Oyster Holiday Rentals

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Holiday Rentals in Oyster

Next to the park and 2 blocks to the Beach and restaurants! RIGHT side of Duplex

9.8 out of 10, Exceptional, (85)
"We had a great trip, the rental was a good size, clean and perfect location"
Next to the park and 2 blocks to the Beach and restaurants! RIGHT side of Duplex

The Captains Quarters located in Cape Charles, VA offers breathtaking views.

9.6 out of 10, Exceptional, (40)
"Nice apartment overlooking a yacht marina and Coast Guard station. Very scenic and charming. An easy walk to restaurants and coffee shops in town, and a long sandy beach."
The Captains Quarters located in Cape Charles, VA offers breathtaking views.

Nassawadox Creek Waterfront Home with Private Pool

10.0 out of 10, Exceptional, (47)
"We had everything we needed. A very quiet, relaxing weekend. "
Nassawadox Creek Waterfront Home with Private Pool

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

9.6 out of 10, Exceptional, (136)
"We planned a quick get-a-way and decided to come to Cape Charles to spend the day and stay over night. The house was charming with plenty of room. The owners communicated well and they were very accommodating on my last minute trip planning. The beach wasn’t far at all and town was in walking distance with nice weather. We came in March so it wasn’t perfect beach weather but we are hoping to come back when it’s warmer! "
Bay cottage, Beach 100 yards away! RESERVE NOW!!!

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

10.0 out of 10, Exceptional, (2)
"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"
Rendezvous at the Bay, Resort Condo in charming Cape Charles. Relaxation awaits

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

9.6 out of 10, Exceptional, (129)
"Prime location, great stay!"
Downtown, Sleeps 9, Dog-friendly, Short Walk to the Beach

Perfect Cozy Vacation Rental on the Eastern Shore

8.2 out of 10, Very good, (23)
"Great location, close to town, beach, fishing spots. very clean, safe and spacious parking for boats."
Perfect Cozy Vacation Rental on the Eastern Shore

Delmarva - Brand new condo in downtown Cape Charles!

Delmarva - Brand new condo in downtown Cape Charles!

Pet Friendly Tiny Livin 3min from Cape Charles

10.0 out of 10, Exceptional, (8)
"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...
The price is NZ$557
includes taxes & fees
21 July - 22 July
Pet Friendly Tiny Livin 3min from Cape Charles

Cape Utopia - sister to existing ID# 7559899

9.8 out of 10, Exceptional, (33)
"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

The Back 9 | Chesapeake Properties

3.0 star property
10.0 out of 10, Exceptional, (3)
"Great place ...pool great. ... beach and town great ..."
The Back 9 | Chesapeake Properties

Cape Charles home with pool and golf cart 5 minutes from the beach!

8.6 out of 10, Excellent, (9)
"We had a wonderful stay at Sunshine Bay Dream! The house was clean, lovely and very relaxing. The bed was incredibly comfortable. We loved having access to the golf cart (a must for the full Cape Charles experience) and the nostalgic fun of the Ms. Pac-Man table. It was the perfect setting for much-needed R&R. Typically, we stay in town, but this tranquil location was a refreshing change of pace. Highly recommend for a fun and relaxing getaway!"
Cape Charles home with pool and golf cart 5 minutes from the beach!

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

10.0 out of 10, Exceptional, (58)
"Beautiful house on the bay. Well equipped kitchen. Plenty of beds. Gorgeous sunsets."
Coastal Bliss: 3500 sqft Beachfront Haven, Steps Away from Your Private Beach - Your Ultimate Cape Charles Getaway

Crabba-Dabba-Doo | Chesapeake Properties

10.0 out of 10, Exceptional, (3)
Crabba-Dabba-Doo | Chesapeake Properties

Family Friendly 3 Blocks to Beach with Great Amenities

9.8 out of 10, Exceptional, (84)
"The house was very cute and comfortable! Even better than the pictures showed. We had two families with small children and we were very comfortable. Good proximity to the beach and the park with a nice playground!"
Family Friendly 3 Blocks to Beach with Great Amenities

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

9.6 out of 10, Exceptional, (10)
"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!

Sea Salt Cottage: Your Tranquil Getaway 3 min to beach

9.8 out of 10, Exceptional, (36)
"Very clean, tidy & convenient for our stay."
Sea Salt Cottage: Your Tranquil Getaway 3 min to beach

Only 2 Night Minimum Stay! Custom home w/boat slip, fenced yard, swimming pool.

10.0 out of 10, Exceptional, (1)
"Great house and kitchen ! "
Only 2 Night Minimum Stay! Custom home w/boat slip, fenced yard, swimming pool.

Counting Corks - Waterfront, Pet friendly, private dock!

10.0 out of 10, Exceptional, (7)
"Smith Beach is small and beautiful so the area is very quiet and relaxing. Nice house with dock and the Florida room was cool! We really enjoyed crabbing right out back. "
Counting Corks - Waterfront, Pet friendly, private dock!

Cozy RV with 1 bedroom in enchanting Cape Charles

Cozy RV with 1 bedroom in enchanting Cape Charles
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.
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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?

Next to the park and 2 blocks to the Beach and restaurants! RIGHT side of Duplex: This holiday home rental outside of Oyster is located in the city centre, and has a patio, 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. Make the most of games in this rental home to help you unwind.

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.