
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.

2 Bedroom Beach Condo Block Off Boardwalk
Come enjoy everything Virginia Beach has to offer. Our newly renovated condo has all of the comforts of home and accommodates 6 adults or perfect for families. Bedroom 1 has a king size bed, bedroom 2 has a queen size bed, and Living room has sofa that pulls out into a full size sofa bed. TVs in all rooms. 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.

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.

Va Beach Oceanfront Studio, Boardwalk, Pool, Beach
Nestled in the heart of the coastal city of Virginia Beach where all of the area’s greatest attractions will be right at your fingertips. This coastal beach studio offers a space-maximizing layout which includes kitchenette with full size appliances. All on the desirable north end of the Virginia Beach boardwalk. This small oceanfront complex is one of a kind, a great place for couples or a small family. Enjoy an early morning cup of coffee while enjoying beautiful views of the Atlantic Ocean.

Spacious Captain’s Beach Suite Near Rudee Inlet
Take advantage of the seasonal rates plan a winter escape to the beach! Don’t miss all the wonderful holiday activities to include the holiday lights, holiday parade & more! 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.

2 Bedroom Condo One Block from the Oceanfront!
Our newly renovated 2 bedroom condo ONE block from the boardwalk accommodates 6 people and is also perfect for families. Each bedroom has a flat screen TV; one with a queen bed and the other with a king bed. There is also a pull out sofa bed in the living room along with a large TV. This is a 2nd floor unit with one designated parking spot. Plenty to do for the whole family with the beach, boardwalk, shopping, restaurants, amusement parks, and many more activities all within walking distance.

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!

Condo living just steps from the sand
Come see what Virginia Beach has to offer. Our newly renovated condo has all of the comforts of home and accommodates 4 adults or perfect for families of 5. Bedroom 1 has a queen size bed, bedroom 2 has 2 twin beds, and Living room has a sofa that folds out into a twin size bed. Cable TVs and WiFi, and a beautiful lake view. We are located on the second floor so you will have steps to walk up. 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.

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.

*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

Pacific Paradise

*New* Oceanside,Pool,Walk 2 the beach,No Stairs

Sandbridge Beach - DeepSeaSide Retreat

1 Block to Oceanfront & Boardwalk

Oceanfront Penthouse

Chic's Beach Rental and Fishing

Beach Studio - Oceanside, Pool, Boardwalk, Bikes

Boutique Oceanfront Condo - Boardwalk & Top Dining
Pet-friendly condo rentals

2 bdr: Steps to Sand, Dog-Friendly!

Ocean Bliss: Cozy Apt Retreat(D)

Enjoy Sea Life! Steps to the Beach!

Beachfront Getaway, Pet Friendly, Dolphin Suite

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

1b/1bath beach condo, unobstructed ocean views

The White Pearl A Modern 3 Bed w/Private Hot Tub!

Modern 2 bedroom, near beach and village
Condo rentals with a pool

1BR / Boardwalk Location / Hot Tub / Heated Indoor

Beach Please! 2 bedroom Single Level

Good Vibes at the Beach

Oyster & Pearl Beautiful New Single Level Condo

2BD/2BA Villa across Currituck Beach Lighthouse

Oceanfront, beach, boardwalk, fun, dolphin, sunris

Coastal Beach condo-amazing view and indoor pool

Paradise Cove
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 | $188 NZD | $184 NZD | $181 NZD | $176 NZD | $174 NZD | $177 NZD | $188 NZD | $191 NZD | $215 NZD | $191 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
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- 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
- Jamestown Settlement
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- Ocean Breeze Waterpark
- Norfolk Botanical Garden
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- Chrysler Museum of Art
- Cape Charles Beachfront
- Wilkins Beach
- James River Country Club
- Red Wing Lake Golf Course
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