Here are Chesapeake listings for rentals and roommates -- find yourself a whole new living arrangement by choosing from apartments, homes for rent, and other rooms for rent.

Also, if you're only passing through Chesapeake for a brief period of time, find short term rentals or vacation rentals.

1312 Rellen St
	1312 Rellen St Chesapeake, VA $2,250 Vacation Rentals, Unknown  NEW! Beautiful 3 bedroom 2 bath ranch home on a corner lot in the Alden Square neighborhood. Large living room with cathedral ceilings and fireplace. Converted garage adds another large living area to......

905 Porte Crayon St
	905 Porte Crayon St Chesapeake, VA $3,100 Vacation Rentals, Unknown Like new, 5 bed, 3.5 bath, plus flex room with French doors that could be an office, formal dining room or playroom. The finished FROG and bath is the 5th bedroom. There are plantation shutters......

604 Sail Fish Quay
	604 Sail Fish Quay Chesapeake, VA $2,100 Vacation Rentals, Unknown Adorable end unit condo in the Riverwalk area of Chesapeake. Move in ready with family room, large kitchen with dining area and pantry. Two bedrooms each with a full bath and a half bath......

9 Upton Cir
	9 Upton Cir Chesapeake, VA $1,750 Vacation Rentals, Unknown This freshly renovated home is a great find! This duplex connected at the garage features brand new windows and sliding glass door. Three bedrooms, two full baths and a half bath. Spacious kitchen......

2205 Hilton Ct
	2205 Hilton Ct Chesapeake, VA $2,200 Vacation Rentals, Unknown 2205 Hilton Court is a 4 bedroom and 2 and a half single family home located in the South Norfolk municipality in Chesapeake. Spacious bedrooms, galley style kitchen, partially converted garage for......

612 Bottom Quay
	612 Bottom Quay Chesapeake, VA $3,200 Vacation Rentals, Unknown Beautiful red brick home in the immaculately kept River Walk neighborhood of Chesapeake! This home has 3 bedrooms + a FROG that could function as bedroom #4 or as another upstairs living space.......

410 Fernwood Farms Rd
	410 Fernwood Farms Rd Chesapeake, VA $2,475 Vacation Rentals, Unknown Available now! The owner requests 680+ credit scores. 4-year-old 2-story single-family home with attached garage near schools, restaurants and expressways. Pergo floors, granite countertops......

148 Horse Run Dr
	148 Horse Run Dr Chesapeake, VA $1,795 Vacation Rentals, Unknown This spacious townhome offers open floor plan. Separate dining area and eat in kitchen. New carpet throughout and new upgrades. Two master suites. Eat in kitchen with all appliances. Conveniently......

932 Redstart Ave
	932 Redstart Ave Chesapeake, VA $1,695 Vacation Rentals, Unknown Beautiful home on a terrific lot. Single family ranch with remodeled kitchen and bathrooms. Living room with wood laminate flooring. Eat in kitchen with stainless steel appliance package to include......

317 Wimbledon Chase #A
	317 Wimbledon Chase #A Chesapeake, VA $1,695 Vacation Rentals, Unknown Great location near Chesapeake General hospital. Close to interstate and shopping. Just painted throughout. End unit with lots of privacy. Only one pet considered with pet restrictions and deposit.......

1110 Fenton Quay
	1110 Fenton Quay Chesapeake, VA $3,195 Vacation Rentals, Unknown Elevate your lifestyle with this impeccable 4-bedroom haven nestled within a tranquil cul-de-sac in the heart of Greenbrier. Cathedral ceilings soar above, inviting in an abundance of natural......

3425 Challis Dr
	3425 Challis Dr Chesapeake, VA $1,800 Vacation Rentals, Unknown 3 BEDROOM 1.5 BATH IN WESTERN BRANCH SCHOOL DISTRICT BIG YARD FOR FAMILY COOK OUTS, WITHIN MINTUES TO INTERSTATES TO ALL MAJOR MILITARY BASES, SHIPYARDS AND GREAT SHOPPING. FRESH PAINT....

320 Snowberry Ln
	320 Snowberry Ln Chesapeake, VA $2,495 Vacation Rentals, Unknown This spacious unit has a gorgeous backyard, open concept living area, and so much closet space! Ready for immediate move in. Tenant is responsible for all utilities and maintaining their half of......

