Oyster Holiday Rentals from €302: Search Short-Term Rentals

Q: What are some of the best holiday rentals that Oyster has to offer?

Bay cottage, Beach 100 yards away! RESERVE NOW!!! : This holiday home rental outside of Oyster is located near the beach, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

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Holiday Rentals in Oyster

Enjoy a serene beachside escape with undulating sand dunes and lush grassy outcroppings.

includes taxes & fees

21 Jul - 22 Jul

Escape to a serene beach with natural dunes and lush grasses, perfect for relaxation and nature appreciation.

"This was a great stay, we loved everything about it. Highly recommended. We will definitely return."

includes taxes & fees

16 Jul - 17 Jul

Enjoy a serene beachfront setting with a pier extending into the calm waters.

"I enjoyed staying here, solid place!"

includes taxes & fees

16 Jul - 17 Jul

Sit around the fire pit in this serene outdoor space, surrounded by trees and a fence.

"The room was very clean and well equipped. The grounds were very well maintained. Short drive to downtown Cape Charles. Host communication was excellent would stay again. "

includes taxes & fees

10 Aug - 11 Aug

Experience serene beach tranquility with expansive sandy dunes and gentle waves.

"Adorable tiny livin…. The entire property is just quaint and cozy!"

includes taxes & fees

10 Aug - 11 Aug

Enjoy a serene beach experience with warm sand and calm waters.

"We booked this tiny house for a spontaneous night away to do some fishing in Cape Charles. The property and house were absolutely adorable and the accommodations were exactly what we needed for a weekend away. The property had an amazing bonfire pit and grill if you don’t want to eat out, and there’s plenty of space with a fence and grassy areas if you’re traveling with a dog. The owners were extremely communicative and even went to the trouble of mailing us back something we left. We would...

includes taxes & fees

16 Jul - 17 Jul

Enjoy a serene beach experience with a pier extending into the calm waters.

"We love staying in the tiny home, Eric was such a nice host"

includes taxes & fees

10 Aug - 11 Aug

Cozy room with a comfortable bed, flat-screen TV, and warm wooden accents.

"We absolutely enjoyed our little tiny home! The property was great and the things to do close by were great! We would definitely stay again! "

includes taxes & fees

10 Aug - 11 Aug

Charming single-story house with a porch, garage, and garden.

"We had a blast on our first trip to Cape Charles. The cottage was immaculate when we arrived. The kitchen is beautiful and has everything you need to prepare meals. There were plenty of supplies for our stay. This area is very charming and steeped in history. There were many things to do and we were thrilled that a lot of places were dog friendly. The walking trail nearby was amazing and utilized daily. It is only about a 10 minute walk down the trail to the beach. The property managers...

includes taxes & fees

1 Aug - 2 Aug

Relax in this stylish living room with a flat-screen TV, comfortable sofa, and ample storage.

"We had a great time at this property. It was clean, spacious, and convenient to beach, town, playground. Perfect for our weekend getaway!"

includes taxes & fees

13 Jul - 14 Jul

Kitchen with brick chimney, cabinetry, and wooden floor, featuring a dishwasher and sink.

"My friends and I go to Cape Charles once or twice a year and always have an amazing time. This NYE trip was no exception. We really had a nice time and the property was perfect! Very clean and communication with the owners was amazing. I highly recommend. "

Enjoy cooking in this well-equipped kitchen with a microwave, oven, and toaster, along with ample countertop space.

"We had a wonderful time visiting Cape Charles it was our first time there we were celebrating one of our kids, birthdays and just had a tremendous time not only in Cape Charles, but in the house as well. As well appointed clean close to everything and the secret of getting a golf cart to drive around made it even better Will definitely do it again next year "

includes taxes & fees

26 Jul - 27 Jul

Charming single-story houses with gabled roofs and welcoming front porches.

"We really enjoyed our stay at Bayside, specifically the location. With our young kiddos, it was perfect for us to pop over to the park to play several times a day. The house had all the necessities, even a pack & play and high chair which were unexpected bonuses. We could hear a little noise from our neighbors, but nothing disruptive. It could’ve used a bit more cleaning and a water filtration system, but the house was great for our family to enjoy a sweet vacation together. "

includes taxes & fees

12 Jul - 13 Jul

Enjoy cooking in this well-equipped kitchen with a stainless steel refrigerator, microwave, oven, and dishwasher.

"The house was a beautiful mix of modern and historic. It was close to everything! Perfect location! Super easy check in and check out process! And to top it off everything you could possibly think of was included! We had an absolute blast!"

Cozy living area with a dining table, chairs, sofa, and modern kitchen featuring a black countertop and white cabinetry.

"Thoroughly warm & cozy house - great space throughout the house, feels much bigger than actual is - definitely on repeat list!"

includes taxes & fees

10 Aug - 11 Aug

Guests can enjoy the beach with umbrellas and chairs available for shade.

"Lovely home, great location - never had such a fully equipped kitchen. The Murphy bed room is extremely small but was fine for our 8 & 10 year olds. Will certainly book it again"

includes taxes & fees

30 Jul - 31 Jul

includes taxes & fees

22 Jul - 23 Jul

Enjoy cooking in this well-equipped kitchen with a central island, bar stools, microwave, and coffee machine.

