Title: Chesapeake Vacation Rentals from $126: Search Short-Term Rentals | Expedia.com [Chesapeake Travel Guide](https://expedia.com/Chesapeake.dx6612)[Hotels in Chesapeake](https://expedia.com/Chesapeake-Hotels.d6612.Travel-Guide-Hotels)[Flights to Chesapeake](https://expedia.com/Cheap-Flights-To-Chesapeake.d6612.Travel-Guide-Flights)[Things to do in Chesapeake](https://expedia.com/Things-To-Do-In-Chesapeake.d6612.Travel-Guide-Activities)[Car Rentals in Chesapeake](https://expedia.com/Car-Rentals-In-Chesapeake.d6612.Car-Rental-Guide)[Chesapeake Vacation Packages](https://expedia.com/Chesapeake.d6612.Destination-Travel-Guides) ![Lodging Image](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_bundle_and_save.svg) ### Bundle & Save Get more, spend less whenever you see Bundle & Save deals - ![](https://a.travel-assets.com/travel-assets-manager/pictograms-expedia/light__onekey.svg) ### OneKeyCash Earn OneKeyCash on all your eligible bookings - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_ftc.svg) ### Upfront pricing We are not like the others - we include taxes and fees ## Check prices for these dates In two weeks [Feb 27 - Mar 1](https://www.expedia.com/Hotel-Search?regionId=6612&startDate=2026-02-27&endDate=2026-03-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Apr 10 - Apr 12](https://www.expedia.com/Hotel-Search?regionId=6612&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [May 8 - May 10](https://www.expedia.com/Hotel-Search?regionId=6612&startDate=2026-05-08&endDate=2026-05-10&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jun 5 - Jun 7](https://www.expedia.com/Hotel-Search?regionId=6612&startDate=2026-06-05&endDate=2026-06-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chesapeake vacation rentals ![Beach/ocean view](https://images.trvl-media.com/lodging/2000000/1160000/1154700/1154697/3711adde.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/2000000/1160000/1154700/1154697/04d0c199.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1160000/1154700/1154697/c01f9eb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Food and drink](https://images.trvl-media.com/lodging/2000000/1160000/1154700/1154697/80f01e26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia [](https://www.expedia.com/Virginia-Beach-Hotels-The-Ocean-Sands-Resort-By-VSA-Resorts.h1154697.Hotel-Information) Northeast Virginia Beach 8.2/10 Very Good (1,185 reviews) "We had a great stay. The staff was very helpful. The room was amazing and clean. We will be back" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rod $180 nightly $209 total Feb 23 - Feb 24 Total with taxes and fees [](https://www.expedia.com/Virginia-Beach-Hotels-The-Ocean-Sands-Resort-By-VSA-Resorts.h1154697.Hotel-Information) ![Beach nearby](https://images.trvl-media.com/lodging/2000000/1150000/1141900/1141831/b72945f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1150000/1141900/1141831/9cbad6e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/2000000/1150000/1141900/1141831/ffb83e76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![One-Bedroom Suite | Living area | 32-inch LCD TV with cable channels, TV](https://images.trvl-media.com/lodging/2000000/1150000/1141900/1141831/d74d21ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Atrium Resort, Virginia Beach by Vacatia [](https://www.expedia.com/Virginia-Beach-Hotels-The-Atrium-Resort-By-VSA-Resorts.h1141831.Hotel-Information) Northeast Virginia Beach 8.2/10 Very Good (1,479 reviews) "Clean, spacious, short walk to beach, nice staff, I will be back definitely " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sy $151 nightly $176 total Mar 1 - Mar 2 Total with taxes and fees [](https://www.expedia.com/Virginia-Beach-Hotels-The-Atrium-Resort-By-VSA-Resorts.h1141831.