Title: Chesapeake, VA Cottage Rentals from $291 | Expedia.com [Chesapeake Travel Guide](https://expedia.com/Chesapeake.dx6612)[Hotels in Chesapeake](https://expedia.com/Chesapeake-Hotels.d6612.Travel-Guide-Hotels)[Vacation Rentals in Chesapeake](https://expedia.com/Chesapeake-Vacation-Rentals.d6612.Travel-Guide-VacationRentals)[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 [Apr 24 - Apr 26](https://www.expedia.com/Hotel-Search?regionId=6612&startDate=2026-04-24&endDate=2026-04-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two 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) In three months [Jul 3 - Jul 5](https://www.expedia.com/Hotel-Search?regionId=6612&startDate=2026-07-03&endDate=2026-07-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jul 31 - Aug 2](https://www.expedia.com/Hotel-Search?regionId=6612&startDate=2026-07-31&endDate=2026-08-02&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chesapeake cottages ![Property grounds](https://images.trvl-media.com/lodging/123000000/122770000/122760200/122760136/a3318414.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/123000000/122770000/122760200/122760136/9b2950ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/123000000/122770000/122760200/122760136/09c3ec15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/123000000/122770000/122760200/122760136/95f33da1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 900 A Seaside 2BR Duplex Steps to Bay w/ Veranda [](https://www.expedia.com/Norfolk-Hotels-900-A-Seaside-2BR-Duplex-Steps-To-Bay-W-Veranda.h122760136.Hotel-Information) Willoughby Spit $970 nightly $1,111 total Apr 20 - Apr 21 Total with taxes and fees [](https://www.expedia.com/Norfolk-Hotels-900-A-Seaside-2BR-Duplex-Steps-To-Bay-W-Veranda.h122760136.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/85000000/84050000/84048300/84048231/w3329h4096x0y0-fe9e2a32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/85000000/84050000/84048300/84048231/45b8c186.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/85000000/84050000/84048300/84048231/7e7cfb78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player](https://images.trvl-media.com/lodging/85000000/84050000/84048300/84048231/825456ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfortable & Private 2 Bedrm Cottage w/ King bed. [](https://www.expedia.com/Portsmouth-Hotels-Comfortable-Private-2-Bedrm-Cottage-W-King-Bed.h84048231.Hotel-Information) Portsmouth 9.4/10 Exceptional (18 reviews) "Very clean, the beds were comfortable! It was a great place to stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lee S. $250 nightly $291 total Apr 7 - Apr 8 Total with taxes and fees [](https://www.expedia.com/Portsmouth-Hotels-Comfortable-Private-2-Bedrm-Cottage-W-King-Bed.h84048231.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/34000000/33560000/33556500/33556489/93fd401c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33560000/33556500/33556489/da4b144a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/34000000/33560000/33556500/33556489/159a3612.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sun loungers, beach towels](https://images.trvl-media.com/lodging/34000000/33560000/33556500/33556489/b918f4ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Norfolk Beach Cottage Rental [](https://www.expedia.com/Norfolk-Virginia-Beach-Hotels-Norfolk-Beach-Cottage-Rental.h33556489.Hotel-Information) East Ocean View 9.0/10 Wonderful (282 reviews) "Great location. Very close to the beach and a park. Great place for families. Large dining table worked great for us for Thanksgiving. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cody H. $345 nightly $400 total Apr 12 - Apr 13 Total with taxes and fees [](https://www.expedia.com/Norfolk-Virginia-Beach-Hotels-Norfolk-Beach-Cottage-Rental.h33556489.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/124000000/123850000/123849300/123849297/w4320h3213x0y11-09e6607c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/124000000/123850000/123849300/123849297/w4320h3209x0y0-902a2623.