Compare Cottages, Resorts, & Rentals in Chesapeake, Virginia, USA
About Chesapeake Vacation Rentals
There are over 179 amazing vacation rentals available in Chesapeake. Choose from a variety of options including villas, hotels, and other rental properties. Explore a vast selection of luxury amenities at unbeatable prices, providing you with the ideal spot for your next getaway. Life is Better at the Cottage with Vacation Cottage, where you can discover fantastic stays in Chesapeake.
Vacation Cottage offers numerous last-minute deals on villas, hotels, and rentals, both near you and across the globe. Whether you need accommodations for a group or event, such as a hotel or vacation rental (including cabins and private luxury villas), let us assist you. With Vacation Cottage in Chesapeake, you can easily compare options from multiple suppliers with just a click to find the perfect price point, amenities, and style of stay for you. Whether you're seeking group discounts, private pools, hot tubs, pet-friendly options, or spacious master suite bedrooms with open-air showers, you can find it all with Vacation Cottage vacation rentals, resorts, and Airbnb-style properties in Chesapeake. The average size of places to stay near Chesapeake is approximately 438.86 ft², with prices averaging US $186 per night.
Vacation Cottage helps you discover the perfect holiday rental to create lasting travel memories in Chesapeake. Prices listed often feature discounts compared to rack rates. Simply search for your destination and secure your ideal place to stay today.
Find Vacation Cottage Rentals in these Cities and Neighborhoods Chesapeake, VA
Frequently Asked Questions About Chesapeake?
What are the top cottages, summer homes, and lake houses 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
- The Full House
- King Suite. Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!
- NEWLY REMODELED 2 BEDROOM DUPLEX
How many rentals, hotels, or resorts are available in Chesapeake?
Vacation Cottage consistently updates its selection, offering a blend of new options alongside well-established accommodations in prime locations. Currently, there are over 179 properties listed by Vacation Cottage in the Chesapeake area for the year 2026, with this number increasing daily. By aggregating listings from various websites and travel providers, Vacation Cottage ensures a diverse array of choices for the best luxury stays in Chesapeake.
Nearby Neighborhood (7)
| Neighborhood | Property Count |
|---|---|
| Greenbrier East Rental Cottages and Private Getaways in Chesapeake, Virginia | 27 |
| Western Branch North Rental Cottages and Private Getaways in Chesapeake, Virginia | 70 |
| Greenbrier West Rental Cottages and Private Getaways in Chesapeake, Virginia | 60 |
| Great Bridge Rental Cottages and Private Getaways in Chesapeake, Virginia | 103 |
| Deep Creek South Rental Cottages and Private Getaways in Chesapeake, Virginia | 145 |
| Churchland Rental Cottages and Private Getaways in Chesapeake, Virginia | 63 |
| Great Bridge East Rental Cottages and Private Getaways in Chesapeake, Virginia | 27 |
