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.

1616 Chestnut Ave

1616 Chestnut Ave

Chesapeake, VA
$2,500
Vacation Rentals, Unknown  NEW!
Modern two story home with a beautiful floorplan and a huge backward. Spacious kitchen and rooms. Tile, carpet and laminate floors. 2 car garage. Close to shopping and dinning ....

1231 Kay Ave

1231 Kay Ave

Chesapeake, VA
$1,350
Vacation Rentals, Unknown
Cozy 2 bedroom, 1 bath home! Beautiful kitchen featuring a double sink and lots of storage space. Huge backyard with plenty of space for activities and Detached Garage! Pet Friendly! Pet screening......

1433 Oleander Ave

1433 Oleander Ave

Chesapeake, VA
$1,995
Vacation Rentals, Unknown
Beautiful 2 Bedroom 2 full bathroom home as new laminate flooring throughout dwelling. Spacious living room with working fireplace. Large kitchen with plenty of cabinet storage, refrigerator,......

601 Lord Byron Ct

601 Lord Byron Ct

Chesapeake, VA
$2,300
Vacation Rentals, Unknown
Looking for your next dream rental in Chesapeake? Look no further! This stunning 3-bedroom, 2.5-bathroom home is now ready for you to move in. Located in a serene neighborhood, this home offers......

863 Redleafe Cir

863 Redleafe Cir

Chesapeake, VA
$3,600
Vacation Rentals, Unknown
Beautiful 2 story home in Greystone neighborhood. Downstairs features gorgeous entry with formal living and dinning rooms, 1st floor bedroom, full bathroom, large living area w/ gas fireplace with......

641 Baywood Trl

641 Baywood Trl

Chesapeake, VA
$3,200
Vacation Rentals, Unknown
COMPLETELY RENOVATED!! 4BR/2BA, single story brick ranch on 2 acres in desirable Oak Manor! Freshly painted, spacious floor plan with generously sized bedrooms and large living spaces! Brand new:......

516 Birchwater Ave

516 Birchwater Ave

Chesapeake, VA
$3,200
Vacation Rentals, Unknown
Beautiful family home with 4 bedrooms, 2.5 bathrooms, and a huge fenced-in yard. This home is located in the best area of Chesapeake short distances from shopping, restaurants, and military bases.......

857 Mains Creek Rd

857 Mains Creek Rd

Chesapeake, VA
$2,100
Vacation Rentals, Unknown
This is a single house, just up grad a inside with new appliances. Nice quiet and stable neighborhood. Open kitchen and living room area, extra Den. Big fenced yard, easy access high way i-64,get......

504 Tuskegee Ave

504 Tuskegee Ave

Chesapeake, VA
$2,395
Vacation Rentals, Unknown
3 Bedroom, 2.5 bath home in Crestwood Area of Chesapeake in the desirable Great Bridge High School District. Large kitchen with eating area is open to the Family Room with a gas fire place. The......

568 River Gate Rd

568 River Gate Rd

Chesapeake, VA
$3,400
Vacation Rentals, Unknown
All brick home on lake with 3 car garage. Approximately 3700 sq ft, 6 bedrooms and 3 1/2 baths. Owners suite on First Floor. Minimum 2 year lease....

1331 Hazel Ave

1331 Hazel Ave

Chesapeake, VA
$950
Vacation Rentals, Unknown
Lovely room for a single professional, student ,or military member wanting a room in a quiet house. Room has a closet and window that gets sun in the afternoon. The room has no shared walls with......

1000 Butt St

1000 Butt St

Chesapeake, VA
$1,495
Vacation Rentals, Unknown
Coming Soon: This property is not currently available, please join the Rently Waitlist for more updates. Don't miss out on FREE RENT! Welcome to your new sanctuary, a snug 3-bedroom ranch that......

1110 Hazel Ave

1110 Hazel Ave

Chesapeake, VA
$1,400
Vacation Rentals, Unknown
Refreshed and Move-in ready, 2 bedroom, 1 bath! Updated with new flooring and appliances. Also features a spacious fenced in back yard. Located in Chesapeake near restaurants and shopping. Laundry......

4644 Indiana Ave

4644 Indiana Ave

Chesapeake, VA
$2,695
Vacation Rentals, Unknown
Magnificent 2-Story Home featuring 4 bedrooms and 2.5 baths! Great open concept living room and kitchen. The kitchen is equipped with stainless steel appliances, granite countertops, bar-top......

