Chesapeake Bay Rentals

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55 Houses

(23) Excellent 

19

Big Bay- A Private Beach front Home on the Chesapeake Bay

Chesapeake / Chesapeake Bay

Chesapeake house

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0 mi
  • Child Friendly
“Beautiful Beach Front” The house is well laid out and has great views from the living room. The sandy beach is spacious. The kitchen is well equipped and modern and is open to the living room. Comfortable chairs are on the deck and the wide bay view
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Price per night from

$229

Price per night from

$229

Great rentals within 20 miles that match your search

Distance approx 15.83 km from Chesapeake Bay

24

NEW! Chesapeake Bay Apt- 2 Blocks from the Beach!

Virginia / Hampton

Hampton apartment

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Child Friendly
  • Air conditioning

Price per night from

$109

Responds fast!
avg. 9 minutes

Price per night from

$109

Distance approx 16.24 km from Chesapeake Bay

(2) Excellent 

27

11th Heaven Golf and Beach at Bay Creek

Virginia / Cape Charles

Cape Charles apartment

3 8 2 nights min

  • 3 bedrooms
  • sleeps 8
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.8 mi
  • Swimming pool

Price per night from

$297

Responds fast!
avg. 1 hour 43 minutes

Price per night from

$297

Distance approx 12.9 km from Chesapeake Bay

12

Spacious One-bedroom Suite with Full Kitchen

Virginia / Yorktown

Yorktown b and b

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Nearest beach 0.5 mi
  • Child Friendly
  • Air conditioning

Price per night from

$166

Responds fast!
avg. 1 hour 35 minutes

Price per night from

$166

Distance approx 15.84 km from Chesapeake Bay

13

2 Blocks to Beach in Cape Charles ( Duplex style)

Virginia / Cape Charles

Cape Charles house

3 7 1 night min

  • 3 bedrooms
  • sleeps 7
  • 1 night min
  • Child Friendly
  • Car not necessary
  • Air conditioning

Price per night from

$115

Price per night from

$115

Distance approx 16.99 km from Chesapeake Bay

(4) Excellent 

20

Find unspoiled natural beauty, slower pace and genuine southern hospitality...

Virginia / Cape Charles

Cape Charles house

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.5 mi
  • Child Friendly

Price per night from

$172

Responds fast!
avg. 1 hour 17 minutes

Price per night from

$172

Distance approx 14.48 km from Chesapeake Bay

(8) Excellent 

23

Chesapeake Bay Waterfront Cottage: Pool Pier Wifi

Virginia / Mathews

Mathews cottage

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Air conditioning
“Just Plain Perfect!” My 3 children and I arrived at Grandview on July 5th, 2011 for a one night stay in "The Crab Shack." I'm not much for words or for "padding the stats," but I would easily give the Scanlan's little gem on the East River 6 stars acr
…see more

Price per night from

$252

Price per night from

$252

Distance approx 15.85 km from Chesapeake Bay

28

Downtown Cape Charles and 3 blocks to the beaches

Virginia / Cape Charles

Cape Charles house

4 12 4 nights min

  • 4 bedrooms
  • sleeps 12
  • 4 nights min
  • Child Friendly

Price per night from

$343

Price per night from

$343

Distance approx 15.65 km from Chesapeake Bay

18

Beach front historic Dryden House, Chesapeake Bay views w/2 King Master Bedrooms

Virginia / Cape Charles

Cape Charles house

5 12 3 nights min

  • 5 bedrooms
  • sleeps 12
  • 3 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$425

Price per night from

$425

Distance approx 17.86 km from Chesapeake Bay

14

Cozy 1 br near the Beach

Virginia / Norfolk

Norfolk house

1 3 2 nights min

  • 1 bedroom
  • sleeps 3
  • 2 nights min
  • Child Friendly
  • Pet Friendly

Price per night from

$63

Price per night from

$63

Distance approx 16.19 km from Chesapeake Bay

(1) Excellent 

24

Modern Beach House with great amenities in the heart of Cape Charles!

