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From $420 per night (USD)
VRBO
Crabba-Dabba-Doo | Chesapeake Properties
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Luxurious Bay Creek Condo with Golf Course Views in Cape Charles. Experience tranquility at this charming first ...
From $420 per night (USD)
VRBO
From $203 per night (USD)
Expedia
Luxury country living!
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
You are only 25 minutes from Va, Beach, country living combined with modern finishes and rustic country charm. Inside yo ...
From $203 per night (USD)
Expedia
From $1370 per night (USD)
VRBO
Bring the whole family to the Summer House. 6 bedroom, 2 bath sleeps 13.
Bedrooms:
2
Bathrooms:
6
Sleeps:
13
Still hoping for a house large enough for your whole family to visit Cape Charles? Come and stay at The Summer House. ...
From $1370 per night (USD)
VRBO
From $210 per night (USD)
Expedia
Quaint costal farm cottage, on a working farm, just mere miles from beaches!
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Welcome to ESVA! We are surrounded by beautiful waters, wildlife, farms, and trails. Don’t fret, because we also have sm ...
From $210 per night (USD)
Expedia
From $184 per night (USD)
VRBO
Have fun with the whole family!
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Get ready to relax in this delightful 3-bedroom mobile home in Exmore. This enchanting property offers a cozy retreat fo ...
From $184 per night (USD)
VRBO
From $108 per night (USD)
Expedia
Thomas Inn Q 6 miles from Cape Charles - double room
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Lovely old colonial home, 2 story brick with great amenities, located only 6 miles from Cape Charles, beautiful Beach, b ...
From $108 per night (USD)
Expedia
From $280 per night (USD)
VRBO
Stately historic 3bdr shore house near Cape Charles, boat parking, pet friendly
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Bring the whole family, pets included, to Pine and Pecan Shore Estate with lots of room for fun. This large stately home ...
From $280 per night (USD)
VRBO
From $495 per night (USD)
Expedia
Historic Spacious 4-bedroom corner house on the Park
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
Brickhaven By The Park - Step into a piece of history with this stunning updated 1917 home, gracefully preserving its or ...
From $495 per night (USD)
Expedia
From $869 per night (USD)
VRBO
Minchew- 5 Bedrooms, Bay Creek, Beach Access
Bedrooms:
4
Bathrooms:
5
Sleeps:
14
Welcome to this charming new rental Minchew, a delightful 4-bedroom, 3.5-bathroom house that mixes modern amenities with ...
From $869 per night (USD)
VRBO
From $527 per night (USD)
Expedia
Oyster Shack - true gem in heart of downtown!
Bedrooms:
3
Bathrooms:
3
Sleeps:
9
Introducing the newest gem in Cape Charles! Perfect for those seeking a serene retreat, this charming vacation rental bo ...
From $527 per night (USD)
Expedia
From $361 per night (USD)
VRBO
Seaside - Traditional duplex in historic downtown!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to "Seaside", your next relaxation haven! This charming 3-bedroom, 2-bathroom pet friendly duplex offers the per ...
From $361 per night (USD)
VRBO
From $374 per night (USD)
Expedia
Bayside - Classic duplex in historic downtown!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to Bayside, your next relaxation haven! This charming 3-bedroom, 2-bathroom pet friendly duplex offers the perfe ...
From $374 per night (USD)
Expedia
From $365 per night (USD)
VRBO
1903 By the Sea - Minutes from Cape Charles
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Our spacious American foursquare style home built in 1903 is the perfect family retreat! Located in quaint Cheriton, we ...
From $365 per night (USD)
VRBO
From $431 per night (USD)
Expedia
Blue Skies Hideaway First Floor - Just 5 miles away from downtown Cape Charles
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Newly renovated 3 bedroom, 2 bath home is perfect for your get away. With a large yard over 1 acre and circle drive, you ...
From $431 per night (USD)
Expedia
From $454 per night (USD)
VRBO
Blue Skies Hideaway - Just 5 miles away from downtown Cape Charles
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Newly renovated 3 bedroom, 2 bath home is perfect for your get away. With a large yard over 1 acre and circle drive, you ...
From $454 per night (USD)
VRBO
$Home w\/ Fire Pit < 1 Mi to Willis Wharf Boat Ramp!$
From $324 per night (USD)
Expedia
Home w\/ Fire Pit < 1 Mi to Willis Wharf Boat Ramp!
