Holiday houses in Chesapeake Beach

4.9 out of 5 average rating, 645 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 1st level with your own private entrance, but no kitchen. There is small microwave and a coffee machine in the unit , & a small fridge on the screened-in-porch.

Cottage in Virginia Beach

4.97 out of 5 average rating, 181 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.

4.94 out of 5 average rating, 115 reviews

Home in Portsmouth

Wooded Wonderland Miniature Golf Hot tub Pool

Make yourself at home! This property offers a warm and welcoming environment for guest, located in a quiet and established neighborhood in the middle of Portsmouth, VA. Guests should expect a clean space equipped with modern technology and appliances. Attractions aren’t too far; 41mi from Busch Gardens, 24 mi from Virginia Beach Ocean Front, 7.3 mi from Waterside District Norfolk, and 2.9 mi from Rivers Casino Portsmouth. Peaceful mornings and a comfortable stay awaits at Wooded Wonderland!

4.98 out of 5 average rating, 304 reviews

Home away from home~Private,quiet, mins to bay

Home away from home is a spacious, comfortable, and private apartment with 1 Queen bedroom, full bath w/ tub, living area, work space, and fully equipped kitchen. Conveniently and centrally located in historic neighborhood: 3 mins to bay, 15 mins to oceanfront. We are within 4 miles of Norfolk Premium Outlets and IKEA, and are within 5 miles to Virginia Wesleyan and 15 miles to ODU. Walk to local favorite restaurants (New River Tap House, The Rustic Spoon, 1608 Crafthouse, Comfy Belly).

Guest suite in Chesapeake

4.95 out of 5 average rating, 570 reviews

Sweet Suite!

Private attached MOTHER IN LAW suite (not the whole house) in a quiet neighborhood in the heart of Hampton Roads. We offer keyless entry and a private parking space, private pool and backyard grill area. All are welcome here, including pets. We ask that you tell us if you are bringing a pet(s) and I'll message you about the added pet fee. We are minutes away from all major attractions and less than 5 minutes from major highways. Our location gives you easy access to the Outer Banks.

4.97 out of 5 average rating, 116 reviews

Home in Cape Charles

Wander Cape Charles

A sanctuary, an oasis, a one of a kind experience communing with nature while lounging in civilized splendor—all are apt descriptions of this New York architect designed beach house on the shores of the Chesapeake Bay. Guests enjoy stunning waterfront views from a finished floor height of 36 feet. The Eastern Shore of Virginia is famous for its flat tidewaters, but this property is perched amongst unusual relic Sandhills, complete with pines, gum trees and vast sea and sunset vistas.

4.99 out of 5 average rating, 134 reviews

Cottage in Norfolk

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. Can accommodate up to 8 people.

4.84 out of 5 average rating, 112 reviews

Private Guest Suite Cozy Stay w/ Separate Entrance

Welcome to your own brand-new guest suite in Virginia Beach—just a quick drive to the beaches, Town Center, and all the best spots. Built in 2023 with full city permits, this sleek space is totally private, with its own exterior entrance and a peaceful vibe. Nestled on a quiet street in the popular Thalia neighborhood, it’s the perfect home base for beach days, nights out, or just unplugging in comfort. Relax, recharge, and enjoy VB like a local.

4.92 out of 5 average rating, 256 reviews

Home in Virginia Beach

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.

4.99 out of 5 average rating, 348 reviews

Guesthouse in Hampton

Sun Sea and Sand

Welcome to Sun Sea and Sand, a Caribbean theme in Hampton, Virginia. Sun, Sea and Sand is a beautiful, waterfront, second story, two-bedroom, one-bath guest house located on a private drive providing lots of privacy including your own private entrance as well as stairs leading from your private balcony directly to the waterfront. High-speed fiber-optic wifi and cable with blue ray player provided.

4.94 out of 5 average rating, 231 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!

