Title: Chesapeake Vacation Rentals from $103: 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)

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## 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 vacation rentals

![Terrace/patio](https://images.trvl-media.com/lodging/108000000/107190000/107183300/107183271/f19c225c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/108000000/107190000/107183300/107183271/26c9c3f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/108000000/107190000/107183300/107183271/1781b7d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, foosball, printers](https://images.trvl-media.com/lodging/108000000/107190000/107183300/107183271/7823d509.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 3-bedroom home away from home in fabulous Chesapeake, Virginia.

[](https://www.expedia.com/Chesapeake-Hotels-2-Bedroom-House-In-Fabulous-Chesapeake-With-WiFi.h107183271.Hotel-Information)

Chesapeake

10/10

Exceptional

(43 reviews)

"This was a wonderful place that was perfect for girls trip! I would definitely recommend and stay again!!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Tabitha P.

$264 nightly

$306 total

Apr 14 - Apr 15

Total with taxes and fees

[](https://www.expedia.com/Chesapeake-Hotels-2-Bedroom-House-In-Fabulous-Chesapeake-With-WiFi.h107183271.Hotel-Information)

![Indoor pool](https://images.trvl-media.com/lodging/88000000/87920000/87917000/87916951/d0696f96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/88000000/87920000/87917000/87916951/09a84eba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/88000000/87920000/87917000/87916951/475fb7bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/88000000/87920000/87917000/87916951/6d1c6f86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 1 Bedroom | Free Breakfast. Indoor Pool & Hot Tub

[](https://www.expedia.com/Chesapeake-Hotels-1-Bedroom-Free-Breakfast-Indoor-Pool-Hot-Tub.h87916951.Hotel-Information)

Chesapeake

$181 nightly

$208 total

Apr 6 - Apr 7

Total with taxes and fees

[](https://www.expedia.com/Chesapeake-Hotels-1-Bedroom-Free-Breakfast-Indoor-Pool-Hot-Tub.h87916951.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/116000000/115340000/115333200/115333185/97612ed9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/116000000/115340000/115333200/115333185/3e0a9e18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/116000000/115340000/115333200/115333185/38b2366a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/116000000/115340000/115333200/115333185/123730b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!

[](https://www.expedia.com/Chesapeake-Hotels-Free-Breakfast-Indoor-Pool-Hot-Tub-Near-The-Virginia-Beach-Business-District.h115333185.Hotel-Information)

Chesapeake

$204 nightly

$234 total

Apr 5 - Apr 6

Total with taxes and fees

[](https://www.expedia.com/Chesapeake-Hotels-Free-Breakfast-Indoor-Pool-Hot-Tub-Near-The-Virginia-Beach-Business-District.h115333185.Hotel-Information)

![Indoor pool](https://images.trvl-media.com/lodging/88000000/87430000/87427500/87427432/8c7ccd63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/88000000/87430000/87427500/87427432/1cd4693d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/88000000/87430000/87427500/87427432/13f5bdc5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/88000000/87430000/87427500/87427432/188bbad5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Studio | Free Breakfast. Indoor Pool & Hot Tub.

[](https://www.expedia.com/Chesapeake-Hotels-Studio-Free-Breakfast-Indoor-Pool-Hot-Tub.h87427432.Hotel-Information)

Chesapeake

$190 nightly

$219 total

Apr 19 - Apr 20

Total with taxes and fees

[](https://www.expedia.com/Chesapeake-Hotels-Studio-Free-Breakfast-Indoor-Pool-Hot-Tub.h87427432.Hotel-Information)

![Indoor pool](https://images.trvl-media.com/lodging/89000000/88180000/88179800/88179795/0a114823.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/89000000/88180000/88179800/88179795/95f6e444.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/89000000/88180000/88179800/88179795/6113856d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/89000000/88180000/88179800/88179795/41222787.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Studio | Free Breakfast. Indoor Pool & Hot Tub

[](https://www.expedia.com/Chesapeake-Hotels-Studio-Free-Breakfast-Indoor-Pool-Hot-Tub.h88179795.Hotel-Information)

Chesapeake

$195 nightly

$224 total

Apr 6 - Apr 7

Total with taxes and fees

[](https://www.expedia.com/Chesapeake-Hotels-Studio-Free-Breakfast-Indoor-Pool-Hot-Tub.h88179795.Hotel-Information)

![Indoor pool](https://images.trvl-media.com/lodging/85000000/84550000/84543900/84543812/c53925b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/85000000/84550000/84543900/84543812/f76cf892.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/85000000/84550000/84543900/84543812/a32364b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/85000000/84550000/84543900/84543812/1fb27dfa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Great Studio | Pool & Hot Tub. Your Next Vacation

[](https://www.expedia.com/Chesapeake-Hotels-Great-Studio-Pool-Hot-Tub-Your-Next-Vacation.h84543812.Hotel-Information)

Chesapeake

10/10

Exceptional

(3 reviews)

"Impressed with the whole experience. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Patricia M.

