunes-Sleeps 14, Steps From Private Beach Community Pool and...
Guests14
Bedrooms5
Bathrooms5
Wonderful 4.8 / 5
$386 avg/night
5 beds
5 Bathrooms
Guests 14
17 reviews
BAYCATION-2 BLOCKS TO THE BEACH!
Guests8
Bedrooms4
Bathroom1
Wonderful 4.3 / 5
$145 avg/night
4 beds
1 Bathroom
Guests 8
4 reviews
Enjoy Sandpiper House on Chincoteague's Peaceful Piney Island!
Guests8
Bedrooms3
Bathrooms2
Wonderful 4.7 / 5
$166 avg/night
3 beds
2 Bathrooms
Guests 8
24 reviews
Sunset View, 4 Bedroom Family Size Home 300 Feet From Beach
Guests10
Bedrooms4
Bathrooms2
Wonderful 4.7 / 5
$343 avg/night
4 beds
2 Bathrooms
Guests 10
3 reviews
Chesapeake Bay Sunsets Abound. Discounted Rates December thru...
Guests6
Bedrooms2
Bathrooms2
Wonderful 4.9 / 5
$220 avg/night
2 beds
2 Bathrooms
Guests 6
32 reviews
1st Year Listing - Park Place 1 - No reviews yet. See PP2 Reviews...
Guests6
Bedrooms3
Bathroom1
Wonderful 4.2 / 5
$175 avg/night
3 beds
1 Bathroom
Guests 6
6 reviews
Park Place - Comfy Condo Close to Beach
Guests7
Bedrooms3
Bathrooms2
Wonderful 4.3 / 5
$138 avg/night
3 beds
2 Bathrooms
Guests 7
4 reviews
Flip Flop Inn and Relax!
Guests5
Bedrooms2
Bathroom1
Wonderful 4.6 / 5
$147 avg/night
2 beds
1 Bathroom
Guests 5
30 reviews
As close as you can get to the ocean south of Chincoteague
Guests6
Bedrooms2
Bathrooms2
Wonderful 4.8 / 5
$257 avg/night
2 beds
2 Bathrooms
Guests 6
11 reviews
SUNSET BEACH - Exquisite sunsets at this luxury home - steps away...
Guests8
Bedrooms3
Bathrooms2
Wonderful 4.5 / 5
$399 avg/night
3 beds
2 Bathrooms
Guests 8
10 reviews
Relax & Enjoy, You're On Island Time... 10% Military discount.
Guests8
Bedrooms3
Bathrooms2
Wonderful 4.9 / 5
$179 avg/night
3 beds
2 Bathrooms
Guests 8
38 reviews
Secluded Waterfront Farm
Guests8
Bedrooms4
Bathrooms3
Wonderful 4.9 / 5
$286 avg/night
4 beds
3 Bathrooms
Guests 8
14 reviews
Starborough: A Beautiful Home In Historic Cape Charles That Sleeps...
Guests8
Bedrooms3
Bathrooms2
Wonderful 4.9 / 5
$200 avg/night
3 beds
2 Bathrooms
Guests 8
36 reviews
Beachfront Luxury Home with fabulous garden and splendid sunset...
Guests14
Bedrooms5
Bathrooms3
Wonderful 4.9 / 5
$376 avg/night
5 beds
3 Bathrooms
Guests 14
41 reviews
Popular 5-Bedroom Family Rental By Town & Water - BOOKING NOW
Guests15
Bedrooms5
Bathrooms2
Wonderful 4.8 / 5
$199 avg/night
5 beds
2 Bathrooms
Guests 15
47 reviews
Room for the Whole Family or Several Families and Just a Walk to...
Guests15
Bedrooms5
Bathrooms2
Wonderful 4.7 / 5
$185 avg/night
5 beds
2 Bathrooms
Guests 15
12 reviews
LARGE HOME perfect for Extended Family Vacations or Group Trips or...
Guests14
Bedrooms4
Bathrooms2
Wonderful 4.4 / 5
$158 avg/night
4 beds
2 Bathrooms
Guests 14
17 reviews
Family-Friendly Bay View Home With Private Beach
Guests9
Bedrooms3
Bathrooms2
Wonderful 4.8 / 5
$107 avg/night
3 beds
2 Bathrooms
Guests 9
20 reviews
Breathtaking Views of Chincoteague Bay & Chincoteague Island...
Guests8
Bedrooms3
Bathrooms2
Wonderful 4 / 5
$183 avg/night
3 beds
2 Bathrooms
Guests 8
2 reviews
Spacious Upscale Vacation House With Hot Tub, Sleeps 15, 3 Kings...
Guests15
Bedrooms5
Bathrooms3
Wonderful 4.9 / 5
$350 avg/night
5 beds
3 Bathrooms
Guests 15
21 reviews
Orange Crush! Backyard Paradise-Beach, Marina, Pool, Fire Pit...
Guests9
Bedrooms4
Bathrooms3
Wonderful 4.9 / 5
$325 avg/night
4 beds
3 Bathrooms
Guests 9
16 reviews
Bayside Beauty/Waterfront facing Chincoteague Island
Guests8
Bedrooms4
Bathrooms2
Wonderful 4.4 / 5
$257 avg/night
4 beds
2 Bathrooms
Guests 8
14 reviews
Chesapeake Dream-Restored Victorian 1 Blocks To Beach
Guests11
Bedrooms4
Bathrooms3
Wonderful 5 / 5
$230 avg/night
4 beds
3 Bathrooms
Guests 11
13 reviews

