
Holiday rentals with beach access in Chesapeake
Find and book unique rentals with beach access on Airbnb
Top-rated rentals with beach access in Chesapeake
Guests agree: these rentals with beach access are highly rated for location, cleanliness and more.

Just Steps Away to the Beach
Enjoy Nov. thru Feb. at Va. Bch--average day temp. in 60s and 50s. Just steps or bike through a nice area to the beach, restaurants, culture, The Dome, Convention Ctr & other activities. Take a 10-min. walk or bike to the beach (7 short blocks). No traffic or parking hassles! We are close to I264, several military bases & Hilltop Shopping area. This is a quiet neighborhood & convenient location. Perfect for couples & solo travelers. NO animals or pets allowed! NO children under 13 yrs. of age!

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.

Guesthouse at Vessel Farm & Winery, Waterfront
Just 5 miles from Cape Charles and 30 minutes from Virginia Beach, our contemporary Guesthouse gives you the peace and solitude characteristic of the Eastern Shore along with the convenience of being close to town. Our twenty acre waterfront farm, home to both a Vineyard and an Oyster Farm, has plenty of nearby walking or biking and a dock on a secluded arm of the Chesapeake Bay. Our farm is perfect for solo travelers, couples or small families looking for a memorable trip to the Eastern Shore.

Purple Room- Rare Luxury Ste w/prkg - 1 of a kind!
Welcome to The Purple Room, get ready for an AirBnB experience unlike any others. This one of a kind AirBnB not only offers a memorable staying experience, but will be a welcome end to an exciting day at the beach, dinner and drinks at a local restaurant or bar, or an adventurous day exploring all the culture and history the area has to offer. We are centrally located, offer free parking, wifi and kitchenette. We have local art, free wine and food samples. Come see what the excitement is about!

One block from the Beach
Stay at one of the highest rated homes in Willoughby Beach. It has everything you need to have a relaxing getaway. Enjoy the breezes of the Willoughby Bay on the back 2 decks, and the Chesapeake Bay on the front 2 decks. 500 ft walk to Chesapeake beach access, and an outdoor shower ready when you return. We have been hosting since 2018 and you can read our reviews to see that this property is our pride and joy. Let us show you what a five star experience is on Airbnb... Mandy and Kevin

Cozy Cottage - NEW hot tub, dogs OK, fenced yard
Welcome to Wayland Beach Cottage, your home away from home! Here are some of the things you can look forward to: - queen beds - smart TVs in each room - fully equipped kitchen & laundry room - fully fenced backyard - 6-person hot tub *new!* - outdoor seating under a pergola - 4-burner gas grill - long, private driveway - speedy Wi-Fi We're nearby to so many fun things to do, shop, and eat! Bring the family, see the sights, and come relax at Wayland Beach Cottage. We'd love to have you!

Spanish Style Casita • 2BR/2BA • Dogs Welcome
✨ Welcome to Casita on Granby! ✨ Enjoy a short drive to the beach (less than 2 miles, about 5 minutes), restaurants, grocery stores, and easy nearby highway access to downtown Norfolk, Virginia Beach, and Hampton! We LOVE pups! 🐶 Bring your 4-legged best friend along to bask in our fenced backyard. Must be pre-approved, and additional fees apply. Please read the house rules for additional info. Your perfect getaway is waiting at Casita on Granby. Book now for a stay you won’t forget!

Peaceful beach @Courtyard Cottage+No Cleaning Fee!
There is no congestion, crowds, or large commercial beach resorts here. Experience the exact opposite at Courtyard Cottage, steps away from a quiet, peaceful beach surrounded by sand dunes for a special getaway. A park across the street offers playgrounds and pet-friendly walks, and a local farmers' market opens from 9 a.m. to noon. Saturdays, May 4 - Nov 23. A past guest wrote, "This place brings beach home nostalgia, peace, and a time to relax". No parties, quiet hours after 10 pm.

