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Beachfront holiday rentals in Chesapeake

Find and book unique beachfront homes on Airbnb

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Popular amenities for beachfront rentals in Chesapeake

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 Norfolk
4.97 out of 5 average rating, 249 reviews

Positano Villa

RhondaRating, 5 stars4 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!!!
Top guest favourite
Apartment in Norfolk
4.99 out of 5 average rating, 91 reviews

Beachfront Getaway, Pet Friendly, Mermaid Suite

SaraRating, 5 stars1 month ago
What an amazing stay! I've never been satisfied with an Airbnb, the photos always are so much nicer than the reality - but Big Blue was actually even better than advertised! Merlyn's communication prior to arrival made things very easy. Accessing the unit was simple, and I felt safe with the self-locking doors. The unit was clean and so comfortable, with many personal touches - I instantly felt at home. I was overjoyed when I arrived and toured the unit. Really exceeded my expectations which was such a different feeling than all the other Airbnb I've rented over the years. The beach access was tidy and pretty, the gym and beach gear a nice touch, and the foot wash station was appreciated after my morning walks with the dog. I really can't say enough great things about my stay here. Hosts were friendly and helpful every step of the way. We mostly spent our time traveling around the area from VA Beach to OBX so I can't speak much about Norfolk/Ocean View. I would def rent Big Blue again.
Guest favourite
Home in East Ocean View
4.89 out of 5 average rating, 142 reviews

Modern. Spacious. Pets Yes! 2Min Walk to Beach

VimarisRating, 5 stars3 weeks ago
The house as advertised! Clean and very supplied. The beach was small and the area does not have much options to eat. Neighborhood was ok.
Superhost
Home in Virginia Beach
4.88 out of 5 average rating, 104 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.
Top guest favourite
Home in East Ocean View
4.98 out of 5 average rating, 55 reviews

The Seaglass Cottage

BarbaraRating, 5 starstoday
The host was so kind and made sure we had a comfortable stay! The AC ended up not working due to an accidental mishap when she was working on her yard! She was able to get the AC fixed as we arrived to the Air BNB and we had the coolest room ever ( which we love) especially on a hot day! We are thankful for the time she took to get that done ASAP! She also had a wonderful cute cottage with all that you’d need for a short stay! It was equipped with great dishes and all the things you’d need for a perfect stay in a home :) it was extremely clean and decorated nicely for your small family! It also has a beautiful back yard oasis to sit out and relax or go for a swim :) you won’t want to miss this Airbnb!! Located near the beach and a great park and walking paths for you kiddos!! All you need nearby just a short walk away!! It was a great getaway for the weekend with a very kind host who is always there to help if needed :)
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!

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 stars4 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 stars2 weeks 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
Apartment in Sandbridge
4.92 out of 5 average rating, 131 reviews

Ocean & Bay Views - Local Family Owned & Operated

MarieRating, 5 stars6 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
Apartment 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
Apartment 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, 129 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

Sunrise, North End Beach

BeatriceRating, 5 stars2 weeks ago
The best spot. Super nice amenities and very clean, great location, right across the street from beach access.

Private beachfront home rentals

Top guest favourite
Home in Buckroe Beach
5 out of 5 average rating, 63 reviews

The Canary Island … Keep Calm and Fish On

TimothyRating, 5 stars1 month ago
We made wonderful memories at this beautiful place. Would definitely recommend!
Guest favourite
Apartment in Norfolk
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.
Top guest favourite
Cottage in Norfolk
4.98 out of 5 average rating, 85 reviews

Life on a Sandbar right on Chesapeake Bay

CatherineRating, 5 stars6 months ago
The cottage was perfect for us and had everything that we needed! Jimmy was an awesome host and even shared that there was a pod of dolphins in the vicinity of the cottage! We had an amazing time!
Guest favourite
Home in Virginia Beach
4.89 out of 5 average rating, 88 reviews

Paradise On Pacific

LakeyshaRating, 5 stars3 days ago
We love to place. Everything was wonderful. Thank you again.
Top guest favourite
Flat in Virginia Beach
4.96 out of 5 average rating, 80 reviews

North End Beach Cottage Apt - One Block from Beach

EricRating, 5 stars5 days ago
Our stay here was fantastic! Very close to the beach which you can walk to, and only a short drive away from the waterfront that has great restaurants and lots to do! The place itself was clean, quiet and the perfect size for 2 people. If you’re looking for something with great amenities for the size, and in a great location this is it!
Superhost
Home in East Ocean View
5 out of 5 average rating, 4 reviews

Modern 4br beach house - Norfolk

SarahRating, 5 stars1 month ago
Beautiful home close to the beach with walkable restaurants/ coffee shops/ brewery/ farmers market/ Chesapeake bay. We particularly preferred the bay for calmer waters as we have young children. Beautiful spacious home. Huge fenced in yard. Convenient side spigot for rinsing fear post beach. Helpful responsive hosts. Thanks for having us!!
Guest favourite
Flat in Virginia Beach
4.92 out of 5 average rating, 318 reviews

5 Minute Walk to the Beach!

TonniRating, 5 stars1 week ago
We had a wonderful stay at Carrie’s place! Conveniently located for the beach and numerous other activities! Bed was very comfortable and the rest of the place was clean and well kept. Would love to stay here again!
Guest favourite
Home in East Ocean View
4.97 out of 5 average rating, 63 reviews

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

PatrickRating, 5 stars1 day ago
Fran's place was amazing. The house was extremely clean, the beds were very comfortable, and the water pressure in the showers was excellent. The house was a short walk from the beach and was in a nice quiet neighborhood. We would definitely stay at Fran's house again!

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