Holiday rentals in Oyster

Farm stay in Cape Charles

5 out of 5 average rating, 384 reviews

Private Guesthouse on Secluded Waterfront Farm

Just 5 miles from Cape Charles and 30 minutes from Virginia Beach, our contemporary Guesthouse gives you the peace and solitude characteristic of the Eastern Shore along with the convenience of being close to town. Our twenty acre waterfront farm, home to both a Vineyard and an Oyster Farm, has plenty of nearby walking or biking and a dock on a secluded arm of the Chesapeake Bay. Our farm is perfect for solo travelers, couples or small families looking for a memorable trip to the Eastern Shore.

4.93 out of 5 average rating, 245 reviews

Loft in Cape Charles

The Cheriton Loft

Located in the heart of Cheriton, The Loft is a bright and sunny apartment. It is perfect for a couple and one child, three friends or one person. Cheriton is an up and coming village which is home to several galleries and an art center. It is less than 4 miles to the charming town and beach of Cape Charles, 3 miles to Oyster Boat Landing and 8 miles to Kiptopeke State Park. The apartment is owned and decorated by"The Sheep Lady", a local painter, illustrator and writer of children's books.

Guest house in White Stone

5 out of 5 average rating, 246 reviews

Waterfront Guesthouse II on the Rappahannock

The “Beach House” is a guest cottage at Snug Harbor, a 2 acre private property overlooking the Rappahannock River and Chesapeake Bay. Perfect for a couple’s getaway, this well-appointed cottage has beautiful water views and includes access to our private beach & dock (with guest slip) with use of our paddle boards and kayaks. The cottage’s 1st floor features an open liv/din/kit area, full bath with large shower and a covered patio. The 2nd floor features a large loft bedroom with a queen bed.

4.94 out of 5 average rating, 123 reviews

Bakery Next Door | Renovated | Golf Cart Avail.

Nectarine 13 is a centrally located. Next door, you’ll find the Coastal Bakery. A great place for breakfast or Treat. Relax on the charming front porch and soak in the calm, historic vibe of Cape Charles. A Quick walk to historic Downtown, Take a swim in the bay or cast a line off the dock. Central Park is also nearby, offering a great spot for a family picnic while the kids enjoy the playground. Golf carts are available to rent(Cart Rentals are only available during the House rental period)

4.99 out of 5 average rating, 102 reviews

Palm Beach by the Bay

This bright and cheery 3-bedroom, 2.5-bath home in the historic section of Cape Charles sleeps up to 8. Great mix of historic charm with all the comforts of a modern home. Located six blocks from the beach, with a direct walk to the gazebo and beach entrance, and one block from the iconic Cape Charles charm of Mason Avenue. This beautiful, completely renovated house includes a well-appointed kitchen, two living spaces (one with daybeds), main bedroom with en suite, and backyard paradise.

Tiny home in Cape Charles

4.98 out of 5 average rating, 318 reviews

The Laughing King Retreat Honeymoon Island Cottage

Honeymoon Island Cottage is an adults-only lodging experience like no other. You and your guest will stay in a charming tiny farmhouse that is located just steps from the Chesapeake Bay on a USDA certified organic farm. Enjoy access to a private saltwater pool, private beach, Chesapeake Bay water access for boating, swimming, paddleboarding, fishing or just soaking, dig for clams, collect wild oysters, or just sit and marvel at the beauty. We look forward to welcoming you.

4.89 out of 5 average rating, 101 reviews

"Live Life Sunnyside Up" - Minutes From The Beach!

Welcome to "Live Life Sunnyside Up" on the Shore! Take a trip off the busy beaten path and kick your feet up at our little slice of paradise. Kid friendly with plenty of amenties for you and your family. On a quiet street, less than 4 miles from the historic town of cape charles and beach, get ready to take a load off and enjoy the many treasures Cape Charles has to offer! Just 5 short minutes from the Oyster Boat Ramp, fishermen are sure to find their honey hole here!

4.96 out of 5 average rating, 177 reviews

Cabin in Cape Charles

Ultimate Cabin Farm Stay Cape Charles

Tucked away in the woods on a historic Eastern Shore farm lies this stunning pond side Cabin just 10 mins from Cape Charles. The classic yet modern cabin is a dreamy getaway or remote work space. Wake up to the birds singing in the trees that completely surround the cabin and enjoy the deck - watching the deer and goats foraging. Take a walk on our trails, collect fresh eggs, visit Cape Charles for restaurants and shopping, and enjoy the farms’ fire pit in the evening.

