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Compare 290 Vacation Homes in Diggs 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

Relaxing 1 bedroom 2019 Camper beside the Seven River

9.4 out of 10, Exceptional, (18)
" The location was great if you want a quiet place and close to the river. We enjoyed walking down to edge and watching the water. We also enjoyed walking around the neighborhood. The camper was very clean. Kimberly and her husband were very nice and helped with the few little problems that we had. We really enjoyed our stay there."
The price is AED 246
AED 621 total
includes taxes & fees
21 Jan - 22 January 2025
Relaxing 1 bedroom 2019 Camper beside the Seven River

"Bee Haven" Cottage Retreat Near Colonial Williamsburg

10.0 out of 10, Exceptional, (88)
"We loved our stay. We were looking for somewhere away from the chaos of holiday in Williamsburg but accessible. It fit perfectly. House was quiet, clean and comfortable. Made for a wonderful weekend. "
"Bee Haven" Cottage Retreat Near Colonial Williamsburg

Oyster Shack - true gem in heart of downtown!

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

MILLION $ VIEWS NO EXTRA CHARGE! HOT TUB! POOL! BEACH! RESORT-LIKE AMENITIES!

10.0 out of 10, Exceptional, (148)
"I knew when I found this listing that I may have uncovered a hidden gem and I was right! We stayed just for a long weekend but everything was cozy and the local towns were so friendly. We definitely enjoyed White Dog Bistro, Southwind Pizza and Richardsons. Even though we ate out most of our time, the house had most of the essentials if you chose to cook there. The hot tub and fire pit were favorites, we stopped at Food Lion just to get Marshmallows to roast. My husband caught lots of fish...
MILLION $ VIEWS NO EXTRA CHARGE! HOT TUB! POOL! BEACH! RESORT-LIKE AMENITIES!

Large 4bed 2.5b home w/ fenced in back yard & deck

10.0 out of 10, Exceptional, (2)
"We stayed here for a wedding, there were seven adults and one toddler and one pup. It was great! Loved all the space, fenced in backyard for the pup and nice yard for kiddo games. Would definitely stay here again. "
The price is AED 1,150
AED 2,248 total
includes taxes & fees
19 Jan - 20 January 2025
Large 4bed 2.5b home w/ fenced in back yard & deck

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
1 Jan - 2 January 2025
The Strand: Free Golf Carts, Paddle Boards, Tennis & Pool, 1 Blk to Beach

Cozy Country setting with comforts of home

8.8 out of 10, Excellent, (15)
"Was very warm and inviting atmosphere. Easy to find and off the main traffic at the same time very convenient. "
Cozy Country setting with comforts of home

Sunset Shores | Chesapeake Properties

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

Cozy cottage on the Chesapeake Bay

9.8 out of 10, Exceptional, (40)
"We have stayed at Glenda’s place multiple times and love it every time. It’s the perfect place to reconnect with my family and enjoy the peace of the Rivah. Everything is clean and comfortable and well stocked. Thank you Glenda!"
Cozy cottage on the Chesapeake Bay

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!

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!

Heart of Irvington w/Fireplace Walk to Tides Inn & restaurants - Dog friendly!

9.8 out of 10, Exceptional, (159)
"We enjoyed our stay so close to the Tides Inn for the Taste of the Bay. Irvington is a quaint walkable town, perfect for getting away from the hustle and bustle of fast paced locations."
Heart of Irvington w/Fireplace Walk to Tides Inn & restaurants - Dog friendly!

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

Monthly discount- beautiful house, Gloucester VA

10.0 out of 10, Exceptional, (18)
"Our weekend stay was perfect and cozy. The home was clean and had everything we needed. "
Monthly discount- beautiful house, Gloucester VA

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
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 Diggs

Private 5-acre Waterfront Peninsula with Beach

9.4 out of 10, Exceptional, (34)
"We had such a wonderful time! The location was absolutely beautiful and so peaceful. The house was very comfortable and clean making it easy to just relax. Note to future renters - the property and it's amenities have been greatly loved. The peddle boat rudder wasn't working, one of the kayaks was cracked and leaking, hot tub never got up to temperature, several nails were popping up out of the deck which had several loose boards and splinters, and the kitchen needed some work as the knobs were...
The price is AED 158
AED 2,749 total
includes taxes & fees
20 Jan - 21 January 2025
Private 5-acre Waterfront Peninsula with Beach

Relaxing 1 bedroom 2019 Camper beside the Seven River

9.4 out of 10, Exceptional, (18)
" The location was great if you want a quiet place and close to the river. We enjoyed walking down to edge and watching the water. We also enjoyed walking around the neighborhood. The camper was very clean. Kimberly and her husband were very nice and helped with the few little problems that we had. We really enjoyed our stay there."
The price is AED 246
AED 621 total
includes taxes & fees
21 Jan - 22 January 2025
Relaxing 1 bedroom 2019 Camper beside the Seven River

"Bee Haven" Cottage Retreat Near Colonial Williamsburg

10.0 out of 10, Exceptional, (88)
"We loved our stay. We were looking for somewhere away from the chaos of holiday in Williamsburg but accessible. It fit perfectly. House was quiet, clean and comfortable. Made for a wonderful weekend. "
"Bee Haven" Cottage Retreat Near Colonial Williamsburg
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.