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sun loungers, beach towels](https://images.trvl-media.com/lodging/124000000/123850000/123849300/123849297/w4320h3225x0y7-3b239459.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, foosball, table tennis, books](https://images.trvl-media.com/lodging/124000000/123850000/123849300/123849297/w4320h3240x0y0-09e990b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wild Horses - 4x4 Beach - Quiet & Cozy [](https://www.expedia.com/Corolla-Hotels-Salty-Sea-Dog-Cottage-4x4-Beach-Quiet-Cozy.h123849297.Hotel-Information) Corolla 10/10 Exceptional (1 review) "This is an adorable, comfy home. Regan, our host, very communicative and welcoming. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Maureen A. $398 nightly $449 total Apr 13 - Apr 14 Total with taxes and fees [](https://www.expedia.com/Corolla-Hotels-Salty-Sea-Dog-Cottage-4x4-Beach-Quiet-Cozy.h123849297.Hotel-Information) ![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) ![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/124000000/123420000/123412000/123411909/4ca87ed2.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/adf90b11.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 Apr 30 - May 1 Total with taxes and fees [](https://www.expedia.com/Portsmouth-Hotels-Centrally-Located-Hampton-Roads-Home-W-Game-Room.h123411909.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/123000000/122810000/122804300/122804217/73aa526c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/123000000/122810000/122804300/122804217/a1f9aa06.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/123000000/122810000/122804300/122804217/a4cc259a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/123000000/122810000/122804300/122804217/a37bcd1f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 900\. B Seaside 2 Br Cottage with Bay Views, Veranda, High Ceilings, Hot Tub, Private Beach, Beachfront Grilling, & Kayaks [](https://www.expedia.com/Norfolk-Hotels-900-B-Seaside-2BR-Cottage-W-Bay-Views-Veranda.h122804217.Hotel-Information) Willoughby Spit $910 nightly $1,042 total Apr 12 - Apr 13 Total with taxes and fees [](https://www.expedia.com/Norfolk-Hotels-900-B-Seaside-2BR-Cottage-W-Bay-Views-Veranda.h122804217.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=2026-04-20&endDate=2026-04-21®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=2026-07-05&d1=2026-07-05&endDate=2026-07-08&d2=2026-07-08&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=2026-07-05&d1=2026-07-05&endDate=2026-07-08&d2=2026-07-08&lodging=APARTMENT) 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=2026-07-05&d1=2026-07-05&endDate=2026-07-08&d2=2026-07-08&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=2026-07-05&d1=2026-07-05&endDate=2026-07-08&d2=2026-07-08&lodging=COTTAGE) 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=2026-07-05&d1=2026-07-05&endDate=2026-07-08&d2=2026-07-08&lodging=CONDO) 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=2026-07-05&d1=2026-07-05&endDate=2026-07-08&d2=2026-07-08&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=2026-07-05&d1=2026-07-05&endDate=2026-07-08&d2=2026-07-08&lodging=HOUSE_BOAT) ![](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-Cottages.d6612-aaCottages.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChesapeake-Cottages.d6612-aaCottages.Travel-Guide-Accommodation) ## Top Chesapeake Hotel Reviews ![Hyatt Place Virginia Beach / Oceanfront](https://images.trvl-media.com/lodging/76000000/75960000/75958000/75957909/7980bf30_y.jpg) ### Hyatt Place Virginia Beach / Oceanfront 8/10 Good "I recently stayed at this hotel and had a mostly great experience. The front desk staff were incredibly welcoming, professional, and helpful throughout my stay—they really set the tone from the moment I arrived. The rooms were clean, comfortable, and well-maintained, making it easy to relax. Valet parking was also a standout—quick, efficient, and very convenient. The only area that could use improvement is the breakfast. While it was decent, the variety and overall presentation could definitely be enhanced to better match the quality of the rest of the hotel experience. Overall, I would still recommend this