
Vacation rentals in Chesapeake Beach
Find and book unique accommodations on Airbnb
Top-rated vacation rentals in Chesapeake Beach
Guests agree: these stays are highly rated for location, cleanliness, and more.

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.

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.

Beautiful Cottage Waterfront Near Downtown Norfolk
A Beautiful Secluded Paradise! We respond quickly This spacious Non-Smoking cozy cottage has a great view of the Elizabeth River. It's 5 miles from downtown Norfolk and a 5 minute walk to a lightrail stop nearby. A day pass is $4.50 including a ferry to Portsmouth. Great amenities Renovated interior Beautiful Fireplace New floor/fully equipped kitchen Fresh organic eggs/yogurt/snacks/juice/coffee included WiFi-CableTV/HBO Bluetooth sound bar Luxury linens New waterview sunroom Washer/dryer

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.

Carriage House at the Historic Church Point Manor
Relax in the luxurious Carriage House: a 3-bedroom French-country style retreat at the historic Church Point Manor (circa 1860). Restored in 2021 with modern amenities, the Carriage House features a king bedroom and two queen bedrooms, each with its own private, full bathroom. Enjoy our private nature trail, tennis court, and lush gardens. The Manor has hosted some of Virginia Beach’s most VIP guests, including President Obama, and is also listed on the city's Historic Register.

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.

Private Beach Access at The OV Beach House
Here at the OV Beach House, you have your own private access to the beach and STUNNING water views of the Chesapeake Bay. The sunrises and sunsets are incredible! My husband and I renovated the interior of the house this past year. We poured all of our love (and sweat) designing and crafting a home away from home with you in mind!! You'll find the kitchen stocked with all of the essentials. Towels, soap, shampoo, and conditioner are all provided.

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.

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!

Steps to Beach at Chics Beach! Sleeps 12 & Garage!
Experience the perfect blend of convenience and excitement at this beautiful 3 bedroom, 3 1/2 bath home in Virginia Beach. Featuring 3 king size beds and 2 full size beds, it’s ideal for a family getaway. Enjoy a fully stocked kitchen, Wi-Fi, Smart TV, and laundry. We are only a 20 second walk from the beach! Whether for a weekend or an extended stay, this home has it all!
Popular amenities for Chesapeake Beach vacation rentals
Chesapeake Beach beach vacation rentals

Life on a Sandbar right on Chesapeake Bay

VB. Oceanfront/ Boardwalk,Beach, Pool, Balcony

New Beach Home on the Chesapeake Bay

902C Poseidon’s Cottage: Sauna & Charm By The Sea

2BD+Den: BeachAccess| KingBedsI FencedYard| DogsOk

Exclusive Beachfront Home w/ 180° Views & Hot Tub!

A Block to Beach | 5 Beds, King Suite, Walkable

Quaint and Comfortable Buckroe Beach Getaway.
Other great vacation rentals in Chesapeake Beach

Beach House~Hot Tub~3 Min to Sand~HUGE Kitchen

Cozy Home Near Hospitals & Beach

Charming Single Family Home by the Chesapeake Bay

Beach Stay

2 king beds 2nd fl walk 2 Beach apt2

Peninsula Suite on the Lynnhaven River

Ocean Bungalo-WiFi, fire pit, beach, pet friendly

This inviting 3-bedroom ranch perfect for families
Destinations to explore
- New York Vacation rentals
- Washington Vacation rentals
- East River Vacation rentals
- Myrtle Beach Vacation rentals
- Jersey Shore Vacation rentals
- Philadelphia Vacation rentals
- South Jersey Vacation rentals
- Mount Pocono Vacation rentals
- Outer Banks Vacation rentals
- Charlotte Vacation rentals
- Ocean City Vacation rentals
- Jersey City Vacation rentals
- Family-friendly rentals Chesapeake Beach
- Rentals with a fireplace Chesapeake Beach
- Apartment rentals Chesapeake Beach
- Rentals with outdoor seating Chesapeake Beach
- Rentals with beach access Chesapeake Beach
- Fitness-friendly rentals Chesapeake Beach
- Rentals with a patio Chesapeake Beach
- House rentals Chesapeake Beach
- Rentals with a washer and dryer Chesapeake Beach
- Hotel rentals Chesapeake Beach
- Beachfront rentals Chesapeake Beach
- Waterfront rentals Chesapeake Beach
- Townhouse rentals Chesapeake Beach
- Pet-friendly rentals Chesapeake Beach
- Rentals with pools Chesapeake Beach
- Chesapeake Bay
- Virginia Beach Oceanfront
- Carova Beach
- Busch Gardens Williamsburg
- Corolla Beach
- Buckroe Beach
- Water Country USA
- First Landing State Park
- Haven Beach
- Buckroe Beach and Park
- Grandview Beach
- Jamestown Settlement
- Bethel Beach
- Outlook Beach
- Kiptopeke Beach
- Ocean Breeze Waterpark
- Norfolk Botanical Garden
- Virginia Beach National Golf Club
- Golden Horseshoe Golf Club
- Chrysler Museum of Art
- Cape Charles Beachfront
- James River Country Club
- Wilkins Beach
- Little Creek Beach