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.
533 Tennis Dr |
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533 Tennis DrChesapeake, VA$3,500
Vacation Rentals, Unknown NEW!
All brick 4 bd/2 bth single family home on a corner lot centrally located to amenities in Greenbrier including a stocked pond on the exterior of the property. The home was just renovated with a new...... |
4133 Stephanie Boyd Dr |
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4133 Stephanie Boyd DrChesapeake, VA$3,600
Vacation Rentals, Unknown
Beautiful 5 bedroom 3.5 bath Cape Cod that sits on a generous corner lot. If you have been looking for that perfect place, look no further. Located off the Dock Landing exit. Excellent schools,...... |
1762 Watershed Ct |
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1762 Watershed CtChesapeake, VA$3,500
Vacation Rentals, Unknown
5 bedroom, 3 bathroom home located in highly desirable Grassfield School District. The home contains a guest bedroom with semi attached full bath on the main level of the home. Kitchen has a large...... |
3408 Seneca Ave |
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3408 Seneca AveChesapeake, VA$2,395
Vacation Rentals, Unknown
Totally updated home in 2018. Amazing eat-in kitchen with plenty of cabinets and a pot filler over the stove. Large great room. 2 first floor bedrooms, master plus additional bedroom and bonus room...... |
5109 James St |
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5109 James StChesapeake, VA$2,200
Vacation Rentals, Unknown
Please Read Carefully: TOURING TO BE SCHEDULED AFTER APPLICATION. CHECK OUT THE 41 PHOTOS, WALKTHROUGH VIDEOS & DRIVE BY THE PROPERTY @ YOUR CONVENIENCE. Security Deposit=$2,200+1st Mo Rent Of...... |
4110 Hamilton St |
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4110 Hamilton StChesapeake, VA$3,000
Vacation Rentals, Unknown
Here's a polished and complete version of your listing with the added features: Spacious 4 Bed / 2.5 Bath Home for Rent Chesapeake, VA Located at Hamilton St, Chesapeake, this beautiful home offers...... |
1115 Wright Ave |
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1115 Wright AveChesapeake, VA$2,000
Vacation Rentals, Unknown
Marvel at the charm and warmth of this inviting four-bedroom haven, nestled in the heart of Chesapeake at 1115 Wright Ave. With 1303 sq ft of thoughtfully designed living space, this delightful...... |
2968 Bruce Sta |
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2968 Bruce StaChesapeake, VA$3,000
Vacation Rentals, Unknown
Beautiful home in the heart of Western Branch with newer carpet throughout! Enjoy the spacious first floor, complete with a formal living room, dining room, and great room with a gas fireplace and...... |
817 Englewood Dr |
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817 Englewood DrChesapeake, VA$2,900
Vacation Rentals, Unknown
Like New! Wonderful brick ranch in the heart of Greenbrier! Large treed corner lot with side loading garage! Large ranch with formal dining room, gourmet kitchen with huge over sized center island...... |
816 Mullen Rd |
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816 Mullen RdChesapeake, VA$1,595
Vacation Rentals, Unknown
This charming 3 bedroom, 2.5 bath Ranch Style single family home is available for lease starting end of April Some of the amenities this beautiful rancher has to offer: A well natural lighted and...... |
Mark St |
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Mark StChesapeake, VA$2,000
Vacation Rentals, Unknown
Please message directly for the price, and to schedule a tour. Thank you! Welcome to your new home, a spacious and inviting home in the heart of Chesapeake, Virginia. This beautiful property...... |
3410 Bangor Ct |
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3410 Bangor CtChesapeake, VA$2,100
Vacation Rentals, Unknown
Three bedrooms Two bath home in Dunedin area of Chesapeake. Private parking private backyard, French door refrigerator ceramic tile floor. Laundry hook up. Close to the interstate and shopping areas.... |
1128 Hazel Ave |
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1128 Hazel AveChesapeake, VA$1,995
Vacation Rentals, Unknown
Well maintained and recently renovated 3-bedroom, 2-bathroom single-family home located in Central Chesapeake, featuring carpet and vinyl flooring, along with updated kitchen cabinets and...... |
1207 Madeline Ryan Way |
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1207 Madeline Ryan WayChesapeake, VA$3,550
Vacation Rentals, Unknown
AVAILABLE 16 June 2026 -- PRIME LOCATION!! This beautiful, 3,000 sq ft home features 5 beds, 3 bath and is built on a cul-de-sac with no thru traffic. Home is located in southern Chesapeake/Great...... |
305 Nottaway Ct |
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305 Nottaway CtChesapeake, VA$2,100
Vacation Rentals, Unknown
Welcome home to this charming 3-bedroom, 2.5-bath townhome in the heart of Chesapeake. Designed for both comfort and convenience, this home features an open-concept layout where the spacious family...... |