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/530000/529400/529337/87f7858a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![One-Bedroom Suite, Ocean View | View from room](https://images.trvl-media.com/lodging/1000000/530000/529400/529337/07c04cd6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/530000/529400/529337/41a7c97e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, in-room safe, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/530000/529400/529337/6ee8a946.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Ocean Key Virginia Beach Resort [](https://www.expedia.com/Virginia-Beach-Hotels-The-Ocean-Key-Resort-By-VSA-Resorts.h529337.Hotel-Information) Northeast Virginia Beach 7.8/10 Good (1,462 reviews) "Clean and nice room" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Curtis $115 nightly $134 total Mar 12 - Mar 13 Total with taxes and fees [](https://www.expedia.com/Virginia-Beach-Hotels-The-Ocean-Key-Resort-By-VSA-Resorts.h529337.Hotel-Information) ![Cottage, 3 Bedrooms | Terrace/patio](https://images.trvl-media.com/lodging/79000000/78280000/78276200/78276199/3bdb2e99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage, 3 Bedrooms | Living room | Smart TV](https://images.trvl-media.com/lodging/79000000/78280000/78276200/78276199/ecce39cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage, 3 Bedrooms | Beach | On the beach](https://images.trvl-media.com/lodging/79000000/78280000/78276200/78276199/b0f90467.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage, 3 Bedrooms | Living room | Smart TV](https://images.trvl-media.com/lodging/79000000/78280000/78276200/78276199/36c79d61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Manor And Mutts #2 3 Bedroom Cottage by RedAwning [](https://www.expedia.com/Norfolk-Hotels-Manor-And-Mutts-2-3-Bedroom-Cottage.h78276199.Hotel-Information) Willoughby Spit $514 nightly $594 total Feb 14 - Feb 15 Total with taxes and fees [](https://www.expedia.com/Norfolk-Hotels-Manor-And-Mutts-2-3-Bedroom-Cottage.h78276199.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/110000000/109200000/109190600/109190515/ddee3953.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Full-size fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/110000000/109200000/109190600/109190515/79d8e1d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Full-size fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/110000000/109200000/109190600/109190515/17eb91ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/110000000/109200000/109190600/109190515/f999c98e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### stayAPT Suites Suffolk-Chesapeake [](https://www.expedia.com/Suffolk-Hotels-StayAPT-Suites-Suffolk-Chesapeake.h109190515.Hotel-Information) Suffolk 9.4/10 Exceptional (60 reviews) "The staff was so friendly. The rooms were so nice. I loved the kitchen and breakfast bar." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nicole $109 nightly $126 total Mar 3 - Mar 4 Total with taxes and fees [](https://www.expedia.com/Suffolk-Hotels-StayAPT-Suites-Suffolk-Chesapeake.h109190515.Hotel-Information) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/124000000/123420000/123412000/123411909/adf90b11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/124000000/123420000/123412000/123411909/4ca87ed2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/124000000/123420000/123412000/123411909/3324a4c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/124000000/123420000/123412000/123411909/93497329.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Centrally Located Hampton Roads Home w/ Game Room! [](https://www.expedia.com/Portsmouth-Hotels-Centrally-Located-Hampton-Roads-Home-W-Game-Room.h123411909.Hotel-Information) Portsmouth $535 nightly $618 total Feb 28 - Mar 1 Total with taxes and fees [](https://www.expedia.com/Portsmouth-Hotels-Centrally-Located-Hampton-Roads-Home-W-Game-Room.h123411909.