Chesapeake Rentals

Close

Enter dates for more accurate prices

Payment Protection
Your payment for this rental is protected when you pay through FlipKey. Learn more

784 Houses

(2) Excellent 

30

Stay at the Quay!

Virginia / Chesapeake

Chesapeake townhouse

3 8 2 nights min

  • 3 bedrooms
  • sleeps 8
  • 2 nights min
  • Nearest beach 20 mi
  • Child Friendly
  • Air conditioning

Price per night from

$99

Price per night from

$99

(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
…see more

Price per night from

$229

Price per night from

$229

Great rentals within 20 miles that match your search

Distance approx 17.43 km from Chesapeake Show on Map

(1) Excellent 

13

Ocean Front View at Virginia Beach Beach Quarters Aug 03 - Aug 10 2019

Virginia / Virginia Beach

Virginia Beach villa

1 4 7 nights min

  • 1 bedroom
  • sleeps 4
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$270

Price per night from

$270

Distance approx 17.75 km from Chesapeake Show on Map

5

Ocean Sands 2207 Atlantic Ave Oceanfront Va.Beach

Virginia / Virginia Beach

Virginia Beach apartment

1 4 7 nights min

  • 1 bedroom
  • sleeps 4
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$171

Price per night from

$171

Distance approx 17.43 km from Chesapeake Show on Map

(3) Excellent 

12

Virginia Beach Vacation Rental

Virginia / Virginia Beach

Virginia Beach condo

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Child Friendly
  • Car not necessary
  • Air conditioning

Price per night from

$140

Price per night from

$140

Distance approx 17.76 km from Chesapeake Show on Map

(1) Excellent 

10

The Rimini at Plaza 2700

Virginia / Virginia Beach

Virginia Beach condo

2 8 3 nights min

  • 2 bedrooms
  • sleeps 8
  • 3 nights min
  • Nearest beach 0.33 mi
  • Child Friendly
  • Car not necessary

Price per night from

$159

Price per night from

$159

Distance approx 18.24 km from Chesapeake Show on Map

24

NEW! Virginia Beach Studio-Oceanfront Complex!

Virginia / Virginia Beach

Virginia Beach studio

Studio 4 min stay varies

  • Studio
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$155

Responds fast!
avg. 55 minutes

Price per night from

$155

Distance approx 17.74 km from Chesapeake Show on Map

16

Ocean Front Condo Virginia Beach Boardwalk Kamla

Virginia / Virginia Beach

Virginia Beach apartment

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0 mi
  • Air conditioning

Price per night from

$203

Price per night from

$203

Distance approx 17.61 km from Chesapeake Show on Map

49

Seaward Bound

Virginia / Virginia Beach

Virginia Beach house

5 12 7 nights min

  • 5 bedrooms
  • sleeps 12
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$888

Responds fast!
avg. 3 hours 0 minutes

Price per night from

$888

Distance approx 17.31 km from Chesapeake Show on Map

43

The Contemporary Castle in Sandbridge Beach...ten bedrooms and a freeform pool

Virginia / Virginia Beach

Virginia Beach house

10 22 7 nights min

  • 10 bedrooms
  • sleeps 22
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool

Price per night from

$641

Price per night from

$641

Distance approx 17.4 km from Chesapeake Show on Map

14

Oceanfront condo Virginia Beach Boardwalk Dolphin Run

Virginia / Virginia Beach

Virginia Beach condo

2 6 7 nights min

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

Price per night from

$256

Price per night from

$256

Distance approx 18.11 km from Chesapeake Show on Map

23

Cutty Sark Historic Beach Cottage Triplex 2

Virginia / Virginia Beach

Virginia Beach apartment

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool

Price per night from

$169

Price per night from

$169

Distance approx 17.44 km from Chesapeake Show on Map

(5) Excellent 

Certificate of Excellence

13

Vacation Paradise

Virginia / Virginia Beach

Virginia Beach house

4 8 3 nights min

  • 4 bedrooms
  • sleeps 8
  • 3 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Certificate of Excellence

