Chesapeake vacation rentals
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Top-rated vacation rentals in Chesapeake
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
Apartment in Newport News
4.97 out of 5 average rating, 143 reviewsCentrally Located Sleek Studio Apartment
Private guest studio apartment with separate parking/entrance in a quiet neighborhood. Centrally located to shopping, restaurants , and parks. Airport:12 min CNU:6 min Riverside Medical Center:7 min Sentara Hospital:8 min Langley AFB:11 min Patrick Henry Mall:8 min Willimasburg/Bush Gardens: approx 30 min Virgina Beach Oceanfront: 45 min Wifi available with a 55" TV with streaming services (no cable). Coffee table folds into dining/work table. Stools under table. Full bath/kitchen/laundry unit.
Nov 16 – 23
Guest suite in Chesapeake
4.97 out of 5 average rating, 227 reviewsPurple Room- Rare Luxury Ste w/prkg - 1 of a kind!
Welcome to The Purple Room, get ready for an AirBnB experience unlike any others. This one of a kind AirBnB not only offers a memorable staying experience, but will be a welcome end to an exciting day at the beach, dinner and drinks at a local restaurant or bar, or an adventurous day exploring all the culture and history the area has to offer. We are centrally located, offer free parking, wifi and kitchenette. We have local art, free wine and food samples. Come see what the excitement is about!
Jun 8 – 15
Guesthouse in Norfolk
4.98 out of 5 average rating, 549 reviewsPrivate Guesthouse, Ghent/Downtown near ODU, EVMS
Legally licensed and permitted with the City of Norfolk! We did it right here! European-style guesthouse between Ghent and the Heart of Downtown. Walking access to many restaurants and hotspots, and across from “The Tide” light rail, and YMCA, Chrysler Museum of Art, Granby St, Colley Ave, EVMS, Town Point Park! 15-min from the ocean. FREE PRIVATE PARKING: designated driveway parking spot; Kitchenette includes– cooktop, sink, microwave, coffee, fridge; Wifi, separate HVAC, bath, FREE laundry.
Sep 27 – Oct 4
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Chesapeake vacation rentals
Other great vacation rentals in Chesapeake
Apartment in Portsmouth
4.84 out of 5 average rating, 285 reviewsSpacious 2 bedroom apt in Historic Port Norfolk
Aug 15 – 22
Guesthouse in Hampton
4.99 out of 5 average rating, 280 reviewsSun Sea and Sand
Aug 26 – Sep 2
Place to stay in Virginia Beach
4.99 out of 5 average rating, 106 reviewsSalty Willow-a “suite retreat” in the heart of VB!
May 4 – 11
Townhouse in Chesapeake
4.92 out of 5 average rating, 106 reviewsTasha's Townhouse *King, Queen, Twin*
Aug 20 – 27
Apartment in Portsmouth
4.96 out of 5 average rating, 239 reviewsCozy Ground Floor Apt in Historic Home
Jan 16 – 23
Home in Smithfield
4.96 out of 5 average rating, 198 reviewsMason Manor - Downtown Smithfield next to WCP
Nov 28 – Dec 5
Guest suite in Virginia Beach
4.85 out of 5 average rating, 348 reviewsGuest Suite Studio w/ Kitchenette & Private bath.
May 20 – 27
Tiny home in Hampton
4.92 out of 5 average rating, 171 reviewsHampton River Retreat Tiny House
Nov 9 – 16
Guesthouse in Portsmouth
4.97 out of 5 average rating, 151 reviewsSpring Hill Guest Cottage - Portsmouth
Jan 29 – Feb 5
Apartment in Chesapeake
5.0 out of 5 average rating, 25 reviewsEntire Apartment - No Cleaning Fees!