Bedrooms:
3
Bathrooms:
5
Sleeps:
8
Private Deck | Gas Grill | Beach Gear Provided Get the most out of your next stop on the Virginia coast when you stay a ...
From $324 per night (USD)
Expedia
From $413 per night (USD)
VRBO
Cute Cottage Awaits You! First Floor Primary Bedroom
Bedrooms:
3
Bathrooms:
3
Sleeps:
10
The cutest cottage awaits you in the newest community in Cape Charles! This home features 3 bedrooms 2.5 bathrooms with ...
From $413 per night (USD)
VRBO
From $727 per night (USD)
Expedia
FREE Luxury Golf Cart - across from CC Beach
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Escape to Cape Charles and unwind at our charming waterfront ranch, nestled in the heart of the historic district. This ...
From $727 per night (USD)
Expedia
$Bungalow w\/ Large Yard: 8 Mi to Cape Charles Beach$
From $332 per night (USD)
VRBO
Bungalow w\/ Large Yard: 8 Mi to Cape Charles Beach
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Hot Tub Soaks | Barbecue Feasts w/ Gas Grill | Board Game Nights | ‘Whitney Bungalow' Nestled in the heart of Cape Char ...
From $332 per night (USD)
VRBO
$\Beach Escape\-3BR, 3BA Beautiful Home With Private Soft Sand Beach Access!$
From $730 per night (USD)
Expedia
\"Beach Escape\"-3BR, 3BA Beautiful Home With Private Soft Sand Beach Access!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
"Beach Escape" is a beautiful 3 bedroom, 3 bathroom home located in the Bayside Village of Bay Creek Golf Resort. A love ...
From $730 per night (USD)
Expedia
From $1444 per night (USD)
VRBO
Waterfront, Chesapeake Bay | Littleton Tazewell
Bedrooms:
6
Bathrooms:
4
Sleeps:
12
Summary: This is a waterfront, luxurious, custom home overlooking the Chesapeake Bay! Expansive decks on all three floor ...
From $1444 per night (USD)
VRBO
From $457 per night (USD)
Expedia
The Waverly Tree House
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This is a 1 of a kind custom built tree house. It is specifically designed to help you escape the city and reconnect wit ...
From $457 per night (USD)
Expedia
From $578 per night (USD)
VRBO
Seascape, Spacious Family Rental Close to Beach and Town!
Bedrooms:
3
Bathrooms:
5
Sleeps:
14
Seascape is a 5BR, 2 1/2BA spacious family rental located in the heart of Historic Cape Charles & a quick walk to the be ...
From $578 per night (USD)
VRBO
From $436 per night (USD)
Expedia
A Charming, Low-Key Luxe Retreat, Steps from the Beach in Historic Cape Charles,
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Get ready for the ultimate Cape Charles escape! With new ownership and a fresh 2025 listing, this charming, newly decora ...
From $436 per night (USD)
Expedia
From $694 per night (USD)
VRBO
Near Beach & Trails: Elegant Home in Cape Charles!
Bedrooms:
5
Bathrooms:
6
Sleeps:
14
Pets Welcome w/ Fee Your peaceful retreat with family and friends awaits at this recently built vacation rental in Cape ...
From $694 per night (USD)
VRBO
From $398 per night (USD)
Expedia
Sandy Cheeks – Where Coastal Charm Meets Modern Comfort<br>
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Sandy Cheeks – Where Coastal Charm Meets Modern Comfort Newly Renovated | Pet-Friendly | Prime Location | Fa ...
From $398 per night (USD)
Expedia
$New 2025 Luxury Waterfront Retreat w\/Private Beach, Views & Mesmerizing Sunsets!$
From $825 per night (USD)
VRBO
New 2025 Luxury Waterfront Retreat w\/Private Beach, Views & Mesmerizing Sunsets!
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
Welcome to Corona Cove, a pristine beachfront gem constructed in 2025! This luxurious waterfront retreat boasting a priv ...
From $825 per night (USD)
VRBO
$Sans Sou\sea\ Come visit our groovy 3 bedroom house in Cape Charles, Va.$
From $369 per night (USD)
Expedia
Sans Sou\"sea\" Come visit our groovy 3 bedroom house in Cape Charles, Va.
