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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.

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Guest favourite
Guest suite in Virginia Beach
4.9 out of 5 average rating, 700 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.

Top guest favourite
A spacious studio apartment features a queen-size bed adorned with a colorful coral-themed quilt. Nearby, a small seating area is visible, alongside a well-equipped kitchen. Warm wood flooring enhances the inviting atmosphere, complemented by a modern ceiling fan and natural light entering through the window.
Flat in Newport News
4.98 out of 5 average rating, 232 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.

Top guest favourite
A cheerful cottage is framed by tall trees and surrounded by a spacious lawn. The front porch features white railings and a welcoming green door. A mailbox stands at the edge of a quiet road, highlighting the tranquil neighborhood setting.
Cottage in Sunbury
4.97 out of 5 average rating, 129 reviews

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.

Top guest favourite
A modern kitchen features white cabinetry and a granite countertop, equipped with stainless steel appliances including a stove and a refrigerator. Under-cabinet lighting enhances the space, and ample storage is provided by multiple upper and lower cabinets. A sink is positioned near a window, allowing natural light.
Home in East Ocean View
5 out of 5 average rating, 141 reviews

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.

Top guest favourite
A cozy living room is featured, showcasing a light-colored sofa paired with two yellow accent chairs. A wooden coffee table sits at the center, and two windows are dressed with sheer curtains, allowing gentle light to brighten the space. A ceiling fan is present above.
Home in Chesapeake
4.96 out of 5 average rating, 125 reviews

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 brand new central heat and air conditioning, new stainless steel refrigerator and smooth top stove, microwave, and new carpeting. It’s centrally located and there is plenty of space for parking. This is truly a home away from home.

Guest favourite
A spacious studio area is highlighted by a king-size bed with a white bedspread and decorative pillows. A cozy seating arrangement and dining table are seen, alongside a fireplace and wall-mounted TV. Soft lighting enters through the windows adorned with wooden blinds.
Guest suite in Virginia Beach
4.97 out of 5 average rating, 178 reviews

Quiet Suite with Private Entrance

Looking for a place to relax away from the chaos of the oceanfront? Quiet, private and secluded but conveniently located. Less than a 10 minute drive to the beach. Walking distance to breweries, local restaurants, grocery stores and other amenities Beautiful 2 acre property with plenty of outdoor space to find a place to relax, play games or take a nap Leesa king size mattress Luxurious bathroom with soaker tub Microwave and fridge, Kurig, k-cups snacks and popcorn Smart TV, WiFi

Top guest favourite
The exterior of a private attached suite is shown, featuring a welcoming entrance with white steps and a small porch. Lush greenery and colorful flowers frame the walkway, leading to a paved driveway. A wooden fence provides privacy, while a well-maintained lawn enhances the setting.
Guest suite in Chesapeake
4.95 out of 5 average rating, 618 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.

Guest favourite
A spacious living room features a comfortable sectional sofa, a wooden entertainment center with a large TV, and a decorative console table. Light-colored walls complement the area rug, and framed artwork adds interest. A staircase is visible, leading to the upper level.
Home in Norfolk
4.91 out of 5 average rating, 179 reviews

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.

Guest favourite
A spacious room features a king-size bed with a soft white bedspread and dark accent pillows. A seating area with a leather futon and dining table for four is present. Natural light enters through a large window, complemented by dark curtains. A small fridge is positioned nearby.
Guest suite in Chesapeake
4.92 out of 5 average rating, 298 reviews

King Guest Suite - A Family Vacation Rental

Come enjoy a great stay in this beautiful private In-law suite, located in the heart of Chesapeake where you can get lost in nature, peruse the fare at a farmer's market, or picnic on the water's edge with your family. Just within 15 to 30 minutes from surrounding Naval bases, Virginia Beach Oceanfront and Downtown Norfolk. All you have to do us gas-up and unplug. We'll take it from there. Reserve your stay today and let your moments begin!

Guest favourite
A bright and spacious living area features comfortable seating on a large sofa and armchairs. A flat-screen TV is mounted on the wall across from the seating. Natural light enters through multiple windows, and a decorative plant adds a touch of greenery to the room.
Home in Norfolk
4.83 out of 5 average rating, 131 reviews

The Chesapeake St Retreat - Pet and Kid Friendly!

The kid and pet friendly retreat your family will love! This beautiful 2,200 sqft, four bedroom home is PERFECT for your beach get away and is less than a 5-minute walk from the beach. This home features a stylish design, a dining room table that can seat up to 10, a fenced in back yard for your furry friends. There are two decks with outdoor seating, modern washer and dryer, games and toys, and much much more. Can't wait to host you!!

Top guest favourite
A spacious living area features a large, L-shaped gray sectional sofa adorned with decorative pillows. Two side tables with lamps flank the sofa, while a central coffee table holds a decorative tray. Coastal-themed artwork and a shelf with accents are visible above, enhancing the beach-inspired decor.
Townhouse in Virginia Beach
4.97 out of 5 average rating, 155 reviews

Entire Home - Close to Beach - Pet Friendly

Welcome to "The Crab Shack" located in Salt Marsh Point. This is our newly renovated home located just minutes from the oceanfront. Everything here is brand new, upscale, comfy and just waiting for you. Imagine relaxing on the front veranda in upscale patio furniture, offset umbrella, outdoor grill and privacy fence. Or take it inside to the professionally decorated beach themed setting, with everything brand new and waiting for you.

Top guest favourite
A charming two-story home is seen from the street, featuring a welcoming front porch with white railing. Large windows allow natural light to fill the space. The yard is well-maintained and bordered by a sidewalk, surrounded by trees that provide shade.
Home in Norfolk
4.99 out of 5 average rating, 134 reviews

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

When is the best time to visit Chesapeake?

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Avg. price$130 SGD$127 SGD$134 SGD$142 SGD$148 SGD$149 SGD$156 SGD$152 SGD$137 SGD$139 SGD$147 SGD$155 SGD
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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 $25 SGD 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 & child-friendly amenities

  • Holiday rentals with a pool

    50 properties feature pools

  • Rentals with dedicated workspaces

    180 properties have a dedicated workspace

  • Wifi availability

    290 of Chesapeake holiday rentals include wifi 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