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Compare 226 Vacation Homes in Cheriton with updated reviews, rates, and availability.

Cape Charles Newly Updated Family-friendly Beach House, 1 Block to Private Beach

10.0 out of 10, Exceptional, (19)
"We had an incredible weekend in Cape Charles at Drop Anchor. We've been renting places in CC for the past 10 years, and this was the cleanest and most well-appointed home we've ever rented. My husband and I invited 4 friends to CC for the weekend bc they had never been, and they fell in love with everything! The golf cart was amazing, and we had the best time. Timely responses and detailed notes and emails from property manager. Thank you so much for having us at Drop Anchor! We’ll definitely...
Cape Charles Newly Updated Family-friendly Beach House, 1 Block to Private Beach

Lil' Miss Clementine 2-bedroom home in Historic District with Golfcart option

2.0 star property
10.0 out of 10, Exceptional, (1)
"Very nice place and Cheri was available and communication was spot on. I would definitely book with Cheri again "
Lil' Miss Clementine 2-bedroom home in Historic District with Golfcart option

Oyster Shack - true gem in heart of downtown!

2.0 star property
Oyster Shack - true gem in heart of downtown!

Stunning Chesapeake Bay Farmhouse w/ Dock & Kayaks

10.0 out of 10, Exceptional, (4)
"We had a great time and stay at this property!! Would love to stay here again!"
Stunning Chesapeake Bay Farmhouse w/ Dock & Kayaks

The Strand: Free Golf Carts, Paddle Boards, Tennis & Pool, 1 Blk to Beach

10.0 out of 10, Exceptional, (12)
"Had a great time at the strand. Property was immaculate and as advertised. The included golf carts are a huge bonus and it’s nice to not have a hidden $650 “host fee” like most other properties on here. Will be back for sure. "
The price is AED 1,175
AED 3,644 total
includes taxes & fees
3 Jan - 4 January 2025
The Strand: Free Golf Carts, Paddle Boards, Tennis & Pool, 1 Blk to Beach

Sunset Shores | Chesapeake Properties

10.0 out of 10, Exceptional, (2)
Sunset Shores | Chesapeake Properties

Nassawadox Creek Waterfront Home with Private Pool

10.0 out of 10, Exceptional, (39)
"This is a beautiful house and Nancy is an outstanding host. We enjoyed sitting by the pool and birdwatching. My wife wanted to take the scenic main room home with us. "
Nassawadox Creek Waterfront Home with Private Pool

Sisters 3 by the Sea, 400 Feet To The Beach

9.4 out of 10, Exceptional, (153)
"Wonderful home in a great location. Plenty of space. Well stocked home. Owner was great. Will be back again. "
Sisters 3 by the Sea, 400 Feet To The Beach

Minutes to the BEACH! Large yard w/fire pit, bocci, ample parking and fun!

10.0 out of 10, Exceptional, (13)
"Clean, welcoming home with huge backyard for kids to play in! Firepit was a big hit. Very easy access to Cape Charles (it's literally right down the road) and right off 13. Great place for a great time... we loved it! all 10 us!"
Minutes to the BEACH! Large yard w/fire pit, bocci, ample parking and fun!

Newly renovated, 4BD 2 BA, 1 full acre, sleeps 9, and is pet friendly.

10.0 out of 10, Exceptional, (18)
"Even though we were there off-season for a wedding, this VRBO is super close to the beach. Also close is a grocery store. Only possible issue is a super squeaky floor in master bedroom could disturb a light sleeper or a baby. Kitchen is masterfully stocked, great deck, quiet neighborhood, awesome water pressure (although you may prefer bottled water due to the minerals). You'll need to bring your own shampoo as well. It was perfect for our needs and super cute!"
Newly renovated, 4BD 2 BA, 1 full acre, sleeps 9, and is pet friendly.

Bayfront Retreat w/ Game Room + Outdoor Pool!

9.8 out of 10, Exceptional, (32)
"Our second time staying at the house. We absolutely love the property and all its surrounding wildlife. Enjoyed spending time hiking, fishing, crabbing, and watching eagles flying over the water. The house is clean and well stocked, and the game room is a great place to spend time in the evenings or rainy days. The hosts are attentive and helpful. Looking forward to visiting again!"
Bayfront Retreat w/ Game Room + Outdoor Pool!