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
This Cape Charles house boasts 3 inviting bedrooms. Each bedroom offers a comfortable sleep with options like a queen be ...
From $369 per night (USD)
Expedia
From $374 per night (USD)
VRBO
Charming Renovated Beach Cottage a Few Blocks from Beach in Cape Charles, VA
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Charming renovated house in the Historic District of Cape Charles, VA. Perfect for a long weekend getaway. Golf cart fri ...
From $374 per night (USD)
VRBO
From $1583 per night (USD)
Expedia
Bayfront Home Featuring Private Beach Access in Bay Creek!
Bedrooms:
6
Bathrooms:
5
Sleeps:
12
The Alexander Lee is a luxurious custom built Bayfront home offering modern features mixed with timeless design, idyllic ...
From $1583 per night (USD)
Expedia
$Saratoga Charmer.w\/Communtiy Pool and Private Beach$
From $417 per night (USD)
VRBO
Saratoga Charmer.w\/Communtiy Pool and Private Beach
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
PRIME DATES STILL AVAILABLE-SUMMER IS RIGHT AROUND THE CORNER! PLEASE INQUIRE ON RATES FOR STAYS LESS THAN A WEEK. Tuck ...
From $417 per night (USD)
VRBO
From $734 per night (USD)
Expedia
Southern Living II On The Eastern Shore
Bedrooms:
5
Bathrooms:
6
Sleeps:
15
Sip a drink on the front porch, ride a bike, walk to the beach, go antiquing/fishing/sailing/golfing or just watch the ...
From $734 per night (USD)
Expedia
$Stunning New Construction in Historic Cape Charles 3 1\/2 Blocks to the Beach$
From $430 per night (USD)
VRBO
Stunning New Construction in Historic Cape Charles 3 1\/2 Blocks to the Beach
Bedrooms:
3
Bathrooms:
3
Sleeps:
9
This stunning new construction home is ready for you and your family! With 3 bedrooms and 2.5 baths there is room for ev ...
From $430 per night (USD)
VRBO
From $478 per night (USD)
Expedia
Family Friendly 3 Blocks to Beach with Great Amenities
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
New for ‘23 🚨DISHWASHER🚨!! We ...
From $478 per night (USD)
Expedia
From $526 per night (USD)
VRBO
Coastal Charmer | Chesapeake Properties
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Summary: Coastal Charmer - 4 bedroom, 2 bath, sleeps 8-10 with 2 sets of bunk beds. - Completely Renovated! Cozy and com ...
From $526 per night (USD)
VRBO
From $341 per night (USD)
Expedia
Cape Serendipity - sister to existing ID#2395726
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Cape Serendipity - we found it by chance and stayed because we love it! We are sure you will feel the same! This 2 stor ...
From $341 per night (USD)
Expedia
From $599 per night (USD)
VRBO
Bay Creek Meets Historic Cape Charles! pool access!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Best of both worlds - first house off the historic center of Cape Charles, but part of the gated Bay Creek community wit ...
From $599 per night (USD)
VRBO
From $528 per night (USD)
Expedia
Five Minute Walk to the Beach Sleeps 10
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Located in the gated community of Marina Village, this updated home is close to everything - private community beach, sh ...
From $528 per night (USD)
Expedia
From $984 per night (USD)
VRBO
your own Private beach, adjacent nature preserve-Sunset Dunes Cape Charles, VA
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
Indulge in the serenity of Sunset Dunes, where your private beach is just 80 steps from the house. Perched atop a timele ...
From $984 per night (USD)
VRBO
From $321 per night (USD)
Expedia
Beach, beach, beach in historic Cape Charles. Lovely 2BR Apt1Block from beach
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
Beach, beach, beach! Many local shops, cafes, and restaurants that can be easily strolled to in this cozy historic beach ...
From $321 per night (USD)
Expedia
From $356 per night (USD)
VRBO
3 BR 1.5 BA on Jefferson Ave, fenced yard
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to "Just One More..." our families home away from home. Our 3 bedroom 1.5 bath house is on a corner street just ...
From $356 per night (USD)
VRBO
From $691 per night (USD)
Expedia
Spacious Beach House: Oystermen's Pearl: Golf Cart Included
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
Spacious beach house with a luxury touches: GOLF CART INCLUDED in price. Great place to escape with your family and enjo ...
