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Beachfront holiday rental in Chesapeake

Find and book unique beachfront homes on Airbnb

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Popular amenities for Chesapeake beachfront rentals

Pet-friendly beachfront home rentals

Guest favourite
Home in Chic's Beach
4.96 out of 5 average rating, 132 reviews

Water Oaks at Chic's Beach

EmmaRating, 5 stars1 month ago
Tommy and Janet were very responsive! They were extremely friendly and went above and beyond to make our wedding weekend special. The house was a wonderful experience!
Top Guest favourite
Cottage in Bayview
4.97 out of 5 average rating, 249 reviews

Villa Positano

RhondaRating, 5 stars3 days ago
We had an amazing time. The house was perfect for us. We really enjoyed the pool and short walk to the beach. We could hear the ocean from the master suite. The upstairs deck had view of the water. Everything about our stay was perfect. The area was nice and was quiet and peaceful. We will definitely go back and stay longer next year. Thank you!!!
Guest favourite
Apartment in Bayview
5 out of 5 average rating, 7 reviews

LiveEOV: Beachcomber Two

PamRating, 5 stars2 weeks ago
The place was great it had everything that we needed it was walking distance to the beach
Superhost
Home in Virginia Beach
4.87 out of 5 average rating, 103 reviews

The Happy Place-Quiet, North End 1 block to ocean!

HaroldRating, 5 stars1 week ago
Our stay was fantastic! The location couldn't be better, just a stone's throw from the beach. The property itself was clean and well-stocked with everything we needed. Mary was prompt and helpful in addressing the one minor issue that came up. We highly recommend this spot for a worry-free beach getaway!
Guest favourite
Home in Buckroe Beach
4.96 out of 5 average rating, 80 reviews

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

KathleenRating, 5 stars2 weeks ago
I could not wait to write a review about our stay. So much so that we are not even home yet. We had a glorious week at Bay Bliss! Bliss is the perfect description. Anywhere in this beautiful home you can hear the waves of the ocean. There was nothing better than listening to that while falling asleep on the comfiest bed in the master bedroom. Hosts were extremely responsive, helpful with local recommendations and extremely friendly. I have stayed at lot of AirBnb’s and hotels. Honestly, I have never felt so at home and I felt that way from the second I walked in the door. We will definitely be back.
Guest favourite
Home in Norfolk
4.95 out of 5 average rating, 104 reviews

Gorgeous Vacation House

AlexisRating, 5 stars6 days ago
The house was super clean when we got there, the temperature of the house was great the entire stay. The pool was certainly clean, but since we went early, June the water was a little bit cold, but it felt really nice and refreshing honestly. There were three beach chairs and a wagon there that were helpful for traveling to the beach. There were available cups plate, utensils, and all the necessities that you would need, they even had shampoo and conditioner bottles there for us. We weren’t aware that there was a code to get into the house so instructions for check-in were a little bit unclear, but all I had to do is message and they responded. Overall, I would recommend staying here because even though the area surrounding isn’t the nicest, I felt safe the entire time at that house!
Guest favourite
Bungalow in East Ocean View
4.99 out of 5 average rating, 77 reviews

BaysideBungalow | 5 Beds, King Suite, Walkable

AnnRating, 5 stars2 weeks ago
Andria was an accommodating host who communicated and assisted to our needs. The home is beautiful and well stocked for a comfortable stay. Great location to restaurants and the beach within walking distance. Our dog loved the fenced in backyard. We cannot wait to book again!
Guest favourite
Cottage in Sandbridge
5 out of 5 average rating, 22 reviews

Epic Sunsets | Waterfront Cottage | Pet Friendly

CateRating, 5 stars3 days ago
This place was the most charming airbnb I have ever stayed in. Badria and Jay made every detail of our stay perfect with all of their extra touches, including saltwater taffy and a box of croissants, slippers and a lavender mask, and a fully stocked coffee station with syrups. We instantly felt at home and in vacation mode at their place and literally laid out on the dock the entire time. A perfect spot for kayaking, laying out in the sun, and I even brought out my mat and did some yoga on the dock. The views were unreal. The couch was so comfortable I accidentally fell asleep there the whole night and woke up to the gorgeous window views. Amazing hosts and location!

