
House holiday rentals in Chesapeake Beach
Find and book unique houses on Airbnb
Top-rated house rentals in Chesapeake Beach
Guests agree: These houses are highly rated for location, cleanliness and more.

Wooded Wonderland Miniature Golf Hot tub Pool
Make yourself at home! This property offers a warm and welcoming environment for guests, located in a quiet and established neighborhood in the middle of Portsmouth, VA. Guests should expect a clean space equipped with modern technology and appliances. Attractions aren’t too far; 41mi from Busch Gardens, 24 mi from Virginia Beach Ocean Front, 7.3 mi from Waterside District Norfolk, and 2.9 mi from Rivers Casino Portsmouth. Peaceful mornings and a comfortable stay awaits at Wooded Wonderland!

Oceanview Oasis- Close Beach, Game Rm & Volleyball
Take a load off and relax at the beach! This open concept home is walking distance from the beach (3-5 mins). It has everything you need to enjoy your stay. Enjoy the updated decor, multiple dining areas and plenty of comfortable beds to go around. There's 3 additional pull out beds and an extra mattress for additional sleeping arrangements. In the garage, you'll see plenty of games foosball, ping pong, darts. Enjoy a game of volleyball! Cook out on the grill or sit next to the firepit!

Beachfront 2 Dwellings EV charger
Blue Marlin is a private, beachfront home on the Chesapeake Bay in Hampton, VA! The property features two separate dwellings. All four bedrooms, including the fourth bedroom located in the second dwelling, are on the second floor and require climbing stairs. Therefore, this home may not be suitable for guests with mobility difficulties. Nestled within 30 miles of Busch Gardens, Colonial Williamsburg, and Virginia Beach, our location offers the perfect blend of relaxation and adventure.

Play by the Bay 1 MIN TO WATER
LESS THAN 1 MIN WALK TO WATERS EDGE. Fantastic beach home with 3 bdrms, 3 baths, Living room-dining rm combo with vaulted ceilings, kitchen, TV in 4 rooms, Wi-Fi, large deck with natural gas Weber grill, Washer-dryer. Great water views while you are relaxing on the deck. Many amenities! Just bring your bathing suit. Our guests have all said they love this place! Very close to many wedding venues, restaurants, state park, oceanfront boardwalk is closeby, military bases, etc.

THE POINT! Private waterfront Oasis!
Enjoy breath taking views & a fully equipped home w/ many amenities. Looking for a private & intimate experience of quality time & a relaxing retreat w/ nature & ample space to spread out, this is IT! Convenient to VB Oceanfront, Downtown Norfolk, Rivers Casino, Waterside & a host of popular attractions. Wheelchair accessible, Tesla charging stations 3 minutes away, perfect family/friends group trips, 12 minutes from Carnival Cruise Port. Bring your fishing poles!

Stylish Beach House, Hot Tub, Pet Friendly
Welcome to your coastal oasis of relaxation & fun. Enjoy beach fun, hot tub & games in a modern open concept living space. This stylish, pet friendly home away from home is perfect for families. It's 1.5 blocks from the beach. This charming SFH offers 2 bedrooms, loft, chef's kitchen, game room, spacious backyard with deck, hot tub, fire pit, BBQ grill, & volleyball/badminton court. It's centrally located near VA Beach, Williamsburg, & Downtown Norfolk.

The Cozy Beach House
We keep it simple here in this small, cozy, clean, and charming, home. House is great for 1 or 2 maybe 3 people. A 10 minute walk, to a public access, that takes you straight to the beach. Golf cart available for use . There are a few public parking spaces. 10 minutes to Norfolk International Airport. The Oceanview Pier is a great place to fish and have dinner and is only 3 miles away. Come and enjoy! There is also a NEW CASINO only 20 minutes away.

Cozy 3BD Beachfront | Foosball & Yard Games w/ BBQ
Escape to our charming Airbnb, just steps from the beach! Perfect for groups up to 8, our home offers ultra-fast 1Gbps fiber internet, a dedicated workspace, and delightful amenities including a SCA-approved coffee maker, a grinder, and fun games like a giant Connect 4 and Foosball. Enjoy the outdoors with our two patios and a BBQ grill. With numerous local restaurants nearby, it’s the ideal getaway for both relaxation and adventure.

