
Apartment holiday rentals in Chesapeake
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Top-rated apartment rentals in Chesapeake
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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.

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!

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! Dogs welcome
Step inside our stylish and cozy space in Hampton, thoughtfully decorated to make you feel right at home. Featuring 2 bedrooms with 1 king bed and 2 queens, this is the perfect getaway for families or couples. The fully equipped kitchen has everything you need to cook 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! Whether for a weekend or an extended stay, this home has it all!

Oceanfront Studio: Boardwalk, Beach, & Pool Views
Atlantic Ocean views from the comfort of an Oceanfront studio, perfect for beach-loving travelers. Reserved parking space just steps from the beach, indulge in the sand & surf without having to cross a street. Park your car, & let your toes sink into the sand for a truly relaxing stay. Equipped with Wi-Fi & Roku TV, you can stay connected throughout your visit. Take a refreshing dip in the saltwater pool or lounge on the lawn just steps from the beach.

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
Popular amenities for Chesapeake apartment rentals
Weekly apartment rentals

Sandbridge Beach - DeepSeaSide Retreat

21st Street Condo - 1 block from the Dome

Coastal Beach condo-amazing view and indoor pool

Boutique Oceanfront Condo - Boardwalk & Top Dining

Lovely Beachfront 3-Bedroom Condo

Prime Location: Steps to Beach & Attractions

Trendy 2024 Seaside Retreat

WOW Location! Beach Paradise on Boardwalk w/Pool
Pet-friendly apartment rentals

Welcome to Waves of Fun Single Level, Dog Friendly

2 bdr: Steps to Sand, Dog-Friendly!

Beachfront Getaway, Pet Friendly, Mermaid Suite

OceansideLuxuryCondo*Walk2Beach*Pool*Pets*NoStairs

Ocean Bliss: Cozy Apt Retreat(D)

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

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

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

1BR / Boardwalk Location / Hot Tub / Heated Indoor

The Historic Powhatan 2 bdrm

Good Vibes at the Beach

2BD/2BA Villa across Currituck Beach Lighthouse

Oceanfront, beach, boardwalk, fun, dolphin, sunris

Oceanfront - Balcony Views - Walk to Beach & Shops

Beach Studio - Oceanside, Pool, Boardwalk, Bikes

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 | € 93 | € 93 | € 93 | € 91 | € 89 | € 87 | € 86 | € 87 | € 93 | € 94 | € 106 | € 94 |
| 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 apartment rentals in Chesapeake

Total holiday rentals
Explore 30 holiday rentals in Chesapeake

Nightly prices starting at
Chesapeake holiday rentals start at € 42 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 & child-friendly amenities

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
30 of Chesapeake holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi 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 Cinemark Chesapeake Square
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- Apartment 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
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- Buckroe Beach
- Jamestown Settlement
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- Chrysler Museum of Art
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- Red Wing Lake Golf Course
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