
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.

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.

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.

3 bedroom private home a block from the beach!
Relax with the whole family at this peaceful home. A block to the beach! 3 bedrooms and 2 bathrooms, with an outdoor shower and finished basement with extra living space. Outdoor patio with gas grill and patio furniture. All amenities included sheets, towels, cooking utensils, etc. Fast Wi-Fi throughout the home. Can sleep up to 8! Pets always welcome. All bedrooms are on main level no stairs required. Weekly and monthly discounted rates upon inquiry.

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!

The Chesapeake St Retreat - Pet and Kid Friendly!
The kid and pet friendly retreat your family will love! This beautiful 2,200 sqft, four bedroom home is PERFECT for your beach get away and is less than a 5-minute walk from the beach. This home features a stylish design, a dining room table that can seat up to 10, a fenced in back yard for your furry friends. There are two decks with outdoor seating, modern washer and dryer, games and toys, and much much more. Can't wait to host you!!

Entire Home - Close to Beach - Pet Friendly
Welcome to "The Crab Shack" located in Salt Marsh Point. This is our newly renovated home located just minutes from the oceanfront. Everything here is brand new, upscale, comfy and just waiting for you. Imagine relaxing on the front veranda in upscale patio furniture, offset umbrella, outdoor grill and privacy fence. Or take it inside to the professionally decorated beach themed setting, with everything brand new and waiting for you.

Ghent on the Corner: Cozy 3 bed 2.5 bath home
My cozy, 3 bed / 2.5 bath Norfolk home has a spacious 1st floor primary suite with a full bathroom, 2 bedrooms upstairs along with a 2nd full bathroom. No cleaning fee or checkout instructions. Pet-friendly! Free Wi-Fi, parking for 4 cars, grill & gazebo. Distances: CHKD - 5 min EVMS - 5 min Sentara Norfolk General - 5 min Waterside / Downtown - 10 min Ocean View - 20 min VB Oceanfront - 25 min
Popular amenities for Chesapeake pet-friendly home rentals
Pet-friendly house rentals

Colonial Retreat

Charming Single Family Home by the Chesapeake Bay

Quiet Stay near Bay. Walk to Oceanview access

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

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

Family hideaway

Gorgeous Vacation House

Newport Nook: 5/2.5 Home in Norfolk - Sleeps 10!
Pet-friendly home rentals with a pool

Villa Positano

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

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

The White Lotus - Oceanview Retreat + Wild Horses

The Seaglass Cottage

Corolla Oceanside Hideaway, 5 min walk to beach

MillerLight

Ocean Escape
Private, pet-friendly home rentals

Chesapeake. Comfy & Cozy. 4 Beds 2 Bath

Southern Charm Warm and Welcome

Country Escape - Next DOOR - Hidden Gem

B Walk to Beach and Sports Center. Dogs Welcome!

The Booker: Modern Retreat by the Beach

Hidden Gem.4/bedroom cozy home fenced in yard

Ocean Bungalo-WiFi, fire pit, beach, pet friendly

Cozy Waterfront Barn Loft
When is the best time to visit Chesapeake?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $130 SGD | $127 SGD | $134 SGD | $142 SGD | $148 SGD | $149 SGD | $156 SGD | $152 SGD | $137 SGD | $139 SGD | $147 SGD | $155 SGD |
| 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 $25 SGD 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
- Outlook Beach
- Norfolk Botanical Garden
- Ocean Breeze Waterpark
- Chrysler Museum of Art
- Virginia Living History Museum
- Old Dominion University
- Colonial Williamsburg's Merchants Square
- Virginia Zoological Park
- Town Point Park
- Nauticus
- First Landing Beach
- Currituck Beach Lighthouse
- Chrysler Hall
- Currituck Club
- USS Wisconsin (BB-64)