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

9.8 out of 10, Exceptional, (146)
"I loved the property and location except for the music from the restaurant that didn’t stop until after 11:00. The second floor room had hot air coming from the back of what looked like an in room air conditioner. I think the air was supposed to go outside through a vent…. So hot one of us had to sleep on sofa…. Also might co spider taking out small white bar and putting in a round table for eating and cards…sunsets were beautiful and we would co spider coming back. Oh also the golf cart might...
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, (56)
"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

Game Barn! Next to Central Park! 2 Blocks 2 Beach/Resturants/Shops

10.0 out of 10, Exceptional, (47)
"This was the greatest house and we loved the game barn. It was just as advertised. My kids had a blast. We even played some of the games that were in the living room. The kitchen is very well stocked and the grill worked great. This place was amazing!!"
Game Barn! Next to Central Park! 2 Blocks 2 Beach/Resturants/Shops

Cape Utopia - sister to existing ID# 7559899

9.8 out of 10, Exceptional, (31)
"What a great trip! Our first trip to the Eastern Shore and it won't be out last. What a terrific VRBO. It had everything we needed and more. Loved the historic home. Our host, Elizabeth, was attentive and welcoming. We will be back to Cape Charles and we will return to this home. The location was centrally located and we enjoyed our walks to the beach and to the main street area. Can't recommend more highly!"
Cape Utopia - sister to existing ID# 7559899

Family Rental, Best location to Central Park and beach!

10.0 out of 10, Exceptional, (26)
"Great "
Family Rental, Best location to Central Park and beach!

Whimsical Tiny House, Cape Charles Virginia

9.8 out of 10, Exceptional, (11)
"We love staying in the tiny home, Eric was such a nice host"
The price is AED 539
AED 974 total
includes taxes & fees
5 Jan - 6 January 2025
Whimsical Tiny House, Cape Charles Virginia

Huntington Farm - Great Family Retreat

9.6 out of 10, Exceptional, (54)
"Great place to stay and beautiful views. Was perfect for our group. Highly recommend!"
Huntington Farm - Great Family Retreat

Spacious Restored Victorian with 5 Bedrooms and 4 Bathrooms

10.0 out of 10, Exceptional, (42)
"We like the house so much we are repeat customers! The house is wonderful, the Host is amazing and Cape Charles is one of my favorite places to visit. The house is very well arranged, very clean and well supplied. The house is located in a prime spot and it's really nice to be able to walk to everything. I highly recommend the house!"
Spacious Restored Victorian with 5 Bedrooms and 4 Bathrooms

Salt Box, One Block to the Beach

10.0 out of 10, Exceptional, (9)
"The property was in an AMAZING location. It was quiet, quaint, and SO close the beach. We walked over to watch the sunset on the beach each night. We realized that alot of the locals did this and it was cool to chat with them during that time. Speaking of locals, everyone was SO friendly (we're not used to that here in Virginia, unfortunately). It was a nice change of pace and scenery for us. We were looking for a place to unwind and just connect with each other and this place gave us all of...
The price is AED 581
AED 1,554 total
includes taxes & fees
3 Jan - 4 January 2025
Salt Box, One Block to the Beach
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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Other property types in Cheriton

Nassawadox Creek Waterfront Home with Private Pool

10.0 out of 10, Exceptional, (39)
"This is a beautiful house and Nancy is an outstanding host. We enjoyed sitting by the pool and birdwatching. My wife wanted to take the scenic main room home with us. "
Nassawadox Creek Waterfront Home with Private Pool

Cape Charles Newly Updated Family-friendly Beach House, 1 Block to Private Beach

10.0 out of 10, Exceptional, (19)
"We had an incredible weekend in Cape Charles at Drop Anchor. We've been renting places in CC for the past 10 years, and this was the cleanest and most well-appointed home we've ever rented. My husband and I invited 4 friends to CC for the weekend bc they had never been, and they fell in love with everything! The golf cart was amazing, and we had the best time. Timely responses and detailed notes and emails from property manager. Thank you so much for having us at Drop Anchor! We’ll definitely...
Cape Charles Newly Updated Family-friendly Beach House, 1 Block to Private Beach

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

9.6 out of 10, Exceptional, (129)
"Loved everything about this lovely cottage and especially walking to the bay! Rick was extremely kind and helpful. Hope to come back!"
The price is AED 698
AED 1,751 total
includes taxes & fees
3 Jan - 4 January 2025
Bay cottage, Beach 100 yards away! RESERVE NOW!!!
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.