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

Total vacation rentals
Explore 280 vacation rentals in Chesapeake

Nightly prices starting at
Chesapeake vacation rentals start at G$4,186 GYD per night before taxes and fees

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

Family-friendly vacation rentals
180 properties offer extra space & kid-friendly amenities

Vacation rentals with a pool
40 properties feature pools

Rentals with dedicated workspaces
170 properties have a dedicated workspace

Wi-Fi availability
280 of Chesapeake vacation rentals include wi-fi 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.

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.

All 4 One | Beach Living
Come enjoy time at the beach in our seaside oasis! All4One is located on the semi-private beach of Croatan in Virginia Beach. This means that although you are but a bike ride away from the hustle and bustle of the Boardwalk, you also have the beach to yourself in a quiet neighborhood setting- best of both worlds right? We certainly think so! My grandma built this home in the 1960's and my husband and have called it home for over a decade. Come enjoy your stay at the beach at our home!

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!

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.

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!

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.

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

Sweet Suite!
Private attached MOTHER IN LAW suite (not the whole house) in a quiet neighborhood in the heart of Hampton Roads. NOTE: Pool is open from Memorial Day to Labor Day. 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.
Popular amenities for Chesapeake pet-friendly home rentals
Pet-friendly house rentals

Water Oaks at Chic's Beach

Wooded Wonderland Miniature Golf Hot tub Pool

Cozy beach cottage! One block to the beach!

The Chesapeake St Retreat - Pet and Kid Friendly!

The Bird’s Nest

Family hideaway

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

Quiet 3/2 beautiful Chesapeake
Pet-friendly home rentals with a pool

Villa Positano

Nautical Cottage

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

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

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

Gorgeous Vacation House

Key Lime Cabana at Surfside

Ocean Escape
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

Seaglass Cottage

Beach Bungalow • Navy Base • Quiet St • Dogs OK

2BR Self Check-in, Fast Wi-Fi

Cozy apartment close to a beach

Ocean Bungalo-WiFi, fire pit, beach, pet friendly
When is the best time to visit Chesapeake?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$24,486 GYD | G$24,277 GYD | G$25,742 GYD | G$23,440 GYD | G$24,486 GYD | G$24,695 GYD | G$25,742 GYD | G$25,114 GYD | G$22,603 GYD | G$23,021 GYD | G$24,277 GYD | G$25,533 GYD |
| 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 |
Destinations to explore
- New York Vacation rentals
- Myrtle Beach Vacation rentals
- Philadelphia Vacation rentals
- Washington Vacation rentals
- Charlotte Vacation rentals
- Ocean City Vacation rentals
- North Myrtle Beach Vacation rentals
- Raleigh Vacation rentals
- Virginia Beach Vacation rentals
- Wilmington Vacation rentals
- Newark Vacation rentals
- Jersey City Vacation rentals
- Rentals with a fire pit Chesapeake
- Beachfront rentals Chesapeake
- Beach house rentals Chesapeake
- Rentals with lake access Chesapeake
- Mansion rentals Chesapeake
- Private suite rentals Chesapeake
- Rentals with pools Chesapeake
- Rentals with a washer and dryer Chesapeake
- Apartment rentals Chesapeake
- Guesthouse rentals Chesapeake
- Family-friendly rentals Chesapeake
- Rentals with a patio Chesapeake
- Rentals with beach access Chesapeake
- Condo rentals Chesapeake
- Rentals with a fireplace Chesapeake
- Rentals with breakfast Chesapeake
- Rentals with a kayak Chesapeake
- Fitness-friendly rentals Chesapeake
- Townhouse rentals Chesapeake
- Rentals with a hot tub Chesapeake
- Rentals with outdoor seating Chesapeake
- Waterfront rentals Chesapeake
- Rentals with an EV charger Chesapeake
- Cottage rentals Chesapeake
- House rentals Chesapeake
- Smoking-friendly rentals Chesapeake
- Pet-friendly rentals Virginia
- Pet-friendly rentals United States
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Corolla Beach
- Carova Beach
- Buckroe Beach
- Cape Charles Beachfront
- Water Country USA
- First Landing State Park
- Jamestown Settlement
- Norfolk Botanical Garden
- Outlook Beach
- Old Dominion University
- Regent University
- Ocean Breeze Waterpark
- Chrysler Museum of Art
- Colonial Williamsburg's Merchants Square
- Neptune's Park
- First Landing Beach
- Currituck Club
- Currituck Beach Lighthouse
- The Military Aviation Museum
- The Mariners' Museum
- Nauticus
- Back Bay National Wildlife Refuge-N





