Title: Chesapeake Vacation Home Rentals from CA $317: Search Top Private Vacation Homes for Rent | Expedia.ca [Chesapeake Travel Guide](https://expedia.ca/Chesapeake.dx6612)[Hotels in Chesapeake](https://expedia.ca/Chesapeake-Hotels.d6612.Travel-Guide-Hotels)[Vacation Rentals in Chesapeake](https://expedia.ca/Chesapeake-Vacation-Rentals.d6612.Travel-Guide-VacationRentals)[Flights to Chesapeake](https://expedia.ca/Cheap-Flights-To-Chesapeake.d6612.Travel-Guide-Flights)[Chesapeake Car Rentals](https://expedia.ca/Car-Rentals-In-Chesapeake.d6612.Car-Rental-Guide)[Chesapeake Vacation Packages](https://expedia.ca/Chesapeake.d6612.Destination-Travel-Guides) ![Hidden Gems. #trovember #chesapeake #virginia #november #fall #golden #hiddengems](https://images.trvl-media.com/place/6612/dba409e5-c541-4029-b3b6-3ea7a408a4c8.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Sarah Chiricosta # Chesapeake Vacation Rentals - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates In two weeks [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=6612&startDate=2025-12-12&endDate=2025-12-14&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=6612&startDate=2026-01-23&endDate=2026-01-25&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Feb 20 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=6612&startDate=2026-02-20&endDate=2026-02-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Mar 20 - Mar 22](https://www.expedia.ca/Hotel-Search?regionId=6612&startDate=2026-03-20&endDate=2026-03-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Chesapeake Vacation Homes ![Terrace/patio](https://images.trvl-media.com/lodging/108000000/107190000/107183300/107183271/f19c225c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/108000000/107190000/107183300/107183271/f4772987.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/108000000/107190000/107183300/107183271/bd83a370.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107190000/107183300/107183271/aba77227.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Chesapeake 10/10 Exceptional (39) "Everything was great! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nikki S. CA $169 CA $349 total includes taxes & fees Dec 3 - Dec 4 [](https://www.expedia.ca/Chesapeake-Hotels-2-Bedroom-House-In-Fabulous-Chesapeake-With-WiFi.h107183271.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/101000000/100370000/100360100/100360069/9bd5f725.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/101000000/100370000/100360100/100360069/81cbb459.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100370000/100360100/100360069/64624c19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/101000000/100370000/100360100/100360069/f5b8f4b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Norfolk 10/10 Exceptional (1) "Very nice property to stay at plenty to do staying there. Good location plenty of places around for anything you may need. Host was nice and available to answer any questions I had. Would love staying there again sometime!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Zachary C. CA $139 CA $465 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Norfolk-Hotels-10min-To-Ocean-View-BBQ-Volleyball-Fire-Pit.h100360069.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/111000000/111000000/110997100/110997037/0dcb9772.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/111000000/111000000/110997100/110997037/ff6dbf41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/111000000/111000000/110997100/110997037/370f86ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/111000000/111000000/110997100/110997037/a61328fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Portsmouth 9.6/10 Exceptional (4) "Property is well maintained. Great AC. Perfect for a couple to get away for a week. Central location was perfect for everything we planned to do for the week. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Paige M. CA $112 CA $369 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Portsmouth-Hotels-Charming-1-Bedroom-1-Bath-Unit-With-Beautiful-Riverfront-Sunsets-In-Portsmouth.h110997037.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/96000000/95740000/95731500/95731452/8d9c63c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/96000000/95740000/95731500/95731452/ed97d9b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, coffee/tea maker, toaster](https://images.trvl-media.com/lodging/96000000/95740000/95731500/95731452/w905h683x60y0-303d9406.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hair dryer, towels, toilet paper](https://images.trvl-media.com/lodging/96000000/95740000/95731500/95731452/w903h683x61y0-bc39f103.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Coinjock 9.6/10 Exceptional (4) "The whole process was very easy and smooth. The property was clean and comfortable. I would definitely stay here again in the future!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Pam P. CA $133 CA $317 total includes taxes & fees Dec 3 - Dec 4 [](https://www.expedia.ca/Coinjock-Hotels-Knot-Three-Balcony-View-Of-ICW-Dog-Friendly.h95731452.