House holiday rentals in Chesapeake Beach

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Top-rated house rentals in Chesapeake Beach

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

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Guest favourite

Home in Smithfield

4.97 out of 5 average rating, 205 reviews

Mason Manor - Downtown Smithfield next to WCP

Historic Smithfield 233 S Mason Street 2 Bedrooms 1 Bath Located in the heart of historic Smithfield boasts old world charm and character with a touch of today’s conveniences. The living room has gas fireplace for cool evenings & leads to dining area & updated fully equipped kitchen. The full bath is updated with jetted tub. Front porch swing for relaxing and back deck for entertainment. Windsor Castle Park just steps away. Located just around the corner from restaurants, shopping & more.

17–24 Apr

$156 SGD per night

Guest favourite

Home in Hampton

4.97 out of 5 average rating, 176 reviews

The Water's Edge

The "Water's Edge": a fantastic 100-year old waterfront home.Owner/host lives next door.(Please also check out their additional property, "Sun, Sea and Sand".) At The Water's Edge, the base rate includes 2 bedrooms and 2 full bathrooms.Additional bedrooms to accommodate additional guests may be available upon request for additional nightly fees. Great view of a Chesapeake Bay inlet.Private deck & dock. Modern appliances.Washer/dryer.Smart TVs.Free wifi.Keurig coffee maker.Fully equipped kitchen.

16–23 Sep

$236 SGD per night

Guest favourite

Home in Virginia Beach

4.96 out of 5 average rating, 112 reviews

Beach Cottage #2 19th - 3 Blocks from Beach

Welcome to ResortCottages19. Cozy authentic beach cottage with many original features centrally located on 19th street, the heart of the VIBE district; boardwalk, beach, convention and sports center within 3 blocks. Walk or bike to local coffee shops, breweries, and restaurants. Take in the live music from various venues along the boardwalk. Shop at the Old Beach Farmer's Market on Saturdays. Enjoy the privacy of your own deck and backyard with plenty of parking. Easy access to the interstate.

18–25 Feb

$201 SGD per night

Guest favourite

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.

30 Aug – 6 Sep

$724 SGD per night

Guest favourite

Home in Virginia Beach

4.88 out of 5 average rating, 115 reviews

Half house w/pool & new patio all to yourself

PLEASE READ TO THE END!!!!!! Our home is close to restaurants, parks, the resort oceanfront and art and culture. You’ll love our place because of the location and the ambiance. Our space is good for couples, solo adventurers, business travelers or small families. Please know that my wife and I live in the other half of the house. There is NO shared space!!! You have a private entrance with full & private access to all amenities. Our home is LGBTQ+ friendly because LOVE IS LOVE!

24 Apr – 1 May

$171 SGD per night

Superhost

Home in Norfolk

4.84 out of 5 average rating, 121 reviews

Cozy Coastal Home

Cozy Coastal Home is located on the second floor of a duplex. It is a quiet 2 Bedroom 1 bath less than a block away from the beach. Close to shops and restaurants in the Ocean View area of Norfolk. Fully furnished with refrigerator, stove, microwave & wine fridge. Come back from the beach, relax and take a chilled bottle of wine and enjoy. Enjoy the 55" smart TV or just take a short stroll to the local COVA Brewery or local restaurants. Food Lion is 1.1 miles and H-Teeter 3 miles

16–23 Dec

$111 SGD per night

Guest favourite

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.

9–16 Mar

$436 SGD per night

Guest favourite

Home in Hampton

4.95 out of 5 average rating, 123 reviews

1950s bungalow, 2-1/2 blocks from Buckroe Beach

Enjoy shore life on the Chesapeake Bay 2 blocks from Buckroe Beach Park. 1400 sq ft-- 2 bedrooms w/ Florida room, dining room, galley kitchen and sleeping porch w/ double daybed. Linens and beach gear provided. Fenced backyard. Wiifi package for up to 10 devices. Explore restaurants, antiques and a brewery/cidery in historic Phoebus. Fort Monroe's beach, moat, fishing dock, biking, playgrounds and a brewery, while nearby Grandview Nature Preserve is a remote wetland beach.

9–16 Dec

$184 SGD per night

Guest favourite

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 !

2–9 Oct

$231 SGD per night

Guest favourite

Home in Virginia Beach

4.9 out of 5 average rating, 208 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.

4–11 Dec

$120 SGD per night

Guest favourite

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.

25 Dec – 1 Jan

$358 SGD per night

Guest favourite

Home in Virginia Beach

4.94 out of 5 average rating, 144 reviews

Steps to Beach At Chics Beach! Spacious + Clean!

Welcome to our Beach House! Nestled right in the ♡ of Chic's Beach, you won't find a better location! A 20 second walk to the beach or you can enjoy the beach views from the multiple decks! 3 spacious bedrooms with 3 king sized beds, 2 full beds & 3.5 bathrooms. Perfect for big groups with a bathroom attached to each bedroom. Book your beach getaway now!

7–14 May

$415 SGD per night