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 favourite

Home in Smithfield

4.97 out of 5 average rating, 205 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.

Dec. 8 – 15

$183 CAD per night

Guest favourite

Apartment in Newport News

4.97 out of 5 average rating, 148 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.

Nov. 5 – 12

$147 CAD per night

Guest favourite

Guest suite in Virginia Beach

4.89 out of 5 average rating, 551 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.

Dec. 4 – 11

$146 CAD per night

Guest favourite

Townhouse in Virginia Beach

4.92 out of 5 average rating, 121 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

$364 CAD per night

Guest favourite

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. 20 – 27

$195 CAD per night

Guest favourite

Apartment in Williamsburg

4.84 out of 5 average rating, 361 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.

Nov. 9 – 16

$163 CAD per night

Guest favourite

Camper/RV in Hampton

4.99 out of 5 average rating, 160 reviews

M&M’s Modern RV

RELAX in our cozy and modern RV with dependable blazing fast internet or sit outside and enjoy the view of our 2 acre property on the edge of a wooded area. We are centrally located: 5-15 minutes to a golf course, the beach, walking paths, parks, playgrounds, museums, AMC 24, shopping malls, Historic Yorktown Battlefields, Mini Golf, Whole Foods & many restaurants. 24mins to Busch Gardens & Water Country, 35mins to Williamsburg & Jamestown, and 45-50min to VA Beach's Oceanfront.

Aug. 27 – Sep. 3

$202 CAD per night

Guest favourite

Home in Moyock

4.93 out of 5 average rating, 285 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.

Sep. 23 – 30

$297 CAD per night

Guest favourite

Cabin in Cape Charles

4.96 out of 5 average rating, 100 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.

Oct. 25 – Nov. 1

$353 CAD per night

Guest favourite

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. 21 – 28

$372 CAD per night

Guest favourite

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.

Sep. 10 – 17

$406 CAD per night

Guest favourite

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!

Nov. 30 – Dec. 7

$302 CAD per night