
Pet-friendly holiday rentals in Chesapeake
Find and book unique pet-friendly homes on Airbnb
Quick stats about holiday rentals that are pet-friendly in Chesapeake

Total holiday rentals
Explore 280 holiday rentals in Chesapeake

Nightly prices starting at
Chesapeake holiday rentals start at $26 SGD per night before taxes and fees

Verified guest reviews
Over 10,870 verified reviews to help you choose

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

Holiday rentals with a pool
40 properties feature pools

Rentals with dedicated workspaces
170 properties have a dedicated workspace

Wifi availability
280 of Chesapeake holiday rentals include wifi access

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

4.7 Average rating
Chesapeake stays receive an average rating of 4.7 out of 5 from guests

Nearby attractions
Chesapeake’s top spots include Chrysler Museum of Art, Nauticus and Cinema Cafe-Greenbrier Mall
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.

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.

Hidden Gem.4/bedroom cozy home fenced in yard
Make yourself at home!Hidden Gem offers a clean welcoming space for guests, located in a quiet established neighborhood. Guests should expect a clean and comfortable stay. Conveniently located near parks,shopping, and dining options. Attractions aren’t too far away Rivers casino.2.9. Virginia Beach Ocean Front.23miles. Waterside district Norfolk 8.5 miles. Town center 17.miles. Busch Gardens 40 miles. Old Dominion University 9.8 miles. Norfolk State University 8.8 miles.Hampton University23miles

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.

Wooded Wonderland Miniature Golf Hot tub Pool
Make yourself at home! This property offers a warm and welcoming environment for guests, located in a quiet and established neighborhood in the middle of Portsmouth, VA. Guests should expect a clean space equipped with modern technology and appliances. Attractions aren’t too far; 41mi from Busch Gardens, 24 mi from Virginia Beach Ocean Front, 7.3 mi from Waterside District Norfolk, and 2.9 mi from Rivers Casino Portsmouth. Peaceful mornings and a comfortable stay awaits at Wooded Wonderland!

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.

Sportsman's Paradise ( Hunting & Fishing )
Sportsman's Paradise is just minutes away from the Currituck Sound which is famous for it's duck hunting and fishing. It overlooks Tull's Bay and Tull's Creek and is surrounded by the Northwest River Marsh Game Lands. The kitchen and living room have 9 windows so you can look out three sides of the house at the water. The walls are old rough cut boards and the ceilings are plywood. The living room and bedrooms are carpeted and the bathrooms and kitchen are laminate wood floor.

Dog Friendly, Large Yard, Spacious & Sleeps 6!
Experience the perfect blend of tranquility and convenience in this charming 3-bed, 2-bath Norfolk home. With a spacious layout and cozy beds, it’s ideal for families and their four-legged friends (pre-approval required; inquire for rules before booking). Features include a fenced yard, a fully stocked kitchen, Wi-Fi, and a quiet cul-de-sac setting. Just a short walk to the beach, you’ll have easy access to the sand and nearby attractions. Book your extended getaway today!

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 central heat and air conditioning, updated appliances, and carpeting. It’s centrally located and there is plenty of space for parking. This is a perfect place to recharge whether you’re visiting for work or a getaway!

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, walk over the sand dune to a quiet, peaceful beach 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. No parties, quiet hours after 10 pm. A past guest wrote, "This place brings beach home nostalgia, peace, and a time to relax".

Perfect Getaway!
Home away from home!! Beautiful 2 story house with 3 bedrooms, 3 bathrooms, and a huge playroom over the garage. The master suite has a beautiful bathroom with a jacuzzi tub, and huge walk in shower. The fenced in backyard has plenty of space to run around, and has an awesome saltwater inground pool for fun! In addition, there is a 2 level, new deck, and patio furniture to sit and relax on. There is something for everyone to do here.. I’m positive you will love it!

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

Cozy beach cottage! One block to the beach!

@Whit’s End? Come in and Relax

Norfolk Beach Casita | Fenced Yard | Dog Friendly

Chicks Beachfront

Gorgeous Vacation House

Family Holiday House. Events and Beaches Nearby

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

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

Oceanfront | 7BR | Pool | Hot Tub | Sleeps 20

Positano Villa

Serenity Sound House: Sandbridge Oasis with pool

Nautical Cottage

North End Home with pool, beach & state park.

Sunrise, North End Beach / Oceanfront Area

Key Lime Cabana at Surfside

Waterfront Cottage w/ Dock/Kayaks + Dog Friendly
Private, pet-friendly home rentals

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

Country Escape - Next DOOR - Hidden Gem

Spacious 3 Bedroom Home | Near many Shops & Dining

Lovely Ocean View Cottage

Chic's Beach Rental and Fishing

Quiet 3/2 beautiful Chesapeake

Quiet Suite with Private Entrance

Cozy Waterfront Barn Loft
When is the best time to visit Chesapeake?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $151 SGD | $150 SGD | $159 SGD | $145 SGD | $151 SGD | $152 SGD | $159 SGD | $155 SGD | $140 SGD | $142 SGD | $150 SGD | $158 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 |
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- Pet-friendly rentals Virginia
- Pet-friendly rentals United States
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Corolla Beach
- Carova Beach
- Cape Charles Beachfront
- Buckroe Beach
- Water Country USA
- First Landing State Park
- Jamestown Settlement
- Outlook Beach
- Norfolk Botanical Garden
- Old Dominion University
- Ocean Breeze Waterpark
- Regent University
- First Landing Beach
- Chrysler Museum of Art
- Neptune's Park
- Colonial Williamsburg's Merchants Square
- Currituck Club
- Currituck Beach Lighthouse
- The Military Aviation Museum
- Nauticus
- The Mariners' Museum
- Town Point Park