Enjoy meals with family and friends at this dining area, featuring a round table and comfortable seating for four.

"Very clean and well set to house. The space was very well utilized and met all our needs. Thanks for an incredible week."

includes taxes & fees

24 Jul - 25 Jul

Enjoy a serene beach experience with calm waters and a picturesque pier in the distance.

"Clean, neat and extremely close to the sea"

includes taxes & fees

25 Jul - 26 Jul

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Find out more about Oyster

Everything you need to know about Oyster holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Oyster holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Oyster holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Oyster holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Oyster. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Oyster holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Oyster holiday rentals we have selected for you start as low as €302 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Oyster rentals

At Expedia, we put the best Oyster holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Oyster rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Oyster holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Oyster. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Recent reviews of Oyster properties

Hampton Inn & Suites Exmore - Eastern Shore

5/5 Excellent

"The room was pretty spacious, clean and quiet. Everything that we looked for! "

A verified traveller stayed at Hampton Inn & Suites Exmore - Eastern Shore

Posted 4 days ago

Nassawadox Creek Waterfront Home with Private Pool

5/5 Excellent

Wonderful vacation spot

"We have been staying in the area for over 7 years, and by far, this is the best house we have ever rented. The house is comfortable and spacious. I loved having a place to put out food in the pantry. The house was well-equipped with the essentials, like toilet paper, paper towels, cleaners, beach towels, etc. The pool is amazing and the views are amazing! The water was also deep enough for our boat, which has been a challenge to find down here! We had the best time and hope to return next year!"

A verified traveller stayed at Nassawadox Creek Waterfront Home with Private Pool

Posted 6 days ago

Minutes to the BEACH! Boat friendly, fire pit, bocci & large yard for famly fun!

5/5 Excellent

Wonderful spot for family

"We had a great time in Cape Charles. This property was perfect for our extended family (5 adults and 5 teens). The owners were attentive and great with communication. We're already planning a return visit!"

A verified traveller stayed at Minutes to the BEACH! Boat friendly, fire pit, bocci & large yard for famly fun!

Posted 6 days ago

Rendezvous at the Bay, Resort Condo in charming Cape Charles. Relaxation awaits

5/5 Excellent

Great hosts!

"We had an amazing time for a family getaway. There was ample room for six adults and two kids to and under the host were great and super accommodating and helpful with helping us to get everything set up so that we were able to enjoy the golf course and the pool we would love to come again"

A verified traveller stayed at Rendezvous at the Bay, Resort Condo in charming Cape Charles. Relaxation awaits

Posted 11 days ago

Frequently asked questions

Are there holiday rentals in Oyster?

Yes, there are holiday rentals close to the most popular sights in Oyster, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Oyster has to offer?

Bay cottage, Beach 100 yards away! RESERVE NOW!!!: This holiday home rental outside of Oyster is located near the beach, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

What can I see and do in Oyster?

While you're exploring the area, Cape Charles Beach and Cape Charles Harbor are a couple of picturesque spots to get outside and enjoy nature. In the wider area, you’ll find Cape Charles Museum & Welcome Center and Bay Creek Golf Club.

What are holiday rentals like in Oyster?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Oyster. Holiday rentals feature extras such as patios, hot tubs and fire pits so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, holiday rentals can offer a sense of security away from shared hotel lifts and bustling concierge desks while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental a great option for family trips.

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Holiday Rentals in Oyster

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Holiday Rentals in Oyster

Restored 1930’s Tiny Home 3 min to Cape Charles

Hippie Hideaway - Tiny House w/ Fire Pit & BBQ

Tiny House close to the Beaches of Cape Charles

Tiny House 3 min from Down Town Cape Charles

Experience Tiny Living, in Cape Charles, Va

Pet Friendly Tiny Livin 3min from Cape Charles

Whimsical Tiny House, Cape Charles Virginia

Tiny House Hideaway with King sized Bed

Flip Flop Cottage | Chesapeake Properties

Serene Beach Haven in Cape Charles

Luxury Beach Getaway in Cape Charles

Bring the whole family to the Summer House. 6 bedroom, 2 bath sleeps 13.

Bayside - Classic duplex in historic downtown!

Anchors Aweigh

Coral Haven 2 | Chesapeake Properties

Peach Perfect | Chesapeake Properties

Firepit/BBQ, Minutes to Beach & Park | Deja Blu II

Walk to Beach & Park, Firepit & BBQ | Deja Blu I

Wild Blue Cottage | Chesapeake Properties

Sisters 3 by the Sea, 400 Feet To The Beach

Find out more about Oyster

Recent reviews of Oyster properties

Hampton Inn & Suites Exmore - Eastern Shore

The Baywood Bed & Breakfast

Budget Inn By OYO Nassawadox Hwy 13

Nassawadox Creek Waterfront Home with Private Pool

Minutes to the BEACH! Boat friendly, fire pit, bocci & large yard for famly fun!

Rendezvous at the Bay, Resort Condo in charming Cape Charles. Relaxation awaits

Holiday Inn Express and Suites Exmore, Eastern Shore by IHG

Cape Charles Tiny Livin

Quality Inn & Suites

Frequently asked questions