
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.

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.

Spacious 3BR | 1-mile to the Oceanfront & The Dome
Welcome to your home away from home about 1 mile from the Virginia Beach Oceanfront and The Dome and within walking distance to the VA Beach sports center! Perfect for groups up to 9, our home offers ultra-fast 1Gbps internet, 2 dedicated workspaces, and delightful amenities including FREE Parking (up to 4 vehicles). Enjoy the outdoors with our outdoor dining area and a BBQ grill. With numerous local restaurants activities nearby, it’s the ideal getaway for both relaxation and adventure.

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.

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.

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.

Artful Retreat with a Private Pool
Take a break and unwind at your private pool! Stylish, updated interior and a spacious backyard with pool and lounge area. Rinse off at the outdoor shower after a day at the beach and enjoy your private retreat! The Rudee Inlet is less than a block away with great restaurants, fishing, and water activities. A path along the Rudee Inlet leads to the beach and shops - a quick 4 block trip with the included bikes! Outdoor seating and gas fire pit added for the cooler months!

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!

Ultimate Cabin Farm Stay Cape Charles
Tucked away in the woods on a historic Eastern Shore farm lies this stunning pond side Cabin just 10 mins from Cape Charles. The classic yet modern cabin is a dreamy getaway or remote work space. Wake up to the birds singing in the trees that completely surround the cabin and enjoy the deck - watching the deer and goats foraging. Take a walk on our trails, collect fresh eggs, visit Cape Charles for restaurants and shopping, and enjoy the farms’ fire pit in the evening.
Popular amenities for Chesapeake pet-friendly home rentals
Pet-friendly house rentals

Quiet family location and close to BEACH!

Charming Single Family Home by the Chesapeake Bay

Norfolk Beach Casita | Fenced Yard | Dog Friendly

Gorgeous Vacation House

Family Holiday House. Events and Beaches Nearby

The Tree House at Old Beach

Beachfront 2 Dwellings EV charger

3 bedroom 3 bathroom beach house pets welcome
Pet-friendly home rentals with a pool

Positano Villa

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

Quiet Retreat (Pet friendly)

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

The White Lotus - Oceanview Retreat + Wild Horses

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

Key Lime Cabana at Surfside

Modern 2 bedroom near beach, sound and lighthouse!
Private, pet-friendly home rentals

Spacious 3 Bedroom Home | Near many Shops & Dining

Country Escape - Next DOOR - Hidden Gem

The Bartlett Inn

Entire Apartment - No Cleaning Fees!

The Bird’s Nest

The Main House

Norfolk Beach Bungalow • Cozy & Convenient

Quiet 3/2 beautiful Chesapeake
When is the best time to visit Chesapeake?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $177 NZD | $171 NZD | $182 NZD | $192 NZD | $201 NZD | $202 NZD | $211 NZD | $206 NZD | $185 NZD | $189 NZD | $199 NZD | $209 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 $34 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, 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
Destinations to explore
- New York City Holiday rentals
- Washington Holiday rentals
- Myrtle Beach Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- South Jersey Holiday rentals
- Outer Banks Holiday rentals
- Charlotte Holiday rentals
- Cape Fear River Holiday rentals
- Ocean City Holiday rentals
- Jersey City Holiday rentals
- Rappahannock River Holiday rentals
- Rentals with lake access Chesapeake
- Rentals with a washing machine and dryer Chesapeake
- Mansion rentals Chesapeake
- Private suite rentals Chesapeake
- Rentals with pools Chesapeake
- Rentals with an EV charger Chesapeake
- Apartment rentals Chesapeake
- Guesthouse rentals Chesapeake
- Rentals with a fireplace Chesapeake
- Waterfront rentals Chesapeake
- Rentals with breakfast Chesapeake
- Cottage rentals Chesapeake
- Rentals with a hot tub Chesapeake
- Rentals with beach access Chesapeake
- Rentals with a kayak Chesapeake
- Beach house rentals Chesapeake
- Townhouse rentals Chesapeake
- Rentals with outdoor seating Chesapeake
- Rentals with a fire pit Chesapeake
- Rentals with a patio Chesapeake
- Condo rentals Chesapeake
- Beachfront rentals Chesapeake
- House rentals Chesapeake
- Fitness-friendly rentals Chesapeake
- Family-friendly rentals Chesapeake
- Pet-friendly rentals Virginia
- Pet-friendly rentals United States
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Corolla Beach
- Carova Beach
- Buckroe Beach
- Water Country USA
- First Landing State Park
- Jamestown Settlement
- Cape Charles Beachfront
- Norfolk Botanical Garden
- Ocean Breeze Waterpark
- Outlook Beach
- Chrysler Museum of Art
- Nauticus
- Colonial Williamsburg's Merchants Square
- Virginia Zoological Park
- Town Point Park
- First Landing Beach
- Hampton University
- Currituck Beach Lighthouse
- Old Dominion University
- Currituck Beach
- Chrysler Hall
- Regent University