$160 nightly

$184 total

Apr 5 - Apr 6

Total with taxes and fees

[](https://www.expedia.com/Chesapeake-Hotels-Great-Studio-Pool-Hot-Tub-Your-Next-Vacation.h84543812.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/116000000/115340000/115333200/115333190/87af226c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/116000000/115340000/115333200/115333190/95e0c52b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/116000000/115340000/115333200/115333190/518922cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/116000000/115340000/115333200/115333190/668f3bfe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### King Suite. Free Breakfast. Indoor Pool & Hot Tub. Great for Business Travelers!

[](https://www.expedia.com/Chesapeake-Hotels-King-Suite-Free-Breakfast-Indoor-Pool-Hot-Tub-Great-For-Business-Travelers.h115333190.Hotel-Information)

Chesapeake

$208 nightly

$240 total

Apr 19 - Apr 20

Total with taxes and fees

[](https://www.expedia.com/Chesapeake-Hotels-King-Suite-Free-Breakfast-Indoor-Pool-Hot-Tub-Great-For-Business-Travelers.h115333190.Hotel-Information)

![Indoor pool](https://images.trvl-media.com/lodging/50000000/49150000/49149800/49149734/09547181.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/50000000/49150000/49149800/49149734/38f0dea5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/50000000/49150000/49149800/49149734/e9f96ab0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/50000000/49150000/49149800/49149734/5da4f642.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### King Suite. Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!

[](https://www.expedia.com/Chesapeake-Hotels-King-Suite-Free-Breakfast-Indoor-Pool-Hot-Tub-Near-The-Virginia-Beach-Business-District.h49149734.Hotel-Information)

Chesapeake

9.0/10

Wonderful

(2 reviews)

"Very clean , great location. Will stay there again!!!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Tony H.

$171 nightly

$197 total

Apr 5 - Apr 6

Total with taxes and fees

[](https://www.expedia.com/Chesapeake-Hotels-King-Suite-Free-Breakfast-Indoor-Pool-Hot-Tub-Near-The-Virginia-Beach-Business-District.h49149734.Hotel-Information)

![Indoor pool](https://images.trvl-media.com/lodging/107000000/106270000/106262300/106262204/77f922da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/107000000/106270000/106262300/106262204/f7175697.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/107000000/106270000/106262300/106262204/7d849880.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/107000000/106270000/106262300/106262204/65cc89ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Free Breakfast. Indoor Pool & Hot Tub. Close to the Virginia Beach business district!

[](https://www.expedia.com/Chesapeake-Hotels-Free-Breakfast-Indoor-Pool-Hot-Tub-Close-To-The-Virginia-Beach-Business-District.h106262204.Hotel-Information)

Chesapeake

8.0/10

Very Good

(4 reviews)

"Perfect for what we needed for one day layover before outer Banks"

![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg)

Michael L.

$204 nightly

$234 total

Apr 5 - Apr 6

Total with taxes and fees

[](https://www.expedia.com/Chesapeake-Hotels-Free-Breakfast-Indoor-Pool-Hot-Tub-Close-To-The-Virginia-Beach-Business-District.h106262204.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/107000000/106240000/106236500/106236428/ba6ecdc8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/107000000/106240000/106236500/106236428/2a425a16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/107000000/106240000/106236500/106236428/771c267a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/107000000/106240000/106236500/106236428/acfdaf58.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Luxurious RV

[](https://www.expedia.com/Virginia-Beach-Hotels-Luxurious-RV.h106236428.Hotel-Information)

Sandbridge

8.4/10

Very Good

(17 reviews)

"Excellent accommodation close to beach I would stay here again !!! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Scott E.

