Chesapeake Accommodations - Hotels & Rentals
About Chesapeake Vacation Rentals
Discover More than 179 Incredible Getaway Rentals Available in Chesapeake. Choose from a Wide Selection of Villas, Hotels, and Other Rental Options. Explore Luxury Amenities at Affordable Prices, Creating the Ideal Base for Your Next Vacation. Plan Your Perfect Escape with Online Reservations and Uncover Fantastic Stays in Chesapeake.
Online Reservations Offers Numerous Last-Minute Deals on Villas, Hotels, and Rentals, Both Near You and Across the Globe. Whether You Need Accommodation for a Group or an Event, Be it a Hotel or Vacation Rental (Including Cabins and Private Luxury Villas), We're Here to Assist. With Online Reservations in Chesapeake, You Can Easily Compare Options from Multiple Suppliers with a Single Click to Find the Perfect Price Point, Amenities, and Style of Stay That Suit Your Needs. Looking for Group Deals, Properties with Private Pools, Hot Tubs, Pet-Friendly Options, or Spacious Master Suite Bedrooms with Open-Air Showers? You Can Find It All in the Online Reservations Vacation Rentals, Resorts, and Airbnb-Style Properties in Chesapeake. The Average Size of Places to Stay Near Chesapeake is 438.86 ft², with Prices Averaging US $186 per Night.
Let Online Reservations Help You Discover the Ideal Holiday Rental to Create Lifelong Travel Memories in Chesapeake. Our Listed Prices Are Often Discounted Compared to Rack Rates. Simply Search for Your Destination and Secure the Perfect Place to Stay Today.
Top Hotels & Vacation Rentals in Chesapeake
| Type | Count |
|---|---|
| Vacation Homes | 67 |
| Holiday Apartments | 20 |
| Cottages | 2 |
Use these Quick Filters to Find a Vacation Rental in Chesapeake
★ Pro Tip: Online Reservations is a vacation rental website specializing in cottages, lake houses, and exclusive summer home rentals. We curate a vast selection of incredible properties from trusted suppliers, allowing you to compare prices and locations to find the perfect fit for your getaway. Create lasting memories in Chesapeake with Online Reservations.
Weather in Chesapeake, VA
View the weather forecast for Chesapeake before booking your Chesapeake Vacation Rentals to confirm your best time to go.
Activities ChesapeakeGuest Reviews Local Attractions
A Large Selection of Hotels and Vacation Rentals from Around the World ChesapeakeGuest Reviews Discover Exciting Activities and Must-Visit Destinations for Your Upcoming Journey
Find Hotels & Vacation Rentals in these Cities and Neighborhoods
Frequently Asked Questions About Chesapeake?
What are the top hotels, lake houses & vacation rentals in Chesapeake?
We provide an array of great vacation destinations in Chesapeake. If you are looking to stay in or around the Chesapeake area, make sure to browse our options to find a premium rental location in a top vacation destination. Whether it is a few nights, a week, or more, we've got the luxury stays that rank among the Top Vacation Rentals in Chesapeake:
- Fully renovated and Modernized home in Chesapeake
- Bright Chesapeake Home Near Shopping & Dining
- Southern Charm Warm and WelcomenEntire home hosted by Annetten4 guests
- The Sparks Home! Relaxing Space + Lux Kitchen
- Beautiful home in Chesapeake
- Looking for 30 days or more contact me via VRBO for special pricing. Hot Tub
- Great Studio | Pool & Hot Tub. Your Next Vacation
- Fenced Yard & Patio! 2,400-Sq-Ft Chesapeake Home
- The Full House
- NEWLY REMODELED 2 BEDROOM DUPLEX
How many Hotels & Vacation Rentals have private pools in Chesapeake?
We have 3 Hotels & Vacation Rentals featuring a private pool in and near Chesapeake. Some of the best destinations to stay that feature or have access to a swimming pool are:
- Wingate by Wyndham Chesapeake
- Sleep Inn & Suites Chesapeake - Portsmouth
- Comfort Inn & Suites Chesapeake - Portsmouth
Which hotel, lake house, or vacation rental in Chesapeake is best for families?
Searching for a family-friendly getaway in Chesapeake? We've got you covered. Check out one of these luxurious getaways that are highly-rated and perfect fits for families of all sizes.
- Shop, Golf and Explore Family Home in Chesapeake!
- Hilton Garden Inn Chesapeake/Greenbrier
- Homewood Suites by Hilton Chesapeake-Greenbrier
How many hotels, resorts, or rentals are available in Chesapeake?
Online Reservations™ offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by Online Reservations™ in 2026 is over 179 in the Chesapeake area, and that number rises every day. By combining listings from multiple websites and travel providers, Online Reservations™ can provide you with a diverse amount of choices of the best luxury stays in Chesapeake.
Nearby Neighborhood (7)
| Neighborhood | Property Count |
|---|---|
| Greenbrier East Vacation Rentals in Chesapeake, Virginia | 27 |
| Western Branch North Vacation Rentals in Chesapeake, Virginia | 70 |
| Greenbrier West Vacation Rentals in Chesapeake, Virginia | 60 |
| Great Bridge Vacation Rentals in Chesapeake, Virginia | 103 |
| Deep Creek South Vacation Rentals in Chesapeake, Virginia | 145 |
| Churchland Vacation Rentals in Chesapeake, Virginia | 63 |
| Great Bridge East Vacation Rentals in Chesapeake, Virginia | 27 |