1133 Lady Ashley Dr
	1133 Lady Ashley Dr Chesapeake, VA $2,595 Vacation Rentals, Unknown Look no further!! This fantastic 3 bedroom, 2.5 bath home is ready for move-in! Nice open and spacious floorplan with lovely neutral colors to fit any decor. Large kitchen offers stainless......

623 Partridge Ave
	623 Partridge Ave Chesapeake, VA $1,550 Vacation Rentals, Unknown Charming 3-Bedroom Home in Central Chesapeake available in September 2023. Welcome to your new rental home! This delightful 3-bedroom, 1-bathroom residence offers a cozy and convenient living......

4338 Stafford Dr
	4338 Stafford Dr Chesapeake, VA $1,300 Vacation Rentals, Unknown GREAT END UNIT TOWNHOME IN DESIRABLE WESTERN BRANCH! 2 PRIMARY BEDROOMS, GALLEY STYLE KITCHEN AND LARGE FAMILY RM. W/ WOOD BURNING FIREPLACE! LARGE LOT W/ PATIO AREA AND STORAGE SHED. THIS RENTAL......

1827 Elizabeth Ave
	1827 Elizabeth Ave Chesapeake, VA $2,295 Vacation Rentals, Unknown Beautiful and spacious single family home! Formal dining room, sit-in kitchen area and open living room. Kitchen features granite countertops and stainless steel appliances. HUGE primary bedroom......

837 Shillelagh Rd
	837 Shillelagh Rd Chesapeake, VA $2,850 Vacation Rentals, Unknown Immaculate 3,000 sq ft home on 2 acres! 4 bedrooms and 3 bath with possible 5th bedroom. Large open kitchen with NUMEROUS cabinets and an island, a two story two car detached garage- PLENTY of......

2432 Watermill Grv
	2432 Watermill Grv Chesapeake, VA $6,000 Vacation Rentals, Unknown Ready to move in home that is completely furnished in a beautiful and very quiet neighborhood with water views of the Elizabeth River in Chesapeake VA. Very private and quiet location yet within......

1452 Culpepper Ave
	1452 Culpepper Ave Chesapeake, VA $1,650 Vacation Rentals, Unknown Single family home with 3 bedrooms and 2 full baths. Laminate flooring in bedrooms, hallway, and living room. Tile in bathrooms and kitchen. Fenced back yard. Single car garage attached to house.......

1479 Atlantic Ave
	1479 Atlantic Ave Chesapeake, VA $1,900 Vacation Rentals, Unknown Modern home located in Chesapeake in close proximity to naval bases, shopping centers, schools and entertainment. Master bedroom has a walk in closet, spacious private bathroom with double sink......

1317 Fairway Dr
	1317 Fairway Dr Chesapeake, VA $2,695 Vacation Rentals, Unknown Located in the heart of Greenbrier, this four bedroom 2.5 bath has an open floor plan with a large kitchen, family room w/ FP, Living room/office, and formal dining room. 2 Car garage and sprinkler......

2637 N Elizabeth Harbor Dr
	2637 N Elizabeth Harbor Dr Chesapeake, VA $2,750 Vacation Rentals, Unknown Look no further!! This 4 bedroom Waterfront Rancher is spacious, well maintained and move-in ready!! The kitchen has been updated and offers lovely corian counters, soft close cabinets, lots of......

301 Meadow Creek Dr
	301 Meadow Creek Dr Chesapeake, VA $1,650 Vacation Rentals, Unknown 3 BEDROOM 1 BATH BIG FAMILY ROOM, HARDWOOD FLOORS THROUGH OUT. HUGE DET. GARAGE FENCED IN YARD, WITHIN MINTUES TO ALL MAJOR HIGHWAYS. CLOSE TO ALL MILITARY BASES,SHIPYARDS AND HOSPITALS....

627 Sail Fish Quay
	627 Sail Fish Quay Chesapeake, VA $1,750 Vacation Rentals, Unknown Spacious contemporary style condo located in the Mariners Quay section of Riverwalk. This condo offers 2 ensuite bedrooms, one with jetted tub. Open floor plan with cathedral ceilings, skylights,......

913 Swain Ave
	913 Swain Ave Chesapeake, VA $1,799 Vacation Rentals, Unknown Gorgeous 3 bedroom, 1 bath home! The kitchen features stainless steel appliances, granite countertops and bar-top seating! Spacious primary bedroom with en suite. Lovely backyard oasis! Relax under......