2620 Sunrise Ave |
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2620 Sunrise AveChesapeake, VA$1,900
Vacation Rentals, Unknown
3 bedroom 1.5 bath, townhome in nice neighborhood, new flooring, painted cabinets, new windows. Off street parking in rear of home. Central Air/Heat pump. Stove, Refrigerator, washer/dryer hook up....... |
3100 Holly Ridge Dr |
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3100 Holly Ridge DrChesapeake, VA$3,400
Vacation Rentals, Unknown
Looking to rent our home- we have decided to move closer to family in another state. It is a four bedroom two bathroom house, Two car garage I absolutely love our home and I'm hoping to rent it to...... |
220 Stubbs Dr |
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220 Stubbs DrChesapeake, VA$3,200
Vacation Rentals, Unknown
Stunning 5 Bedroom Waterfront Home with 2 car garage... |
2012 Midway Ave |
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2012 Midway AveChesapeake, VA$2,425
Vacation Rentals, Unknown
Welcome to 2012 Midway Ave - a spacious and versatile 3-bedroom, 2-bath home offering room to live, work, and unwind comfortably. Inside, you'll find a flexible layout with generously sized...... |
852 Parapet Rd |
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852 Parapet RdChesapeake, VA$790
Vacation Rentals, Unknown
Private room available in a clean, well-kept home located in a quiet and safe neighborhood. The home features durable laminate flooring throughout and secure access with a personal entry code for...... |
2408 Sunset Dr |
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2408 Sunset DrChesapeake, VA$1,850
Vacation Rentals, Unknown
Adorable ranch home for rent and available by 5/15/2026. This home is fully updated throughout. Kitchen features beautiful shaker cabinets with granite countertops. Laminate flooring throughout the...... |
2414 Fieldsway Dr |
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2414 Fieldsway DrChesapeake, VA$3,000
Vacation Rentals, Unknown
Beautiful 3 bedroom condo in sought after community. Very well maintained unit with upgraded cabinets and countertops; master bedroom with ensuite and walk in closet; 1 car garage with a bunch of...... |
912 Hastings Ct |
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912 Hastings CtChesapeake, VA$2,795
Vacation Rentals, Unknown
ONE LEVEL LIVING! 3 bedrooms and 2 full baths, plus garage, and HUGE fully fenced in backyard! This is it! Available NOW! Open concept living area with cathedral ceiling, upgraded kitchen with...... |
927 Gene Cres |
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927 Gene CresChesapeake, VA$2,000
Vacation Rentals, Unknown
Welcome to this quiet single-family home in Chesapeake, offering comfort, privacy, and plenty of garage space. This 3-bedroom, 1-bath home provides a practical layout with comfortable living areas...... |
612 Reunion St |
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612 Reunion StChesapeake, VA$2,395
Vacation Rentals, Unknown
DON'T WAIT, you will want to see this home FIRST. This well-maintained, 3 story condo has a spacious, open floorplan, tall ceilings and tons of natural light. First floor bonus room could be...... |
2923 Scotia Dr |
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2923 Scotia DrChesapeake, VA$2,100
Vacation Rentals, Unknown
Well-maintained 3BR/1BA rental in the heart of Chesapeake offering 1,011 sq ft of comfortable living space. This home features a bright and open living area with durable flooring and neutral tones...... |
1503 Freeman Ave |
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1503 Freeman AveChesapeake, VA$2,700
Vacation Rentals, Unknown
This charming two-story home has 5 bedrooms, 2 bathrooms, a garage, and a screened in porch that looks out to the fenced in backyard. This property offers a spacious layout with comfortable living...... |
300 Windy Oak Run |
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300 Windy Oak RunChesapeake, VA$3,200
Vacation Rentals, Unknown
Quiet 4BD/2BA Rental in Central Chesapeake! Enjoy peace and quiet while being centrally located to all Chesapeake has to offer. Features include a spacious floorplan, fenced-in backyard, and plenty...... |
931 Painted Lady Pl |
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931 Painted Lady PlChesapeake, VA$3,950
Vacation Rentals, Unknown
5BR Home in Grassfield District | Upgrades + Large Yard + Walk to School Description: Beautifully upgraded 5-bedroom, 2.5-bath single-family home in Dominion Meadows, located in the highly...... |
2238 Sanibel Ln |
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2238 Sanibel LnChesapeake, VA$3,500
Vacation Rentals, Unknown
Beautiful 4 bedroom 2.5 bathroom with bonus room. First floor primary bedroom, with tray ceiling, has an en-suite that includes a soaking tub and 5' shower. Main living open floor plan. Kitchen...... |