4.96 out of 5 average rating, 124 reviews

Home in Gloucester Point

Charming coastal home w/ outdoor area and river views

Tucked away at the end of a quiet road, our home welcomes you. This spacious, thoughtfully designed 1 BR/1.5 BA home on 4 acres is ideal for those looking to relax and get away from it all while still being just minutes away from some of the areas best dining and attractions. Whether you want to watch the sun rise over the York River, spend the day exploring the historic triangle, or just take it easy around the house and enjoy the outdoor area, the choice is yours.

4.95 out of 5 average rating, 108 reviews

Sunshine Rays: Historic district backyard bliss!

Situated on a peaceful block of Cape Charles' charming historic district, Sunshine Rays was designed as a retreat for families visiting the Eastern Shore. With space for up to eight guests, an incredible backyard, and thoughtful amenities throughout, it's the perfect base for your Cape Charles getaway. We are just six blocks from the beach and even closer to our Central Park and the town's main street with all of its restaurants, bakeries, and shops.

4.96 out of 5 average rating, 253 reviews

Steps to the Sea at Salt Box

Escape to The Salt Box, a charming 1915 duplex just one block from the beach in the heart of Cape Charles' Historic District. This cozy, private retreat sits on a peaceful, tree-lined street and is a short stroll to the beach, pier, shops, restaurants, and more! Check out our local Guidebooks or text us anytime—we're happy to share our favorite local spots! Looking for even more space? You can also book the other half of our duplex, Salt Box II!

Superhost

Cottage in Cape Charles

4.78 out of 5 average rating, 113 reviews

Sea Salt Cottage: Tranquil Getaway 5 min to beach

Escape to the Eastern shore! Sea Salt Cottage is your quiet, off-the-beaten path getaway in charming Cape Charles. -Peaceful, rural feel with a 5 min drive to beach, quaint shops & restaurants. -Dog & kid friendly w/ large yard to park boats, RV's, etc. -Hammock, tree swing, outdoor dining, fire pit, romantic sunsets. -2 min to groceries, 10 min to Kiptopeake State Park, 70 min to Chincoteague Island

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Popular amenities for Oyster holiday rentals

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Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Oyster

5 out of 5 average rating, 4 reviews

Holiday Blues vacation rental

ScottRating, 5 stars2 weeks ago

The home was a described. Rhona was very responsive. Made sure we got in and settled in the house. Will book again! Thank you!

4.91 out of 5 average rating, 23 reviews

FREE Luxury Golf Cart - across from CC Beach

GailRating, 5 stars2 weeks ago

We enjoyed everything about this place! The location was so perfect being steps from the beach & the house so charming! Loved the comfy beds, beautiful decor & the movie projector & screen were a big hit after the day at the beach! Khyber was very responsive to our questions. We would love to stay here again! Thank you, Khyber!

Tiny home in Cape Charles

4.88 out of 5 average rating, 181 reviews

Unique, luxurious creekside stay in Cape Charles

ChristopherRating, 5 stars2 weeks ago

The tiny home was a perfect fit for our vacation. It is a great place for a couple to stay on a vacation. It is reasonably close to downtown Cape Charles and Virginia Beach, with beach access a short walk away. It is a good fit for whatever beach type vacation you're looking for.

5 out of 5 average rating, 7 reviews

Flat in Cape Charles

Historic Charm & Modern Comfort : Downtown Escape

RobinRating, 5 stars1 month ago

This Airbnb was perfect for a weekend getaway. The place was conveniently close to the beach, shops and restaurants. The apartment is pristine and I felt very comfortable and safe during my stay. The bed was very comfortable too!

4.93 out of 5 average rating, 27 reviews

Cottage in Cape Charles

The Crew's Quarters: Steps from the Bay

SueRating, 5 stars3 weeks ago

Caryn’s home was perfect for our needs. She was very responsive to our question and provided valuable information about the area.

Superhost

4.95 out of 5 average rating, 37 reviews

Beach Front Home 5 Bedrooms 9 beds 2 kings 3 baths

Laura & ChapmanRating, 5 stars1 week ago

We had a fantastic stay at the Dryden house. Paul and Kim were extremely responsive, proactive hosts and they had so many thoughtful touches and amenities throughout the home which made our stay comfortable, fun, and easy with a large group of folks. The location cannot be beat and the charm and history of the home make for a unique and unforgettable experience. Cape Charles is a true gem as is the Dryden house and we definitely hope to be back someday!

5 out of 5 average rating, 72 reviews

The BeeHouse

JennyRating, 5 stars4 days ago

We loved loved loved The Bee House! We have stayed in several homes in Cape Charles, and this one was the best in every way. It was so comfortable and beautifully decorated with lots of windows. Large functional kitchen. Floor plan was exceptionally well thought out. There were so many well cared for beach items available for use. Enjoyed the private backyard and the swing and the fire pit too!! Very quiet location w friendly neighbors. Comfy mattresses, big front porch w lots of seating. We will definitely be coming back!