Pet-friendly vacation 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.

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Guest favorite

Home in Smithfield

4.97 out of 5 average rating, 204 reviews

Mason Manor - Downtown Smithfield next to WCP

Historic Smithfield 233 S Mason Street 2 Bedrooms 1 Bath Located in the heart of historic Smithfield boasts old world charm and character with a touch of today’s conveniences. The living room has gas fireplace for cool evenings & leads to dining area & updated fully equipped kitchen. The full bath is updated with jetted tub. Front porch swing for relaxing and back deck for entertainment. Windsor Castle Park just steps away. Located just around the corner from restaurants, shopping & more.

Mar 29 – Apr 5

G$23,748 GYD per night

Guest favorite

Apartment in Newport News

4.97 out of 5 average rating, 147 reviews

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.

Dec 2 – 9

G$18,358 GYD per night

Guest favorite

Guest suite in Virginia Beach

4.89 out of 5 average rating, 550 reviews

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.

Aug 27 – Sep 3

G$18,113 GYD per night

Guest favorite

Townhouse in Virginia Beach

4.92 out of 5 average rating, 120 reviews

Charming 3 BR / 3.5 BA with a Private Backyard

Charming and quiet 3 Bedroom / 3.5 Bathroom townhouse available in Town Center of Virginia Beach. Newer Construction built in 2021 with a private AstroTurfed and fenced backyard perfect for pets. Top Golf under 1 mile away! Wegmans, Walmart, and Town Center dining are a 4-minute drive from the house. Centrally located a 3-minute drive from VB town center and all the dining imaginable. The townhome is a 15-minute drive from Chicks Beach and a 20-minute drive to the Oceanfront & Boardwalk.

Jan 19 – 26

G$44,685 GYD per night

Guest favorite

Guest suite in Chesapeake

4.95 out of 5 average rating, 479 reviews

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.

Sep 8 – 15

G$45,091 GYD per night

Guest favorite

Apartment in Williamsburg

4.84 out of 5 average rating, 360 reviews

The Nook

Enjoy a getaway in this cozy 1 bedroom apartment attached to a classic 1940s Cape Cod home minutes from Colonial Williamsburg and Jamestown. You'll be within biking distance to many local attractions such as Williamsburg Winery, Jamestown Island, Jamestown Settlement, Jamestown Beach, and Billsburg Brewery. Busch Gardens & Water Country are a 15 minute drive. The Nook was completely refinished in 2020. Need more space or traveling with a group? Inquire about our other units.

Jan 10 – 17

G$20,544 GYD per night

Guest favorite

Home in Moyock

4.93 out of 5 average rating, 284 reviews

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.

Oct 13 – 20

G$36,791 GYD per night

Guest favorite

Cabin in Cape Charles

4.96 out of 5 average rating, 99 reviews

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.

Mar 29 – Apr 5

G$45,433 GYD per night

Guest favorite

Cottage in Norfolk

4.98 out of 5 average rating, 174 reviews

Peaceful beach @Courtyard Cottage+No Cleaning Fee!

No congestion, crowds, or commercial big beach resorts here. Experience the exact opposite at Courtyard Cottage just steps away from a quiet and peaceful beach surrounded by sand dunes for a special getaway. A park across the street provides playgrounds and pet-friendly walks and is the home to a local farmers market, 9 a.m. to noon. Saturdays, May 4 through Nov. 23. A past guest wrote "This place brings beach home nostalgia. peace, and a time to relax".

Feb 22 – Mar 1

G$48,316 GYD per night

Guest favorite

Apartment in Chesapeake

5.0 out of 5 average rating, 145 reviews

Modern Luxury Peace & Quiet.

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, Hulu, High Speed WiFi, washer, dryer, fully equipped kitchen. With a Keurig! Brand new Heat and Air Condition! Plus 2 dedicated parking spots.

Jun 30 – Jul 7

G$57,428 GYD per night

Guest favorite

Home in Williamsburg

4.97 out of 5 average rating, 177 reviews

Casita on the Corner

Our cozy little 2 bedroom, one bath, small dog friendly home is on a corner lot in a family friendly neighborhood just minutes from major attractions like Busch Gardens/Water Country. This area is rich with historical sites. Be sure to visit Colonial Williamsburg, Jamestown and Yorktown. Take a tour on The Colonial Parkway or If you are a cyclist bring your bike and ride the Capitol trail or hit the trails at Freedom Park or New Quarter Park.

Mar 19 – 26

G$26,976 GYD per night

Guest favorite

Cottage in Virginia Beach

4.94 out of 5 average rating, 303 reviews

Seaglass Cottage

Brand new, sparkling clean, "Seaglass cottage" in a quiet, beach neighborhood! Two blocks from the exciting, artsy, "VIBE" district, with murals, marketplace and unique restaurants. Five blocks from the active, Virginia Beach Boardwalk with shopping, music and dining! Don't do the usual, hotel lobbies and crowds, come to a clean place that you can call your own!

Sep 24 – Oct 1

G$36,211 GYD per night