Oct 8 – 15
Apartment in Chesapeake
4.95 out of 5 average rating, 39 reviewsBlissful Nook @ Washington
May 8 – 15
Guest suite in Chesapeake
4.91 out of 5 average rating, 44 reviewsGuest Suite with Private entrance & bathroom
Jun 29 – Jul 6
Other great vacation rentals in Chesapeake
Home in Chesapeake
4.91 out of 5 average rating, 33 reviewsHidden Gem in Chesapeake, Virginia
Sep 28 – Oct 5
Bungalow in Chesapeake
4.93 out of 5 average rating, 69 reviewsPrivate and Cozy Bungalow Loaded with Amenities
Apr 30 – May 7
Townhouse in Chesapeake
4.82 out of 5 average rating, 28 reviewsBest Temporary Rental in Chesapeake
Jan 16 – 23
Condo in Portsmouth
4.96 out of 5 average rating, 84 reviews‘Captains Corner’ 1 Bedrm CONDO Historic Old Towne
Apr 22 – 29
Guesthouse in Suffolk
4.9 out of 5 average rating, 50 reviewsThe Magnolia Guesthouse With A Private Entrance
Sep 2 – 9
Townhouse in Chesapeake
4.9 out of 5 average rating, 99 reviewsFamily friendly townhouse
May 17 – 24
Apartment in Suffolk
5.0 out of 5 average rating, 69 reviewsCountry Living Guest House (Upstairs/Downstairs)
Mar 17 – 24
Townhouse in Virginia Beach
4.84 out of 5 average rating, 76 reviews3 bedroom townhome by Town Center
Feb 25 – Mar 4
Home in Chesapeake
4.93 out of 5 average rating, 14 reviewsModern Escape King Suite! 2 BDR
Dec 16 – 23
Apartment in Chesapeake
4.84 out of 5 average rating, 25 reviews2BR Self Check-in, Fast Wi-Fi
Apr 3 – 10
Camper/RV in Chesapeake
4.84 out of 5 average rating, 85 reviewsWaterfront Airstream in peaceful central location!
May 12 – 19
Home in Portsmouth
4.96 out of 5 average rating, 26 reviewsPenny’s Palace 1 Bed/1 Bath Home
Jun 9 – 14
Quick stats about vacation rentals in Chesapeake
Total rentals | 1.1K properties |
---|---|
Rentals with dedicated workspaces | 620 properties have a dedicated workspace |
Rentals with a pool | 140 properties have a pool |
Pet-friendly rentals | 370 properties allow pets |
Family-friendly rentals | 520 properties are a good fit for families |
Total number of reviews | 31K reviews |
Frequently Asked Questions
Where should I stay in Chesapeake?
Make yourself at home in Chesapeake by choosing from our most frequently booked neighborhoods. We have over 320 vacation rentals in Ghent, over 580 vacation rentals in Downtown Norfolk, over 580 vacation rentals in Olde Towne, and over 110 vacation rentals in Salem.
Are there vacation rentals with a dedicated workspace in Chesapeake?
Yes! Work meets play with ease at over 620 vacation rentals in Chesapeake featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Chesapeake?
Four-legged friends are welcome in Chesapeake. Choose from more than 370 vacation rentals for guests traveling with pets.
Are there Chesapeake vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 140 vacation homes with pools in Chesapeake, available on Airbnb. Make a splash and soak up the sun in style!
How much does it cost to stay in townhouse rentals in Chesapeake?
Experience the best of Chesapeake with our townhouse rentals, starting at about $20 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Chesapeake have a bbq area?
Absolutely! We offer over 120 house rentals with a bbq area in Chesapeake. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Chesapeake have a gym?
Absolutely! We offer over 80 apartment rentals with a gym in Chesapeake. Enjoy a tailored experience with all the comforts you desire.
Do guesthouse rentals in Chesapeake have wifi?
Absolutely! We offer over 20 guesthouse rentals with wifi in Chesapeake. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Chesapeake have self check-in?
Absolutely! We offer over 170 house rentals with self check-in in Chesapeake. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly house rentals in Chesapeake?
Chesapeake has more than 310 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
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