Eastern Shore of Virginia, USA Vacation Rentals

Fall Rates Starting @ $50/Ngt. Charming Chincoteague Cottage...

Bargain Rates Starting@ $50/Ngt.-Fall is Spectacular in Oyster...

AT LAST Cottage-PET FRIENDLY-Sleeps 6, Two Blocks To Beach, 1...

Chincoteague Island Bungalow W/ 2 Bedrooms And Guest House

Newly Renovated Cottage On Main Street

Charming Accommodations Backing Misty's Pasture

Dog-Friendly Tranquil Retreat

The Fishing Cottage located on a Scenic Eastern Shore farm

Grand Escape - Featured on HGTV's Beachfront Bargain Hunt

Breezy Pines- Relax on the Dock of the Bay!

Smith Beach Waterfront Cottage

Sisters 3 by the Sea, 400 Feet To The Beach

The Only Thing We Overlook Is The Bay

Stately Home on Chincoteague Island

ROMANTIC GETAWAY 1 BLOCK TO BEACH, BAY & SUNSETS- KAYAK INCLUDED...

Chesapeake Bay Memories of a Lifetime-GREAT 5 STAR REVIEWS!

'Gone to the Beach' Cape Charles, VA. Stunning Sunsets, Fishing...

Pink Pearl-Comfortable and Affordable

The Quarter Master has been sold. New name and new listing 4547183

Serene Bayfront Cottage on Private Beach - Waterfront Beach House

Historic Home on Onancock Creek

THE LIGHTHOUSE INN..Imagine Walking 2 Blocks And Having Your Feet...

Onancock Creek Waterfront Cottage-Premier Location

Up to 25% Off - 4BR Golf Course Front Home at Bay Creek Resort!

Paradise on the Chesapeake Bay,sunsets over the Bay & steps away...

WOW- FALL VACATION WITH SUMMER WEATHER AND GREAT RATES

Beautiful Sunsets Over The Chincoteague Bay* Panoramic Water...

Bay Dunes-Sleeps 14, Steps From Private Beach Community Pool and...

BAYCATION-2 BLOCKS TO THE BEACH!

Enjoy Sandpiper House on Chincoteague's Peaceful Piney Island!

Sunset View, 4 Bedroom Family Size Home 300 Feet From Beach

Chesapeake Bay Sunsets Abound. Discounted Rates December thru...

1st Year Listing - Park Place 1 - No reviews yet. See PP2 Reviews...

Park Place - Comfy Condo Close to Beach

Flip Flop Inn and Relax!

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

SUNSET BEACH - Exquisite sunsets at this luxury home - steps away...

Relax & Enjoy, You're On Island Time... 10% Military discount.

Secluded Waterfront Farm

Starborough: A Beautiful Home In Historic Cape Charles That Sleeps...

Beachfront Luxury Home with fabulous garden and splendid sunset...

Popular 5-Bedroom Family Rental By Town & Water - BOOKING NOW

Room for the Whole Family or Several Families and Just a Walk to...

LARGE HOME perfect for Extended Family Vacations or Group Trips or...

Family-Friendly Bay View Home With Private Beach

Breathtaking Views of Chincoteague Bay & Chincoteague Island...

Spacious Upscale Vacation House With Hot Tub, Sleeps 15, 3 Kings...

Orange Crush! Backyard Paradise-Beach, Marina, Pool, Fire Pit...

Bayside Beauty/Waterfront facing Chincoteague Island

Chesapeake Dream-Restored Victorian 1 Blocks To Beach