From $691 per night (USD)
Expedia
From $323 per night (USD)
VRBO
Historic Waterfront Home With Big Views Of The Chesapeake Bay
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Foxcroft, a lovely, two-story home sits on 5 acres overlooking the Nassawadox Creek and the Chesapeake Bay. This perfec ...
From $323 per night (USD)
VRBO
From $762 per night (USD)
Expedia
Handicap Accesible, with Beach, Pool & Tennis!
Bedrooms:
4
Bathrooms:
4
Sleeps:
13
This luxurious handicap accessible beach home, is less than a 1 minute walk to the soft sand community private beach! Th ...
From $762 per night (USD)
Expedia
From $255 per night (USD)
VRBO
Seabreeze Cottage ... your home base for exploring Virginia's Eastern Shore!
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Seabreeze Cottage is located on a country lane just outside the seaside village of Cheriton, less than 5 miles from down ...
From $255 per night (USD)
VRBO
From $1049 per night (USD)
Expedia
Privacy & tranquility at Beauty on the Beach, Beachfront!
Bedrooms:
5
Bathrooms:
5
Sleeps:
12
Pamper yourself to the privacy and tranquility of Beauty on the Beach - a magnificent manor nestled on 3+ acres of beach ...
From $1049 per night (USD)
Expedia
From $469 per night (USD)
VRBO
Stunning Historic Home Two Blocks from Beach, Town & Central Park
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Welcome to Cape Charles Retreat! Come on up to the porch, grab an ice-cold lemonade and settle into the porch swing for ...
From $469 per night (USD)
VRBO
From $555 per night (USD)
Expedia
Beautiful Lindal Cedar Home Near Beach! Private Pool!
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
A beautiful getaway located on the Eastern Shore of Virginia that is perfect for anyone needing a vacation from the busi ...
From $555 per night (USD)
Expedia
$Family vacation retreat w\/ In-ground Pool with private Chesapeake Bay access!$
From $914 per night (USD)
VRBO
Family vacation retreat w\/ In-ground Pool with private Chesapeake Bay access!
Bedrooms:
4
Bathrooms:
6
Sleeps:
12
Located for easy access to our private beach, Kiptopeke State Park, Cape Charles, and Virginia Beach. This is the ideal ...
From $914 per night (USD)
VRBO
From $539 per night (USD)
Expedia
Only 1 Block to the Beach - Community Pool - Featured on HGTV!
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Shore Thing Cape Charles (formerly known as Purple Daze on HGTV’s Beachfront Bargain Hunt S26 E12) is a beautiful beach ...
From $539 per night (USD)
Expedia
From $420 per night (USD)
VRBO
HISTORIC DISTRICT: 1st Floor Primary, Great Location and Views!
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
*From Memorial Day weekend through Labor Day weekend, 7-day rentals are required. During this period, please only selec ...
From $420 per night (USD)
VRBO
From $363 per night (USD)
Expedia
Cape Escape-Short Walk to Beach, Pet Friendly, Fenced Yard & Optional GC Rental
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Beautiful beach house with fenced in yard, double porches and the comfort of a "home away from home" for your Cape Charl ...
From $363 per night (USD)
Expedia
From $560 per night (USD)
VRBO
As seen on HGTV! 4 BR, 2 blocks to beach. Newly renovated. Golf Cart Included.
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
As featured on HGTV! Newly renovated downstairs including dining room, bathroom and GORGEOUS Instagram-worthy kitchen! ...
From $560 per night (USD)
VRBO
From $813 per night (USD)
Expedia
Historic Beach Front Home: Victorian Elegance. Large Rooms with AMAZING bay view
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
The Dryden House offers the most amazing sunsets the Chesapeake bay has to offer and the ultimate in flexible amenities ...
From $813 per night (USD)
Expedia
From $588 per night (USD)
VRBO
Relaxing Condo in Golf Community With Access to Club Amenities!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Bay Getaway is a second floor condo that is just steps from the Fairway's pool. This condo sleeps 6 guests comfortably w ...
From $588 per night (USD)
VRBO
From $974 per night (USD)
Expedia
Gorgeous 6 Bed, 5 Bath Beachfront Home With Private Beach!
