Chesapeake Rentals

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60 Houses

Chesapeake Bay Beach House in Reedville Virginia

Reedville house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 14

Price per night from

$687

Price per night from

$201

786 N. First Street

Hampton house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$373

My Pan-O-Sea-A on the Chesapeake Bay.

White Stone cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

“Great View!” Loved the bedroom view, priceless! We could not have had a better view! Great place, very clean and has everything you could possibly need!

Price per night from

$229

Mobjack Bay Cottage Overlooking East River & Mobjack Bay

Foster cottage

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$332

Stunning, Newer Chesapeake Waterfront Estate, Pool - 7 Bedrms 5 Baths

Cambridge house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 18

“Outstanding Vacation Rental” Our extended family (22 people - 13A/9K) had a great week at Saddle Beach. The house was beautiful and in very good condition. The option of being in the pool or the river during the day was wonderful. The house was clean and well furnished. The dining room table and table on the porch provided plenty of seating for meals. There was plenty of hot water for showers and clean-up after meals. The pool was clean and the river was awesome, with a gradual slope that was perfect for kids and adults. We used the crab traps provided and caught 2 dozen crabs that made a great contribution to dinner on Friday. Crabbing was best by the dock. We caught all but 3 crabs there, rather than out closer to the middle of the river. The AC on the ground floor stopped working on Tuesday, but one call to the owner and the repair team was on-site in less than 2 hours. The issue was resolved before noon on Wednesday. We have been renting vacation properties for years and issues crop up from time to time. We appreciated the quick response and resolution. The one recommendation we will make is to bring bug spray (mosquitos and horse flies). We anticipated it being right on the river, but if you haven't had that experience, you need to be prepared.

Price per night from

$1,030

Hoopers Island Bayside Studio, 360 Degrees WATER VIEWS near IRONMAN Cambridge

Fishing Creek apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

“What a fantastic stay!” As soon as we stepped out of our car, we felt like we hit the jackpot. The views in front and in back of the house are breathtaking, with water stretching to the horizons. Inside the house, we found all that we could need and more. The décor was adorable, though both aesthetically and functionally vintage. We found a very thoughtful welcome bag and bottle of wine on the dining table as soon as we walked in. A variety of items found throughout the house make for a very comfortable and carefree stay (including a blender, coffee maker, coffee, a wide variety of DVD/VHS movies, and more). The kitchen was fully stocked with all of the essentials, as well as a great assortment of spices. It truly feels like your home away from home. Fishing Creek is a modest town, but houses some of the friendliest people. There is only one general store and one restaurant – both terrific. We arrived at the general store five minutes after closing and they still opened the doors for us. The restaurant, Old Salty’s, has fast, friendly, and accommodating service and the food is very good. Not to mention, the largest and cleanest oysters we have ever tried. We spent much of our time relaxing and enjoying the amenities that the Haven provides. The screened porch makes for a wonderful place to have an outdoor dinner. The fire pit in the back kept us warm as we took in some of the most beautiful sunsets we have ever seen. We even caught a few crabs just off the dock up front, using the crab traps that Debi provided. Unfortunately, we found no luck with catching any fish. Debi was out of town during our stay, yet she still provided wonderful service. Her responses to text messages and e-mails were always very prompt. She left the Haven very tidy for us, and included a detailed instruction manual that covered scenario we may have come across. It’s obvious she puts a lot of thought into giving her guests a pleasant stay, and it surely pays off. We really enjoyed our time at the Haven, and have already talked about a possible return trip in the future. Thanks Debi!

Price per night from

$207

Peaceful on the Albemarle Sound

Hertford house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$172

Furnished 1BR/1.5BA Luxury Condo

Norfolk condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$118

Price per night from

$340

Luxurious 4 Bedroom 2200 sqft East Ocean View Villa. "

Norfolk house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$636

Waterfront 1 Bd Full Kitchen Water & Nature Preserve Views ALL Windows

Hampton apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“Absolute Dream Location” Clancy, my dog and I spent an amazing week at this location. Kim and her family were amazing. The rental had absolutely everything you could ask for and much more. Clearly Kim and Co. have made this an upscale, homey spot for anyone wanting beach time. Speaking of the beach, the views off the deck are some of the finest I've ever seen both morning and night. I got up early every morning, just to watch the sunrise. The beach is clean, an easy walk and friendly for kids, dogs and people. Thank you for making our stay a wonderful vacation.

Price per night from

$166

Cottage at Heron Cove, Chesapeake Bay, Cambridge

Cambridge cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

Responds fast! avg. 32 minutes

Price per night from

$257

Sloop Creek Cottage

Reedville house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

Price per night from

$315

Shirley’s Buckroe Beach Vacation Rental

Hampton house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

Price per night from

$567

Mai Villa Hampton - Where Good Times Happen!

Hampton house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

Price per night from

$457

Spacious House by Beach, AFB, Stores & more

Hampton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

Price per night from

$343

Dolphin Point - A beach lovers retreat

Hampton condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Price per night from

$114

The Chesapeake Gray

Norfolk house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$342

The Conquest ⭐️ 4BR Beach Retreat Home w/ Balcony

Norfolk house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 14

Price per night from

$569

Our Little Place at the Beach for Two!

Hampton house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$148

Life on a Sandbar

Norfolk house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$287

Price per night from

$108

Beautiful Waterfront Home, Private Pool and Water Amenities- Sleeps 16

Cambridge house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 18

Price per night from

$859

The Wyatt, an H4N Fully Furnished Apartment

Norfolk apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$123

*NEW* Family friendly home 3 mins to Buckroe Beach

Hampton house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 10

Price per night from

$401

Dances Bay Room 1

Elizabeth City private room

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$75

The Eddington, an H4N Fully Furnished Apartment

Hampton apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$187

Trust n Travel

Lusby guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Price per night from

$201

Victorian Waterfront Downtown Oasis Charm

Hampton house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 12

Price per night from

$481

Big & beautiful at the beach 2

Hampton house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$515

Beach House w/ hot tub and Bay view

Norfolk house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$219

Nautical Farmhouse Near Reedville/Smith Point Marina in Northern Neck VA

Reedville house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$229

Buckroe Beach Affordable for 4 - Walk to the Beach!

Hampton house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$171

The Cottage House

Hampton house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

Price per night from

$98

Granby Loft

Norfolk apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 1 hour 8 minutes

Price per night from

$207

Cozy King Size Bed 1st Floor (Apt. 1)

Norfolk apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Price per night from

$85

Luxurious Alberta Beach House

Hampton house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 14

Price per night from

$1,065

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