Smith Beach Holiday Rentals

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Holiday Rentals in Smith Beach

Nassawadox Creek Waterfront Home with Private Pool

10.0 out of 10, Exceptional, (53)
"We enjoyed the beautiful view of the creek and the house has wonderful amenities. The property manager kindly came over the first day to welcome us. It was a little cool for a dip in the pool, but we enjoyed sitting on the deck. We will be back!!"
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 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

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 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

The Beach Peach - Downtown location with new charm!

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

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!

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

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!

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 NZ$871
includes taxes & fees
19 Sept - 20 Sept
Bay cottage, Beach 100 yards away! RESERVE NOW!!!

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!

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, (92)
"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!

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!

The Farm Overlook Treehouse At Blanchard Farm

10.0 out of 10, Exceptional, (1)
The price is NZ$214
includes taxes & fees
20 Aug - 21 Aug
The Farm Overlook Treehouse At Blanchard Farm

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

Beach House Getaway, exclusive location on "Chesapeake Bay" with private beach

10.0 out of 10, Exceptional, (12)
"Sunrise and sunsets were beautiful!"
Beach House Getaway, exclusive location on "Chesapeake Bay" with private beach

A Mermaid Vacation Beach Rental BAY VIEW CAPE CHARLES

9.0 out of 10, Wonderful, (18)
"Had a great time. Wonderful location. Great views. Close access to everything. Relaxing. "
A Mermaid Vacation Beach Rental BAY VIEW 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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Top Smith Beach Hotel Reviews

Frequently asked questions

Are there holiday rentals in Smith Beach?

Yes, there are holiday rentals close to the most popular sights in Smith Beach, 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 Smith Beach 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 Smith Beach 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 Smith Beach?

While you're exploring the area, Dog Beach and Cape Charles Beach are a couple of picturesque spots to get outside and enjoy nature. Barrier Islands Center and Chatham Vineyards are a couple of places you'll find in the wider area.

What are holiday rentals like in Smith Beach?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Smith Beach. Holiday rentals feature amenities like laundry facilities and kitchens so you'll have everything you need. If you're concerned about cleanliness, a holiday rental can offer a sense of seclusion away from public hotel lifts and lobbies packed with people while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular option for a family getaway.