Price per night from

$288

Responds fast!
avg. 1 hour 44 minutes

Price per night from

$288

Distance approx 17.36 km from Chesapeake Show on Map

16

Ocean Key Resort 1BR 1BA TOP FLOOR with OCEAN VIE

Virginia / Virginia Beach

Virginia Beach condo

1 4 3 nights min

  • 1 bedroom
  • sleeps 4
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$228

Responds fast!
avg. 2 hours 26 minutes

Price per night from

$228

Distance approx 17.07 km from Chesapeake Show on Map

(1) Very Good 

33

Coral Point

Virginia / Virginia Beach

Virginia Beach house

4 10 7 nights min

  • 4 bedrooms
  • sleeps 10
  • 7 nights min
  • Child Friendly
  • Car not necessary

Price per night from

$396

Responds fast!
avg. 3 hours 0 minutes

Price per night from

$396

Distance approx 17.78 km from Chesapeake Show on Map

(2) Excellent 

12

Virginia Beach, 28th Street

Virginia / Virginia Beach

Virginia Beach condo

2 6 7 nights min

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

Price per night from

$171

Price per night from

$171

Distance approx 18.05 km from Chesapeake Show on Map

(1) Excellent 

9

Ocean Beach Club and Oceanairre - the Nicest Place in Virginia Beach; 4 Stars

Virginia / Virginia Beach

Virginia Beach condo

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Nearest beach 0 mi
  • Swimming pool
  • Child Friendly

Price per night from

$224

Responds fast!
avg. 3 hours 42 minutes

Price per night from

$224

Distance approx 17.79 km from Chesapeake Show on Map

9

OCEANFRONT PENTHOUSE 1 BEDROOM UNIT - SLEEPS 4

Virginia / Virginia Beach

Virginia Beach condo

1 4 7 nights min

  • 1 bedroom
  • sleeps 4
  • 7 nights min
  • Child Friendly

Price per night from

$164

Price per night from

$164

Distance approx 17.76 km from Chesapeake Show on Map

7

The Napoli at Plaza 2700

Virginia / Virginia Beach

Virginia Beach condo

2 8 3 nights min

  • 2 bedrooms
  • sleeps 8
  • 3 nights min
  • Nearest beach 0.33 mi
  • Child Friendly
  • Car not necessary

Price per night from

$169

Price per night from

$169

Distance approx 16.84 km from Chesapeake Show on Map

100

Bella Vita Virginia Private Home

Virginia / Virginia Beach

Virginia Beach house

11 32 min stay varies

  • 11 bedrooms
  • sleeps 32
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$1,374

Responds fast!
avg. 3 hours 0 minutes

Price per night from

$1,374

Distance approx 18.22 km from Chesapeake Show on Map

(13) Very Good 

11

Oceanfront Condo in Virginia Beach

Virginia / Virginia Beach

Virginia Beach condo

1 4 3 nights min

  • 1 bedroom
  • sleeps 4
  • 3 nights min
  • Beach / lakeside relaxation
  • Ask about children
  • Air conditioning

Price per night from

$180

Responds fast!
avg. 3 hours 22 minutes

Price per night from

$180

Distance approx 15.96 km from Chesapeake Show on Map

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

$224

Price per night from

$224

Distance approx 17.76 km from Chesapeake Show on Map

(3)  

8

The Cinque Terre at Plaza 2700

Virginia / Virginia Beach

Virginia Beach condo

2 8 3 nights min

  • 2 bedrooms
  • sleeps 8
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.33 mi
  • Child Friendly
“Everything went pretty good.” It's a five minute walk to the beach. Neighborhood is pretty quiet at night we only woke up early at one time because there was two drunk guys talking pretty loudly outside our window. You can hear the military planes fly
…see more

Price per night from

$179

Price per night from

$179

Distance approx 17.76 km from Chesapeake Show on Map

7

The Torino at Plaza 2700

Virginia / Virginia Beach

Virginia Beach condo

2 7 3 nights min

  • 2 bedrooms
  • sleeps 7
  • 3 nights min
  • Nearest beach 0.33 mi
  • Child Friendly
  • Car not necessary