$343 nightly

$402 total

Mar 24 - Mar 25

Total with taxes and fees

[](https://www.expedia.com/Virginia-Beach-Hotels-Luxurious-RV.h106236428.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 | 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)

![Apartment | 2 bedrooms](https://images.trvl-media.com/lodging/110000000/109380000/109375900/109375809/w3000h2000x0y0-a6c5a857.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

$198 nightly

$229 total

Mar 24 - Mar 25

Total with taxes and fees

[](https://www.expedia.com/Newport-News-Hotels-The-Speakeasy-Downtown-Newport-News.h109375809.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/85000000/84050000/84048300/84048231/7e7cfb78.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)

### 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)

![TV](https://images.trvl-media.com/lodging/93000000/92370000/92360800/92360757/18e03d55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/93000000/92370000/92360800/92360757/4869a696.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/93000000/92370000/92360800/92360757/a2e25621.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)

### The Art Door Duplex only minutes from beach

[](https://www.expedia.com/Virginia-Beach-Hotels-The-Art-Door-Only-Minutes-From-Beach.h92360757.Hotel-Information)

Northeast Virginia Beach

9.6/10

Exceptional

(108 reviews)

"Many restaurants and shopping nearby. Excellent place to stay."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Daniel A.

$199 nightly

$231 total

Mar 24 - Mar 25

Total with taxes and fees

[](https://www.expedia.com/Virginia-Beach-Hotels-The-Art-Door-Only-Minutes-From-Beach.h92360757.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/96000000/95740000/95731500/95731452/973ed4ed.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)

### Knot Three- Balcony View of ICW- Dog Friendly!

[](https://www.expedia.com/Coinjock-Hotels-Knot-Three-Balcony-View-Of-ICW-Dog-Friendly.h95731452.Hotel-Information)

Coinjock

9.6/10

Exceptional

(5 reviews)

"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.

$208 nightly

$234 total

Mar 24 - Mar 25

Total with taxes and fees

[](https://www.expedia.com/Coinjock-Hotels-Knot-Three-Balcony-View-Of-ICW-Dog-Friendly.h95731452.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/127000000/126620000/126614400/126614340/e76a24e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/127000000/126620000/126614400/126614340/1572c294.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Hair dryer, towels, soap, toilet paper](https://images.trvl-media.com/lodging/127000000/126620000/126614400/126614340/2e828f74.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/127000000/126620000/126614400/126614340/6d2ab586.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Large cozy private room

[](https://www.expedia.com/Newport-News-Hotels-Large-Cozy-Private-Room.h126614340.Hotel-Information)

Marshall

$138 nightly

$160 total

Mar 24 - Mar 25

Total with taxes and fees

[](https://www.expedia.com/Newport-News-Hotels-Large-Cozy-Private-Room.h126614340.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117510000/117501200/117501164/a616c353.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117510000/117501200/117501164/3562ee2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/118000000/117510000/117501200/117501164/69a96aaa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/118000000/117510000/117501200/117501164/b172392b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 2 king beds -2nd floor walk 2 beach apt2

[](https://www.expedia.com/Norfolk-Hotels-2-King-Beds-2nd-Floor-Walk-2-Beach-Apt2.h117501164.Hotel-Information)

East Ocean View

10/10

Exceptional

(2 reviews)

"I can’t say enough how perfect this place was for us! Clean, beautifully decorated, short walking distance from the beach. I would definitely stay again and again! :)"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Shelby R.

$251 nightly

$292 total

Mar 24 - Mar 25

Total with taxes and fees

[](https://www.expedia.com/Norfolk-Hotels-2-King-Beds-2nd-Floor-Walk-2-Beach-Apt2.h117501164.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/104000000/103020000/103019400/103019316/9fd3db04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Game room](https://images.trvl-media.com/lodging/104000000/103020000/103019400/103019316/w2094h1573x3y0-08463f2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/104000000/103020000/103019400/103019316/acc6be0f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/104000000/103020000/103019400/103019316/0594eb88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Roomy Beachfront Apartment! Game room, big deck, 2 bed/2 bath!

[](https://www.expedia.com/Norfolk-Hotels-Roomy-Beachfront-Apartment-Game-Room.h103019316.Hotel-Information)

Cottage Line

9.0/10

Wonderful

(26 reviews)

"Super clean and absolutely amazing location. Would definitely go back with friends."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Joseph A.

$196 nightly

$228 total

Mar 25 - Mar 26

Total with taxes and fees

[](https://www.expedia.com/Norfolk-Hotels-Roomy-Beachfront-Apartment-Game-Room.h103019316.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/110000000/109590000/109587300/109587259/w1017h683x4y0-a1249302.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/110000000/109590000/109587300/109587259/w1018h683x3y0-76532017.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, WiFi](https://images.trvl-media.com/lodging/110000000/109590000/109587300/109587259/w1018h683x3y0-7149d515.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/110000000/109590000/109587300/109587259/w1016h683x4y0-1d4972e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Private 1 Bed Apt - Historic Olde Towne Portsmouth

[](https://www.expedia.com/Portsmouth-Hotels-Private-1-Bed-Apt-Historic-Olde-Towne-Portsmouth.h109587259.Hotel-Information)

Portsmouth

10/10

Exceptional

(2 reviews)

"Great place. Nice area. Parking was confusing at first but host was very responsive "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Ed and Laura S.