Bedrooms:
5
Bathrooms:
6
Sleeps:
12
Watch the waves of the Chesapeake Bay roll in from the spacious back deck of "Beachfront Bliss"! “Beachfront Bliss” is ...
From $974 per night (USD)
Expedia
From $263 per night (USD)
VRBO
The Farmhouse at Chatham Vineyards
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
THE VINEYARD HOUSE AT CHATHAM FARM, A RESTORED CA. 1920 FARMHOUSE, OVERLOOKS VINEYARDS, BARNS, WOODS, AND FIELDS. The Vi ...
From $263 per night (USD)
VRBO
From $593 per night (USD)
Expedia
Spacious First Floor Condo in Golf Community With Access to Club Amenities!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Get to the golf course early. No stairs in this lovely downstairs condo. The master bedroom features a king bed, flat sc ...
From $593 per night (USD)
Expedia
From $166 per night (USD)
VRBO
Near Cape Charles and Kiptopeke Beaches
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
Newly renovated mid-19th century farm house located on a picturesque 3 acre setting. Wooden floors. Near Arnold Palmer a ...
From $166 per night (USD)
VRBO
From $390 per night (USD)
Expedia
Feed Your Soul at Silver Beach Cove
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Silver Beach Cove is a sanctuary from the workaday world. This last year we have added a pier with floating dock, and ...
From $390 per night (USD)
Expedia
From $493 per night (USD)
VRBO
Modern spacious home one block from the beach
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
We are excited to share our home away from home with you! This is a 3 bedroom, 2.5 bathroom, spacious home. The first fl ...
From $493 per night (USD)
VRBO
From $320 per night (USD)
Expedia
Across from the park and 2 blocks from beach & restaurants- LEFT side of duplex
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Perfect for families with children; And for Two Families to Rent Side-by-side! We offer BOTH mirror image sides of our v ...
From $320 per night (USD)
Expedia
From $283 per night (USD)
VRBO
Next to the park and 2 blocks to the Beach and restaurants! RIGHT side of Duplex
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Perfect for families with children; And for Two Families to Rent Side-by-side! We offer BOTH mirror image sides of our ...
From $283 per night (USD)
VRBO
From $499 per night (USD)
Expedia
Perfect Location in the heart of Cape Charles
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Everyone that comes to Cape Charles falls in love with the charm and beauty of this small town. Peach Retreat is nestle ...
From $499 per night (USD)
Expedia
From $579 per night (USD)
VRBO
Coastal Elegance Meets Small Town Charm
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
Seablues is located in the private Marina Village neighborhood of Bay Creek and is one block away from the private neigh ...
From $579 per night (USD)
VRBO
From $392 per night (USD)
Expedia
Your Private Beach Awaits! Fall is the best time!
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
Plan your beach vacation now! BayWatch features a private beach, spectacular water views and fresh, casual well-appointe ...
From $392 per night (USD)
Expedia
Click For Pricing
VRBO
Luxury Beachfront 5 Bedroom, 3.5 Bath home with 200 ft. of PRIVATE BEACH!
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
Luxury Beachfront Living is what you can expect from the moment you enter The SandCastle, a 5 Bedroom, 3.5 Bath, 4,900 s ...
Click For Pricing
VRBO
From $536 per night (USD)
Expedia
Family-Friendly Home in historic downtown; Wrap-Around Porch, Steps from the Bay
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Welcome to Endless Tides in Cape Charles, VA - named “the best little beach town in Virginia” by Southern Living magazin ...
From $536 per night (USD)
Expedia
From $697 per night (USD)
VRBO
The Oyster Bed Inn, NEW CONSTRUCTION in Historic District, One block from beach
Bedrooms:
5
Bathrooms:
5
Sleeps:
11
Brand new 4 bedroom, 3.5 Bathroom sleeps 10 with incredible views of the Chesapeake Bay from the first and second floor ...
From $697 per night (USD)
VRBO
$Fish Tales-FISH\/EAT\/STAY$
From $198 per night (USD)
Expedia
Fish Tales-FISH\/EAT\/STAY
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This cozy eastern shore cottage is perfect for any visitor and is also ideal for fisherman. Ample boat parking. Fish cle ...
