Title: Chesapeake, VA Cottage Rentals from $288 | 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) ## Check prices for these dates In two weeks [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 two months [May 22 - May 24](https://www.expedia.com/Hotel-Search?regionId=6612&startDate=2026-05-22&endDate=2026-05-24&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Jun 19 - Jun 21](https://www.expedia.com/Hotel-Search?regionId=6612&startDate=2026-06-19&endDate=2026-06-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jul 17 - Jul 19](https://www.expedia.com/Hotel-Search?regionId=6612&startDate=2026-07-17&endDate=2026-07-19&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/123000000/122810000/122807400/122807341/b4d7d7d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/123000000/122810000/122807400/122807341/c6d7e69e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/123000000/122810000/122807400/122807341/75e87133.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/123000000/122810000/122807400/122807341/3c51c4eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 902 C Coastal King Retreat Steps from Beach + Sauna [](https://www.expedia.com/Norfolk-Hotels-902C-Coastal-King-Retreat-Steps-From-Beach-Sauna.h122807341.Hotel-Information) Willoughby Spit $848 nightly $971 total Mar 29 - Mar 30 Total with taxes and fees [](https://www.expedia.com/Norfolk-Hotels-902C-Coastal-King-Retreat-Steps-From-Beach-Sauna.h122807341.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) ![Interior](https://images.trvl-media.com/lodging/85000000/84050000/84048300/84048231/ee6a7245.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player](https://images.trvl-media.com/lodging/85000000/84050000/84048300/84048231/79a31f08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/85000000/84050000/84048300/84048231/d64e83d8.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. $248 nightly $288 total Mar 30 - Mar 31 Total with taxes and fees [](https://www.expedia.com/Portsmouth-Hotels-Comfortable-Private-2-Bedrm-Cottage-W-King-Bed.h84048231.Hotel-Information) ![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) ![Outdoor dining](https://images.trvl-media.com/lodging/123000000/122770000/122760200/122760136/95f33da1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/123000000/122770000/122760200/122760136/707db8b5.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 $938 nightly $1,074 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) ![Property grounds](https://images.trvl-media.com/lodging/123000000/122810000/122805900/122805878/65991cc0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/123000000/122810000/122805900/122805878/71137cbe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/123000000/122810000/122805900/122805878/1ef75f5e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/123000000/122810000/122805900/122805878/b47eb50b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 902 CH Historic Carriage House 20 Steps to Beach + Hot Tub, Kayaks, Beachfront Grilling [](https://www.expedia.com/Norfolk-Hotels-902-CH-Historic-Carriage-House-Hot-Tub-Access.h122805878.Hotel-Information) Willoughby Spit $808 nightly $925 total Apr 2 - Apr 3 Total with taxes and fees [](https://www.expedia.com/Norfolk-Hotels-902-CH-Historic-Carriage-House-Hot-Tub-Access.h122805878.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) ![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) ![Interior](https://images.trvl-media.com/lodging/34000000/33560000/33556500/33556489/695576fe.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 (280 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. $344 nightly $399 total Mar 26 - Mar 27 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/w1080h809x0y3-83ae0511.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) ![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 $397 nightly $448 total Mar 27 - Mar 28 Total with taxes and fees [](https://www.expedia.com/Corolla-Hotels-Salty-Sea-Dog-Cottage-4x4-Beach-Quiet-Cozy.h123849297.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/124000000/123810000/123802500/123802418/54731b11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/124000000/123810000/123802500/123802418/w1200h753x0y1-e36e7039.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/124000000/123810000/123802500/123802418/w1200h752x0y1-13bad001.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby, sun loungers](https://images.trvl-media.com/lodging/124000000/123810000/123802500/123802418/5441b123.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Steps to the Ocean! A Family and Dog-Friendly North End Cottage w/ Rsrv Parking [](https://www.expedia.com/Virginia-Beach-Hotels-3-Min-Walk-To-Beach-Cozy-North-End-Cottage-Oceanside-Of-Atlantic-Dog-Friendly.h123802418.Hotel-Information) Northeast Virginia Beach 9.8/10 Exceptional (261 reviews) "Great location and communication" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Katherine E. $514 nightly $593 total Apr 3 - Apr 4 Total with taxes and fees [](https://www.expedia.com/Virginia-Beach-Hotels-3-Min-Walk-To-Beach-Cozy-North-End-Cottage-Oceanside-Of-Atlantic-Dog-Friendly.h123802418.