Virginia / Cape Charles

Cape Charles house

4 8 3 nights min

  • 4 bedrooms
  • sleeps 8
  • 3 nights min
  • Child Friendly

Price per night from

$286

Price per night from

$286

Distance approx 16.32 km from Chesapeake Bay

(1) Excellent 

23

Spectacular Bay View Retreat *NEW LISTING*

Virginia / Cape Charles

Cape Charles house

3 10 3 nights min

  • 3 bedrooms
  • sleeps 10
  • 3 nights min
  • Nearest beach 0.7 mi
  • Swimming pool
  • Child Friendly

Price per night from

$487

Price per night from

$487

Distance approx 9.6 km from Chesapeake Bay

4

131 N. First Street Apt#3

Virginia / Hampton

Hampton apartment

1 2 7 nights min

  • 1 bedroom
  • sleeps 2
  • 7 nights min
  • Nearest beach 0 mi
  • Child Friendly
  • Air conditioning

Price per night from

$107

Price per night from

$107

Distance approx 8.94 km from Chesapeake Bay

(1) Excellent 

12

786 N. First Street

Virginia / Hampton

Hampton house

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$229

Price per night from

$229

Distance approx 9.6 km from Chesapeake Bay

(2) Very Good 

7

134 N. First Street

Virginia / Hampton

Hampton condo

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$172

Price per night from

$172

Distance approx 15.76 km from Chesapeake Bay

(1) Excellent 

13

Waters Edge at Pickett's Harbor, 'a Perfect Private Beach-Front' Estate

Virginia / Capeville

Capeville house

4 9 7 nights min

  • 4 bedrooms
  • sleeps 9
  • 7 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$818

Price per night from

$818

Distance approx 15.53 km from Chesapeake Bay

41

Sand Hills Retreat- Great for Families and Golfers

Virginia / Cape Charles

Cape Charles house

4 12 7 nights min

  • 4 bedrooms
  • sleeps 12
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.8 mi
  • Swimming pool

Price per night from

$458

Price per night from

$458

Distance approx 18.1 km from Chesapeake Bay

(3) Excellent 

18

Rigby Retreat on the Chesapeake Bay

Virginia / Diggs

Diggs cottage

3 7 2 nights min

  • 3 bedrooms
  • sleeps 7
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0 mi
  • Child Friendly

Price per night from

$171

Price per night from

$171

Distance approx 15.83 km from Chesapeake Bay

(1) Very Good 

24

Norfolk Apartment - Walk to Beach & Chesapeake Bay

Virginia / Norfolk

Norfolk apartment

2 5 3 nights min

  • 2 bedrooms
  • sleeps 5
  • 3 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$144

Responds fast!
avg. 9 minutes

Price per night from

$144

Distance approx 17.93 km from Chesapeake Bay

27

NEW! Norfolk Home w/Balcony - Block From the Beach

Virginia / Engleside

Engleside townhouse

4 12 min stay varies

  • 4 bedrooms
  • sleeps 12
  • min stay varies
  • Child Friendly
  • Air conditioning

Price per night from

$258

Responds fast!
avg. 9 minutes

Price per night from

$258

Distance approx 15.05 km from Chesapeake Bay

(1) Excellent 

13

Mobjack Bay Cottage Overlooking East River & Mobjack Bay

Virginia / Foster

Foster cottage

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Child Friendly

Price per night from

$332

Price per night from

$332

Distance approx 19.86 km from Chesapeake Bay

24

NEW! Cozy Norfolk Home 4 Mi. to Waterside District

Virginia / Engleside

Engleside house

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$86

Responds fast!
avg. 9 minutes

Price per night from

$86

Distance approx 17.84 km from Chesapeake Bay

(1) Excellent 

7

Cozy Mother-in-Law Suite

Virginia / Norfolk

Norfolk house

1 3 2 nights min

  • 1 bedroom
  • sleeps 3
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$58

Price per night from

$58

Distance approx 9.68 km from Chesapeake Bay

(2) Very Good 

6

4 Buckroe Ave.

Virginia / Hampton

Hampton condo

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$172

Price per night from

$172

Distance approx 9.6 km from Chesapeake Bay

8

131 N. First Street Apt#1

Virginia / Hampton

Hampton apartment

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Nearest beach 0 mi
  • Child Friendly
  • Air conditioning