From $198 per night (USD)
Expedia
From $514 per night (USD)
VRBO
Bay cottage, Beach 100 yards away! RESERVE NOW!!!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
'A Bayview Beauty' sits 100 Yards from the Chesapeake bay on a quiet, crape myrtle lined blvd. Relax and enjoy views of ...
From $514 per night (USD)
VRBO
From $444 per night (USD)
Expedia
Downtown, Sleeps 9, Dog-friendly, Short Walk to the Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
11
When it came to our family and Cape Charles, it was love at first sight. The peace and quiet, the beauty of the Bay, the ...
From $444 per night (USD)
Expedia
From $549 per night (USD)
VRBO
Bicycles, Beach Toys, Kayaks, Chairs & Umbrella - 6 blocks to Beach!
Bedrooms:
4
Bathrooms:
4
Sleeps:
12
You will be in awe this newly-renovated Victorian home located in historic Cape Charles. Come relax in the rocking chair ...
From $549 per night (USD)
VRBO
From $276 per night (USD)
Expedia
Smith Beach Beachfront Rental, Bay View Cottage, near Cape Charles, Virginia
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Bay View Cottage is located in the quiet little bayside village of Smith Beach, Virginia. It is situated on a beautiful ...
From $276 per night (USD)
Expedia
From $478 per night (USD)
VRBO
Baydream Believer Cape Charles
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
This charming newly-renovated home was built in 1888 and is right in the heart of Cape Charles on a corner lot. It is cl ...
From $478 per night (USD)
VRBO
From $355 per night (USD)
Expedia
SALE 100Acre Private Seaside Home Photographers and NatureLovers Paradise&Views!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Mockhorn Bay Retreat is an exclusive 100-acre seaside property with modern home and complete privacy, 180° Atlantic view ...
From $355 per night (USD)
Expedia
From $287 per night (USD)
VRBO
Wonderfully Updated and Renovated in the Historic District. 2-3 Night Min Stay
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Located in the Cape Charles Historic District, this completely renovated cottage is close to everything - beaches, shopp ...
From $287 per night (USD)
VRBO
From $383 per night (USD)
Expedia
Walk to Beach and Shopping from Vibrant Duplex
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Looking for a comfortable and memorable stay, look no further than this fabulously located 1700 era duplex where you can ...
From $383 per night (USD)
Expedia
From $353 per night (USD)
VRBO
Trendy Duplex Close to Beach and Mason Ave
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Nestled in the downtown Mason Avenue area, you can’t get closer to the shops, restaurants, bakeries and galleries that t ...
From $353 per night (USD)
VRBO
From $507 per night (USD)
Expedia
'Southern Living' On The Eastern Shore
Bedrooms:
2
Bathrooms:
4
Sleeps:
12
Southern Living is a home that is just that. Your biggest decision will be to have your coffee / drinks on the front por ...
From $507 per night (USD)
Expedia
From $305 per night (USD)
VRBO
All the comforts of home!
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
You will LOVE Virginia's nature! If getting away from it all is what you desire, consider this; The Eastern Shore of V ...
From $305 per night (USD)
VRBO
From $209 per night (USD)
Expedia
Share Splendid Sunsets Over the Beautiful Chesapeake Bay!
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
"Shore's Fun" is located at Silver Beach, a small, charming Chesapeake Bay cottage community, established years ago when ...
From $209 per night (USD)
Expedia
From $761 per night (USD)
VRBO
4BR, 3 & a half BA home, private beach access
Bedrooms:
4
Bathrooms:
4
Sleeps:
12
“Sunset” is a luxurious, custom 4 BR, 3.5 BA home offering exquisite postcard perfect views of the shimmering blue water ...
From $761 per night (USD)
VRBO
From $528 per night (USD)
Expedia
THE LIGHTHOUSE INN..Imagine Walking 2 Blocks And Having Your Feet In The Sand!!!
Bedrooms:
5
Bathrooms:
4
Sleeps:
14
We are so excited to share our long awaited dream home in the beautiful town of Cape Charles. We named our home 'The Lig ...
From $528 per night (USD)
Expedia
From $880 per night (USD)
VRBO
SUNRISE 2 SUNSET VIEWS! Enjoy our beautiful, spacious home steps from the beach!
Bedrooms:
5
Bathrooms:
6
Sleeps:
15
Find your home away from home at our Cape Charles beach retreat—a perfect blend of relaxation and adventure! Dive into ...