1108 Myrtle Ave

1108 Myrtle Ave

Chesapeake, VA
$2,095
Vacation Rentals, Unknown
Gorgeous renovated single family home almost move-in ready. All new kitchen with quartz countertops on peninsula and coffee station, new bathroom vanities with quartz top , fresh new carpet, fresh......

1132 Commerce Ave

1132 Commerce Ave

Chesapeake, VA
$1,450
Vacation Rentals, Unknown
Charming rancher, Dishwasher, Refrigerator, Microwave, Stove, Washer, and Drier. Fenced-in yard. Tenant responsible for utilities and yard. Pets with owner approval. To qualify we are looking for......

1001 Hillwell Rd

1001 Hillwell Rd

Chesapeake, VA
$2,700
Vacation Rentals, Unknown
This home offers a unique open floor plan. Downstairs has wood floors, 1/2 bath, living dining area, family room. Kitchen has breakfast bar with gas stove, refrigerator, microwave, dishwasher &......

3345 Country Cir

3345 Country Cir

Chesapeake, VA
$2,300
Vacation Rentals, Unknown
Spacious home - large primary bedroom w/sitting room & large closet. Washer/dryer connections. 2-car garage. Large fenced backyard. Pets accepted w/additional deposit and pet rent. No cats....

1117 George Olah Dr

1117 George Olah Dr

Chesapeake, VA
$3,500
Vacation Rentals, Unknown
This home was built in 2016 in the beautiful neighborhood of Olah's Landing in the Great Bridge area of Chesapeake! It was the neighborhood's model home, with many amenities and updated features.......

2420 Annie Cir

2420 Annie Cir

Chesapeake, VA
$3,200
Vacation Rentals, Unknown
Large open floor plan with 4 bedrooms, 2.5 baths in highly desirable Grassfield high school district!! * Contemporary & luxurious upgrades * Automated lighting throughout house * Granite kitchen......

1028 Woodsmans Reach

1028 Woodsmans Reach

Chesapeake, VA
$2,400
Vacation Rentals, Unknown
Beautifully maintained 3 bedroom 2.5 bathroom home in golf course community, highly sought after Greenbrier area. Home is tucked away on a quiet and peaceful cul-de-sac. This home has tastefully......

1112 Turtle Rock Trce

1112 Turtle Rock Trce

Chesapeake, VA
$2,300
Vacation Rentals, Unknown
Amazing 3 bedroom 2.5 bathroom home in Greenbrier! Huge Kitchen w/ SS appliances, granite counter tops, 6ft-island w/cabinets & seating for 5+,deep sink, separate faucet for drinking filtered......

913 Saddleback Trail Rd

913 Saddleback Trail Rd

Chesapeake, VA
$2,395
Vacation Rentals, Unknown
Take advantage of this rare rental opportunity! Gorgeous well maintained ranch home in the sought after Great Bridge community in Chesapeake! This home has tons of updates throughout including......

1212 Corden Ave

1212 Corden Ave

Chesapeake, VA
$1,800
Vacation Rentals, Unknown
Gorgeous Cape Cod home on a large corner lot in a quiet neighborhood. This 4 bedroom 2.5 bath has been beautifully updated. Spacious Master bedroom with french doors leading to the ensuite bath and......

2012 Sunset Maple Ln

2012 Sunset Maple Ln

Chesapeake, VA
$3,000
Vacation Rentals, Unknown
Beautifully maintained home in the heart of Grassfield school district. You will love everything about this home. Beautiful hardwood floors, newer carpets, stainless steel appliances, above ground......

3 Exeter Cir

3 Exeter Cir

Chesapeake, VA
$1,715
Vacation Rentals, Unknown
3 bedroom, 2.5 baths, privacy fence with a new back deck. Woods behind property give it a peaceful feeling. Trails for walking and riding bikes, community pool. Pets considered on a case by case......

971 N Haven Cir

971 N Haven Cir

Chesapeake, VA
$2,595
Vacation Rentals, Unknown
This beautiful single story home sits in a quiet cul-de-sac in the Waterford area of Chesapeake! You'll love the gorgeous open floor plan and over 2,000 square feet ready to be made a home. Take......

2518 Fieldsway Dr

2518 Fieldsway Dr

Chesapeake, VA
$2,450
Vacation Rentals, Unknown
Beautiful new construction home built in 2021. Shows pride in ownership. Come see the 1900sqft corner lot home with a lake view. This home features vinyl flooring, fresh carpet, walk in closets,......

408 Millwright Way

408 Millwright Way

Chesapeake, VA
$2,495
Vacation Rentals, Unknown
Well - maintained 4-bedroom, 2.5 -bathroom home in Sawyer's Mill is situated in cul-de-sac, perfect for those seeking a sense of community. Features include a large primary bedroom with en suite......

3820 Stonebridge Lndg

3820 Stonebridge Lndg

Chesapeake, VA
$2,850
Vacation Rentals, Unknown
Gorgeous 4 bedroom, 2.5 bathroom, Brick Ranch, 2 side car loading garage with multi-car driveway, Large Foyer with closet, 3 sliding glass doors, Huge Primary bedroom with dressing room, Updated......

712 Renee Ln

712 Renee Ln

Chesapeake, VA
$3,450
Vacation Rentals, Unknown
This Grassfield beauty features a beautiful open floor design with 5 bedrooms and 4 full baths, including a 1st floor en-suite for guest or multi generational needs. Beautiful LVP flooring covers......

4021 Oak Moss Ct

4021 Oak Moss Ct

Chesapeake, VA
$1,795
Vacation Rentals, Unknown
Fresh and Ready for immediate move in! Western Branch Schools. This 2 bedroom 1.5 bath home has fresh paint and new flooring throughout. Updated Kitchen with pantry and room for small table- Brand......

1244 Jackson Ave

1244 Jackson Ave

Chesapeake, VA
$2,500
Vacation Rentals, Unknown
DO NOT MESSAGE NOR CALL FOR SHOWINGS OR TO ASK IF WE TAKE SECTION 8 THE INFORMATION IS ALL IN THE DESCRIPTION PLEASE READ SHOWING WILL ONLY BE ON THE WEEKEND ON March 3,2024 - March 10, 2024 -......

108 Pile Ave

108 Pile Ave

Chesapeake, VA
$2,300
Vacation Rentals, Unknown
This gorgeous home is 4 bedrooms, 2.5 bathrooms. Large eat in kitchen and dining room. Living room is spacious with fireplace. This property boasts a two car garage and large fenced front and side......

3516 Raytee Dr

3516 Raytee Dr

Chesapeake, VA
$4,300
Vacation Rentals, Unknown
Beautiful home on a cul-de-sac. Inground pool with several acres of private land and fire pit out back. Harwood floors throughout. Upstairs laundry. Refinished deck. Two car garage. Private fenced......

420 Wickwood Dr

420 Wickwood Dr

Chesapeake, VA
$2,995
Vacation Rentals, Unknown
Title: Modern and Spacious Home for Rent in Chesapeake, VA Location: 420 Wickwood Dr, Chesapeake, VA Description: Welcome to 420 Wickwood Dr, a stunning and spacious home nestled in the heart of......

1104 Brandon Ct

1104 Brandon Ct

Chesapeake, VA
$2,450
Vacation Rentals, Unknown
Lovely 3 bedroom, 2.5 bath in a quiet cut de sac. Primary bedroom with bath located on the first floor. High ceilings with lots of natural light. Newer stainless steel appliances, quartz counter......

804 Arcadia Rd

804 Arcadia Rd

Chesapeake, VA
$2,500
Vacation Rentals, Unknown
Cul-de-sac ranch home! Four bedrooms, 2.5 baths. Through the foyer you enter the open family room with vaulted ceilings and fireplace. Huge eat in kitchen with workstation and pantry. Formal dining......

2001 English Ave

2001 English Ave

Chesapeake, VA
$2,000
Vacation Rentals, Unknown
Cozy cape cod in the heart of Chesapeake located close to Greenbrier, the interstate, shopping, and dining. Large eat-in kitchen, spacious rooms, fireplace, and attached garage. The back yard hosts......

404 Covington Ct

404 Covington Ct

Chesapeake, VA
$2,400
Vacation Rentals, Unknown
Spacious 3 bedroom condo in the heart of Chesapeake. 2 car garage and plenty of parking. All Keyrenter Hampton Roads residents are enrolled in the Resident Benefits Package (RBP) for $45.95/month......

Chesapeake, VA

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