Search for vacation rentals in Chesapeake.
Whether it's vacation home rentals, apartments, condos, or cabins/cottages, we have you covered -- search for rental properties in the entire Chesapeake area to find the perfect spot for your vacay.
910 Cantor St |
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910 Cantor StChesapeake, VA$2,900
Vacation Rentals, Unknown
Better than NEW! A recently rehabbed, first-time rental situated on a massive fenced lot on a quiet cul-de-sac in sought-after Stonegate! A pet-friendly 4-bedroom, 2 1/2 bath home with attached...... |
517 Hardwood Ct |
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517 Hardwood CtChesapeake, VA$2,195
Vacation Rentals, Unknown
Wonderfully renovated three bedroom one bath situated in the heart of Great Bridge, expansive kitchen and dining area, updated bathrooms, lvp flooring. Huge backyard with a small enclosed patio.... |
1023 Keel St |
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1023 Keel StChesapeake, VA$1,665
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 this lovely 3-bedroom, 1.5-bath residence nestled in...... |
812 Brightleaf Pl |
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812 Brightleaf PlChesapeake, VA$2,495
Vacation Rentals, Unknown
Gorgeous 4-bedroom home in Brightleaf Meadows available 05-28-24! 2-car attached garage with opener PLUS driveway parking! Great open floor-plan with spacious rooms and updates galore!! Kitchen has...... |
1933 Flintshire Dr |
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1933 Flintshire DrChesapeake, VA$3,999
Vacation Rentals, Unknown
Custom built by Steven Alexander! Beautiful open floor plan with 1st & 2nd floor master suites! Quiet St. - Grassfield school district! Large gourmet kitchen w/granite counter tops, upgraded...... |
535 Kings Gate |
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535 Kings GateChesapeake, VA$2,950
Vacation Rentals, Unknown
Recent updates have elevated the interior, boasting quartz countertops, modern stainless steel appliances, and updated flooring throughout, infusing the space with a contemporary feel. The fully...... |
516 Cavendish Way |
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516 Cavendish WayChesapeake, VA$3,600
Vacation Rentals, Unknown
Brand new model home. Be the first occupants!! Highly upgraded with a landscaped backyard/patio, top line appliances, etc! YouTube promotional video on this page shows the actual home, but none of...... |
503 Frances Ct |
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503 Frances CtChesapeake, VA$2,295
Vacation Rentals, Unknown
Lovely 3 bedroom 2 bathroom brick ranch house with a spacious yard in Great Bridge East/Hickory in Chesapeake, VA. It has beautiful wood floor in the family room, and laminated flooring throughout...... |
1128 Sir Galahad Dr |
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1128 Sir Galahad DrChesapeake, VA$3,300
Vacation Rentals, Unknown
Beautiful Fully Furnished pet friendly Downtown Chesapeake Home just 4 minutes away from main Highway and Downtown Chesapeake area! Our Amazing home comes with all utilities included plus free...... |
Arbuckle St |
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Arbuckle StChesapeake, VA$3,500
Vacation Rentals, Unknown
Beat the Spring/Summer rush to Culpepper Landing, the best neighborhood in Chesapeake! This beautiful home sits on .20 acres that back up to the Great Dismal Swamp National Wildlife Refuge for...... |
348 Kempsville Rd |
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348 Kempsville RdChesapeake, VA$1,600
Vacation Rentals, Unknown
Spacious 3 bedroom 2 bedroom brick ranch in the heart of Chesapeake. Brand New Renovation which includes new paint, LVP flooring, quartz counters, and shaker cabinets! This is a one of a kind...... |
1016 Sullivan Ln |
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1016 Sullivan LnChesapeake, VA$3,750
Vacation Rentals, Unknown
Excellent rental in a quiet, safe neighborhood in the Cedar Road Elementary and Grassfield High school zones. This is a 2006 Stephen Alexander home with several upgrades and improvements, to...... |
304 Oak Hill Way |
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304 Oak Hill WayChesapeake, VA$2,200
Vacation Rentals, Unknown
Welcome home to this meticulously kept single family detached condo in the heart of greenbrier. Convenient to everything, this home offers 3 bedrooms, 2.5 baths, updated kitchen including black...... |
2837 Crossings Dr |
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2837 Crossings DrChesapeake, VA$2,850
Vacation Rentals, Unknown
Come check out this gorgeous two story rental located in Chesapeake. This spacious home includes 4 beds and 2.5 baths with close to 3000 SQFT! Right from the entrance it feels like home with the...... |
303 Middleton Way |
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303 Middleton WayChesapeake, VA$2,800
Vacation Rentals, Unknown
Bright like new Single Family condo in the Hickory School District ready to move into now. Space galore with three bedrooms, two and a half baths and great room open to kitchen. Great floor plan!...... |
624 Creekside Ct |
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624 Creekside CtChesapeake, VA$1,695
Vacation Rentals, Unknown
BRICK FRONT END UNIT TOWNHOME IN SOUGHT AFTER RIVERWALK. LIVING ROOM WITH FIREPLACE, DINING AREA. EAT IN KITCHEN WITH ALL APPLIANCES INCLUDING REFRIGERATOR, GAS STOVE, DISHWASHER, DISPOSAL.VERY...... |
2436 Strawberry Ln |
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2436 Strawberry LnChesapeake, VA$1,625
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! Step into the serene and picturesque of this lovely 3-bedroom 1...... |
5213 Willow Lake Rd |
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5213 Willow Lake RdChesapeake, VA$2,800
Vacation Rentals, Unknown
Gorgeous 4 bedroom, 3.5 bath single family home. Great open floor plan, excellent for entertaining. Big sized bedrooms, large yard with deck in backyard. Pets considered with owners approval and...... |
1616 Chestnut Ave |
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1616 Chestnut AveChesapeake, VA$2,500
Vacation Rentals, Unknown
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 |
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1231 Kay AveChesapeake, 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 |
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1433 Oleander AveChesapeake, 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 |
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601 Lord Byron CtChesapeake, 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 |
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863 Redleafe CirChesapeake, 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 |
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641 Baywood TrlChesapeake, 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 |
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516 Birchwater AveChesapeake, 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 |
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857 Mains Creek RdChesapeake, 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 |
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504 Tuskegee AveChesapeake, 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 |
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568 River Gate RdChesapeake, 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 |
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1331 Hazel AveChesapeake, 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 |
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1000 Butt StChesapeake, 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 |
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1110 Hazel AveChesapeake, 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 |
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4644 Indiana AveChesapeake, 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 |
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1108 Myrtle AveChesapeake, 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 |
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1132 Commerce AveChesapeake, 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 |
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1001 Hillwell RdChesapeake, 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 |
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3345 Country CirChesapeake, 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 |
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1117 George Olah DrChesapeake, 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 |
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2420 Annie CirChesapeake, 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 |
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1028 Woodsmans ReachChesapeake, 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 |
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1112 Turtle Rock TrceChesapeake, 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...... |