hotel and would gladly stay here again." [](https://expedia.com/Virginia-Beach-Hotels-Hyatt-Place-Virginia-Beach-Oceanfront.h75957909.Hotel-Information) ![Hilton Vacation Club Oceanaire Virginia Beach](https://images.trvl-media.com/lodging/6000000/5200000/5190800/5190701/35a4a7e3_y.jpg) ### Hilton Vacation Club Oceanaire Virginia Beach 2/10 Terrible "Went to check in at " [](https://expedia.com/Virginia-Beach-Hotels-Oceanaire-By-Diamond-Resorts.h5190701.Hotel-Information) ![Embassy Suites by Hilton Hampton Convention Center](https://images.trvl-media.com/lodging/2000000/1180000/1172300/1172219/f5721060_y.jpg) ### Embassy Suites by Hilton Hampton Convention Center 6/10 Okay "We were excited to stay a suite but that quickly turned into disappointment as there was a leak from somewhere which caused by clothes and shoes to be soaked." [](https://expedia.com/Newport-News-Hotels-Embassy-Suites-By-Hilton-Hampton-Convention-Center.h1172219.Hotel-Information) ![Hilton Vacation Club Ocean Beach Club Virginia Beach](https://images.trvl-media.com/lodging/2000000/1370000/1367400/1367330/44e2a487_y.jpg) ### Hilton Vacation Club Ocean Beach Club Virginia Beach 10/10 Excellent "I was very pleased with my stay here. I have nothing negative to say at all." [](https://expedia.com/Virginia-Beach-Hotels-Ocean-Beach-Club-By-Diamond-Resorts.h1367330.Hotel-Information) ![Country Inn & Suites by Radisson, Virginia Beach (Oceanfront)](https://images.trvl-media.com/lodging/1000000/10000/5400/5363/be66f1fd_y.jpg) ### Country Inn & Suites by Radisson, Virginia Beach (Oceanfront) 10/10 Excellent "Nice room, great, friendly staff" [](https://expedia.com/Virginia-Beach-Hotels-Country-Inn-Suites-By-Radisson.h5363.Hotel-Information) ![Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/20000/12800/12727/26394a34_y.jpg) ### Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel 10/10 Excellent "Great location!" [](https://expedia.com/Virginia-Beach-Hotels-Surfbreak-Oceanfront-Hotel.h12727.Hotel-Information) ![The Ocean Key Virginia Beach Resort](https://images.trvl-media.com/lodging/1000000/530000/529400/529337/87f7858a_y.jpg) ### The Ocean Key Virginia Beach Resort 2/10 Terrible "Dirty rooms unprofessional staff pool not open just trash in elevator " [](https://expedia.com/Virginia-Beach-Hotels-The-Ocean-Key-Resort-By-VSA-Resorts.h529337.Hotel-Information) ![Wingate by Wyndham Chesapeake](https://images.trvl-media.com/lodging/2000000/1520000/1513300/1513238/0d94729b_y.jpg) ### Wingate by Wyndham Chesapeake 8/10 Good " Yes " [](https://expedia.com/Chesapeake-Hotels-Wingate-By-Wyndham-Chesapeake.h1513238.Hotel-Information) ![Coastal Hotel and Suites Virginia Beach Oceanfront](https://images.trvl-media.com/lodging/1000000/10000/10000/9977/77100d53_y.jpg) ### Coastal Hotel and Suites Virginia Beach Oceanfront 10/10 Excellent "Bonnie the breakfast staff was very, very friendly. Good worker and very pleasant. The check inn people were very friendly. Will be back. Excellent room." [](https://expedia.com/Virginia-Beach-Hotels-Coastal-Hotel-And-Suites-Virginia-Beach-Oceanfront.h9977.Hotel-Information) ## Find out more about Chesapeake ## Chesapeake Cottages information | Number of reviews | 301 | | ----------------- | ------------ | | Accommodation | 162 Cottages | | Lowest Price | $291 | | Highest Price | $1,111 | ## Frequently asked questions ### Why book your cottage in Chesapeake with Expedia? ### How can I find cheap cottages in Chesapeake? ### What is there to do in Chesapeake near my cottage? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - Other - [Hotels near Oak Grove Lake Park ](https://www.expedia.com/Oak-Grove-Lake-Park-Hotels.0-l6301205-0.Travel-Guide-Filter-Hotels) - [Hotels near Greenbrier West ](https://www.expedia.com/Greenbrier-West-Chesapeake-Hotels.0-n553248635976480700-0.Travel-Guide-Filter-Hotels) - [Norfolk Hotels ](https://www.expedia.com/Norfolk-Hotels.d2689.Travel-Guide-Hotels) - [Hotels near Cahoon Plantation Golf Course ](https://www.expedia.com/Cahoon-Plantation-Golf-Course-Hotels.0-l6083003-0.Travel-Guide-Filter-Hotels) - 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