
Condo holiday rentals in Chesapeake
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Top-rated condo rentals in Chesapeake
Guests agree: These condos are highly rated for location, cleanliness and more.

Tropical 2BR Condo Getaway 1 Block from the Beach!
Unwind at this gorgeous fully renovated getaway for your family and friends! This two bedroom, one bath beach home is one block from the ocean. This unit accommodates up to 4 adults. Each room is equipped with a smart TV and internet is provided. Our kitchen provides refrigerator, microwave, oven, dishwasher, toaster, Keurig, dishes, cutlery, bowls, pots and pans, and much more! Steps away from shopping and restaurants! This highly sought after vacation spot really is a home away from home.

Ocean & Bay Views - Local Family Owned & Operated
Just steps away from the sand, "Carolina on My Mind" is a 2b/2ba oceanside condo at the exclusive Sanctuary at False Cape, the only Oceanfront complex at Sandbridge in Virginia Beach. You'll enjoy a private patio with both Ocean and Bay views and you'll have access to all the exclusive amenities of the complex. The condo features a large open-concept living space and a fully equipped gourmet kitchen. The master has a king bed, the second bedroom has king bed w/ twin loft. Queen sleeper sofa.

Ocean Escape
Ocean Escape, 4th floor condo in the luxuriously upscale Sanctuary Resort at False Cape in Virginia Beach, Virginia, breathtaking views of both the Atlantic Ocean and Back Bay and is a leisurely 100 step stroll to the beautiful beach and surf. Beach chairs, coolers, umbrellas, sand toys for the kids, boogie boards and two beach cruiser bikes. Community pool area, complete with Jacuzzi tub, lounge furniture, and stainless steel gas grills. The elevator is just across from dedicated parking spot.

Luxury Riverfront Condo w/ sunrise & sunset views
Luxury One Bedroom Condo with stunning views of sunrises and sunsets overlooking the James River. Perfect for a romantic getaway or a small family adventure, you can sit on the private balcony and enjoy the serene views of the river and the marina, or venture out for kayaking, jet ski, pontoon boat, Busch Gardens, historic Colonial Williamsburg, wineries, award winning golf courses and restaurants, spa and so much more. Come and experience an unforgettable vacation while making many memories.

Beach Condo Block Off Boardwalk
Come enjoy everything Virginia Beach has to offer. Our condo has all of the comforts of home and accommodates 4 adults or perfect for families. Bedroom has a king size bed and living room has sofa that pulls out into a full size sofa bed. TVs in both rooms. The Boardwalk, Shopping, Restaurants, Amusement parks, and many more activities are all within walking distance. There is plenty to do and you can walk to the beach in 3 minutes or less! Come have a relaxing and fun vacation at the beach.

2 bedroom condo with oceanfront one block away!
Come enjoy everything Virginia Beach has to offer. Our cozy condo has all of the comforts of home and is perfect for families and accommodates 6 adults. Bedroom 1 has a king size bed w/TV, bedroom 2 has a queen size bed w/TV and the living room has a sofa that pulls out into a full size sofa bed w/TV. The Boardwalk, Shopping, Restaurants, and many more activities are all within walking distance. There is plenty to do for the whole family. Come have a relaxing and fun vacation at the beach!

Oceanfront Gem VaB Studio Exceptional Views
Newly renovated modern studio condo, owners personal getaway now open to guests. This corner unit, the largest and most private in Oceans ll Condominium complex, is on the 3rd floor and offers beautiful, expansive views at both sunrise and sunset. Just off the boardwalk with community pool, this unit sleeps three. Right on the oceanfront, you won't find a more peaceful getaway! Beach chairs and towels provided. Please note: due to the open layout of the building, there is no elevator.

Spacious Captain’s Beach Suite Near Rudee Inlet
Location, Location, location! This spacious beautifully decorated 2-bedroom (each with ensuite baths) condo is near Rudee Inlet and all oceanfront activities. Walk across the street & relax on the beach, dine at great restaurants, walk under the bridge next to the city parking lot to enjoy all the water activities that originate from Rudee Inlet (i.e. Dolphin/Whale Watching Tours, Sunset cocktails), or relax on the balcony. Inquire about downstairs guest suite (additional charge)

Cozy & Fun Hampton Condo ~ WIFI & W/D!
Step inside our stylish and cozy space, thoughtfully decorated to make you feel right at home. The fully equipped kitchen has everything you need to cook and dine with ease, while blazing fast WiFi (200 Mbps) keeps you connected for work or entertainment. Enjoy the added convenience of an in-unit washer and dryer, making longer stays effortless. Relax in a peaceful setting while still being close to everything Hampton has to offer.