3364 Brandywine Dr
	3364 Brandywine Dr Chesapeake, VA $2,050 Vacation Rentals, Unknown Available 8/18/2023. Pretty ranch with recent updates to include granite countertops and kitchen appliances, flooring, heat and air conditioning, updated bathrooms with custom tile, newer deck.......

2885 E Point Dr
	2885 E Point Dr Chesapeake, VA $2,000 Vacation Rentals, Unknown SO MUCH SPACE in this charming ranch home! 3 bedrooms and 2 full baths with an attached garage, sunroom, living and dining room as well as large great room with fireplace. Beautiful neighborhood......

701 Rutherford Ct
	701 Rutherford Ct Chesapeake, VA $2,450 Vacation Rentals, Unknown Come view this well maintained 4 bedroom, brick ranch in a cul-de-sac! Newer carpet and luxury vinyl plank floors. Huge living room with wood burning fireplace with wood ceiling beams, large formal......

1311 Summerset Ct
	1311 Summerset Ct Chesapeake, VA $2,495 Vacation Rentals, Unknown Gorgeous 1-Level Ranch Home with Attached Garage on Cul-De-Sac next to Golf Course, Walking/Biking Trails and Park Areas! Open Floor-Plan! Large Fenced Yard With Nice Paver Patio! Hardwood LVP......

3221 Sir Meliot Dr
	3221 Sir Meliot Dr Chesapeake, VA $1,895 Vacation Rentals, Unknown Charming ranch with large backyard. Formal living room, formal dining room and family room with fireplace. Separate utility room. Large backyard that backs up to wooded area....

1240 Richwood Ave
	1240 Richwood Ave Chesapeake, VA $2,595 Vacation Rentals, Unknown Open 4 bedroom 2.5 bathroom home in Chesapeake. Huge kitchen with tons of counter space that looks into the family room. Huge primary bedroom with custom ceiling, walk-in closet, & bath with dual......

1421 Thrasher Lndg
	1421 Thrasher Lndg Chesapeake, VA $3,700 Vacation Rentals, Unknown Magnificent Home featuring 5 bedrooms and 3 full baths! Open concept living room and kitchen with dining area. Kitchen features granite countertops, double oven, wine rack, pantry closet and huge......

579 Seahorse Run
	579 Seahorse Run Chesapeake, VA $1,795 Vacation Rentals, Unknown 3 Bedroom, 2.5 bath condo. Loft on 3rd floor, 3rd floor loft. 3rd bedroom has a private deck. 2 bedrooms on 1st level. The master bedroom has a private balcony. Large great room, kitchen with......

3344 Stilworken Dr
	3344 Stilworken Dr Chesapeake, VA $1,995 Vacation Rentals, Unknown Welcome home to this 4 bed 1.5 bath home that has 1175 sq ft of living space. Big kitchen with new appliances, and a lot of cabinet space. Great yard with additional storage sheds and patio for......

2849 Crossings Dr
	2849 Crossings Dr Chesapeake, VA $2,795 Vacation Rentals, Unknown Stunning 4 bedroom, 2.5 bath home featuring a bright and open floor plan with a large family room with vaulted ceiling and fireplace, formal dining room and a large kitchen with granite counters......

1205 Bainbridge Blvd
	1205 Bainbridge Blvd Chesapeake, VA $1,500 Vacation Rentals, Unknown Established law office including law library/built in bookcases, private offices, reception, and waiting area. Perfect for office space, call center, tutoring center, lash studio, braiding salon......

800 Needlerush Ct
	800 Needlerush Ct Chesapeake, VA $3,195 Vacation Rentals, Unknown What a great house! 4 bedrooms, 2.5 baths, formal living and HUGE dining room, step-down family room w/gas fireplace and built-ins surrounding FP! Kitchen offers a Large eat-in/informal dining......

1314 18th St
	1314 18th St Chesapeake, VA $2,000 Vacation Rentals, Unknown Beautifully remodeled home with new windows, siding, counter tops, paint, flooring, and stainless steel appliances. Also has a new front porch. Master Bedroom has a walk in closet. Centrally......

713 Durham Ave
	713 Durham Ave Chesapeake, VA $2,450 Vacation Rentals, Unknown 4 bedrooms 2.5 bathrooms home available now. Freshly painted. Close to interstate and shopping. Great schools district....