
Pet-friendly holiday rentals in Chesapeake
Find and book unique pet-friendly homes on Airbnb
Top-rated pet-friendly home rentals in Chesapeake
Guests agree: these pet-friendly homes are highly rated for location, cleanliness and more.

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.

The Little House on Park Avenue
Our cottage is a quiet get-away. Sit on the front porch and enjoy the birds and a cup of coffee. Small kitchen provides everything you may need for your stay, including a local yummy treat. A desk in the bedroom gives you a place to work while others in your group utilize the spaces in the living room or dining room. You can leisurely stroll by the Ruritan Park to Studio 32 Gallery and Gift shop on weekends. In 10 minutes drive to Merchants Millpond State Park. Historic Edenton only30 minutes.

Modern Luxury Peace & Quiet.
Covered parking with EV Charger. With one acre fenced in yard. 1000+ sq ft Modern Second Floor Guest House apartment with separate private entrance attached to a 10,000+ sq ft Mansion on 3 acres in a very safe, quiet and private neighborhood. Free private parking. Minutes from restaurants, shopping centers, and a beautiful 30 minute drive to oceanfront. Free Netflix, High Speed WiFi, washer, dryer, full kitchen. With Keurig. Brand new Heat and Air Condition! Plus 2 dedicated parking spots.

Peaceful beach @Courtyard Cottage+No Cleaning Fee!
There is no congestion, crowds, or large commercial beach resorts here. Experience the exact opposite at Courtyard Cottage, steps away from a quiet, peaceful beach surrounded by sand dunes for a special getaway. A park across the street offers playgrounds and pet-friendly walks, and a local farmers' market opens from 9 a.m. to noon. Saturdays, May 4 - Nov 23. A past guest wrote, "This place brings beach home nostalgia, peace, and a time to relax". No parties, quiet hours after 10 pm.

The Cozy Cottage Two Bedroom, King bed House
This is a charming and cozy Cape Cod style house. It’s decorations are eclectic and comfortable. There is a king size bed in the master bedroom and a queen size bed in the second bedroom. There are smart TV’s in each bedroom and the living room. This home has brand new central heat and air conditioning, new stainless steel refrigerator and smooth top stove, microwave, and new carpeting. It’s centrally located and there is plenty of space for parking. This is truly a home away from home.

Quiet Suite with Private Entrance
Looking for a place to relax away from the chaos of the oceanfront? Quiet, private and secluded but conveniently located. Less than a 10 minute drive to the beach. Walking distance to breweries, local restaurants, grocery stores and other amenities Beautiful 2 acre property with plenty of outdoor space to find a place to relax, play games or take a nap Leesa king size mattress Luxurious bathroom with soaker tub Microwave and fridge, Kurig, k-cups snacks and popcorn Smart TV, WiFi

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.

Beautiful renovated 2Bed home!
Your next unforgettable beach getaway awaits with a stay at this charming and completely renovated 2-bedroom, 1-bathroom vacation rental centrally located in Norfolk. Spend sunny summer days at Ocean View Beach, or explore the sights and sounds of nearby First Landing State Park, followed by a quick bite to eat at a local seafood restaurant. At dusk, retreat back to 'Castaway Cottage' for a family BBQ on the propane grill and s'mores shared around the fire pit………………………………

Cozy Cottage w/ Hot Tub, Pool Table, Fenced Yard
Welcome to Wayland Beach Cottage, a relaxed beach retreat with your own private hot tub and separate game room. Unwind under the pergola, soak year-round in the 6-person hot tub, or enjoy movie nights and friendly competition around the full-size 8-foot pool table in your own entertainment space. With a fully fenced yard, smart TVs throughout, fast Wi-Fi, a long private driveway, and easy access to beaches and dining, it’s the perfect getaway for families and friends.

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.