$159 nightly

$186 total

Mar 24 - Mar 25

Total with taxes and fees

[](https://www.expedia.com/Portsmouth-Hotels-Private-1-Bed-Apt-Historic-Olde-Towne-Portsmouth.h109587259.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)

![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/93000000/92790000/92786500/92786454/030d9f20.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/93000000/92790000/92786500/92786454/0287a355.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### #Buckroe Bungalow \~Escape to the Beach 2mins Away!

[](https://www.expedia.com/Hampton-Hotels-Buckroe-Bungalow-Escape-To-The-Beach-2mins-Away.h92786454.Hotel-Information)

Hampton

9.2/10

Wonderful

(19 reviews)

"Enjoyed our staycation .Will be back."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Josie B.

$329 nightly

$355 total

Mar 24 - Mar 25

Total with taxes and fees

[](https://www.expedia.com/Hampton-Hotels-Buckroe-Bungalow-Escape-To-The-Beach-2mins-Away.h92786454.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/118000000/117980000/117979000/117978953/1bf86fd4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/118000000/117980000/117979000/117978953/93ace1f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/118000000/117980000/117979000/117978953/972d662a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/118000000/117980000/117979000/117978953/1195bd52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Beachfront Bungalow w/ BEST Location in Ocean View!

[](https://www.expedia.com/Norfolk-Hotels-Beachfront-Bungalow-W-BEST-Location-In-Ocean-View.h117978953.Hotel-Information)

Willoughby Spit

8.8/10

Excellent

(8 reviews)

"Great view and close to "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Julian M.

$247 nightly

$287 total

Apr 2 - Apr 3

Total with taxes and fees

[](https://www.expedia.com/Norfolk-Hotels-Beachfront-Bungalow-W-BEST-Location-In-Ocean-View.h117978953.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&regionId=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&regionId=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&regionId=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&regionId=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&regionId=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&regionId=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)

Cabins

[](https://www.expedia.com/Hotel-Search?destination=Chesapeake%2C+Virginia%2C+United+States+of+America&regionId=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)

Villas

[](https://www.expedia.com/Hotel-Search?destination=Chesapeake%2C+Virginia%2C+United+States+of+America&regionId=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)

Houseboats

[](https://www.expedia.com/Hotel-Search?destination=Chesapeake%2C+Virginia%2C+United+States+of+America&regionId=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)

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## Top Chesapeake Hotel Reviews

![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

8/10 Good

"Room was clean and comfortable Was booked into a handicap accessible room (not requested) which had no chair or sofa in the room. Was informed that was standard which I found to be unusual. Staff was friendly most especially the valet who made great restaurant recommendations. Thanks "

[](https://expedia.com/Virginia-Beach-Hotels-Holiday-Inn-Oceanside-VA-Beach.h4857.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

8/10 Good

"Hotel was clean. The outside is very dated and the windows on the front were dirty. The staff was very nice. Really no amenities to talk about. No breakfast and the coffee station was pretty basic. I would stay again. "

[](https://expedia.com/Virginia-Beach-Hotels-Surfbreak-Oceanfront-Hotel.h12727.Hotel-Information)

![Schooner Inn](https://images.trvl-media.com/lodging/2000000/1720000/1711400/1711317/7a589703_y.jpg)

### Schooner Inn

10/10 Excellent

"Wonderful hotel! Room was clean and the staff were all very friendly. Checking in was easy and we loved the location. "

[](https://expedia.com/Virginia-Beach-Hotels-Schooner-Inn.h1711317.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

"It was very nice stay"

[](https://expedia.com/Virginia-Beach-Hotels-Country-Inn-Suites-By-Radisson.h5363.Hotel-Information)

![Wingate by Wyndham Chesapeake](https://images.trvl-media.com/lodging/2000000/1520000/1513300/1513238/0d94729b_y.jpg)

### Wingate by Wyndham Chesapeake

10/10 Excellent

"Good place to stay"

[](https://expedia.com/Chesapeake-Hotels-Wingate-By-Wyndham-Chesapeake.h1513238.Hotel-Information)

![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)

![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)

## 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 $103 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

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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?