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=2026-04-06&endDate=2026-04-07®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=2026-06-21&d1=2026-06-21&endDate=2026-06-24&d2=2026-06-24&lodging=VACATION_HOME) 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=2026-06-21&d1=2026-06-21&endDate=2026-06-24&d2=2026-06-24&lodging=CONDO) 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=2026-06-21&d1=2026-06-21&endDate=2026-06-24&d2=2026-06-24&lodging=COTTAGE) 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=2026-06-21&d1=2026-06-21&endDate=2026-06-24&d2=2026-06-24&lodging=APART_HOTEL) 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=2026-06-21&d1=2026-06-21&endDate=2026-06-24&d2=2026-06-24&lodging=APARTMENT) 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=2026-06-21&d1=2026-06-21&endDate=2026-06-24&d2=2026-06-24&lodging=VILLA) 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=2026-06-21&d1=2026-06-21&endDate=2026-06-24&d2=2026-06-24&lodging=CABIN) 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=2026-06-21&d1=2026-06-21&endDate=2026-06-24&d2=2026-06-24&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 House Virginia Beach / Oceanfront](https://images.trvl-media.com/lodging/4000000/3830000/3827100/3827084/w3837h2875x3y0-11f7acb0_y.jpg) ### Hyatt House Virginia Beach / Oceanfront 10/10 Excellent "Great room with fantastic ocean view." [](https://expedia.com/Virginia-Beach-Hotels-Hyatt-House-Virginia-Beach-Oceanfront.h3827084.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 "Outstanding overnight landing pad for our family, and I would love to come back and stay longer. The layout of the rooms is perfect for families, with a quiet room for sleeping and a front room with a queen sleeper sofa facing the ocean for early or late risers. Having the bathroom and kitchenette between rooms minimized disruption. The staff could not have been more welcoming and helpful, and the free self-parking and breakfast made this hotel a great beachfront value in the middle of the best area to jog, eat, or hang out on the beach. Having the 24 hour gym in the lobby in a glass enclosure is great for solo female travelers and makes it a light an airy space, with an easy sight line to the lobby and over to the pool and hot tub. The breakfast buffet is standard, but exceptionally friendly staff kept the area sparking, moving families in and out smoothly. Cappucino and hot chocolate machine along with waffle makers were crowd pleasers. This is an exceptionally well-designed and well-managed hotel from our experience." [](https://expedia.com/Virginia-Beach-Hotels-Coastal-Hotel-And-Suites-Virginia-Beach-Oceanfront.h9977.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 "Room was clean and staff was amazing! Easy to walk to lots of things near by! " [](https://expedia.com/Virginia-Beach-Hotels-Surfbreak-Oceanfront-Hotel.h12727.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) 6/10 Okay "There was a terrible smell on the entire floor leading to my room. Location and view were second to none tho . Rooms were outdated " [](https://expedia.com/Virginia-Beach-Hotels-Country-Inn-Suites-By-Radisson.h5363.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 10/10 Excellent "I’ll admit I was a bit nervous before arriving, based on some of the negative reviews, but we had a great experience. The property is definitely older so everything isn’t perfect, but the renovations in progress are impressive. The only real cons were a slightly odd smell and the door to the balcony wouldn’t open so that was disappointing, but we still had a beautiful view from the large window. Adorable renovated kitchen, very comfy bed (smelled like bleach- nice & clean), clean floors (a big one for me) and clean bathroom. The Roma restaurant food was decent, but very convenient. The lady who worked the restaurant counter was extremely friendly. Would definitely return!" [](https://expedia.com/Virginia-Beach-Hotels-The-Ocean-Key-Resort-By-VSA-Resorts.h529337.Hotel-Information) ![TRU by Hilton Chesapeake, VA](https://images.trvl-media.com/lodging/93000000/92930000/92925200/92925103/7e3313a2_y.jpg) ### TRU by Hilton Chesapeake, VA 8/10 Good "Everything was great! The room and bathroom were neat and clean. The bed was comfortable. Breakfast had many options, more than I was expecting. Check in was a breeze. It was very quiet. The location was perfect—very close to the freeway and there were restaurants very close. The only con I have is that the AC in the room sounded like there were crickets in the room when it was running. It made it somewhat difficult to fall asleep. " [](https://expedia.com/Chesapeake-Hotels-TRU-By-Hilton-Chesapeake.h92925103.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 10/10 Excellent "The best hotel ever!!!!" [](https://expedia.com/Virginia-Beach-Hotels-Oceanaire-By-Diamond-Resorts.h5190701.Hotel-Information) ![Schooner Inn](https://images.trvl-media.com/lodging/2000000/1720000/1711400/1711317/7a589703_y.jpg) ### Schooner Inn 10/10 Excellent "Pool isnt open but the chairs and table on balcony were great to enjoy the beach. Nice amentities in the kitchenette. Super friendly house keeping. Overall nice stay for 3 nights." [](https://expedia.com/Virginia-Beach-Hotels-Schooner-Inn.h1711317.Hotel-Information) ![Holiday Inn Va Beach-Oceanside (21st St) by IHG](https://images.trvl-media.com/lodging/1000000/10000/4900/4857/c65c289f_y.jpg) ### Holiday Inn Va Beach-Oceanside (21st St) by IHG 10/10 Excellent "Terrific location for marathon weekend!" [](https://expedia.com/Virginia-Beach-Hotels-Holiday-Inn-Oceanside-VA-Beach.h4857.Hotel-Information) ## Find out more about Chesapeake ## Chesapeake Cottages information | Number of reviews | 298 | | ----------------- | ------------ | | Accommodation | 152 Cottages | | Lowest Price | $288 | | Highest Price | $1,074 | ## 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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