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.

602 Middleton Way
	602 Middleton Way Chesapeake, VA $3,200 Vacation Rentals, Unknown New construction Bentley floorplan in Hickory Manor, built in 2021. Zoned for Hickory Elementary, Middle, and High school. The best schools in Chesapeake. Great neighborhood for families. Owners......

1318 River Birch Run S
	1318 River Birch Run S Chesapeake, VA $1,825 Vacation Rentals, Unknown Location is everything. Great townhome in the heart of Greenbrier within minutes from the mall, shopping, interstates, and bases. House is being freshened up and ready for you to call it home......

120 Welch Ln
	120 Welch Ln Chesapeake, VA $2,700 Vacation Rentals, Unknown This beautiful home is on a quiet cul-de-sac just off Battlefield Blvd. 4 bedrooms and 3 full baths with One Bedroom with full bath on the first floor. This home has an open floor plan so it is......

420 Harbour North Dr
	420 Harbour North Dr Chesapeake, VA $1,225 Vacation Rentals, Unknown Welcome to your cozy 2 bedroom townhome. Nestled in a fairly quiet court. Despite its less than perfect neighborhood, this charming abode offers a comfortable retreat with its updated interior and......

1108 Magdolna Dr
	1108 Magdolna Dr Chesapeake, VA $3,400 Vacation Rentals, Unknown Exquisite Home Rental in Great Bridge, Chesapeake, VA Welcome to this spacious beautiful new house nestled in a great school district and neighborhood within the heart of Great Bridge, Chesapeake,......

801 Hardwood Dr
	801 Hardwood Dr Chesapeake, VA $2,395 Vacation Rentals, Unknown Very nice corner lot home in sought after Riverwalk community. This home boasts 4 bedrooms, 2.5 baths. The living room opens up to large family room with fireplace, eat-in kitchen combination.......

331 Appaloosa Trl
	331 Appaloosa Trl Chesapeake, VA $2,500 Vacation Rentals, Unknown Beautiful 4 bedroom home with an open floor plan. Formal living room, formal dining room, modern kitchen with breakfast area and bar. Great room opens to large Frog, perfect as 4th bedroom or......

2009 Stalham Rd
	2009 Stalham Rd Chesapeake, VA $1,850 Vacation Rentals, Unknown Coming Soon: This property is not currently available, please join the Rently Waitlist for more updates. Imagine stepping into a light-filled haven. Sunlight streams through a large window, warming......

508 Whisper Walk
	508 Whisper Walk Chesapeake, VA $2,595 Vacation Rentals, Unknown Prepare to fall in love with this adorably updated rental with community pool, playgrounds, tennis courts, community lake, and the front yard landscaping is all included! You will love entertaining......

1301 False Creek Way
	1301 False Creek Way Chesapeake, VA $3,295 Vacation Rentals, Unknown BEST SCHOOL DISTRICT IN HAMPTON ROADS Gorgeous 2 story brick house with 2 car garage on a corner lot within a quaint, quiet and child-friendly neighborhood. Great house for entertaining with......

217 Gregg St
	217 Gregg St Chesapeake, VA $2,800 Vacation Rentals, Unknown Beautifully kept 4 bedroom rental centrally located in Chesapeake near the interstate is ready for it's next family! Modern fixtures throughout this beautiful open concept home complete with......

1022 Stillmeadows Ct
	1022 Stillmeadows Ct Chesapeake, VA $2,750 Vacation Rentals, Unknown Go home to vacation nightly! Nicely renovated home for entertainment with an open floor plan in centrally located Greenwood Estates. Near schools, malls and interstates. 3 bedrooms, 2.5 bathrooms.......

1112 Kingsbury Dr
	1112 Kingsbury Dr Chesapeake, VA $4,295 Vacation Rentals, Unknown Discover spacious elegance in this expansive 4,404 square foot home featuring 5 bedrooms and 3.5 bathrooms. The heart of this home is the impressive kitchen, custom designed with functionality and......

3332 Stilworken Dr
	3332 Stilworken Dr Chesapeake, VA $1,800 Vacation Rentals, Unknown Welcome to the perfect blend of charm and modern updates in this stunning ranch home nestled in the Dunedin area of Chesapeake. Prepare meals in style with the gleaming granite countertops that add......