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### What’s there to see and do in Chesapeake?

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### Expedia's Latest Trends

Hotels

- [Wytheville Hotels](https://expedia.com/Wytheville-Hotels.d6056934.Travel-Guide-Hotels)
- [Fairfax Hotels](https://expedia.com/Fairfax-Hotels.d8062.Travel-Guide-Hotels)
- [Blacksburg Hotels](https://expedia.com/Blacksburg-Hotels.d6056941.Travel-Guide-Hotels)
- [Harrisonburg Hotels](https://expedia.com/Harrisonburg-Hotels.d6056902.Travel-Guide-Hotels)
- [Virginia Beach Cheap Hotels](https://expedia.com/Virginia-Beach-Hotels-Cheap-Hotels.0-0-d10271-tCheapHotels.Travel-Guide-Filter-Hotels)
- [Alexandria Hotels](https://expedia.com/Alexandria-Hotels.d5980.Travel-Guide-Hotels)
- [Charlottesville Hotels](https://expedia.com/Charlottesville-Hotels.d6057012.Travel-Guide-Hotels)
- [Norfolk Hotels](https://expedia.com/Norfolk-Hotels.d2689.Travel-Guide-Hotels)
- [Winchester Hotels](https://expedia.com/Winchester-Hotels.d6056879.Travel-Guide-Hotels)
- [Fredericksburg Hotels](https://expedia.com/Fredericksburg-Hotels.d8145.Travel-Guide-Hotels)
- [Chincoteague Hotels](https://expedia.com/Chincoteague-Hotels.d55637.Travel-Guide-Hotels)
- [Danville Hotels](https://expedia.com/Danville-Hotels.d6056951.Travel-Guide-Hotels)
- [Lynchburg Hotels](https://expedia.com/Lynchburg-Hotels.d2187.Travel-Guide-Hotels)
- [Newport News Hotels](https://expedia.com/Newport-News-Hotels.d6056964.Travel-Guide-Hotels)
- [Virginia Beach Hotels](https://expedia.com/Virginia-Beach-Hotels.d10271.Travel-Guide-Hotels)
- [Roanoke Hotels](https://expedia.com/Roanoke-Hotels.d3020.Travel-Guide-Hotels)
- [Virginia Beach Oceanfront Hotels](https://expedia.com/Virginia-Beach-Hotels-Oceanfront-Hotels.0-0-d10271-tOceanfrontHotels.Travel-Guide-Filter-Hotels)
- [Hampton Hotels](https://expedia.com/Hampton-Hotels.d6067.Travel-Guide-Hotels)
- [Williamsburg Hotels](https://expedia.com/Williamsburg-Hotels.d6296.Travel-Guide-Hotels)
- [Virginia Beach Pet-friendly Hotels](https://expedia.com/Virginia-Beach-Hotels-Pet-Friendly-Hotel.0-0-d10271-tPetfriendlyHotel.Travel-Guide-Filter-Hotels)

Flights

- [Flights to Syria](https://expedia.com/Cheap-Flights-To-Syria.d184113.Travel-Guide-Flights)
- [Flights to Roanoke](https://expedia.com/Cheap-Flights-To-Roanoke.d3020.Travel-Guide-Flights)
- [Flights to Virginia Beach](https://expedia.com/Cheap-Flights-To-Virginia-Beach.d10271.Travel-Guide-Flights)
- [Flights to Charlottesville](https://expedia.com/Cheap-Flights-To-Charlottesville.d6057012.Travel-Guide-Flights)

Cars

- [Car rentals in Newport News](https://expedia.com/Car-Rentals-In-Newport-News.d6056964.Car-Rental-Guide)
- [Car rentals in Virginia Beach](https://expedia.com/Car-Rentals-In-Virginia-Beach.d10271.Car-Rental-Guide)
- [Car rentals in Alexandria](https://expedia.com/Car-Rentals-In-Alexandria.d5980.Car-Rental-Guide)

Activities

- [Things to do in Norfolk](https://expedia.com/Things-To-Do-In-Norfolk.d2689.Travel-Guide-Activities)

Packages

- [Virginia Beach Vacation Packages](https://expedia.com/Virginia-Beach.d10271.Destination-Travel-Guides)

Vacation Rentals

- [Vacation Rentals Virginia Beach](https://expedia.com/Virginia-Beach-Vacation-Rentals.d10271.Travel-Guide-VacationRentals)

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