Beachfront vacation rentals in Chesapeake Beach

Find and book unique beachfront homes on Airbnb

Top-rated beachfront rentals in Chesapeake Beach

Guests agree: these beachfront homes are highly rated for location, cleanliness, and more.

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Guest favorite

Cottage in Virginia Beach

4.98 out of 5 average rating, 140 reviews

The Seaglass Cottage by the Chesapeake Bay

The Seaglass Cottage by the Bay is located in the charming & beautiful neighborhood of Ocean Park just a quick 5-10 minutes stroll to the Chesapeake Bay beach. Our vintage beach house from the 1940’s has been fully remodeled and decorated in local art and beach décor. There are beautiful live oaks on the property and 3 private parking spaces for you and some first-come-first-serve street parking in front of the house. Easy load in with a ramp into the house and a mudroom for all your beach toys.

Sep 26 – Oct 3

G$56,453 GYD per night

Guest favorite

Guest suite in Virginia Beach

4.97 out of 5 average rating, 234 reviews

Scott's Garden Suite At The Crooked House

Just blocks from the beach, Scott's Garden Suite is nestled in the back yard of one of southside's desireable neighborhoods. With a spacious, queen bedroom & small reading/sleeping den, this little private hideaway is ideal for 2/3 adults or small family. Adjacent to the ViBe Art District/restaurants/shopping, it has kitchenette, 3/4 bath & outdoor LR with gas fire table. This is a ‘homeshare’ SRT & is within the in-resident owners’ home - separately entranced & private for convenience/safety.

Sep 16 – 23

G$23,925 GYD per night

Guest favorite

Apartment in Virginia Beach

4.91 out of 5 average rating, 466 reviews

Private apartment only 3 blocks from the Beach

Newly remodeled, super clean one bedroom (in-law) apartment, approx. 375 sf. Three blocks from the beach 7-10 min walk. Covered deck, backyard on water to watch ducks, herons, fish. Concrete benches and firepit near the water. Walking distance to the ocean, boardwalk, Rudee Inlet, dining and entertainment. Hardwood floors, queen size bed, 'pack n play', kitchenette with sink, refrigerator, microwave, Keurig coffee maker, toaster (no oven or stove) 500 mbps Wifi, internet tv. Futon-like couch.

Jan 17 – 24

G$27,979 GYD per night

Guest favorite

Home in Virginia Beach

4.8 out of 5 average rating, 137 reviews

Beach house for 10 people! 1 block to beach!

Welcome to Ocean Beach House! Nestled right in the heart of Chic's Beach. 3 bedroom 2.5 bath beach house with a large hangout spot in the back yard. Plenty of parking space. Less than a minute walk to the beach. PLEASE DO NOT BOOK this unit if you intend to play loud music or host a gathering. Strict Quiet hours 10pm-8am. By making this booking, you agree to forfeit a minimum of $2500 to deploy private security and/or law enforcement for immediate removal of you/your party from the premises.

Jun 23 – 30

G$109,946 GYD per night

Guest favorite

Home in Virginia Beach

4.99 out of 5 average rating, 164 reviews

Play by the bay beach house,

Fantastic beach home with 3 bdrms and 3 baths. Renovated Dec2020 Great views of the Chesapeake Bay from the LR and deck. Just steps away from the beach access. Updated with SS appliances. First floor has Living room-dining rm combo with vaulted ceilings, kitchen, bdrm and bathrm. Second floor has 2 bdrms and 2 private baths . TV in 4 rooms, Wi-Fi, large deck with natural gas Weber grill. Washer-dryer. ONLY ROOM FOR 2 REGULAR SIZE CARS/SUVS IN DRIVEWAY PLUS FREE ON STREET PARKING.

Oct 28 – Nov 4

G$66,150 GYD per night

Guest favorite

Cottage in Norfolk

4.98 out of 5 average rating, 174 reviews

Peaceful beach @Courtyard Cottage+No Cleaning Fee!

No congestion, crowds, or commercial big beach resorts here. Experience the exact opposite at Courtyard Cottage just steps away from a quiet and peaceful beach surrounded by sand dunes for a special getaway. A park across the street provides playgrounds and pet-friendly walks and is the home to a local farmers market, 9 a.m. to noon. Saturdays, May 4 through Nov. 23. A past guest wrote "This place brings beach home nostalgia. peace, and a time to relax".

Feb 21 – 28

G$48,322 GYD per night

Guest favorite

Condo in Virginia Beach

4.9 out of 5 average rating, 182 reviews

Va Beach Oceanfront Studio, Boardwalk, Pool, Beach

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.

Dec 8 – 15

G$31,141 GYD per night

Guest favorite

Cottage in Norfolk

4.97 out of 5 average rating, 201 reviews

Positano Villa

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.

Jan 4 – 11

G$76,472 GYD per night

Guest favorite

Guest suite in Norfolk

4.93 out of 5 average rating, 507 reviews

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

Sep 20 – 27

G$44,934 GYD per night

Guest favorite

Home in Virginia Beach

4.9 out of 5 average rating, 207 reviews

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.

Nov 29 – Dec 6

G$18,255 GYD per night

Guest favorite

Guest suite in Virginia Beach

4.94 out of 5 average rating, 186 reviews

Enjoy your little slice of heaven in Chics Beach!

4-5 min walk to Chic's beach. Avoid the crowds and live with the locals! Surrounded by amazing restaurants, bars, coffee shops, and even an urban winery. We are a convenient 15 min ride from the tourist Oceanfront but you will have plenty to do in our relaxed beach town. This is a guest apartment attached to my home .The motto of Chic's Beach is "No Bad Days". Come see for yourself!

Sep 7 – 14

G$40,397 GYD per night

Guest favorite

Home in Virginia Beach

4.95 out of 5 average rating, 106 reviews

Water Oaks at Chic's Beach

Bright, airy beach home across the street from the Chesapeake Bay beach, a quarter mile east of the Chesapeake Bay Bridge-Tunnel . . . 1600 sf, 3 br, 2.5 ba . . . eclectic residential neighborhood . . . diverse restaurants and a convenience store within easy walking distance . . . five-minute drive from more comprehensive shopping and fifteen minutes from VB oceanfront.

Dec 25 – Jan 1

G$54,236 GYD per night