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/93000000/92370000/92360800/92360757/0255f575.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, bed sheets](https://images.trvl-media.com/lodging/93000000/92370000/92360800/92360757/6ad2f3ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/93000000/92370000/92360800/92360757/a2256842.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/93000000/92370000/92360800/92360757/18e03d55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Northeast Virginia Beach 9.6/10 Exceptional (104) "Great get away stay! Close drive to the shops and the beach. Very cozy. Would definitely stay there again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lizy G. CA $140 CA $324 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Virginia-Beach-Hotels-The-Art-Door-Only-Minutes-From-Beach.h92360757.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/75000000/74880000/74875800/74875772/512bb6dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/75000000/74880000/74875800/74875772/dc8fd476.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/75000000/74880000/74875800/74875772/18856056.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/75000000/74880000/74875800/74875772/acc35d80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Coinjock 10/10 Exceptional (36) "Cute, clean and well appointed. The view over the water is so pretty. We would stay again! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Susan H. CA $140 CA $361 total includes taxes & fees Dec 7 - Dec 8 [](https://www.expedia.ca/Coinjock-Hotels-Waterview-Cottage.h74875772.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/90000000/89550000/89542800/89542716/387a646c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89550000/89542800/89542716/1cffe5a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/90000000/89550000/89542800/89542716/2a777b28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![5 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/90000000/89550000/89542800/89542716/c10a2b3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Virginia Beach 8.8/10 Excellent (42) "It was a nice time. The manager was great to work with. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dawna A. CA $177 CA $494 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Virginia-Beach-Hotels-Beach-Baby-Bingo-Perfect-Spot-For-Exploring-Va-Beach.h89542716.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/91000000/90860000/90851600/90851502/b5b925b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/91000000/90860000/90851600/90851502/54a74646.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/91000000/90860000/90851600/90851502/fb2260d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/91000000/90860000/90851600/90851502/638124a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Elizabeth city 7.0/10 Good (4) "We had a nice stay. Thank you. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rebecca S. CA $119 CA $420 total includes taxes & fees Dec 8 - Dec 9 [](https://www.expedia.ca/Elizabeth-City-Hotels-Comfort-Near-The-Water-And-University.h90851502.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/112000000/111780000/111772000/111771911/40a8c9bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/112000000/111780000/111772000/111771911/5812ceec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/112000000/111780000/111772000/111771911/e762c024.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/112000000/111780000/111772000/111771911/e12e813b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Portsmouth 9.0/10 Wonderful (22) "Great property " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brian C. CA $140 CA $405 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Portsmouth-Hotels-Charming-2-Bedroom.h111771911.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102580000/102571200/102571188/cedeb5c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/103000000/102580000/102571200/102571188/3cfd3d71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102580000/102571200/102571188/936f6fe0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/103000000/102580000/102571200/102571188/947cf998.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Wythe 7.8/10 Good (10) "Clean, convenient and comfortable, would stay again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Riley CA $148 CA $384 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Hampton-Hotels-317A-Perfect-For-Families.h102571188.Hotel-Information) ![On the beach, sun loungers](https://images.trvl-media.com/lodging/68000000/67550000/67547100/67547042/eceda65b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/68000000/67550000/67547100/67547042/41c0b25e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/68000000/67550000/67547100/67547042/a0a32b1f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/68000000/67550000/67547100/67547042/6f583f42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Willoughby Spit 9.0/10 Wonderful (71) "Everything was perfect, a short walk to the beach, getting things delivered was easy, overall the perfect place to stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Elizabeth W. CA $181 CA $366 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Norfolk-Hotels-Cozy-Historic-Beach-House-Only-Steps-Away-From-Beach-And-Fishing-Pier.h67547042.Hotel-Information) ![Beach nearby](https://images.trvl-media.com/lodging/77000000/76680000/76671500/76671407/8102ddfa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/77000000/76680000/76671500/76671407/068b4785.