
Apartment holiday rentals in Chesapeake
Find and book unique apartments on Airbnb
Top-rated apartment rentals in Chesapeake
Guests agree: these apartments are highly rated for location, cleanliness and more.

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.

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 & towels provided in season. Please note: due to the open layout of the building, there is no elevator.

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.

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 Oceanfront!
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!

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

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

WOW Location! Beach Paradise on Boardwalk w/Pool
Enjoy a piece of the Oceanfront with this gorgeous updated condo! Walk out your front door to the beach, pool, boardwalk, the historic Cavalier hotel, restaurants, shops and many entertainments on the beach! Newly renovated, this beachy North End paradise is the perfect getaway for a couple. One parking spot, deck area , a lawn on the beach with lounge chairs and coin operated laundry available on premises.

*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.

Beach Bungalow on the Boardwalk
If you are looking for convenience, comfort, and a pleasant experience than Beach Bungalow on the Boardwalk is for you. We are located only a block from the beach and boardwalk, and there is no shortage of restaurants and entertainment in the area. Our condo has been completely renovated with all new furniture. We know you will enjoy your experience and look forward to being your host.
Popular amenities for Chesapeake apartment rentals
Weekly apartment rentals

Sandbridge Beach - DeepSeaSide Retreat

21st Street Condo - 1 block from the Dome

CLEAN Spacious Getaway near Beaches/Attractions+

Coastal Beach condo-amazing view and indoor pool

Beach Studio - Oceanside, Pool, Boardwalk, Bikes

New! 4 BR/Oceanfront/Ocean & Bay views/3pools/Gym

Lovely Beachfront 3-Bedroom Condo

Prime Location: Steps to Beach & Attractions
Pet-friendly apartment rentals

2 bdr: Steps to Sand, Dog-Friendly!

Cozy & Fun Hampton Condo, WIFI & W/D! Dogs welcome

Beachfront Getaway, Pet Friendly, Mermaid Suite

OceansideLuxuryCondo*Walk2Beach*Pool*Pets*NoStairs

Ocean Bliss: Cozy Apt Retreat(D)

Off The Hook-Luxury Cottage - Heart of Corolla!

1b/1bath beach condo, unobstructed ocean views

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

Rendezvous, a Resort Condo in Cape Charles

Wyndham Kingsgate, 3 Bedroom Lockoff

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

Paradise at the Beach

Charming 1BR Colonial Condo at Wyndham Kingsgate
When is the best time to visit Chesapeake?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £82 | £82 | £81 | £79 | £78 | £76 | £75 | £76 | £81 | £76 | £80 | £77 |
| 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 40 holiday rentals in Chesapeake

Nightly prices starting at
Chesapeake holiday rentals start at £37 per night before taxes and fees

Verified guest reviews
Over 1,000 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

4.8 Average rating
Chesapeake stays are highly rated by guests – averaging 4.8 out of 5!

Nearby attractions
Chesapeake’s top spots include Chrysler Museum of Art, Nauticus and Cinemark Chesapeake Square
Destinations to explore
- New York City Holiday rentals
- Washington Holiday rentals
- Jersey Shore Holiday rentals
- Myrtle Beach Holiday rentals
- Philadelphia Holiday rentals
- South Jersey Holiday rentals
- Charlotte Holiday rentals
- Outer Banks Holiday rentals
- Cape Fear River Holiday rentals
- Jersey City Holiday rentals
- Rappahannock River Holiday rentals
- James River Holiday rentals
- Rentals with beach access Chesapeake
- Family-friendly rentals Chesapeake
- Rentals with a washing machine and dryer Chesapeake
- Cottage rentals Chesapeake
- Mansion rentals Chesapeake
- Private suite rentals Chesapeake
- Rentals with an EV charger Chesapeake
- Fitness-friendly rentals Chesapeake
- Rentals with a kayak Chesapeake
- House rentals Chesapeake
- Rentals with a hot tub Chesapeake
- Rentals with outdoor seating Chesapeake
- Rentals with a fireplace Chesapeake
- Rentals with breakfast Chesapeake
- Flat rentals Chesapeake
- Guest house rentals Chesapeake
- Townhouse rentals Chesapeake
- Beachfront rentals Chesapeake
- Beach house rentals Chesapeake
- Rentals with a firepit Chesapeake
- Waterfront rentals Chesapeake
- Rentals with a patio Chesapeake
- Pet-friendly rentals Chesapeake
- Rentals with pools Chesapeake
- Rentals with lake access Chesapeake
- Apartment rentals Virginia
- Apartment rentals United States
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Corolla Beach
- Carova Beach
- Water Country USA
- First Landing State Park
- Buckroe Beach
- Jamestown Settlement
- Cape Charles Beachfront
- Outlook Beach
- Norfolk Botanical Garden
- Ocean Breeze Waterpark
- Chrysler Museum of Art
- Virginia Living History Museum
- Old Dominion University
- Colonial Williamsburg's Merchants Square
- Virginia Zoological Park
- Nauticus
- Town Point Park
- First Landing Beach
- Currituck Beach Lighthouse
- Chrysler Hall
- Currituck Club
- USS Wisconsin (BB-64)