From $880 per night (USD)
VRBO
From $355 per night (USD)
Expedia
Tiny House 3 min from Down Town Cape Charles
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Welcome to Cape Charles Tiny Livin'. Introducing, our new addition "Stay Awhile". This is just one, of 10 tiny ...
From $355 per night (USD)
Expedia
From $401 per night (USD)
VRBO
Counting Corks - Waterfront, Pet friendly, private dock!
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Welcome to 'Counting Corks' (formerly known as 'Smith Beach Pines'), the moment you step foot in this beautiful waterfro ...
From $401 per night (USD)
VRBO
From $390 per night (USD)
Expedia
Capeville Cottage - modern comfort close to Cape Charles!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Welcome to Capeville Cottage in the heart of Capeville, VA - just 5 miles North of the Chesapeake Bay Bridge Tunnel. The ...
From $390 per night (USD)
Expedia
From $255 per night (USD)
VRBO
Cozy Cape Charles Apartment: Walk to Beaches!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Small-town charm and waterfront fun await at this Cape Charles vacation rental! This 2-bedroom, 2-bath apartment is a un ...
From $255 per night (USD)
VRBO
From $274 per night (USD)
Expedia
Charming historic Home located blocks to Town and Beach.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This historic duplex style home is located in the Cape Charles town district. You can walk to everything. We are less th ...
From $274 per night (USD)
Expedia
$Stunning Chesapeake Bay Farmhouse w\/ Dock & Kayaks$
From $578 per night (USD)
VRBO
Stunning Chesapeake Bay Farmhouse w\/ Dock & Kayaks
Bedrooms:
3
Bathrooms:
8
Sleeps:
10
Hosting picture-perfect views both inside and out, this 4-bedroom, 2.5-bath, Machipongo vacation rental offers waterfron ...
From $578 per night (USD)
VRBO
From $306 per night (USD)
Expedia
The Reserve Lodge” Fish-Beach-Play-Stay
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
"The Reserve Lodge" is a 1926 Bank built to service the Rail Road that ran from Maryland to Kiptopeke to meet the ferry ...
From $306 per night (USD)
Expedia
From $381 per night (USD)
VRBO
Belle is a cute cottage blocks from shops, bay, cafes
Bedrooms:
2
Bathrooms:
4
Sleeps:
11
Spend your days at Belle of the Bay! Belle is a cute cottage located within walking distance to breakfast cafes, shops, ...
From $381 per night (USD)
VRBO
Click For Pricing
Expedia
Traditional Eastern Shore Historic House
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
The Whitehead house is located in the residential district of Eastville, VA near the historic center in the middle of a ...
Click For Pricing
Expedia
Click For Pricing
VRBO
Just Fore Fun | Chesapeake Properties
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Located in a quiet neighborhood in the Bay Creek Community but just minutes from the historic district and the ...
Click For Pricing
VRBO
From $543 per night (USD)
Expedia
Dreamers Bay
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Relax with the whole family at this peaceful place to stay! Off the beaten path enjoy bay front land with 200 feet of wa ...
From $543 per night (USD)
Expedia
From $320 per night (USD)
VRBO
Modern Cape Charles Home: 1 Mi to Kiptopeke Beach!
Bedrooms:
1
Bathrooms:
6
Sleeps:
6
Planning your next adventure to Virginia’s Eastern Shore? You’ll love this spacious 3-bedroom, 1-bath home in Cape Charl ...
From $320 per night (USD)
VRBO
From $425 per night (USD)
Expedia
Charming 3 bedroom beach house in Cape Charles, VA
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Unwind, explore, and create unforgettable memories when you stay at this 3-bedroom, 3-bath vacation rental! Fully equipp ...
From $425 per night (USD)
Expedia
From $433 per night (USD)
VRBO
Bayside Getaways Crab Crib | Chesapeake Properties
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: Welcome to Bayside Getaways–Your Modern Loft Getaway in Historic Cape Charles. Nestled in the heart of downtown ...
From $433 per night (USD)
VRBO
From $431 per night (USD)
Expedia
Bayside Getaways Oyster Oasis | Chesapeake Properties
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: Welcome to Bayside Getaways–Your Modern Loft Getaway in Historic Cape Charles. In the heart of downtown Cape Ch ...
From $431 per night (USD)
Expedia

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