King Guest Suite - A Family Vacation Rental
Come enjoy a great stay in this beautiful private In-law suite, located in the heart of Chesapeake where you can get lost in nature, peruse the fare at a farmer's market, or picnic on the water's edge with your family. Just within 15 to 30 minutes from surrounding Naval bases, Virginia Beach Oceanfront and Downtown Norfolk. All you have to do us gas-up and unplug. We'll take it from there. Reserve your stay today and let your moments begin!

Walk to Beach! Dogs OK, Backyard, Hot Tub, Pool
Welcome to Coral Cove in Corolla! Take it easy at this nearly new, well-appointed condo and relax under the stars in your own private hot tub! - 2bed, 2 bth, sleeps 6, 2 king beds + Queen sleeper sofa - Easy 8-10min walk to beach. - Dogs OK! (fee applies) - Beach Gear included w/wagon. - Linens and Beach towels included! - Single level with no steps to enter or leave. - Private Hot Tub - Private backyard with seating
Popular amenities for Chesapeake pet-friendly home rentals
Pet-friendly house rentals

Colonial Retreat

Charming Single Family Home by the Chesapeake Bay

VB Town Center -4 Parking Spots! -Pets welcome!

Spanish Style Casita • 2BR/2BA • Dogs Welcome

Charming Home by the Sea, a block from the beach!

Relax! Refreshing 3 bedroom Rancher

Sportsman's Paradise ( Hunting & Fishing )

5 Min to Downtown & Ghent, Fenced Yard, Firepit
Pet-friendly home rentals with a pool

Positano Villa

Kingsmill 1bed/1ba on Golf Course 9th Fairway

The Blue Octopus~Private Pool~HotTub~Beach~FirePit

The Seaglass Cottage

Gorgeous Vacation House

MillerLight

Key Lime Cabana at Surfside

Ocean Escape
Private, pet-friendly home rentals

Beach House~Hot Tub~3 Min to Sand~HUGE Kitchen

Serene Tree House Retreat | Spacious 1br/1bth Home

Virginia Beach, Getaway

Southern Charm Warm and Welcome

Country Escape - Next DOOR - Hidden Gem

Quiet 3/2 beautiful Chesapeake

Bayside Bliss - A 5 Minute Walk to the Beach!

Trestles - Loft #5 - 8 min walk to the beach
When is the best time to visit Chesapeake?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | € 87 | € 84 | € 89 | € 94 | € 99 | € 99 | € 104 | € 101 | € 91 | € 93 | € 98 | € 103 |
| Avg. temp | 6°C | 7°C | 10°C | 16°C | 20°C | 25°C | 27°C | 26°C | 23°C | 18°C | 12°C | 8°C |
Quick stats about holiday rentals that are pet-friendly in Chesapeake

Total holiday rentals
Explore 300 holiday rentals in Chesapeake

Nightly prices starting at
Chesapeake holiday rentals start at € 17 per night before taxes and fees

Verified guest reviews
Over 10,480 verified reviews to help you choose

Family-friendly holiday rentals
170 properties offer extra space & child-friendly amenities

Holiday rentals with a pool
50 properties feature pools

Rentals with dedicated workspaces
180 properties have a dedicated workspace

Wifi availability
290 of Chesapeake holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Chesapeake rentals

4.6 Average rating
Chesapeake stays receive an average rating of 4.6 out of 5 from guests

Nearby attractions
Chesapeake’s top spots include Chrysler Museum of Art, Nauticus and Cinemark Chesapeake Square
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- Pet-friendly rentals Virginia
- Pet-friendly rentals United States
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Corolla Beach
- Carova Beach
- Water Country USA
- First Landing State Park
- Buckroe Beach
- Jamestown Settlement
- Cape Charles Beachfront
- Norfolk Botanical Garden
- Outlook Beach
- Ocean Breeze Waterpark
- Chrysler Museum of Art
- The NorVa
- Nauticus
- Colonial Williamsburg's Merchants Square
- Virginia Zoological Park
- Town Point Park
- Old Dominion University
- Currituck Beach Lighthouse
- First Landing Beach
- Virginia Living History Museum
- Chrysler Hall
- Currituck Club




