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

910 Cantor St

Chesapeake, 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

517 Hardwood Ct

Chesapeake, 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

1023 Keel St

Chesapeake, 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

812 Brightleaf Pl

Chesapeake, 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

1933 Flintshire Dr

Chesapeake, 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

535 Kings Gate

Chesapeake, 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

516 Cavendish Way

Chesapeake, 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

503 Frances Ct

Chesapeake, 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

1128 Sir Galahad Dr

Chesapeake, 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

Arbuckle St

Chesapeake, 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

348 Kempsville Rd

Chesapeake, 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

1016 Sullivan Ln

Chesapeake, 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

304 Oak Hill Way

Chesapeake, 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

2837 Crossings Dr

Chesapeake, 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

303 Middleton Way

Chesapeake, 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

624 Creekside Ct

Chesapeake, 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

2436 Strawberry Ln

Chesapeake, 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

5213 Willow Lake Rd

Chesapeake, 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

1616 Chestnut Ave

Chesapeake, 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

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......

Chesapeake, VA

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