Price per night from

$159

Price per night from

$159

Distance approx 17.77 km from Chesapeake Show on Map

(1) Excellent 

10

304 28th Street #101

Virginia / Virginia Beach

Virginia Beach apartment

2 5 7 nights min

  • 2 bedrooms
  • sleeps 5
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$200

Price per night from

$200

Distance approx 17.77 km from Chesapeake Show on Map

10

The Vincenze at Plaza 2700

Virginia / Virginia Beach

Virginia Beach condo

2 8 3 nights min

  • 2 bedrooms
  • sleeps 8
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.33 mi
  • Child Friendly

Price per night from

$179

Price per night from

$179

Distance approx 16.56 km from Chesapeake Show on Map

(2) Average 

27

Private Waterfront Home Minutes To Beaches, Attractions, Restaurants & Shopping

Virginia / Virginia Beach

Virginia Beach house

4 12 min stay varies

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

Price per night from

$150

Responds fast!
avg. 1 hour 58 minutes

Price per night from

$150

Distance approx 17.51 km from Chesapeake Show on Map

24

Retreat at Sandbridge Beach – RV Cottage on Bay

Virginia / Virginia Beach

Virginia Beach caravan/mobile home

1 4 7 nights min

  • 1 bedroom
  • sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Child Friendly

Price per night from

$189

Price per night from

$189

Distance approx 19.05 km from Chesapeake Show on Map

25

Ocean Front! North End! Extra Parking! Beach House!

Virginia / Virginia Beach

Virginia Beach house

5 9 7 nights min

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

Price per night from

$584

Price per night from

$584

Distance approx 16.8 km from Chesapeake Show on Map

37

The Brownley Beach Cottage

Virginia / Virginia Beach

Virginia Beach house

5 12 7 nights min

  • 5 bedrooms
  • sleeps 12
  • 7 nights min
  • Child Friendly
  • Car not necessary
  • Pet Friendly

Price per night from

$609

Responds fast!
avg. 3 hours 0 minutes

Price per night from

$609

Distance approx 17.67 km from Chesapeake Show on Map

21

Coakley

Virginia / Virginia Beach

Virginia Beach house

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Child Friendly
  • Car not necessary

Price per night from

$291

Responds fast!
avg. 3 hours 0 minutes

Price per night from

$291

Distance approx 16.77 km from Chesapeake Show on Map

46

Blue Lagoon

Virginia / Virginia Beach

Virginia Beach house

4 11 1 night min

  • 4 bedrooms
  • sleeps 11
  • 1 night min
  • Swimming pool
  • Car not necessary

Price per night from

$535

Responds fast!
avg. 3 hours 0 minutes

Price per night from

$535

Distance approx 19.17 km from Chesapeake Show on Map

9

108 B 75th Street, Up

Virginia / Virginia Beach

Virginia Beach house

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$179

Price per night from

$179

Distance approx 16.59 km from Chesapeake Show on Map

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

$85

Responds fast!
avg. 55 minutes

Price per night from

$85

Distance approx 18.72 km from Chesapeake Show on Map

33

4 Bedroom Ocean Side Home Ocean Front

Virginia / Virginia Beach

Virginia Beach house

4 7 7 nights min

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

Price per night from

$427

Price per night from

$427

Distance approx 19.63 km from Chesapeake Show on Map

(25) Excellent 

8

OCEANFRONT! North End With Fabulous Ocean View

Virginia / Virginia Beach

Virginia Beach cottage

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Ask about children
  • Air conditioning

Price per night from

$142

Price per night from

$142

Distance approx 17.6 km from Chesapeake Show on Map

(10) Very Good 

28

Lhasa Sunset

Virginia / Virginia Beach

Virginia Beach cottage

2 5 3 nights min

  • 2 bedrooms
  • sleeps 5
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.02 mi
  • Swimming pool

Price per night from

$175

Price per night from

$175

Distance approx 17.77 km from Chesapeake Show on Map

(25) Excellent 

24

Ocean View Condo, Penthouse, Walk to boardwalk

Virginia / Virginia Beach

Virginia Beach condo

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$128

Price per night from

$128