3BR Mid-Century Modern Home • Near Airport
Welcome to our beautifully updated 3-bed, 2-bath home in Norfolk. Featuring a spacious layout with cozy beds, it’s ideal for families or groups. Enjoy a gourmet kitchen, a huge dining space, Wi-Fi, a washer and dryer, and all the amenities needed for a relaxing stay. Located next to Norfolk Airport and the Botanic Gardens, you’ll have easy access to all of Hampton Roads. Book your extended getaway today!

*Escape to the Tangerine Dream*
**ESCAPE TO THE TANGERINE DREAM** in this stunning beachfront oasis, located just steps away from the sandy shores of Captain's Quarters Park, this 3 bedroom/2 bath home offers the perfect blend of luxury and relaxation. Step inside to the open concept living area which boasts breathtaking views from two balconies, perfect for enjoying your morning coffee or watching the sunset over the ocean.

10 min to Ocean View Beach: 20% Off Aug
Welcome to our charming 3-bedroom retreat nestled near the lake and Ocean View beach, just a short 10-minute drive away. Our property has an outdoor patio with firepit and balcony deck for alfresco dining area. Our Volleyball net in the large backyard is also available for use. This cozy haven is designed for comfort and entertainment, with thoughtful touches to make your stay truly memorable.

Cozy beach cottage! One block to the beach!
Beach cottage! Dogs sleep for free! One block to the beach. 3 bedroom. 1 bath. 1 king, 1 queen and 2 twin beds. Large deck with outdoor seating and grill! One block from Karla’s Beach House (brunch and lunch). One block from Jessy’s Taqueria. About a mile from Cova Brewing Co. (Brewery and Coffee) and East Beach Farmer’s Market (Saturdays from 9-12). Up to 2 dogs allowed.
Popular amenities for Chesapeake Beach house rentals
House rentals with a pool

Perfect Getaway!

Designer Beach House | Pool, Hot Tub, Walk to Sand

Gorgeous Vacation House

Artful Retreat with a Private Pool

Ocean Pearl- Canal View and Minutes to the beach

4BD home w/ game room & pool near Langley & PTC!

Condo with pool & beach access!

The Great River Escape *Hot Tub!
Weekly house rentals

Historic Gem - Walk to Dining, Ferry & Waterfront

One block from the Beach

@Whit’s End? Come in and Relax

Beach Hideaway 2 bdr/2bth- Pet friendly!

Bay and Sea

Charming Home by the Sea, a block from the beach!

Norfolk Beach Bungalow | Pet-Friendly + Deck

Dog-Friendly Norfolk Cottage Near Ocean View Beach
Private house rentals

Tiny Home In Buckroe Beach

☼ Coastal Cottage- 5 min walk to beach | parking ☼

Seize the Bay

Beach Bungalow • Navy Base • Quiet St • Dogs OK

Sandy Serenity - On Beach- No Pets or Cleaning Fee

Casa del Pez • Bright Coastal Home Walk to Beach

Private Beachfront Modern Villa: Outdoor Shower!

Eden Lake House Cape Charles
Destinations to explore
- New York Holiday rentals
- Philadelphia Holiday rentals
- Washington Holiday rentals
- Myrtle Beach Holiday rentals
- Charlotte Holiday rentals
- Ocean City Holiday rentals
- North Myrtle Beach Holiday rentals
- Virginia Beach Holiday rentals
- Raleigh Holiday rentals
- Jersey City Holiday rentals
- Wilmington Holiday rentals
- Newark Holiday rentals
- Townhouse rentals Chesapeake Beach
- Rentals with beach access Chesapeake Beach
- Beachfront rentals Chesapeake Beach
- Apartment rentals Chesapeake Beach
- Pet-friendly rentals Chesapeake Beach
- Rentals with pools Chesapeake Beach
- Waterfront rentals Chesapeake Beach
- Hotel rooms Chesapeake Beach
- Family-friendly rentals Chesapeake Beach
- House rentals Virginia Beach
- House rentals Virginia
- House rentals United States
- Virginia Beach Oceanfront
- Chesapeake Bay
- Busch Gardens Williamsburg
- Corolla Beach
- Buckroe Beach
- Cape Charles Beachfront
- Carova Beach
- Water Country USA
- First Landing State Park
- Jamestown Settlement
- Outlook Beach
- Norfolk Botanical Garden
- Old Dominion University
- Regent University
- First Landing Beach
- Neptune's Park
- Colonial Williamsburg's Merchants Square
- Currituck Beach Lighthouse
- The Mariners' Museum
- The Military Aviation Museum
- Back Bay National Wildlife Refuge-N
- Town Point Park
- Nauticus
- Chrysler Museum of Art