Price per night from

$140

Price per night from

$140

Distance approx 18.12 km from Chesapeake Bay

29

NEW! Spacious Norfolk Townhome- 2 Blocks to Beach

Virginia / Engleside

Engleside house

4 12 min stay varies

  • 4 bedrooms
  • sleeps 12
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$229

Responds fast!
avg. 9 minutes

Price per night from

$229

Distance approx 17.36 km from Chesapeake Bay

19

Sandswept Carriage House - Spacious Living at the Beach

Virginia / Norfolk

Norfolk apartment

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies

Price per night from

$61

Price per night from

$61

Distance approx 9.59 km from Chesapeake Bay

(2) Very Good 

6

133 N. First Street Cottage

Virginia / Hampton

Hampton house

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$147

Price per night from

$147

Distance approx 16.6 km from Chesapeake Bay

8

Wake up to a view of the Chesapeake bay, a 100 feet from sand in your toes

Virginia / Norfolk

Norfolk condo

2 6 4 nights min

  • 2 bedrooms
  • sleeps 6
  • 4 nights min
  • Beach / lakeside relaxation
  • Child Friendly

Price per night from

$257

Price per night from

$257

Distance approx 17.93 km from Chesapeake Bay

25

Updated Cape Charles Home - 2.5 Miles From Beach!

Virginia / Cape Charles

Cape Charles house

4 9 min stay varies

  • 4 bedrooms
  • sleeps 9
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$166

Responds fast!
avg. 9 minutes

Price per night from

$166

Distance approx 9.6 km from Chesapeake Bay

5

131 N. First Street Apt #4

Virginia / Hampton

Hampton apartment

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Nearest beach 0 mi
  • Child Friendly
  • Air conditioning

Price per night from

$140

Price per night from

$140

Distance approx 17.35 km from Chesapeake Bay

28

50 Steps from the Beach! WHY NOT Blend Business and Beach?!

Virginia / Norfolk

Norfolk apartment

2 4 30 nights min

  • 2 bedrooms
  • sleeps 4
  • 30 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$54

Price per night from

$54

Distance approx 15.83 km from Chesapeake Bay

24

NEW! Norfolk Apt - 2 Blocks to Beach & Restaurants

Virginia / Hampton

Hampton apartment

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Child Friendly
  • Air conditioning

Price per night from

$81

Responds fast!
avg. 9 minutes

Price per night from

$81

Distance approx 15.02 km from Chesapeake Bay

(1) Excellent 

31

*Waterfront**10 Mile View**Hot Tub**Pet Friendly**

Virginia / Norfolk

Norfolk house

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Nearest beach 0.3 mi
  • Child Friendly
  • Air conditioning

Price per night from

$557

Price per night from

$557

Distance approx 14.89 km from Chesapeake Bay

24

NEW! Pet-Friendly Norfolk Apt. - Blocks from Beach

Virginia / Norfolk

Norfolk apartment

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$137

Responds fast!
avg. 9 minutes

Price per night from

$137

Distance approx 13.94 km from Chesapeake Bay

4

Cozy house near Ft. Eustis for rent

Virginia / Newport News

Newport News house

3 7 2 nights min

  • 3 bedrooms
  • sleeps 7
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$119

Price per night from

$119

Distance approx 15.83 km from Chesapeake Bay

24

Norfolk Apartment Near Chesapeake Bay & Beach!

Virginia / Norfolk

Norfolk apartment

2 5 3 nights min

  • 2 bedrooms
  • sleeps 5
  • 3 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$109

Responds fast!
avg. 9 minutes

Price per night from

$109

Distance approx 18.18 km from Chesapeake Bay

(12) Very Good 

32

Beachfront Bluez the Oceans Melody

Virginia / Norfolk

Norfolk house

4 14 min stay varies

  • 4 bedrooms
  • sleeps 14
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0 mi
  • Child Friendly
“Awesome Place” Came down with family and friends. Area was great great view of the beach which was a short walk away. House very spacious and clean. Nice and quiet area. Loved it and would definitely book again.
…see more

Price per night from

$113

Price per night from

$113