
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.

Centrally Located Sleek Studio Apartment
Private guest studio apartment with separate parking/entrance in a quiet neighborhood. Centrally located to shopping, restaurants , and parks. Airport:12 min CNU:6 min Riverside Medical Center:7 min Sentara Hospital:8 min Langley AFB:11 min Patrick Henry Mall:8 min Willimasburg/Bush Gardens: approx 30 min Virgina Beach Oceanfront: 45 min Wifi available with a 55" TV with streaming services (no cable). Coffee table folds into dining/work table. Stools under table. Full bath/kitchen/laundry unit.

Charming Home by the Sea, a block from the beach!
Single family home steps from the beach. Parking for vehicles including garage. Outdoor/indoor dining areas. Gas grill & fully equipped kitchen with cooking essentials for stay at home meals. 3 bedrooms sleeps 8. Can accommodate additional guests for an up charge with air mattress and sheets provided. Pets welcome! Hardwood flooring and central AC/heat throughout. Walking distance to restaurants in the local area. 15 minutes to Norfolk Naval Station, 10 mins to Airport, 20 mins to VB boardwalk.

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.

Quiet East Beach Bungalow, 1 block to beach!
Brand new construction located exactly one block from the beautiful Chesapeake Bay at East Beach in Oceanview! A quick walk to the beach or Bay Oaks Park, this bungalow is perfect for relaxing getaways. Fireplace, patio, grill, spacious front porch, new appliances, washer/dryer, private off-street parking. A quick trip to the Naval Bases! Guests are provided with linens, towels, toiletries, and high speed internet(SmartTV). Additional rooms available case by case basis. Please ask.

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 cottage a couple blocks from the beach
Cozy home with 1 bedroom and 1 bathroom. Just a short walk to the bay. Large front porch to enjoy your morning coffee. Quick walk to COVA coffee and brewery. Newly remodeled home, super clean. 1 queen bed for sleeping. Large backyard to enjoy your vacation nights. 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. You will truly feel like you're on vacation here…

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.
Popular amenities for Chesapeake pet-friendly home rentals
Pet-friendly house rentals

Wooded Wonderland Miniature Golf Hot tub Pool

Cozy Home Near Hospitals & Beach

The Main House

Family hideaway

Family Holiday House. Events and Beaches Nearby

Newport Nook: 5/2.5 Home in Norfolk - Sleeps 10!

Quiet 3/2 beautiful Chesapeake

Cozy Home in Historic District
Pet-friendly home rentals with a pool

Positano Villa

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

Westgate Historic Williamsburg One Bedroom

The Seaglass Cottage

Corolla Oceanside Hideaway, 5 min walk to beach

Walk to Beach! Dogs OK, Backyard, Hot Tub, Pool

MillerLight

Ocean Escape
Private, pet-friendly home rentals

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

Chesapeake. Comfy & Cozy. 4 Beds 2 Bath

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

Southern Charm Warm and Welcome

Hot Tub~3 Min to Sand~Sparkling Beach Cottage

The Bunny Trail - perfect for travel nurses!

Country Escape - Next DOOR - Hidden Gem

Entire Apartment - No Cleaning Fees!
When is the best time to visit Chesapeake?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $171 NZD | $166 NZD | $176 NZD | $186 NZD | $195 NZD | $196 NZD | $205 NZD | $200 NZD | $180 NZD | $183 NZD | $193 NZD | $203 NZD |
| 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 $33 NZD 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 and kid-friendly amenities

Holiday rentals with a pool
50 properties feature pools

Rentals with dedicated workspaces
180 properties have a dedicated workspace

Wi-Fi availability
290 of Chesapeake holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi 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
- Jamestown Settlement
- Buckroe Beach
- Cape Charles Beachfront
- Outlook Beach
- Norfolk Botanical Garden
- Ocean Breeze Waterpark
- Chrysler Museum of Art
- First Landing Beach
- The NorVa
- Chrysler Hall
- Currituck Beach Lighthouse
- Nauticus
- Virginia Zoological Park
- Old Dominion University
- Hampton University
- Currituck Club
- Virginia Living History Museum
- Town Point Park




