
Vacation rentals with beach access in Chesapeake
Find and book unique beach access rentals on Airbnb
Quick stats about vacation rentals with beach access in Chesapeake

Total vacation rentals
Explore 30 vacation rentals in Chesapeake

Nightly prices starting at
Chesapeake vacation rentals start at G$6,264 GYD per night before taxes and fees

Verified guest reviews
Over 1,420 verified reviews to help you choose

Family-friendly vacation rentals
10 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
30 of Chesapeake vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Chesapeake rentals

4.9 Average rating
Chesapeake stays are highly rated by guests—averaging 4.9 out of 5!

Nearby attractions
Chesapeake's top spots, include Chrysler Museum of Art, Nauticus, and Aerotheater
Top-rated beach access rentals in Chesapeake
Guests agree: these beach access rentals are highly rated for location, cleanliness, and more.

Peaceful beach @Courtyard Cottage Pets Allowed
Escape the crowds and commercial beach resorts. At Courtyard Cottage, you'll enjoy the exact opposite—a peaceful beachfront retreat where a short walk over the sand dunes leads to a quiet, uncrowded beach, perfect for relaxing and unwinding. Proud Superhosts for over four years, we're dedicated to making your stay comfortable, relaxing, and memorable. The host, Richard, lives in a detached garage apartment on the property, allowing guests to enjoy complete privacy in their own accommodations.
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Charming Home by the Sea, a block from the beach!
Single family home steps from the beach. Parking for vehicles including garage. Outdoor/indoor dining areas. Gas grill & fully equipped kitchen with cooking essentials for stay at home meals. 3 bedrooms sleeps 8. Can accommodate additional guests for an up charge with air mattress and sheets provided. Pets welcome! Hardwood flooring and central AC/heat throughout. Walking distance to restaurants in the local area. 15 minutes to Norfolk Naval Station, 10 mins to Airport, 20 mins to VB boardwalk.
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Pet Friendly Beach King Bed
Welcome to Your Vibrant Beach Hideaway! Escape to your own slice of paradise in this vibrant 900 sq. ft. 1950s beach bungalow, just 1 mile from Ocean View Beach. Enjoy a peaceful fenced backyard, fire pit, and grill—perfect after a day in the sun. Skip the crowds of VA Beach Oceanfront and unwind in style. With bold design, modern comforts, and beachy charm, this cozy retreat offers the perfect mix of privacy and convenience. Norfolk is a military town you may experience the sound of aircraft.
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Convenient Beach Home, Beach Access Across Street
Convenient beach house near peaceful East Beach. Beach access across the street. This wonderful home offers 3000 SF, 5 bedrooms, 3.5 bathrooms, 5 off-street parking spaces, tiles, hardwood and laminate floor throughout. Centrally located minutes to Norfolk Outlets Mall, Greenbrier Mall, Town Center, Botanical Garden, Norfolk Airport, and 15 miles from VA Beach ocean front. FOR ADDITIONAL INFORMATION, PLEASE CONTACT THE CO-HOST (Quan-616.340.3328) STR Zoning Permit Number: ZP24-00677
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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.
ViewWalkabilityAir conditioning

Artful Retreat with a Private Pool
Take a break and unwind at your private pool! Stylish, updated interior and a spacious backyard with pool and lounge area. Rinse off at the outdoor shower after a day at the beach and enjoy your private retreat! The Rudee Inlet is less than a block away with great restaurants, fishing, and water activities. A path along the Rudee Inlet leads to the beach and shops - a quick 4 block trip with the included bikes! Outdoor seating and gas fire pit added for the cooler months!
BeachWalkabilityBackyard

Villa Positano
This recently remodeled home build in 1933 and located on the Chesapeake Bay is a perfect place to vacation. Direct private beach access with a beautiful salt water pool to enjoy. Around the pool there is plenty of space for games, grilling, and relaxing. Use the newly renovated kitchen or visit one of several local restaurants serving fresh local seafood to satisfy your appetite. Williamsburg, Jamestown and Yorktown are only a short drive away.
BeachViewHot tub

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.
BeachWalkabilityCheckout

Purple Room- Rare Luxury Ste w/prkg - 1 of a kind!
Welcome to The Purple Room, where every guest is made to feel like royalty. More than an Airbnb, it’s a one-of-a-kind boutique retreat intentionally designed to create unforgettable memories. From the peaceful atmosphere and thoughtful touches to your private entrance and relaxing escape, every detail has been curated to help you unwind, recharge, and experience something truly special. Come discover The Purple Room experience. 💜
WalkabilityBeachAir conditioning

Beachfront stay with kayaks & paddleboards
Private beach access, Chesapeake Bay views, and kayaks and paddle boards included. This waterfront home is made for slow mornings, beach days, sunset evenings, and time on the water. My husband and I renovated the interior ourselves with comfort and simplicity in mind. The kitchen is stocked with the essentials, and towels, soap, shampoo, and conditioner are provided so you can settle in easily and enjoy the bay.
ViewWalkabilityGrill

*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.
BeachViewComfort

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.
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Popular amenities for Chesapeake beach access rentals
Apartment rentals with beach access

The Cottage at Sojourn: Buckroe - one bedroom
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Ocean Getaway
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King Bed WIFI - Work Space - 2 parking space B
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Fully Renovated Beach Loft Block Off OceanFront
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Vibe District, Atlantic Surf Park, VB Sports Ctr
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Historic 1910 Home in Oceanfront Area
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VB Oceanfront Studio Balcony,Beach,Boardwalk, Pool
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Beach Bungalow 4 blocks to the beach
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House rentals with beach access

10 min to Ocean View Beach: 20% Off Aug
BeachWalkabilityCheckout

Water Oaks at Chic's Beach
BeachWalkabilityQuiet

*NEW* Spacious/Standalone 4BR Beach House
BeachWalkabilityCleanliness

Oceanview Oasis- Close Beach, Game Rm & Volleyball
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Bay and Sea
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East Beach Bungalow, 1 block to the beach!
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Beach Ranch House Sleeps 9 and Pet Friendly
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Designer Beach House | Pool, Hot Tub, Walk to Sand
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Condo rentals with beach access

Beachfront Getaway, Pet Friendly, Mermaid Suite
BeachWalkabilityValue

Cher's Place @ The Beach
BeachWalkabilityComfort

Ocean Escape
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2 bedroom condo with oceanfront one block away!
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Tropical 2BR Condo Getaway 1 Block from the Beach!
BeachWalkabilityHospitality

3bd Sandbridge - Sunset Bay views! Newly Remodeled
BeachWalkabilityFamily

Oceanfront Penthouse
ViewWalkabilityLong stay

Cozy 1 Bd condo, 1 block from the beach!
BeachWalkabilityIndoor spaces
When is the best time to visit Chesapeake?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$20,880 GYD | G$18,792 GYD | G$20,671 GYD | G$25,474 GYD | G$25,056 GYD | G$20,045 GYD | G$18,792 GYD | G$18,792 GYD | G$18,792 GYD | G$14,407 GYD | G$18,792 GYD | G$18,792 GYD |
| 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 |
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- Rentals with beach access Virginia
- Rentals with beach access United States
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Corolla Beach
- Buckroe Beach
- Carova Beach
- Cape Charles Beachfront
- Water Country USA
- First Landing State Park
- Jamestown Settlement
- Outlook Beach
- Old Dominion University
- Norfolk Botanical Garden
- 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
- Hampton University