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![5 bedrooms, free WiFi, bed sheets, wheelchair access](https://images.trvl-media.com/lodging/77000000/76680000/76671500/76671407/32f70916.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/77000000/76680000/76671500/76671407/w1080h1042x0y1-c42c8ba8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Corolla 9.8/10 Exceptional (16) "Aaron and Kim were fabulous! From personal escorts at high tide to trips bringing a grill and charcoal. All members of my party were beyond impressed " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jacquie M. CA $190 CA $1,232 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Corolla-Hotels-Octopus-Oasis-On-4x4-Beach-Of-Carova.h76671407.Hotel-Information) ![Beach nearby](https://images.trvl-media.com/lodging/93000000/92790000/92786500/92786454/2166d272.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/93000000/92790000/92786500/92786454/dd4bc02a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, coffee/tea maker, cookware/dishes/utensils](https://images.trvl-media.com/lodging/93000000/92790000/92786500/92786454/ffac4440.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, coffee/tea maker, cookware/dishes/utensils](https://images.trvl-media.com/lodging/93000000/92790000/92786500/92786454/c6785711.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Hampton 9.0/10 Wonderful (18) "Conveniently located by the beach and fun ocean color scheme. The " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Hannah O. CA $141 CA $479 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Hampton-Hotels-Buckroe-Bungalow-Escape-To-The-Beach-2mins-Away.h92786454.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/92000000/91910000/91907700/91907687/af55b300.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/92000000/91910000/91907700/91907687/ae2a6bc1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, offices](https://images.trvl-media.com/lodging/92000000/91910000/91907700/91907687/38bf4374.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, offices](https://images.trvl-media.com/lodging/92000000/91910000/91907700/91907687/686f2a8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Fox Hill 9.6/10 Exceptional (27) "The home was very nice, clean & comfortable. Property manager was great with communication and addressing small concerns. Wished the back doors were a little more secure and there was an oven. But we had no safety concerns at all.Thanks for a comfortable place to stay and we had a good stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Adria K. CA $188 CA $641 total includes taxes & fees Dec 9 - Dec 10 [](https://www.expedia.ca/Hampton-Hotels-Sojourns-Aviators-Dream-On-Back-River.h91907687.Hotel-Information) ![On the beach](https://images.trvl-media.com/lodging/70000000/69540000/69537000/69536918/18a9d006.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/70000000/69540000/69537000/69536918/25f8f073.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/70000000/69540000/69537000/69536918/317971bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/70000000/69540000/69537000/69536918/6aabd7ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Willoughby Spit 9.0/10 Wonderful (69) "Location was amazing and made the house worthwhile " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Misti W. CA $195 CA $385 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Norfolk-Hotels-Rustic-Ocean-View-Beach-House-BEST-Location-In-Ocean-View-2-Bed1-Bath-House.h69536918.Hotel-Information) ![Beach](https://images.trvl-media.com/lodging/101000000/100910000/100903800/100903792/2ead7cf0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/101000000/100910000/100903800/100903792/2a38e5c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/101000000/100910000/100903800/100903792/417ed2a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/101000000/100910000/100903800/100903792/218c853c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Norfolk 9.6/10 Exceptional (4) "We loved staying in this rental…it had everything we needed and more! It is very clean and the perfect location for a beach vacation. After I had asked if there were chairs for the beach, the host voluntarily went out and purchased some…talk about hospitality!! We highly recommend this rental." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Donna B. CA $248 CA $607 total includes taxes & fees Nov 29 - Nov 30 [](https://www.expedia.ca/Norfolk-Hotels-Seaside-Luxury-Retreat-U-In-Norfolk.h100903792.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89010000/89008000/89007920/3f0e3bbd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/90000000/89010000/89008000/89007920/cdfb8169.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/90000000/89010000/89008000/89007920/92ac0d10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, in-room safe, desk, iron/ironing board](https://images.trvl-media.com/lodging/90000000/89010000/89008000/89007920/20919817.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Portsmouth 8.8/10 Excellent (38) "This was a great stay. The location was nice and quiet. Loved the ability to walk to several eateries and bars. Thoroughly enjoyed our stay. Had a great time and the owners were very responsive. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sarah G. CA $181 CA $492 total includes taxes & fees Dec 2 - Dec 3 [](https://www.expedia.ca/Portsmouth-Hotels-Modern-Oasis-Downtown-Luxury-Stay.h89007920.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/75000000/74240000/74236500/74236461/1ff997be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/75000000/74240000/74236500/74236461/bc0559e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/75000000/74240000/74236500/74236461/27308920.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/75000000/74240000/74236500/74236461/d587d827.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Hampton 9.2/10 Wonderful (27) "My overall stay was great! We loved the house and the host is super sweet! We had a minor issue with getting in touch with the host, but that was resolved. Definitely would book it again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveller CA $195 CA $617 total includes taxes & fees Dec 3 - Dec 4 [](https://www.expedia.ca/Hampton-Hotels-4-Bedroom-Cottage-5-Minutes-From-Both-Beaches.h74236461.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/22000000/21130000/21125900/21125830/270-55ec47a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/22000000/21130000/21125900/21125830/00327ce2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/22000000/21130000/21125900/21125830/270-8edd9133.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/22000000/21130000/21125900/21125830/270-4f8e0f32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Norfolk 8.8/10 Excellent (29) "I was very convenient cozy close to everything top tier" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dawn W. CA $223 CA $631 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Norfolk-Hotels-Old-Beach-House-Made-New-Again.h21125830.Hotel-Information) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/109000000/108960000/108952000/108951942/8fdd5a41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/109000000/108960000/108952000/108951942/0ff36c06.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/109000000/108960000/108952000/108951942/0fc4ad5d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/109000000/108960000/108952000/108951942/e65b8cc1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in East Ocean View 10/10 Exceptional (1) "Thank you for the lil incredible paradise. House was clean with alot of rooms. PM was very welcoming and was always available to answer my questions." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Andrew T. CA $222 CA $571 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Norfolk-Hotels-Charming-Beachside-Retreat-Turtle.h108951942.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.ca/Hotel-Search?startDate=2025-12-11&endDate=2025-12-12®ionId=6612&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_CA_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## Black Friday Sale Limited-time deals: save up to 50% on select hotels [Book now](https://expedia.ca/deals?rfrr=AA_BF_PROMO_6612) ## Find vacation rentals that suit your style Apartments [](https://www.expedia.ca/Hotel-Search?destination=Chesapeake%2C+Virginia%2C+United+States+of+America®ionId=6612&latLong=36.767662%2C-76.286817&adults=2&startDate=2026-02-25&d1=2026-02-25&endDate=2026-02-28&d2=2026-02-28&lodging=APARTMENT) Aparthotels [](https://www.expedia.ca/Hotel-Search?destination=Chesapeake%2C+Virginia%2C+United+States+of+America®ionId=6612&latLong=36.767662%2C-76.286817&adults=2&startDate=2026-02-25&d1=2026-02-25&endDate=2026-02-28&d2=2026-02-28&lodging=APART_HOTEL) Private vacation homes [](https://www.expedia.ca/Hotel-Search?destination=Chesapeake%2C+Virginia%2C+United+States+of+America®ionId=6612&latLong=36.767662%2C-76.286817&adults=2&startDate=2026-02-25&d1=2026-02-25&endDate=2026-02-28&d2=2026-02-28&lodging=VACATION_HOME) Condos [](https://www.expedia.ca/Hotel-Search?destination=Chesapeake%2C+Virginia%2C+United+States+of+America®ionId=6612&latLong=36.767662%2C-76.286817&adults=2&startDate=2026-02-25&d1=2026-02-25&endDate=2026-02-28&d2=2026-02-28&lodging=CONDO) Cottages [](https://www.expedia.ca/Hotel-Search?destination=Chesapeake%2C+Virginia%2C+United+States+of+America®ionId=6612&latLong=36.767662%2C-76.286817&adults=2&startDate=2026-02-25&d1=2026-02-25&endDate=2026-02-28&d2=2026-02-28&lodging=COTTAGE) Villas [](https://www.expedia.ca/Hotel-Search?destination=Chesapeake%2C+Virginia%2C+United+States+of+America®ionId=6612&latLong=36.767662%2C-76.286817&adults=2&startDate=2026-02-25&d1=2026-02-25&endDate=2026-02-28&d2=2026-02-28&lodging=VILLA) Cabins [](https://www.expedia.ca/Hotel-Search?destination=Chesapeake%2C+Virginia%2C+United+States+of+America®ionId=6612&latLong=36.767662%2C-76.286817&adults=2&startDate=2026-02-25&d1=2026-02-25&endDate=2026-02-28&d2=2026-02-28&lodging=CABIN) Houseboats [](https://www.expedia.ca/Hotel-Search?destination=Chesapeake%2C+Virginia%2C+United+States+of+America®ionId=6612&latLong=36.767662%2C-76.286817&adults=2&startDate=2026-02-25&d1=2026-02-25&endDate=2026-02-28&d2=2026-02-28&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.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FChesapeake-Private-Vacation-Homes.d6612-aaPrivateVacationHomes.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChesapeake-Private-Vacation-Homes.d6612-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Top Chesapeake Hotel Reviews ![Schooner Inn](https://images.trvl-media.com/lodging/2000000/1720000/1711400/1711317/f35c64c2_y.jpg) ### Schooner Inn 10/10 Excellent "Room looked great, staff was friendly!! " [](https://expedia.ca/Virginia-Beach-Hotels-Schooner-Inn.h1711317.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 "Room and service were excellent!" [](https://expedia.ca/Chesapeake-Hotels-Comfort-Suites-Chesapeake-Norfolk.h6570.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 "Clean and spacious rooms. Nice beach view and very helpful staff! Loved my experience! " [](https://expedia.ca/Virginia-Beach-Hotels-Hyatt-Place-Virginia-Beach-Oceanfront.h75957909.Hotel-Information) ![STUDIOS & SUITES 4 LESS CHESAPEAKE ](https://images.trvl-media.com/lodging/1000000/50000/40500/40428/e945abb1_y.jpg) ### STUDIOS & SUITES 4 LESS CHESAPEAKE 10/10 Excellent "Good price, excellent help at the front desk " [](https://expedia.ca/Chesapeake-Hotels-Econo-Lodge-Chesapeake-Route-13-And-I-464.h40428.Hotel-Information) ![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 "Staff was fantastic, very responsive and helpful." [](https://expedia.ca/Virginia-Beach-Hotels-Country-Inn-Suites-By-Radisson.h5363.Hotel-Information) ![Aloft Chesapeake](https://images.trvl-media.com/lodging/3000000/2180000/2178600/2178508/40b8c7ba_y.jpg) ### Aloft Chesapeake 10/10 Excellent "Clean room" [](https://expedia.ca/Chesapeake-Hotels-Aloft-Chesapeake.h2178508.Hotel-Information) ![Delta Hotels by Marriott Virginia Beach Waterfront Suites](https://images.trvl-media.com/lodging/41000000/40900000/40896500/40896449/6e910a6c_y.jpg) ### Delta Hotels by Marriott Virginia Beach Waterfront Suites 10/10 Excellent "Lovely room. It was so quiet and comfortable. Wonderful for relaxing and unwinding. " [](https://expedia.ca/Norfolk-Virginia-Beach-Hotels-Delta-Hotels-By-Marriott-Virginia-Beach-Bayfront-Suites.h40896449.Hotel-Information) ![Coastal Hotel and Suites Virginia Beach Oceanfront](https://images.trvl-media.com/lodging/1000000/10000/10000/9977/cdf6c338_y.jpg) ### Coastal Hotel and Suites Virginia Beach Oceanfront 10/10 Excellent "Highly recommend. Clean quiet friendly staff..breakfast was delicious..beautiful view of the beach.would stay again." [](https://expedia.ca/Virginia-Beach-Hotels-Coastal-Hotel-And-Suites-Virginia-Beach-Oceanfront.h9977.Hotel-Information) ![Embassy Suites by Hilton Virginia Beach Oceanfront Resort](https://images.trvl-media.com/lodging/84000000/83760000/83750900/83750882/0189125f_y.jpg) ### Embassy Suites by Hilton Virginia Beach Oceanfront Resort 10/10 Excellent "Clean, beautiful, friendly and I don’t give reviews out easily! " [](https://expedia.ca/Virginia-Beach-Hotels-Embassy-Suites-By-Hilton-Virginia-Beach-Oceanfront-Resort.h83750882.Hotel-Information) ## Find out more about Chesapeake ## Chesapeake Vacation Homes information | Number of reviews | 556 | | --- | --- | | Accommodation | 1415 Vacation Homes | | Lowest Price | CA $317 | | Highest Price | CA $1,232 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [Inns in Chesapeake City County](https://www.expedia.ca/Chesapeake-City-County-Inns.d553248635976432419-aaInns.Travel-Guide-Accommodation) - [Hotels near Chesapeake Conference Center](https://www.expedia.ca/Chesapeake-Conference-Center-Hotels.0-l6083013-0.Travel-Guide-Filter-Hotels) - [Adults Only Resorts & in Deep Creek South](https://www.expedia.ca/Deep-Creek-South-Chesapeake-Hotels-Adults-Only-Resorts.0-n553248635976473910-0-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - [Romantic Hotels in Deep Creek South](https://www.expedia.ca/Deep-Creek-South-Chesapeake-Hotels-Romantic-Hotel.0-n553248635976473910-0-tRomanticHotel.Travel-Guide-Filter-Hotels) - 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