Chesapeake vacation rentals
Book unique vacation rentals, houses, and more on Airbnb
Top-rated vacation rentals in Chesapeake
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Chesapeake vacation rentals
Other great vacation rentals in Chesapeake
Home in Smithfield
4.97 out of 5 average rating, 209 reviewsMason Manor - Downtown Smithfield next to WCP
Cottage in Norfolk
5.0 out of 5 average rating, 251 reviewsBeautiful Cottage Waterfront Near Downtown Norfolk
Guesthouse in Portsmouth
4.97 out of 5 average rating, 153 reviewsSpring Hill Guest Cottage - Portsmouth
Home in Virginia Beach
4.92 out of 5 average rating, 264 reviewsMaster bedroom suite 3 blocks from the beach
Home in Norfolk
4.92 out of 5 average rating, 159 reviews@Whit’s End? Come in and Relax
Apartment in Newport News
4.97 out of 5 average rating, 152 reviewsCentrally Located Sleek Studio Apartment
Townhouse in Chesapeake
4.91 out of 5 average rating, 107 reviewsFamily friendly townhouse
Guest suite in Hampton
4.96 out of 5 average rating, 469 reviewsStorybook Cottage
Other great vacation rentals in Chesapeake
Guest suite in Chesapeake
4.99 out of 5 average rating, 139 reviewsBeautiful Two Bedroom King Bed Guest House
Cottage in Norfolk
4.98 out of 5 average rating, 180 reviewsPeaceful beach @Courtyard Cottage+No Cleaning Fee!
Apartment in Portsmouth
4.96 out of 5 average rating, 243 reviewsCozy Ground Floor Apt in Historic Home
Guest suite in Virginia Beach
4.87 out of 5 average rating, 181 reviewsSmall & Cozy Guest Suite w/ Private Bath & Jet-Tub
Cottage in Virginia Beach
4.95 out of 5 average rating, 311 reviewsSeaglass Cottage
Tiny home in Hampton
4.91 out of 5 average rating, 176 reviewsHampton River Retreat Tiny House
Apartment in Chesapeake
4.97 out of 5 average rating, 99 reviews2 BR With King. ⚡️Fast Wifi. 🔐 Easy Self Check-In.
Apartment in Virginia Beach
4.88 out of 5 average rating, 156 reviewsVa.Beach/Oceanfront Studio, Boardwalk, Beach, Pool
Quick stats about vacation rentals in Chesapeake
Total rentals
1.1K properties
Rentals with dedicated workspaces
590 properties have a dedicated workspace
Rentals with a pool
150 properties have a pool
Pet-friendly rentals
340 properties allow pets
Family-friendly rentals
510 properties are a good fit for families
Total number of reviews
31K reviews
Frequently Asked Questions
Where should I stay in Chesapeake?
Make yourself at home in Chesapeake by choosing from our most frequently booked neighborhoods. We have over 320 vacation rentals in Ghent, over 110 vacation rentals in Salem, over 550 vacation rentals in Olde Towne, and over 550 vacation rentals in Downtown Norfolk.
Are there vacation rentals with a dedicated workspace in Chesapeake?
Yes! Work meets play with ease at over 590 vacation rentals in Chesapeake featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Chesapeake?
Four-legged friends are welcome in Chesapeake. Choose from more than 340 vacation rentals for guests traveling with pets.
Are there Chesapeake vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 150 vacation homes with pools in Chesapeake, available on Airbnb. Make a splash and soak up the sun in style!
How much does it cost to stay in apartment rentals in Chesapeake?
Experience the best of Chesapeake with our apartment rentals, starting at about $10 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Chesapeake have a bbq area?
Absolutely! We offer over 120 house rentals with a bbq area in Chesapeake. Enjoy a tailored experience with all the comforts you desire.
Do townhouse rentals in Chesapeake have a gym?
Absolutely! We offer over 10 townhouse rentals with a gym in Chesapeake. Enjoy a tailored experience with all the comforts you desire.
Do condo rentals in Chesapeake have wifi?
Absolutely! We offer over 40 condo rentals with wifi in Chesapeake. Enjoy a tailored experience with all the comforts you desire.
Do condo rentals in Chesapeake have self check-in?
Absolutely! We offer over 10 condo rentals with self check-in in Chesapeake. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly townhouse rentals in Chesapeake?
Chesapeake has more than 70 family-friendly townhouse rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Destinations to explore
- Outer Banks Vacation rentals
- Virginia Beach Vacation rentals
- Richmond Vacation rentals
- Norfolk Vacation rentals
- Williamsburg Vacation rentals
- Nags Head Vacation rentals
- Myrtle Beach Vacation rentals
- Washington Vacation rentals
- Deep Creek Lake Vacation rentals
- Philadelphia Vacation rentals
- Jersey City Vacation rentals
- New York Vacation rentals
- Smoking-friendly rentals Chesapeake
- Townhouse rentals Chesapeake
- Rentals with breakfast Chesapeake
- Rentals with an EV charger Chesapeake
- Waterfront rentals Chesapeake
- Rentals with a hot tub Chesapeake
- Condo rentals Chesapeake
- Monthly Rentals Chesapeake
- Rentals with pools Chesapeake
- Rentals with a home theater Chesapeake
- Rentals with outdoor seating Chesapeake
- Rentals with beach access Chesapeake
- Apartment rentals Chesapeake
- Rentals with a fire pit Chesapeake
- Rentals with lake access Chesapeake
- Fitness-friendly rentals Chesapeake
- Private suite rentals Chesapeake
- Kid-friendly rentals Chesapeake
- Rentals with a patio Chesapeake
- Pet-friendly rentals Chesapeake
- Rentals with a washer and dryer Chesapeake
- Rentals with a fireplace Chesapeake
- Family-friendly rentals Chesapeake
- House rentals Chesapeake
- Cabins United States
- Treehouses United States
- Glamping United States
- Tiny Houses United States
- Beach Houses United States
- Campers and RVs United States
- Lakehouses United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes