orHere 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.
3304 Patrick Henry Dr |
|
 |
3304 Patrick Henry DrChesapeake, VA$3,550
Vacation Rentals, Unknown NEW!
No upfront deposits available! Discover your dream home in the sought-after community of Culpepper Landing! This exquisite 3-story residence boasts over 3,000 sq. ft. of bright and inviting...... |
1206 Copper Knoll Ln |
|
 |
1206 Copper Knoll LnChesapeake, VA$3,295
Vacation Rentals, Unknown NEW!
Welcome to this spacious and beautifully maintained four-bedroom, three-bathroom home located in the heart of Chesapeake! Located in the Albemarle River neighborhood of Chesapeake and is centrally...... |
722 Huntly Dr |
|
 |
722 Huntly DrChesapeake, VA$1,995
Vacation Rentals, Unknown NEW!
COMPLETELY UPDATED & ready NOW!! Come see this charming end-unit townhome with HUGE fenced backyard! Home has just been updated will all-new LVP flooring downstairs, new carpet upstairs, fresh...... |
1407 Yeadon Rd |
|
 |
1407 Yeadon RdChesapeake, VA$1,900
Vacation Rentals, Unknown NEW!
Property will be available 7/28. No upfront deposits available! Beautiful 3 bedroom, 1 bath home! Spacious living room with tons of natural lighting. The kitchen is equipped with stainless steel...... |
905 Hollywood Dr |
|
 |
905 Hollywood DrChesapeake, VA$2,950
Vacation Rentals, Unknown
Available August 1st, 2025 Fully renovated home located near Chesapeake Regional Medical Center. Stainless appliances, granite countertops, hardwood floors, tiled bathroom floors, and carpeted...... |
412 Desertmartin Way |
|
 |
412 Desertmartin WayChesapeake, VA$3,200
Vacation Rentals, Unknown
Welcome home to 412 Desertmartin Way, a beautiful property nestled in the heart of Chesapeake's sought-after Grassfield school district! This freshly renovated 4-bedroom, 2.5-bath gem sits at the...... |
2116 Kingsley Ln |
|
 |
2116 Kingsley LnChesapeake, VA$2,650
Vacation Rentals, Unknown
No upfront deposits available! Fantastic 4 bedroom, 2.5 bath Home in Ships Crossing! Open foyer and living room space. The kitchen is equipped with stainless steel appliances, center island and...... |
642 Willow Bend Dr |
|
 |
642 Willow Bend DrChesapeake, VA$2,850
Vacation Rentals, Unknown
Fabulous updated 4 bedroom, 3 full bath home in the Deep Creek area of Chesapeake! Super spacious with a formal dining room and living room which would make a fantastic office space! The kitchen is...... |
1231 Club Point Rd |
|
 |
1231 Club Point RdChesapeake, VA$2,495
Vacation Rentals, Unknown
Come see this great 3-bedroom home in popular Cedar Crossing featuring a fabulous community pool, playgrounds, tennis courts, community lake, and front yard landscaping all included in your rent!...... |
1343 Cypress Pl |
|
 |
1343 Cypress PlChesapeake, VA$2,350
Vacation Rentals, Unknown
Nice home, big yard backs to community park area with access to bike paths, lakes, play area etc. Fresh Wood-look flooring in all living areas except the bedrooms which have carpet. Stone fireplace...... |
908 Clear Springs Ct |
|
 |
908 Clear Springs CtChesapeake, VA$2,800
Vacation Rentals, Unknown
Spacious and versatile home located in the highly desirable Greenbrier community! The thoughtfully designed layout features four bedrooms upstairs, plus a flexible main-level space ideal for a...... |
Branner Rd |
|
 |
Branner RdChesapeake, VA$3,100
Vacation Rentals, Unknown
Newly built home 2025, high ceilings, pond facing, open floor plan, large island in kitchen, upgraded appliances with quartz counter tops, premium hardwood floors, covered front porch. Closer to...... |
3128 Woodbaugh Dr |
|
 |
3128 Woodbaugh DrChesapeake, VA$2,900
Vacation Rentals, Unknown
Single family ranch , move-in-ready home with fresh paint , new carpet and big backyard is available. Home has 4 bedrooms and 2 Full bathrooms in a highly sought-after location! Ideally situated...... |
602 Barwick Ct |
|
 |
602 Barwick CtChesapeake, VA$1,900
Vacation Rentals, Unknown
Gorgeous end unit condo. This two-bedroom home offers a remarkable amount of space and is designed for comfortable living and entertaining. The downstairs features a large, open floor plan, perfect...... |
1311 Wingfield Ave |
|
 |
1311 Wingfield AveChesapeake, VA$2,400
Vacation Rentals, Unknown
New 2nd bath. New enclosed garage as BR#4 with mini-split HVAC. New floors and paint. More repairs/upgrades to come.... |
2321 Alcott Way |
|
 |
2321 Alcott WayChesapeake, VA$2,200
Vacation Rentals, Unknown
Beautiful open floor plan. Two spacious bedrooms upstairs each with their own bathroom and huge walk-in closets. Beautiful kitchen with breakfast bar, pantry and stainless steel appliances....... |
2437 Annie Cir |
|
 |
2437 Annie CirChesapeake, VA$2,990
Vacation Rentals, Unknown
COMING SOON Available July 21st or Sooner! DM for FREE Showing Renovations are 90% complete on this spacious 5 bed, 2.5 bath home in Chesapeake move-in ready by mid-July or earlier! Located near...... |
801 Brandermill Dr |
|
 |
801 Brandermill DrChesapeake, VA$2,550
Vacation Rentals, Unknown
Single Family One Story Home that contains 1,545 SF with four bedrooms and two bathrooms. The home also has a living and Dining area with a large kitchen. A one car attached garage, with a large...... |
2742 Janice Lynn Ct |
|
 |
2742 Janice Lynn CtChesapeake, VA$1,550
Vacation Rentals, Unknown
If you are searching for a great place to live you do not have to search any further. This newly remodeled three bedroom, 1.5 bathroom townhouse in the Amberly section Deep Creek North, Chesapeake...... |
2726 Janice Lynn Ct |
|
 |
2726 Janice Lynn CtChesapeake, VA$1,850
Vacation Rentals, Unknown
Welcome to this beautifully maintained 3-bedroom, 1.5-bath townhouse the perfect blend of comfort and convenience! Nestled in a desirable neighborhood, this home features a recently updated roof...... |
1305 Simms Arch |
|
 |
1305 Simms ArchChesapeake, VA$3,500
Vacation Rentals, Unknown
Hickory school district! Quiet Cul-de-sac! Ranches like this do not come along everyday! Tastefully renovated, this 4 bedroom 3 full bath ranch features: Great layout with 3 spacious bedrooms on...... |
4010 Ridgewood Ct |
|
 |
4010 Ridgewood CtChesapeake, VA$2,700
Vacation Rentals, Unknown
Amazing waterfront home located on the Elizabeth River of Chesapeake with 4 bedrooms and 2 bathrooms. Highlights: - Central air and heat - Open concept kitchen with granite countertops and...... |
2363 Old Greenbrier Rd |
|
 |
2363 Old Greenbrier RdChesapeake, VA$1,750
Vacation Rentals, Unknown
Newly renovated, well maintained condo located in an established community. This unit is directly across from the community pond, with it's very own fenced-in patio. Complete with new flooring and...... |
908 Levee Ln |
|
 |
908 Levee LnChesapeake, VA$2,250
Vacation Rentals, Unknown
Available for move in 9/22. No in person showings until 9/5. Home is currently rented. Do not contact the tenant asking for the home to be shown. Great 3BR, 2BA home in desirable Deep Creek. Huge...... |
4243 Schooner Trl |
|
 |
4243 Schooner TrlChesapeake, VA$1,500
Vacation Rentals, Unknown
3 Bedroom 2 & 1/2 Bath Condominium unit. Recent construction features HVAC, spacious well laid out kitchen, carpeted living areas, master bedroom features master bathroom, washer and dryer...... |
729 Creekwood Dr |
|
 |
729 Creekwood DrChesapeake, VA$3,300
Vacation Rentals, Unknown
This beautifully maintained 5 - bedroom, 3 - bathroom home offers an impressive 2,800 sqft of living space. Enjoy the beauty of fresh carpet and new paint throughout this spacious home. A fully...... |
4108 Emberhill Ln |
|
 |
4108 Emberhill LnChesapeake, VA$2,295
Vacation Rentals, Unknown
Don't let the price fool you! Beautiful Brick Ranch in a well-established neighborhood of Forest Hills in Western Branch just off Dock Landing Road. Huge Corner Lot with completely fenced in yard....... |
2224 Capri Cir |
|
 |
2224 Capri CirChesapeake, VA$1,800
Vacation Rentals, Unknown
Bedroom, 1.5 Bath Brick Ranch Living Room w/ decorative fireplace Kitchen w/ Eat in Dining Area New Custom Kitchen Cabinetry w/ soft close drawers New LVP and Carpet Throughout New Insulated...... |
604 Barwick Ct |
|
 |
604 Barwick CtChesapeake, VA$1,695
Vacation Rentals, Unknown
Two bedroom two and a half bath end unit townhouse. Close to shopping and interstate. Both bedrooms have private bath. Fenced patio with storage. Tenant has pool privileges.... |
350 Sawyers Mill Xing |
|
 |
350 Sawyers Mill XingChesapeake, VA$2,995
Vacation Rentals, Unknown
Welcome to this beautiful 4-bedroom, 2.5-bath home in sought-after Sawyers Mill and the Grassfield school district! With over 2,700 sq ft of living space, this home offers both comfort and style....... |
1025 Stillmeadows Ct |
|
 |
1025 Stillmeadows CtChesapeake, VA$3,100
Vacation Rentals, Unknown
This beautifully maintained 4-bedroom, 2.5-bathroom home offers comfort and style in every corner. Featuring an open-concept living and dining area, modern kitchen with updated appliances, and a...... |
1127A Willow Ave |
|
 |
1127A Willow AveChesapeake, VA$3,100
Vacation Rentals, Unknown
Updated home with tons of space. 2 living areas downstairs with open kitchen and dining area. Updated appliances. Private bedroom downstairs with its own bathroom. Upstairs is 4 bedrooms, all very...... |
812 Cherry Forest Ct |
|
 |
812 Cherry Forest CtChesapeake, VA$3,500
Vacation Rentals, Unknown
Come Fall In-Love with this Gorgeous Home Nestled in a Cul-De-Sac. Big Deck and Huge fenced yard that is ready for Entertaining. Enjoy the Big Open eat In Kitchen with lots of countertop and...... |
225 Shore Side Rd |
|
 |
225 Shore Side RdChesapeake, VA$2,500
Vacation Rentals, Unknown
4 bedroom, 3 bath home in Great Bridge school district. Bright open floor plan. Granite countertops. Maple hardwood floors throughout. Marble floors and surrounds in Baths. Laundry/mudroom with...... |
1417 Decatur St |
|
 |
1417 Decatur StChesapeake, VA$1,795
Vacation Rentals, Unknown
Welcome to this beautiful 3-bedroom, 1.5-bath home located in the heart of Chesapeake! Renovated in 2008, this property offers a warm blend of comfort and character. Step inside to find spacious...... |
924 Portland St |
|
 |
924 Portland StChesapeake, VA$2,000
Vacation Rentals, Unknown
New, New, New! Everything is new! Enjoy this beautiful home located at center of cul-de-sac with huge fenced backyard. Schedule your appointment today!... |
812 Whisper Hollow Dr |
|
 |
812 Whisper Hollow DrChesapeake, VA$3,495
Vacation Rentals, Unknown
- Spacious 4BR Home with Hardwood Floors - Bright Kitchen with Stainless Steel Appliances - Breakfast Nook - Gas Range with Double Oven - Washer and Dryer Included - Hickory High School, Hickory...... |
1016 Beachstone Quay |
|
 |
1016 Beachstone QuayChesapeake, VA$3,995
Vacation Rentals, Unknown
Welcome to 1016 Beachstone Quay, the first-ever rental opportunity in this highly sought-after neighborhood! This stunning 5-bedroom, 3-full-bath home offers just over 2,800 square feet of open,...... |
920 Green Sea Trl |
|
 |
920 Green Sea TrlChesapeake, VA$2,900
Vacation Rentals, Unknown
No upfront deposits available! Magnificent 4 bedroom, 3 bathroom Home located in Cumberland Farms! Fantastic kitchen equipped with stainless steel appliances, granite countertops, pantry closet and...... |
1615 Hawthorne Dr |
|
 |
1615 Hawthorne DrChesapeake, VA$2,950
Vacation Rentals, Unknown
Welcome to this beautiful updated single-family home with a backyard oasis you won't be able to resist, located on a quiet dead-end street in the desirable Norfolk Highlands neighborhood of...... |