Vacation rentals in Chesapeake Beach

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Top-rated vacation rentals in Chesapeake Beach

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Guest favorite

Cottage in Virginia Beach

4.98 out of 5 average rating, 139 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.

Dec 16 – 23

G$58,978 GYD per night

Guest favorite

Guest suite in Virginia Beach

4.97 out of 5 average rating, 233 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$21,731 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.

May 31 – Jun 7

G$109,884 GYD per night

Guest favorite

Guesthouse in Norfolk

4.98 out of 5 average rating, 552 reviews

Private Guesthouse, Ghent/Downtown near ODU, EVMS

Legally licensed and permitted with the City of Norfolk! We did it right here! European-style guesthouse between Ghent and the Heart of Downtown. Walking access to many restaurants and hotspots, and across from “The Tide” light rail, and YMCA, Chrysler Museum of Art, Granby St, Colley Ave, EVMS, Town Point Park! 15-min from the ocean. FREE PRIVATE PARKING: designated driveway parking spot; Kitchenette includes– cooktop, sink, microwave, coffee, fridge; Wifi, separate HVAC, bath, FREE laundry.

Dec 3 – 10

G$26,980 GYD per night

Guest favorite

Home in Virginia Beach

4.99 out of 5 average rating, 163 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.

Dec 11 – 18

G$66,112 GYD per night

Guest favorite

Guest suite in Virginia Beach

4.89 out of 5 average rating, 547 reviews

Quiet Neighborhood 7 Miles From the Beaches

Be sure to read about the pricing using both bedrooms below in 2nd paragraph. My house is in a quiet neighborhood by a creek of the Lynnhaven River 7 miles from the Oceanfront/Chesapeake Bay with easy access to the interstate and surrounding cities in Hampton Roads. Only minutes from Town Center and local malls. Your private area is the first level with your own private entrance, but no kitchen access. There is small microwave and a coffee machine available in your space.

Oct 7 – 14

G$18,714 GYD per night

Guest favorite

Apartment in Virginia Beach

4.91 out of 5 average rating, 230 reviews

VB. Oceanfront/ Boardwalk,Beach, Pool, Balcony

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 on the balcony 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.

Feb 17 – 24

G$23,709 GYD per night

Guest favorite

Home in Virginia Beach

4.78 out of 5 average rating, 130 reviews

Quaint 2 Bedroom Cottage in Chicks Beach

2 bedroom 1 bathroom quaint cottage, walking distance only 2 blocks to the beach . The beach is great for families with children . This unit is connected to a 1 bedroom unit . Back yard has a single detached unit also . Great for small families. There is a fenced in front yard Back yard and laundry area is shared with guest suite next door. 2 Car max allowed $75 pet fee with pre approval. Starting June 25th 7 night min check in on Friday only !

Oct 1 – 8

G$35,045 GYD per night

Guest favorite

Home in Virginia Beach

4.9 out of 5 average rating, 206 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 28 – Dec 5

G$18,245 GYD per night

Guest favorite

Guesthouse in Chesapeake

4.98 out of 5 average rating, 214 reviews

Beautiful and Chic, One Room Studio Apartment

Chic private apartment is located in a quiet neighborhood at the end of the peninsula were the Indian River flows into the Elizabeth River. Centrally located, we are nestled in the heart of Hampton roads with Virginia Beach 1 mile to the east and Norfolk 1 mile to the north. Twenty minutes from everywhere you'll want to go: the airport, the beach, multiple shopping centers and several universities.

Jan 22 – 29

G$18,455 GYD per night

Guest favorite

Guest suite in Virginia Beach

4.93 out of 5 average rating, 184 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!

May 8 – 15

G$34,165 GYD per night

Guest favorite

Guest suite in Virginia Beach

4.91 out of 5 average rating, 205 reviews

Rest A’Shore-Virginia Beach

Quaint, quiet, one bedroom in-law suite with kitchenette and private entrance, with owners on premises. Guests have access to a large outdoor area, year-round hot tub, and parking on the premises. Located in the Great Neck corridor of Virginia Beach, just minutes to beach access, Virginia Beach General Hospital, Hwy 264 and plenty of shopping. An ideal stay for 1-2 adults.

Sep 10 – 17

G$26,450 GYD per night