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

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.

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)

3bd Sandbridge - Sunset Bay views!
A stone's throw from the sand and water, this is a 3bed-2bath luxury condo in the exclusive Sanctuary at False Cape, the only Oceanfront complex at Sandbridge in Virginia Beach. Two huge private patios with scenic views of the Back Bay await you! Inside, there is space aplenty with a open-space concept living area, a fully-stocked gourmet kitchen, & 3 separate bedrooms with sleeping for 8! Free access to all condo amenities, including 3 pools! Your beach vacation awaits!

VB Condo,Boardwalk/Oceanfront,Beach, Pool,Kitchen
Nestled on the desirable north end of the boardwalk, close to the area’s best attractions, the top restaurants and bars. Just steps to the boardwalk, beach and ocean. Enjoy a nice meal or a early morning cup of coffee while enjoying a beautiful view of the Atlantic Ocean. Our studio includes a reserved parking space, saltwater pool, large BBQ deck area and a lawn on the beach. This small oceanfront complex is a great place for couples or a small 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 apartment rentals
Weekly apartment rentals

Private Luxe Beach Condo

Sandbridge Beach - DeepSeaSide Retreat

The Port - Large condo on Mason Avenue!

1 Block to Oceanfront & Boardwalk

SeaRenity Now! @ Oceanfront

OBC - 2BR/2BA Suite - City View

Beach Studio - Oceanside, Pool, Boardwalk, Bikes

Oceanfront Boardwalk Condo | Walk to Top Dining
Pet-friendly apartment rentals

2 bdr: Steps to Sand, Dog-Friendly!

Beachfront Getaway, Pet Friendly, Mermaid Suite

Cozy & Fun Hampton Condo ~ WIFI & W/D!

Ocean Bliss: Cozy Apt Retreat(D)

Oyster & Pearl Beautiful New Single Level Condo

*New*OceansideCondo PetsOK Pool GameRoom No Stairs

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

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

Beach Please! 2 bedroom Single Level

Good Vibes at the Beach

Wyndham Kingsgate, 2 BR Deluxe

Beach Quarters Resort- Oceanfront 1 bdrm sleeps 6

Paradise at the Beach

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 | £84 | £84 | £83 | £81 | £80 | £78 | £95 | £99 | £90 | £95 | £95 | £84 |
| 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 £38 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 Cinema Cafe-Greenbrier Mall
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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
- 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