Beachfront holiday rentals in Chesapeake Beach
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Top-rated beachfront rentals in Chesapeake Beach
Guests agree: these beachfront homes are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for beachfront rentals in Chesapeake Beach
Pet-friendly beachfront home rentals
Cottage in Norfolk
4.97 out of 5 average rating, 202 reviewsPositano Villa
30 Mar – 6 Apr
Home in Norfolk
4.92 out of 5 average rating, 163 reviewsBeautiful cottage a couple blocks from the beach
11–18 Jul
Villa in Norfolk
4.94 out of 5 average rating, 138 reviews8 minutes walking from Sarah Constant Beach Park
4–11 Jan
Home in Hampton
4.95 out of 5 average rating, 123 reviews1950s bungalow, 2-1/2 blocks from Buckroe Beach
9–16 Dec
Tiny home in Cape Charles
4.98 out of 5 average rating, 275 reviewsThe Laughing King Retreat Honeymoon Island Cottage
27 Dec – 3 Jan
Home in Norfolk
4.89 out of 5 average rating, 115 reviewsNew Renovation! Tons of Space + Dogs ok!
4–11 Sep
Townhouse in Virginia Beach
4.8 out of 5 average rating, 177 reviewsChicks Beach Getaway large yard 500 yards to Beach
5–12 Dec
Home in Virginia Beach
4.99 out of 5 average rating, 128 reviewsQuiet family location and close to BEACH!
27 Nov – 4 Dec
Beachfront home rentals with a pool
Apartment in Virginia Beach
4.85 out of 5 average rating, 109 reviewsNEW! Beach Paradise Studio on the Boardwalk w/Pool
22–29 Sep
Home in Virginia Beach
4.96 out of 5 average rating, 163 reviewsSalida del Sol, North End Beach
30 Oct – 6 Nov
Apartment in Virginia Beach
4.88 out of 5 average rating, 176 reviewsOceanfront Gem VaB Studio Exceptional Views
16–23 Sep
Flat in Cape Charles
4.98 out of 5 average rating, 183 reviewsCape Charles Plantation Home “Nevill’s Nook Suite”
20–27 Aug
Flat in Virginia Beach
4.86 out of 5 average rating, 126 reviewsVA Beach Oceanfront Studio, Beach, Boardwalk, Pool
9–16 Sep
Apartment in Virginia Beach
4.83 out of 5 average rating, 101 reviewsOceanfront, beachfront, boardwalk, fun, dolphins
19–26 Dec
Apartment in Virginia Beach
4.84 out of 5 average rating, 239 reviewsBeautiful Beachfront Condo
24–31 Oct
Guest suite in Virginia Beach
4.92 out of 5 average rating, 104 reviews"Forget About It" Guest Suite- 300 STEPS TO BEACH!
8–15 Jun
Private beachfront home rentals
Home in Norfolk
4.84 out of 5 average rating, 121 reviewsCozy Coastal Home
1–8 Nov
Flat in Virginia Beach
4.92 out of 5 average rating, 253 reviews5 Minute Walk to the Beach!
24–31 Jul
Home in Norfolk
4.92 out of 5 average rating, 290 reviewsNew Beach Home on the Chesapeake Bay
10–17 Sep
Home in Virginia Beach
4.85 out of 5 average rating, 151 reviewsThe Magnificent Meadowlark!
31 Aug – 7 Sep
Guest suite in Virginia Beach
4.92 out of 5 average rating, 110 reviewsKing size space short walk to beach and boardwalk
5–12 Aug
Cottage in Norfolk
4.94 out of 5 average rating, 113 reviews110 Year Old Beach Carriage House @ Poseidon 902CH
13–20 Aug
Home in Hampton
4.92 out of 5 average rating, 13 reviewsTiny Blue Beach House
10–17 Dec
Guest suite in Virginia Beach
4.92 out of 5 average rating, 99 reviewsWaterfront Guest Suite
3–10 Sep
Destinations to explore
- Outer Banks Holiday rentals
- Virginia Beach Holiday rentals
- Richmond Holiday rentals
- Norfolk Holiday rentals
- Williamsburg Holiday rentals
- Nags Head Holiday rentals
- Myrtle Beach Holiday rentals
- Washington Holiday rentals
- Deep Creek Lake Holiday rentals
- Philadelphia Holiday rentals
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- Beachfront rentals Outer Banks
- Beachfront rentals Virginia Beach
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- Rentals with pools Chesapeake Beach
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