Search Holiday Rentals in Oyster

    price find illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Save instantly and earn perks with One Key
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Top Holiday Rentals in Oyster

Nassawadox Creek Waterfront Home with Private Pool

10.0 out of 10, Exceptional, (53)
"We had everything we needed. A very quiet, relaxing weekend. "
Nassawadox Creek Waterfront Home with Private Pool

Downtown, Sleeps 9, Dog-friendly, Short Walk to the Beach

9.6 out of 10, Exceptional, (134)
"Prime location, great stay!"
Downtown, Sleeps 9, Dog-friendly, Short Walk to the Beach

Cape Utopia - sister to existing ID# 7559899

9.8 out of 10, Exceptional, (38)
"Clean, comfortable beds, close to town and beach, beach chairs, beach towels provided and a beautiful porch to sit and watch the world go by. Fantastic stay. Will be back!"
Cape Utopia - sister to existing ID# 7559899

Perfect Cozy Vacation Rental on the Eastern Shore

8.2 out of 10, Very good, (26)
"Dated and not modern, clean but not a getaway or vacation rental, stove and oven dirty, only a few dishwater items available. "
Perfect Cozy Vacation Rental on the Eastern Shore

Cape Escape-Short Walk to Beach, Pet Friendly, Fenced Yard & Optional GC Rental

10.0 out of 10, Exceptional, (160)
"Clean awesome place to stay…handy to all amenities "
Cape Escape-Short Walk to Beach, Pet Friendly, Fenced Yard & Optional GC Rental

Delmarva - Brand new condo in downtown Cape Charles!

10.0 out of 10, Exceptional, (1)
"Just a wonderful place to stay. Walkable to everything but a rented golf cart is nice! Beautiful accommodations esp the kitchen and stocked laundry room. Stunning beach, family friendly and restful vacay spot!"
Delmarva - Brand new condo in downtown Cape Charles!

The Beach Peach - Downtown location with new charm!

8.0 out of 10, Very good, (1)
The Beach Peach - Downtown location with new charm!

Beachfront - unbeatable location - steps to beach & shops - sunsets from porch!

9.8 out of 10, Exceptional, (28)
"Loved the house and a great location."
Beachfront - unbeatable location - steps to beach & shops - sunsets from porch!

The Crows Nest. <br>Sunsets at the Harbor. Enjoy bird’s eye view. Unique location!

9.8 out of 10, Exceptional, (161)
"Loud music from Hook and Harvey was just too damn loud after 10 pm. "
The Crows Nest. <br>Sunsets at the Harbor. Enjoy bird’s eye view. Unique location!

Coastal Bliss: 3500 sqft Beachfront Haven, Steps Away from Your Private Beach - Your Ultimate Cape Charles Getaway

10.0 out of 10, Exceptional, (61)
"Wanted a private place on the water, pictures don’t show a new home built directly behind this house. The fire pit and hot tub are basically in the front yard of the new house. If privacy aren’t an issue and great views are all the matters then this place is perfect."
Coastal Bliss: 3500 sqft Beachfront Haven, Steps Away from Your Private Beach - Your Ultimate Cape Charles Getaway

Gorgeous New 5 BDR, 4 BA Beach Home With Tower Outlook Suite!

9.8 out of 10, Exceptional, (12)
"We loved our recent stay in Cape Charles. The house is a great location to the beach and only minutes into town. We will definitely come back!"
Gorgeous New 5 BDR, 4 BA Beach Home With Tower Outlook Suite!

Bay cottage, Beach 100 yards away! RESERVE NOW!!!

9.6 out of 10, Exceptional, (138)
"We loved our short stay here. The cottage was very nice and located in a great spot. You could see the water from the screened in front porch. The cottage had everything we needed and was very comfortable and clean!The owners were awesome at communicating and everything was a breeze.We love Cape Charles and will definitely stay here when we come back!"
The price is £390
includes taxes & fees
19 Sept - 20 Sept
Bay cottage, Beach 100 yards away! RESERVE NOW!!!

Gorgeous 5 Bedroom, 3 Bath Waterfront Home!

10.0 out of 10, Exceptional, (8)
"Annual visit in Cape Charles Virginia"
Gorgeous 5 Bedroom, 3 Bath Waterfront Home!

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

10.0 out of 10, Exceptional, (5)
"Rendezvous was a perfect location and a wonderful proeperty. Immaculate, fully stocked with whatever you might need. Would definitely ret8rn."
Rendezvous at the Bay, Resort Condo in charming Cape Charles. Relaxation awaits

Overlooking Park with 1st and 2nd Floor Primary Suites.

10.0 out of 10, Exceptional, (93)
"Hosts are great"
Overlooking Park with 1st and 2nd Floor Primary Suites.

Sea Salt Cottage: Your Tranquil Getaway 3 min to beach

9.8 out of 10, Exceptional, (36)
"The weather was amazing. We had such a fun time in Cape Charles thank you guys so much."
Sea Salt Cottage: Your Tranquil Getaway 3 min to beach

Gorgeous water views, a private swimming pool & easy access to private beach!

9.8 out of 10, Exceptional, (19)
"My wife and I visited Charles over the Easter weekend 2025. We were doing some "advance research" to look for a house to host a larger family event scheduled for the summer 2026.Shore E Nuff is an absolutely beautiful property! The home's layout is terrific, the outdoor decks/porches with great views are amazing, and a large well equipped kitchen with and open plan layout connecting to main living space is great for bringing everyone together in one space.Being the off-season, the pool was of...
Gorgeous water views, a private swimming pool & easy access to private beach!

Coral Haven 1 | Chesapeake Properties

9.0 out of 10, Wonderful, (8)
"It was our first time to Cape Charles. We loved the location of the house. We were able to walk to so much - shopping, eating and the beach. The house was the perfect size and layout for my family. Will definitely be back in Cape Charles!"
Coral Haven 1 | Chesapeake Properties

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

10.0 out of 10, Exceptional, (18)
"We had a great stay with the whole family! Minutes from the beach and excellent amenities."
Minutes to the BEACH! Boat friendly, fire pit, bocci & large yard for famly fun!

Wave on Wave | Chesapeake Properties

9.8 out of 10, Exceptional, (23)
"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We had a wonderful stay at Wave on Wave! The house and location were great. The house was clean and in a very private gated neighborhood conveniently located near town and the beach. The house had a slight mildew smell upon our arrival, but it...
Wave on Wave | Chesapeake Properties
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in

Top Oyster Hotel Reviews

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?

Coastal Bliss: 3500 sqft Beachfront Haven, Steps Away from Your Private Beach - Your Ultimate Cape Charles Getaway: This holiday home rental outside of Oyster is located on the waterfront, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, an arcade/games room and 1 hot tub so that you can immerse yourself in your holiday.

What can I see and do in Oyster?

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

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.