Quiet East Beach Bungalow, 1 block to beach!
Brand new construction located exactly one block from the beautiful Chesapeake Bay at East Beach in Oceanview! A quick walk to the beach or Bay Oaks Park, this bungalow is perfect for relaxing getaways. Fireplace, patio, grill, spacious front porch, new appliances, washer/dryer, private off-street parking. A quick trip to the Naval Bases! Guests are provided with linens, towels, toiletries, and high speed internet(SmartTV). Additional rooms available case by case basis. Please ask.

Bungalow at the Bay
This wonderfully decorated home is the perfect spot for a beach getaway with the whole family. Inside you will find a spacious living room, kitchen, bathroom, and two guest rooms with one queen, and a full. Outside there is a backyard porch, perfect for socializing, and a sizable backyard protected by a fence that stretches the property! Free parking is available inside and outside the property. Beach access and free parking is located on 11th view street about a two-minute walk away!

Beachfront Exclusive Bay front Suite
This comfortable private beachfront suite with kitchenette has magnificent views of the sunrise and sunset that you can enjoy from your own private deck, with a 180 degree views of the beach front with easy access to the water's edge, just steps away. If you want to experience life on the beach this is as close as you can get. This suite represents our personalities and everything we love about living at the beach on the Chesapeake Bay

Quilted Quarters by the Bay with Private Entrance
Enjoy beach life, hiking and biking near the Chesapeake Bay in a spacious fully furnished studio with a private entrance and private bath in a very safe and quiet neighborhood with one dedicated parking space as well. Five minute walk to the beach and First Landing State Park with hiking, biking, running trails, locally owned restaurants, bars, shops, breweries, grocery, pharmacy, farmer's market and yoga studio.
Popular amenities for rentals with beach access in Chesapeake
Apartment rentals with beach access

Paradise in Williamsburg next to Busch Gardens

Three blocks from the Beach 2

2 Bedroom Duplex Getaway by the Beach

VA Beach Oceanfront Studio, Beach, Boardwalk, Pool

Relax & Enjoy 2 blocks to beach w/ pool

The Coastal Studio

TreeTopBeach Bungalow 4 blocks 6 min walk to beach

Oceanfront 2BR Luxury • Private Balcony
House rentals with beach access

New Beach Home on the Chesapeake Bay

10 min to Ocean View Beach: 20% Off Jan & Feb

Large 5BR in the Vibe District• Ideal for Groups

Quiet Stay near Bay. Walk to Oceanview access

Country Comfort Close to the Beaches

Play by the Bay 1 MIN TO WATER

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

Beachfront 2 Dwellings EV charger
Apartment rentals with beach access

Tropical 2BR Condo Getaway 1 Block from the Beach!

Cozy 1 Bd condo, 1 block from the beach!

Walk to beach lovely 2/2 in "Kingsmill on James"

Spacious Captain’s Beach Suite Near Rudee Inlet

Good Vibes at the Beach

Oceanfront Gem VaB Studio Exceptional Views

Oceanfront Studio: Boardwalk, Beach, & Pool Views

Oceanfront, beach, boardwalk, fun, dolphin, sunris
When is the best time to visit Chesapeake?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £37 | £42 | £36 | £51 | £68 | £67 | £67 | £67 | £67 | £43 | £51 | £35 |
| 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 holiday rentals with beach access in Chesapeake

Total holiday rentals
Explore 40 holiday rentals in Chesapeake

Nightly prices starting at
Chesapeake holiday rentals start at £22 per night before taxes and fees

Verified guest reviews
Over 1,950 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
30 properties have a dedicated workspace

Wifi availability
40 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
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- Rentals with beach access Virginia
- Rentals with beach access United States
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Carova Beach
- Buckroe Beach
- Corolla Beach
- Water Country USA
- First Landing State Park
- Haven Beach
- Buckroe Beach
- Jamestown Settlement
- Grandview Beach
- Bethel Beach
- Kiptopeke Beach
- Outlook Beach
- Norfolk Botanical Garden
- Ocean Breeze Waterpark
- Virginia Beach National Golf Club
- Golden Horseshoe Golf Club
- Chrysler Museum of Art
- Cape Charles Beachfront
- Wilkins Beach
- James River Country Club
- Red Wing Lake Golf Course
- Little Creek Beach