4.87 out of 5 average rating, 338 reviews

Virginia Beach 2 King BR apt 100 feet from beach

A Two-King-Bedroom apartment is 100 feet from the beach. It is private and secluded. The in-law suite has a private entrance that is separated from the main house. You can watch the sunset while sitting on the beach. The apartment is pet-friendly. 15% discount·3-4-nights minimum 20% discount·5-nights minimum 20% discount·6-nights minimum 25% discount·Weekly (1 week) minimum

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Popular amenities for Chesapeake Beach holiday rentals

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Other great holiday rentals in Chesapeake Beach

4.98 out of 5 average rating, 265 reviews

Private room in Norfolk

Military - Active/Retired/Family at Cape Defoe B&B

ChristineRating, 5 stars2 weeks ago

I stayed at Mark’s place while visiting my daughter, who’s in the Navy, and it was the perfect spot for some peaceful downtime. Even though it’s a shared home, the bedroom and bathroom felt very private and exceptionally clean. I was comfortable the entire time and slept well. The house itself is like walking into an art installation—colorful, unexpected, and full of personality. You never quite know what light or feature will come to life next, which made it fun and memorable. Both hosts are clearly creative souls with a flair for design. The backyard was my favorite part—lush with plants, fountains, and statues, all backing up to the Chesapeake waters. At night, it turns into a magical light show with just the sounds of nature and water features. So peaceful and calming. They even had a little breakfast area set up with bakery items and coffee—such a thoughtful touch. I’d definitely stay again and recommend it to anyone looking for a one-of-a-kind and restful experience.

4.96 out of 5 average rating, 350 reviews

Home sharing with privacy

MarciRating, 5 starstoday

Diana’s Place is just a perfect spot. So clean, private, beautifully decorated and comfortable. I visited after a day at the beach and it was close by and had a great shower. It was quiet and had comfortable mattress and bedding. Thank you!

4.87 out of 5 average rating, 245 reviews

Private room in Norfolk

PRIVATE ROOM near EVMS ODU Ghent Base

LashandaRating, 5 stars3 weeks ago

The bed was everything !!!!! so comfy. Beautiful decor. Nice lighting. And the room was cool enough without the fan and not cold. It was really close to a really good breakfast spot call The Bird. I wasn't driving but I could walk there. It located by the water which is really after break I sat by the dock. Her house is peaceful I'm not a light sleeper but when ready for bed I like peace and quiet and I had just that. If I am headed back this way I will book here if available. I loved my stay.

4.91 out of 5 average rating, 111 reviews

Private room in Norfolk

Upstairs Private Room in Ocean View

AngelaRating, 5 stars2 weeks ago

We loved staying here. Her and her husband were very friendly along with their cat LEO!! We had the bathroom all to ourselves down the hall and we’re not ever bothered by them. We would stay there again in a heartbeat if we go out to Norfolk again. Totally great place to stay!!!

4.8 out of 5 average rating, 476 reviews

Zen East

RachelRating, 5 stars4 days ago

Checkin was easy and the location was quiet. Questions were answered timely and went beyond to mail something left behind for us. Will stay again and recommend to others.

5 out of 5 average rating, 494 reviews

TOP 1% AirBnB - Spirit Bear Lake Private, Peaceful

JulieRating, 5 stars5 days ago

We had a lovely stay! The apartment is beautifully designed and serene. My daughter and I enjoyed early morning paddles on the calm lake. Bob and Rhonda were helpful, kind and approachable. We look forward to staying here again!

4.92 out of 5 average rating, 146 reviews

Comfortable stay at Virginia Beach

LauraRating, 5 stars4 days ago

This was a perfect stay for a long weekend visiting family in the area. There is so much to do & see. The space is a comfortable quiet stay in Virginia Beach. It is about a 25 minute or so ride to the oceanfront/boardwalk & about 9 minutes to Chic's Beach. The mattress is very firm. Zoya was very proactive in making sure we had all the information upon arrival. We did not need anything throughout the duration of our stay and did not need to interact at all though I feel positive she would have been attentive. Thank you so much, Zoya!