2 Bedroom Condo ONE Block from the Oceanfront
Come enjoy a Virginia Beach vacation ONE block from the oceanfront and boardwalk. Our 2 bedroom condo accommodates 4 adults and is also perfect for families. Bedroom 1 has a queen size bed and bedroom 2 has a king size bed. There is also a pull out sofa bed in the living room. The Boardwalk, Shopping, Restaurants, Amusement parks, and many more activities are all within walking distance. There is plenty to do for the whole family.

Walk to beach lovely 2/2 in "Kingsmill on James"
Lovely, quiet, large ground floor 2 bdrm 2 full bath condo in "Kingsmill on the James". Beautiful tree and Audubon bird sanctuaries, trails. Condo backs to greenbelt, within walking distance to Kingsmill's beach, spa, marina, Café. **please note condo is in "Kingsmill on the James", not Kingsmill Resort...there's spa and beach access, for dogs too, but not pool... to use pool and resort, please book directly through the resort

*Mid/Long Term Rental* Cozy Home at Mary Roberts
Bring the whole family to this great place with lots of room for fun. Less than 10 minutes away from Fort Eustis Military Base. Less than 15 min away from Newport News Airport, Christopher Newport University, and plenty of shopping and dining. Short drive to Williamsburg with shopping at the outlet mall, dining and entertainment for the family at Busch Gardens and Water Country USA theme parks.
Popular amenities for Chesapeake condo rentals
Weekly condo rentals

Sandbridge Beach - DeepSeaSide Retreat

1 Block to Oceanfront & Boardwalk

Kingsmill Resort - How do you Romance?

3 Bedroom Suite in Historic Williamsburg!

SeaRenity Now! @ Oceanfront

NEW Updated Oceanfront 3bd 2bth / Beachfront /Pool

OBC - 2BR/2BA Suite - City View

Back Bay Breeze
Pet-friendly condo rentals

2 bdr: Steps to Sand, Dog-Friendly!

Beachfront Getaway, Pet Friendly, Mermaid Suite

Ocean Bliss: Cozy Apt Retreat(D)

Toes In The Sand! 2 Bed 2 Bath and Dog Friendly

*New*OceansideCondo PetsOK Pool GameRoom No Stairs

Oyster & Pearl Beautiful New Single Level Condo

Wonderful & tranquil beach retreat: 2BR/2BA Condo.

The White Pearl A Modern 3 Bed w/Private Hot Tub!
Condo rentals with a pool

Beach Please! 2 bedroom Single Level

2BD/2BA Villa across Currituck Beach Lighthouse

Oceanfront, beach, boardwalk, fun, dolphin, sunris

Paradise at the Beach

Coastal Beach condo-amazing view and indoor pool

Historic Powhatan resort 2 bdrm

1br Colonial in Williamsburg -Fun by Busch Gardens

Seas The Day of Virginia Beach
When is the best time to visit Chesapeake?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $190 NZD | $190 NZD | $189 NZD | $185 NZD | $182 NZD | $176 NZD | $216 NZD | $225 NZD | $206 NZD | $216 NZD | $216 NZD | $192 NZD |
| Avg. temp | 6°C | 7°C | 10°C | 16°C | 20°C | 25°C | 27°C | 26°C | 23°C | 18°C | 12°C | 8°C |
Quick stats about condo rentals in Chesapeake

Total holiday rentals
Explore 30 holiday rentals in Chesapeake

Nightly prices starting at
Chesapeake holiday rentals start at $86 NZD per night before taxes and fees

Verified guest reviews
Over 890 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
30 of Chesapeake holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Chesapeake rentals

4.7 Average rating
Chesapeake stays receive an average rating of 4.7 out of 5 from guests

Nearby attractions
Chesapeake's top spots, include Chrysler Museum of Art, Nauticus, and Cinema Cafe-Greenbrier Mall
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- Condo rentals Virginia
- Condo rentals United States
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Carova Beach
- Buckroe Beach
- Corolla Beach
- Water Country USA
- First Landing State Park
- Haven Beach
- Buckroe Beach and Park
- Grandview Beach
- Jamestown Settlement
- Bethel Beach
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- Kiptopeke Beach
- Ocean Breeze Waterpark
- Norfolk Botanical Garden
- Virginia Beach National Golf Club
- Chrysler Museum of Art
- Golden Horseshoe Golf Club
- Cape Charles Beachfront
- James River Country Club
- Wilkins Beach
- Little Creek Beach
- Red Wing Lake Golf Course