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Find places to stay in Chesapeake

Vacation rentals from professional hosts. Book direct, skip the platform markup.

Chesapeake Vacation Rentals

Chesapeake Vacation Rentals

Find places to stay in Chesapeake

Vacation rentals from professional hosts. Book direct, skip the platform markup.

Stop overpaying for
vacation rentals.

Trending stays in Chesapeake

Birchwood Dream

Apartment in Harbor Springs, MI

Hosted by Holiday Vacation Rentals, LLC

Feb 20 – Mar 22

Birchwood Dream

Apartment in Harbor Springs, MI

Hosted by Holiday Vacation Rentals, LLC

Feb 20 – Mar 22

10% savings

Shop, Golf & Explore: Family Home in Chesapeake!

House in Chesapeake, VA

Hosted by Evolve

Feb 22 – Feb 27

10% savings

Shop, Golf & Explore: Family Home in Chesapeake!

House in Chesapeake, VA

Hosted by Evolve

Feb 22 – Feb 27

8% savings

Spacious Chesapeake Home w/ Pool Table!

House in Chesapeake, VA

Hosted by Evolve

Feb 19 – Feb 24

8% savings

Spacious Chesapeake Home w/ Pool Table!

House in Chesapeake, VA

Hosted by Evolve

Feb 19 – Feb 24

8% savings

Bright Chesapeake Home Near Shopping & Dining

House in Chesapeake, VA

Hosted by Evolve

May 1 – May 6

8% savings

Bright Chesapeake Home Near Shopping & Dining

House in Chesapeake, VA

Hosted by Evolve

May 1 – May 6

Large four bedroom. Great area!

House in Chesapeake, VA

Hosted by Traverse

Oct 1 – Oct 6

Large four bedroom. Great area!

House in Chesapeake, VA

Hosted by Traverse

Oct 1 – Oct 6

18% savings

Great home in the heart of Chesapeake VA.

House in Chesapeake, VA

Hosted by Traverse

18% savings

Great home in the heart of Chesapeake VA.

House in Chesapeake, VA

Hosted by Traverse

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Nearby Cities

Basye, Virginia, United States Arlington, VA, USA Sterling, VA, USA Virginia Beach, VA, USA Norfolk, VA, USA Williamsburg, VA, USA Richmond, VA, USA