Beachfront home rentals with a pool

Superhost
Home in Virginia Beach
4.84 out of 5 average rating, 128 reviews

THE OLD BEACON 1 | Beach Living

HollyRating, 5 stars3 weeks ago
Beautiful home within walking distance to everything you need, especially the beach and restaurants. Clean home with cozy feel. My son never wanted to leave the beautiful pool at the property. Would recommended to families!!
Top Guest favourite
Bungalow in Sandbridge
5 out of 5 average rating, 23 reviews

Beach & Bay Stay at Sandbridge Beach this summer!

TerriRating, 5 stars1 week ago
The host was so informative and friendly. She gave us great tips on local restaurants and resources! She encouraged us to ask questions which was very kind as it was our first trip to Sandbridge. The unit was super clean and well-stocked ! Great windows made it a very light and bright vacation. Excellent bed/mattress and kitchen/living room furnishings. The deck/covered porch was great as well to watch sunsets. We will come back.
Top Guest favourite
Cottage in Sandbridge
5 out of 5 average rating, 100 reviews

Sanctuary on Sandpiper - Bayfront in Sandbridge

ChristineRating, 5 stars3 weeks ago
What a beautiful place to stay. The house is lovely, the back yard was packed full of entertainment: salt water pool, fire pit, corn hole, fishing in the canal and if that isn’t enough it’s a short walk to the beach. The sunrises on the beach and sunsets on the canal were spectacular. We were a family of 8 and there was plenty of room. Christina was very responsive when we reached out and she put together an amazing house manual that included everything you needed to know from A-Z. Couldn’t be happier!!!
Superhost
Condo in Sandbridge
4.92 out of 5 average rating, 131 reviews

Ocean & Bay Views - Local Family Owned & Operated

MarieRating, 5 stars5 days ago
We had a lovely stay at Crystal’s while in town for a graduation. Crystal was proactive with directions, recommendations, and instructions, and she responded quickly to questions. The place was nicely decorated, and well-stocked with kitchen gadgets, beach chairs, games, and other necessities. This is a nice place for a getaway.
Guest favourite
Condo in Virginia Beach
4.9 out of 5 average rating, 221 reviews

Oceanfront Gem VaB Studio Exceptional Views

GingerRating, 5 stars1 week ago
This was our second time staying at one of Rebecca and Sean’s VA Beach condos — and the experience did not disappoint! This is just a perfect location, at the very end of the Boardwalk, with a private grassy lawn and outdoor seating just for the condo residents. Lots of restaurants in the surrounding blocks. Our favorite thing is the view — you look right out onto the ocean from the patio, and you can see the beach and the sunrise from the comfortable bed each morning. We spent unhurried hours sitting on the patio in the evenings enjoying the sound of lapping waves and the night sky. This cozy studio was just right for the two of us. Highly recommend. I’ve no doubt we’ll stay there again in the future!
Guest favourite
Condo in Virginia Beach
4.86 out of 5 average rating, 137 reviews

Oceanfront, beach, boardwalk, fun, dolphin, sunris

AnitaRating, 5 stars1 month ago
We enjoyed staying at Kelly's place in VB. Its an ideal location for anyone who wants to stay right at the boardwalk. We witnessed amazing sunrises and moonrises. The ocean was right in front of us and from the 6th floor, the view was expansive. A lot of restaurants were also nearby. Kelly was always very communicative, polite and professional. The apartment was clean with the kitchen well stocked with utensils The bedrooms were of a pretty large size. And parking was on the premises. Overall, it was a wonderful experience and holiday for us. We strongly recommend Kelly's place.
Superhost
Home in Sandbridge
4.84 out of 5 average rating, 128 reviews

Stunning Views of Back Bay & Seconds to the Beach

GregRating, 5 stars1 week ago
Great location and host. The home was the perfect size for my family and friends.
Top Guest favourite
Home in Virginia Beach
4.97 out of 5 average rating, 201 reviews

Salida del Sol, North End Beach

BeatriceRating, 5 stars1 week ago
The best spot. Super nice amenities and very clean, great location, right across the street from beach access.