704 Arbuckle St
	704 Arbuckle St Chesapeake, VA $3,400 Vacation Rentals, Unknown PREVIOUS CULPEPPER LANDING MODEL HOME AVAILABLE FOR RENT This beautiful 4,000 sqft 5br/4bath single family home was custom built, with all the builder upgrades as Culpepper Landing's Model home -......

1102 Park Ave
	1102 Park Ave Chesapeake, VA $2,195 Vacation Rentals, Unknown Gorgeous 2-Story Home featuring 4 bedrooms and 3 baths! Lovely open concept living room and kitchen. The kitchen is equipped with stainless steel appliances, granite countertops and large center......

1436 Oliver Ave
	1436 Oliver Ave Chesapeake, VA $1,625 Vacation Rentals, Unknown This 2 story home is 1,394 square feet of living space and is centrally located in Chesapeake and features neutral wall colors and beautiful vinyl floors throughout the downstairs. The kitchen is......

1905 Chesapeake Ave
	1905 Chesapeake Ave Chesapeake, VA $2,385 Vacation Rentals, Unknown Application fee is $20 per household for a limited time. Make this charming 4 bedroom 2 bathroom house your new home! This home features a bright and spacious kitchen and dining room perfect for......

306 Middleton Way
	306 Middleton Way Chesapeake, VA $3,350 Vacation Rentals, Unknown LOCATION: - Convenient to Norfolk, VA Beach, Little Creek, Portsmouth and Suffolk - Top rated Elementary, Middle and High Schools (5 minute drive) - Convenient to shopping, restaurants, and outdoor......

N Hill Ln
	N Hill Ln Chesapeake, VA $2,550 Vacation Rentals, Unknown Great Neighborhood! This home is in the heart of the Great Bridge region of Chesapeake. Dining, shopping, and other local attractions in Chesapeake. This open concept Condo features cathedral......

640 Baker Loop
	640 Baker Loop Chesapeake, VA $3,400 Vacation Rentals, Unknown Beautiful 4 bed 2.5 bath 2,625 sq ft, well maintained house zoned for Greenbrier and Indian River HS. Located minutes from restaurants, shopping, and highways. Features dining room, den, open......

2405 Annie Cir
	2405 Annie Cir Chesapeake, VA $2,695 Vacation Rentals, Unknown Don't miss this one! Available for June Lovely Large Home located in the desired Neighborhood of Deep Creek South within a cul-de-sac Fresh paint and cleaned carpet Perfect for a family To qualify......

2808 Cistern Cir
	2808 Cistern Cir Chesapeake, VA $2,900 Vacation Rentals, Unknown Modern luxury updates and amenities. Smart home technology including ring doorbell, Wi-fi enabled thermostat and light switches. Freshly painted throughout. Beautiful natural light. Crown moulding......

1128 Mill Lake Quarter
	1128 Mill Lake Quarter Chesapeake, VA $2,255 Vacation Rentals, Unknown LOCATED IN THE HEART OF THE GREENBRIER COMMUNITY Of CHESAPEAKE. This Convenient Location Puts You Exactly Where You Want To Be With Fast Access To All Point Hampton Roads, Interstates, World Class......

217 Golden Maple Dr
	217 Golden Maple Dr Chesapeake, VA $3,500 Vacation Rentals, Unknown Do not miss this beautiful, spacious single family home in the desirable Chesapeake Colony neighborhood. This 5 bedroom, 3 bath home provides a spacious living space, natural light, large fenced......

1417 Buxton Dr
	1417 Buxton Dr Chesapeake, VA $2,400 Vacation Rentals, Unknown Lovely 4 bedroom brick ranch home located in the Hickory area of Chesapeake. Once you see it, you will know you've found your new home! Great family home! Great schools! Highly desirable area!......

1024 Long Beeches Ave
	1024 Long Beeches Ave Chesapeake, VA $3,295 Vacation Rentals, Unknown Beautiful 5 bedroom 3.5 bath home centrally located in Chesapeake. 1st floor master bedroom with bath. Open spacious floor plan throughout. Gorgeous hardwood flooring, gas fireplace, recently......