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/110000000/109380000/109375900/109375809/w3000h1944x0y0-85007cf2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/110000000/109380000/109375900/109375809/w3000h1840x0y0-254a1ec4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment | 2 bedrooms](https://images.trvl-media.com/lodging/110000000/109380000/109375900/109375809/w3000h2760x0y0-65125647.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment | Private kitchen](https://images.trvl-media.com/lodging/110000000/109380000/109375900/109375809/w3000h1984x0y0-6e336c16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Speakeasy Downtown Newport News [](https://www.expedia.com/Newport-News-Hotels-The-Speakeasy-Downtown-Newport-News.h109375809.Hotel-Information) Downtown Newport News $216 nightly $250 total Feb 10 - Feb 11 Total with taxes and fees [](https://www.expedia.com/Newport-News-Hotels-The-Speakeasy-Downtown-Newport-News.h109375809.Hotel-Information) ![Property entrance](https://images.trvl-media.com/lodging/10000000/9350000/9341300/9341248/57f3f1dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/10000000/9350000/9341300/9341248/dec7de9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 Queen Bed, Kitchenette, Ground Floor | Individually decorated, individually furnished, iron/ironing board](https://images.trvl-media.com/lodging/10000000/9350000/9341300/9341248/7c5bb600.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed, Kitchenette, Ground Floor | Individually decorated, individually furnished, iron/ironing board](https://images.trvl-media.com/lodging/10000000/9350000/9341300/9341248/ece9e738.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Angie's Guest Cottage [](https://www.expedia.com/Virginia-Beach-Hotels-Angies-Guest-Cottage.h9341248.Hotel-Information) Northeast Virginia Beach 8.6/10 Excellent (225 reviews) "The best place I have ever stayed at" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robin $88 nightly $103 total Feb 10 - Feb 11 Total with taxes and fees [](https://www.expedia.com/Virginia-Beach-Hotels-Angies-Guest-Cottage.h9341248.Hotel-Information) ![On the beach, beach towels](https://images.trvl-media.com/lodging/110000000/109380000/109376100/109376084/w3000h1856x0y0-285b9163.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio | Private kitchen](https://images.trvl-media.com/lodging/110000000/109380000/109376100/109376084/ebf0599b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio | 3 bedrooms](https://images.trvl-media.com/lodging/110000000/109380000/109376100/109376084/w3000h1944x0y0-07e731a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio | 3 bedrooms](https://images.trvl-media.com/lodging/110000000/109380000/109376100/109376084/w3000h1872x0y0-5cb656ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Buckroe Bungalow Buckroe Bungalow Escape to the Beach 2mins Away [](https://www.expedia.com/Hampton-Hotels-Buckroe-Bungalow-Buckroe-Bungalow-Escape-To-The-Beach-2mins-Away.h109376084.Hotel-Information) Hampton $312 nightly $361 total Feb 10 - Feb 11 Total with taxes and fees [](https://www.expedia.com/Hampton-Hotels-Buckroe-Bungalow-Buckroe-Bungalow-Escape-To-The-Beach-2mins-Away.h109376084.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/110000000/109380000/109375800/109375774/w3000h1960x0y0-ccf8a5d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/110000000/109380000/109375800/109375774/w3000h1848x0y0-5981932f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment | 4 bedrooms](https://images.trvl-media.com/lodging/110000000/109380000/109375800/109375774/w3000h1824x0y0-9780860b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment | 4 bedrooms](https://images.trvl-media.com/lodging/110000000/109380000/109375800/109375774/fd960bbe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 4BR Waterfront Penthouse Pool Views [](https://www.expedia.com/Virginia-Beach-Hotels-Penthouse-By-The-Sea-Huge-Home-W-Amazing-Views.h109375774.Hotel-Information) Sandbridge $696 nightly $802 total Feb 10 - Feb 11 Total with taxes and fees [](https://www.expedia.com/Virginia-Beach-Hotels-Penthouse-By-The-Sea-Huge-Home-W-Amazing-Views.h109375774.Hotel-Information) ![Apartment | 1 bedroom](https://images.trvl-media.com/lodging/110000000/109380000/109375900/109375825/w3000h1896x0y0-19fdc48a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment | Private kitchen](https://images.trvl-media.com/lodging/110000000/109380000/109375900/109375825/w3000h2000x0y0-01aaf81b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment | 1 bedroom](https://images.trvl-media.com/lodging/110000000/109380000/109375900/109375825/w3000h2816x0y0-e396ee3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment | 1 bedroom](https://images.trvl-media.com/lodging/110000000/109380000/109375900/109375825/w3000h1800x0y0-469e54aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Safe House Downtown Newport News [](https://www.expedia.com/Newport-News-Hotels-The-Safe-House-Downtown-Newport-News.h109375825.Hotel-Information) Downtown Newport News 6.0/10 (1 review) $213 nightly $246 total Feb 10 - Feb 11 Total with taxes and fees [](https://www.expedia.com/Newport-News-Hotels-The-Safe-House-Downtown-Newport-News.h109375825.Hotel-Information) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [View all properties](https://expedia.com/Hotel-Search?startDate=2026-02-23&endDate=2026-02-24®ionId=6612&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## Find vacation rentals that suit your style Private vacation homes [](https://www.expedia.com/Hotel-Search?destination=Chesapeake%2C+Virginia%2C+United+States+of+America®ionId=6612&latLong=36.767662%2C-76.286817&adults=2&startDate=2026-05-10&d1=2026-05-10&endDate=2026-05-13&d2=2026-05-13&lodging=VACATION_HOME) Apartments [](https://www.expedia.com/Hotel-Search?destination=Chesapeake%2C+Virginia%2C+United+States+of+America®ionId=6612&latLong=36.767662%2C-76.286817&adults=2&startDate=2026-05-10&d1=2026-05-10&endDate=2026-05-13&d2=2026-05-13&lodging=APARTMENT) Condos [](https://www.expedia.com/Hotel-Search?destination=Chesapeake%2C+Virginia%2C+United+States+of+America®ionId=6612&latLong=36.767662%2C-76.286817&adults=2&startDate=2026-05-10&d1=2026-05-10&endDate=2026-05-13&d2=2026-05-13&lodging=CONDO) Aparthotels [](https://www.expedia.com/Hotel-Search?destination=Chesapeake%2C+Virginia%2C+United+States+of+America®ionId=6612&latLong=36.767662%2C-76.286817&adults=2&startDate=2026-05-10&d1=2026-05-10&endDate=2026-05-13&d2=2026-05-13&lodging=APART_HOTEL) Cottages [](https://www.expedia.com/Hotel-Search?destination=Chesapeake%2C+Virginia%2C+United+States+of+America®ionId=6612&latLong=36.767662%2C-76.286817&adults=2&startDate=2026-05-10&d1=2026-05-10&endDate=2026-05-13&d2=2026-05-13&lodging=COTTAGE) Villas [](https://www.expedia.com/Hotel-Search?destination=Chesapeake%2C+Virginia%2C+United+States+of+America®ionId=6612&latLong=36.767662%2C-76.286817&adults=2&startDate=2026-05-10&d1=2026-05-10&endDate=2026-05-13&d2=2026-05-13&lodging=VILLA) Houseboats [](https://www.expedia.com/Hotel-Search?destination=Chesapeake%2C+Virginia%2C+United+States+of+America®ionId=6612&latLong=36.767662%2C-76.286817&adults=2&startDate=2026-05-10&d1=2026-05-10&endDate=2026-05-13&d2=2026-05-13&lodging=HOUSE_BOAT) Cabins [](https://www.expedia.com/Hotel-Search?destination=Chesapeake%2C+Virginia%2C+United+States+of+America®ionId=6612&latLong=36.767662%2C-76.286817&adults=2&startDate=2026-05-10&d1=2026-05-10&endDate=2026-05-13&d2=2026-05-13&lodging=CABIN) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.com/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FChesapeake-Vacation-Rentals.d6612.Travel-Guide-VacationRentals)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChesapeake-Vacation-Rentals.d6612.Travel-Guide-VacationRentals) ## Top Chesapeake Hotel Reviews ![Country Inn & Suites by Radisson, Virginia Beach (Oceanfront)](https://images.trvl-media.com/lodging/1000000/10000/5400/5363/c80e2694_y.jpg) ### Country Inn & Suites by Radisson, Virginia Beach (Oceanfront) 10/10 Excellent "Room is clean. We love the ocean front view." [](https://expedia.com/Virginia-Beach-Hotels-Country-Inn-Suites-By-Radisson.h5363.Hotel-Information) ![Embassy Suites by Hilton Hampton Convention Center](https://images.trvl-media.com/lodging/2000000/1180000/1172300/1172219/5d92420f_y.jpg) ### Embassy Suites by Hilton Hampton Convention Center 10/10 Excellent "Everything was amazing. It was convenient to the venue for my concert. The morning breakfast was everything." [](https://expedia.com/Newport-News-Hotels-Embassy-Suites-By-Hilton-Hampton-Convention-Center.h1172219.Hotel-Information) ![Comfort Suites Chesapeake - Norfolk](https://images.trvl-media.com/lodging/1000000/10000/6600/6570/74e17a93_y.jpg) ### Comfort Suites Chesapeake - Norfolk 10/10 Excellent "Clean, comfortable, very nice staff! Bed was extremely comfortable! Nice variety of options for breakfast too. Will continue to use Choice Hotels brand, very happy!" [](https://expedia.com/Chesapeake-Hotels-Comfort-Suites-Chesapeake-Norfolk.h6570.Hotel-Information) ![Schooner Inn](https://images.trvl-media.com/lodging/2000000/1720000/1711400/1711317/f35c64c2_y.jpg) ### Schooner Inn 10/10 Excellent "Perfect for a budget-friendly motel. " [](https://expedia.com/Virginia-Beach-Hotels-Schooner-Inn.h1711317.Hotel-Information) ![Boardwalk Resort and Villas](https://images.trvl-media.com/lodging/1000000/920000/910400/910351/7bb2cf2f_y.jpg) ### Boardwalk Resort and Villas 10/10 Excellent "The room was spotless, amazing view, and last but not least the staff was very pleasant and kind. I will be returning for another stay! " [](https://expedia.com/Virginia-Beach-Hotels-Boardwalk-Resort-And-Villas.h910351.Hotel-Information) ![Fairfield Inn and Suites By Marriott Chesapeake](https://images.trvl-media.com/lodging/1000000/20000/16100/16036/234312b3_y.jpg) ### Fairfield Inn and Suites By Marriott Chesapeake 10/10 Excellent "Tracey at the front desk was a bright light after a very rough LONG day of flights delayed / canceled …. Fast efficient and wonderful! Hotel clean and comfortable! Great breakfast! " [](https://expedia.com/Chesapeake-Hotels-Fairfield-Inn-And-Suites-By-Marriott-Chesapeake.h16036.Hotel-Information) ![Wyndham Garden Norfolk Downtown](https://images.trvl-media.com/lodging/1000000/10000/500/472/0d975282_y.jpg) ### Wyndham Garden Norfolk Downtown 10/10 Excellent "Pleasant room. Very Clean. Wonderful view. Delightful staff. Excellent burger in restaurant. " [](https://expedia.com/Norfolk-Hotels-Wyndham-Garden-Norfolk-Downtown.h472.Hotel-Information) ![Wingate by Wyndham Chesapeake](https://images.trvl-media.com/lodging/2000000/1520000/1513300/1513238/d607b035_y.jpg) ### Wingate by Wyndham Chesapeake 10/10 Excellent "Great customer service" [](https://expedia.com/Chesapeake-Hotels-Wingate-By-Wyndham-Chesapeake.h1513238.Hotel-Information) ![Hyatt Place Virginia Beach / Oceanfront](https://images.trvl-media.com/lodging/76000000/75960000/75958000/75957909/da79c4b1_y.jpg) ### Hyatt Place Virginia Beach / Oceanfront 10/10 Excellent "Very nice staff, with the exception of one person. Nice room, beautiful view, nice breakfast food and eating area. " [](https://expedia.com/Virginia-Beach-Hotels-Hyatt-Place-Virginia-Beach-Oceanfront.h75957909.Hotel-Information) ## Find out more about Chesapeake **Everything you need to know about Chesapeake vacation rentals** Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chesapeake vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on. There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chesapeake vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. **Chesapeake vacation rentals: An excellent choice for every season** Whenever you want to travel, a warm welcome awaits you in Chesapeake. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Chesapeake in high season. Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $126 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals! **How to find incredible deals on Chesapeake rentals** At Expedia, we put the best Chesapeake vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. To find some top Chesapeake rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chesapeake vacation. If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chesapeake. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. ## Explore a world of travel with Expedia - Trending destinations on Expedia.com - All accommodation types in Chesapeake ### Trending destinations on Expedia.com - [Destin Vacation Rentals ](https://www.expedia.com/Destin-Vacation-Rentals.d6906.Travel-Guide-VacationRentals) - [Panama City Vacation Rentals ](https://www.expedia.com/Panama-City-Beach-Vacation-Rentals.d8021.Travel-Guide-VacationRentals) - [Hilton Head Vacation Rentals ](https://www.expedia.com/Hilton-Head-Island-Vacation-Rentals.d601684.Travel-Guide-VacationRentals) - [Gulf Shores Vacation Rentals ](https://www.expedia.com/Gulf-Shores-Vacation-Rentals.d603078.Travel-Guide-VacationRentals) - [Key West Vacation Rentals ](https://www.expedia.com/Key-West-Vacation-Rentals.d1187.Travel-Guide-VacationRentals) - [Gatlinburg Vacation Rentals ](https://www.expedia.com/Gatlinburg-Vacation-Rentals.d7474.Travel-Guide-VacationRentals) - 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[Vacation Homes in Chesapeake ](https://expedia.com/Chesapeake-Private-Vacation-Homes.d6612-aaPrivateVacationHomes.Travel-Guide-Accommodation) - [Apartments in Chesapeake ](https://expedia.com/Chesapeake-Apartments.d6612-aaApartments.Travel-Guide-Accommodation) - [Condo Rentals in Chesapeake ](https://expedia.com/Chesapeake-Condos.d6612-aaCondos.Travel-Guide-Accommodation) - [Cottages in Chesapeake ](https://expedia.com/Chesapeake-Cottages.d6612-aaCottages.Travel-Guide-Accommodation) - [Resorts in Chesapeake ](https://expedia.com/Chesapeake-Resorts.d6612-aaResorts.Travel-Guide-Accommodation) - [Villas in Chesapeake ](https://expedia.com/Chesapeake-Villas.d6612-aaVillas.Travel-Guide-Accommodation) - [Motels in Chesapeake ](https://expedia.com/Chesapeake-Motels.d6612-aaMotels.Travel-Guide-Accommodation) - [Aparthotels in Chesapeake ](https://expedia.com/Chesapeake-Apart-Hotels.d6612-aaApartHotels.Travel-Guide-Accommodation) - [B&B in Chesapeake ](https://expedia.com/Chesapeake-Bed-And-Breakfast.d6612-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Guest Houses in Chesapeake ](https://expedia.com/Chesapeake-Guest-Houses.d6612-aaGuestHouses.Travel-Guide-Accommodation) - [Cabin Rentals in Chesapeake ](https://expedia.com/Chesapeake-Cabins.d6612-aaCabins.Travel-Guide-Accommodation) - [Houseboats in Chesapeake ](https://expedia.com/Chesapeake-Houseboats.d6612-aaHouseboats.Travel-Guide-Accommodation) - [Farmstay in Chesapeake ](https://expedia.com/Chesapeake-Agritourism.d6612-aaAgritourism.Travel-Guide-Accommodation) - [Condo Resorts in Chesapeake ](https://expedia.com/Chesapeake-Condominium-Resort.d6612-aaCondominiumResort.Travel-Guide-Accommodation) - [RV Parks in Chesapeake ](https://expedia.com/Chesapeake-RV-Parks.d6612-aaRVParks.Travel-Guide-Accommodation) - [Residences in Chesapeake ](https://expedia.com/Chesapeake-Residences.d6612-aaResidences.Travel-Guide-Accommodation) - [Inns in Chesapeake ](https://expedia.com/Chesapeake-Inns.d6612-aaInns.Travel-Guide-Accommodation) ## Frequently asked questions ### Are there vacation rentals in Chesapeake? ### What are some of the best vacation home rentals in Chesapeake? ### How many vacation rentals are there in Chesapeake? ### What’s there to see and do in Chesapeake? ### What’s a vacation rental in Chesapeake like? ### Expedia's Latest Trends Hotels - 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