Private beachfront home rentals

Guest favourite
Condo in Ocean View
4.86 out of 5 average rating, 58 reviews

Beachside Condo | 2BR/2BA | Cross street to beach!

HildaRating, 5 stars2 weeks ago
Clean and Spacious for Four people. Great kitchen Space. But could use a better couch Seating in living room. Bedrooms. And beds were great. Would rent again.
Superhost
Home in Willoughby Spit
4.63 out of 5 average rating, 16 reviews

*Escape to Beach Dream*

SamanthaRating, 5 stars1 week ago
I absolutely loved my Airbnb. It was totally more than I expected! The professionalism in booking. Was awesome! The space was so enjoyable. I’ve been under a lot of stress and I needed somewhere to go and just have peace and relax and Jason‘s Airbnb location was exactly what I needed. Thank you so much!! This was my first time renting an Airbnb! Wonderful experience!!
Guest favourite
Home in Bayview
4.95 out of 5 average rating, 41 reviews

Family Getaway | 1 Block from Beach | Game Room

CareyRating, 5 stars3 weeks ago
Brian’s place had everything we needed to make for a relaxing vacation. It was easily walkable to the bay and within 30 mins to all the things we wanted to explore. Loved the layout of the house and the game room ❤️
Top Guest favourite
Home in Virginia Beach
4.99 out of 5 average rating, 196 reviews

Play by the Bay 1 MIN TO WATER

ChristianRating, 5 stars2 weeks ago
This spot was everything we needed and more. The hosts are kind and accommodating, really made us feel at home from the jump. The place itself? Even better than the pictures. Clean, cozy, and had that good energy you hope for when you’re staying somewhere new. It honestly felt like a home away from home. Would 100% stay here again without thinking twice. Big thanks to the hosts for making it such a smooth and comfortable experience for my family.
Guest favourite
Home in East Ocean View
4.97 out of 5 average rating, 62 reviews

Pet Friendly! Newly Built! 1 Block to the Beach!

DezareaRating, 5 stars1 week ago
We had a great time staying here for my sister’s homecoming from deployment. Our family of 7 adults and 1 toddler had a great time and were comfortable in our own spaces while still being able to enjoy each others company in the common areas
Guest favourite
Home in West Park View
4.98 out of 5 average rating, 61 reviews

Waters Edge Retreat!

ChassityRating, 5 stars6 days ago
This was our second time staying here and it was just as great as last year. Leah, our host was very friendly and responsive. She made us feel very welcomed as always. The home is beautiful and they've even made some renovations. The entire family enjoyed indoor and outdoor activities. The kitchen has new appliances which gives the home a modern touch. We felt cozy and right at home our entire stay.
Top Guest favourite
Apartment in East Ocean View
5 out of 5 average rating, 8 reviews

2 Bedroom w/ King Beds walk to beach - top floor 7

Grif and ConnieRating, 5 stars3 weeks ago
We absolutely loved our stay! We we're here for almost a month. I brought quite a few things I thought we would need, but in reality, we didn't need much of anything! They thought of pretty much everything. The only thing I wish I would've brought for this longer stay was my personal blender because I use it daily. Being steps away from the beach was an added bonus, too! The apartment looks exactly like the pictures! I felt safe here and our vehicles were safe as well. The cameras on the property made me feel safe, too. Pip is an amazing host! Very responsive and incredibly helpful. I would stay here again in heartbeat!
Guest favourite
Home in East Ocean View
4.98 out of 5 average rating, 55 reviews

Glam Beach House • 1 block from beach

AngelaRating, 5 stars1 month ago
We felt right at home here. The home was stocked with everything we needed for a long Mother's Day weekend. An easy walk to get to the beach. I would love to stay here again!

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