220 Melonie Dr
	220 Melonie Dr Chesapeake, VA $3,200 Vacation Rentals, Unknown In a word-STUNNING! Go home to vacation every night. This home rests on just over half an acre. 1st floor--Large foyer area, formal sitting room, office w/ French pocket doors and built in......

1120 Priscilla Ln
	1120 Priscilla Ln Chesapeake, VA $1,995 Vacation Rentals, Unknown Beautiful home in Hickory. Hardwood in foyer, hallway, half bath and formal dining area; updated kitchen with granite countertops, stainless appliances and ceramic tile floor; large living room......

1306 Linden Ave #A
	1306 Linden Ave #A Chesapeake, VA $1,300 Vacation Rentals, Unknown Two bedroom, 1 bath, brick duplex centrally located in the Norfolk Highlands area of Chesapeake. Fully renovated with new flooring, paint, fixtures, and appliances. Separate driveway w/ parking for......

1108 Jackson Ave
	1108 Jackson Ave Chesapeake, VA $1,900 Vacation Rentals, Unknown Beautiful 3 Bedroom 2 Bath single family home with new carpet and allure flooring throughout dwelling. Dining room has gas fireplace & ceiling fan w/light. Kitchen includes electric range/oven,......

213 Robert St
	213 Robert St Chesapeake, VA $2,700 Vacation Rentals, Unknown Charming All-Brick Ranch in the Heart of Great Bridge Embrace the blend of comfort and convenience in this impeccably maintained 4-bedroom, 2-bath all-brick ranch, ideally located in a sought-after......

2400 Rock Creek Dr
	2400 Rock Creek Dr Chesapeake, VA $2,795 Vacation Rentals, Unknown Application fee is $20 per household for a limited time! Make this charming 4 bedroom 2 bathroom house your new home! This home features a bright and spacious kitchen and dining room perfect for......

2121 Kingsley Ln
	2121 Kingsley Ln Chesapeake, VA $2,900 Vacation Rentals, Unknown They don't get any better than this! Lakefront Transitional with beautiful lake views from kitchen breakfast area, family room, and master bedroom. Great neighborhood (small, quiet, family......

449 Wittington Dr
	449 Wittington Dr Chesapeake, VA $2,995 Vacation Rentals, Unknown Great Bridge, 4 bedroom, 3 full bath single family home with approximately 2,352sf of living space. Family room with brick gas log fireplace mantle and screen, built-in cabinets and bookshelves,......

4413 Dartmoor Ct
	4413 Dartmoor Ct Chesapeake, VA $1,395 Vacation Rentals, Unknown Two bedroom end unit townhome on small cul-de-sac. Recently painted throughout. Galley style kitchen with room for bar stools. Large bedrooms and closets. 2nd floor laundry room. Fenced yard with......

2053 Allison Dr
	2053 Allison Dr Chesapeake, VA $1,925 Vacation Rentals, Unknown Application fee is $20 per household for a limited time! Make this charming 2 bedroom 2.5 bathroom house your new home! This home features a bright and spacious kitchen and dining room perfect for......

2305 Springdale Rd
	2305 Springdale Rd Chesapeake, VA $2,295 Vacation Rentals, Unknown Newly renovated 3 bedroom, 1.5 bath home in Deep Creek area of Chesapeake. New paint and flooring throughout. Family room has new stone surround and hearth. Open floor plan living with must see......

929 Thatcher Way
	929 Thatcher Way Chesapeake, VA $2,950 Vacation Rentals, Unknown Application fee is $20 per household for a limited time! Make this charming 4 bedroom 2.5 bathroom house your new home! This home features a bright and spacious kitchen and dining room perfect for......

3348 Battlefield Blvd S
	3348 Battlefield Blvd S Chesapeake, VA $1,950 Vacation Rentals, Unknown 4 Bedroom, 1 Bath single-family residence in the highly desired Hickory area of Chesapeake, VA. Fully renovated in 2023 in addition to new paint in 2024. Large fenced-in backyard with back deck and......