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)

![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)

![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.

$246 nightly

$285 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)

![Outdoor dining](https://images.trvl-media.com/lodging/88000000/87920000/87917000/87916951/b70c0249.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)

![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)

![Dining](https://images.trvl-media.com/lodging/116000000/115340000/115333200/115333185/3e0a9e18.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

$213 nightly

$245 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)

![Dining](https://images.trvl-media.com/lodging/88000000/87430000/87427500/87427432/188bbad5.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)

### 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)

![Dining](https://images.trvl-media.com/lodging/89000000/88180000/88179800/88179795/6113856d.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)

![Lobby](https://images.trvl-media.com/lodging/89000000/88180000/88179800/88179795/fe49a58a.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)

![Interior](https://images.trvl-media.com/lodging/85000000/84550000/84543900/84543812/a32364b6.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)

![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.

$169 nightly

$194 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)

![Outdoor dining](https://images.trvl-media.com/lodging/116000000/115340000/115333200/115333190/3545ac87.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)

![Interior](https://images.trvl-media.com/lodging/116000000/115340000/115333200/115333190/95e0c52b.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

$195 nightly

$224 total

Apr 5 - Apr 6

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)

![Dining](https://images.trvl-media.com/lodging/50000000/49150000/49149800/49149734/5da4f642.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)

![Lobby](https://images.trvl-media.com/lodging/50000000/49150000/49149800/49149734/d5fe0f16.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.

$180 nightly

$207 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)

![Lobby](https://images.trvl-media.com/lodging/107000000/106270000/106262300/106262204/65cc89ab.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)

### 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.

$213 nightly

$245 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)

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

![Private kitchen](https://images.trvl-media.com/lodging/107000000/106240000/106236500/106236428/d07de257.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.

$342 nightly

$400 total

Mar 25 - Mar 26

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)

![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)

![Exterior](https://images.trvl-media.com/lodging/110000000/109380000/109375900/109375809/w3000h1840x0y0-254a1ec4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment | 2 bedrooms](https://images.trvl-media.com/lodging/110000000/109380000/109375900/109375809/w3000h2760x0y0-65125647.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Speakeasy Downtown Newport News

[](https://www.expedia.com/Newport-News-Hotels-The-Speakeasy-Downtown-Newport-News.h109375809.Hotel-Information)

Downtown Newport News

$201 nightly

$232 total

Mar 25 - Mar 26

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/85000000/84050000/84048300/84048231/825456ec.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.

$254 nightly

$295 total

Mar 31 - Apr 1

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)

![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)

![Property grounds](https://images.trvl-media.com/lodging/93000000/92370000/92360800/92360757/0255f575.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)

### 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.

$206 nightly

$239 total

Apr 13 - Apr 14

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)

![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)

![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)

![Dining](https://images.trvl-media.com/lodging/96000000/95740000/95731500/95731452/40b792ca.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 25 - Mar 26

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)

![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)

![Miscellaneous](https://images.trvl-media.com/lodging/127000000/126620000/126614400/126614340/b81c1e4f.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)

### Large cozy private room

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

Marshall

$138 nightly

$160 total

Mar 25 - Mar 26

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)

![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)

![Interior](https://images.trvl-media.com/lodging/118000000/117510000/117501200/117501164/69a96aaa.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)

### 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.

$260 nightly

$302 total

Mar 25 - Mar 26

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)

![Interior](https://images.trvl-media.com/lodging/104000000/103020000/103019400/103019316/acc6be0f.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)

![Private kitchen](https://images.trvl-media.com/lodging/104000000/103020000/103019400/103019316/249cb266.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)

![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)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/110000000/109590000/109587300/109587259/w1018h683x3y0-2de6848c.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)

### 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 25 - Mar 26

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)

![Smart TV](https://images.trvl-media.com/lodging/93000000/92790000/92786500/92786454/62198dab.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 25 - Mar 26

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)

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

![Living area](https://images.trvl-media.com/lodging/118000000/117980000/117979000/117978953/977346b8.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)

### 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=2026-04-07&endDate=2026-04-08&regionId=6612&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

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)

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)

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

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

### Schooner Inn

10/10 Excellent

"Well kept, responsive staff, great location and food options nearby."

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

8/10 Good

"The breakfast was great and extremely friendly staff. "

[](https://expedia.com/Virginia-Beach-Hotels-Coastal-Hotel-And-Suites-Virginia-Beach-Oceanfront.h9977.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

"Perfect overall. "

[](https://expedia.com/Virginia-Beach-Hotels-Oceanaire-By-Diamond-Resorts.h5190701.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

"We were there for a run weekend and it was very busy. Our room was very clean and the beds were comfy. Natalie at the front desk was very welcoming and lovely. This is not a fancy property but the rooms were clean, the balconies over look the ocean and we were only a mile from the start."

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

"Gym was ok "

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

![Comfort Suites Chesapeake - Norfolk](https://images.trvl-media.com/lodging/1000000/10000/6600/6570/038be8fc_y.jpg)

### Comfort Suites Chesapeake - Norfolk

8/10 Good

"The lobby was beautifully updated BUT the elevator was not working which make carrying lounge difficult "

[](https://expedia.com/Chesapeake-Hotels-Comfort-Suites-Chesapeake-Norfolk.h6570.Hotel-Information)

![Moxy Virginia Beach Oceanfront](https://images.trvl-media.com/lodging/5000000/4670000/4665200/4665123/8673ad8e_y.jpg)

### Moxy Virginia Beach Oceanfront

10/10 Excellent

"Tge pool was gross and not functional. Beach view was amazing. Balcony room was perfect! The adult slide in the lobby was a hit for my kids. "

[](https://expedia.com/Norfolk-Virginia-Beach-Hotels-Baymont-By-Wyndham-Virginia-Beach-Oceanfront.h4665123.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

"Rooms were clean, beds were ok, bathroom shower took FOREVER to walm up. Door of bathroom is a sliding door which wasn’t great, the door kept coming off the rail. Breakfast also just ok, not well stocked through the morning, pretty boring and tasteless sadly. Old hotel I think they are trying to upkeep but renovations. Parking garage is an absolute nightmare to navigate. We will not stay here again."

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

![Hilton Virginia Beach Oceanfront](https://images.trvl-media.com/lodging/2000000/1160000/1156000/1155964/3b10b192_y.jpg)

### Hilton Virginia Beach Oceanfront

10/10 Excellent

"Overall, it was a great experience. Can’t beat a nice hotel directly on the beach. We had a minor blip, one of the hand towels had fresh mascara on it. The front desk staff quickly got us new ones plus additional towels. Rest of the room was spotless and the view from the 19th floor was absolutely breathtaking! We were able to check into our room two hours early and the front desk staff helped us roll into another nights stay while keeping the same room! Huge thank you to her. We appreciated it! This is a big weekend for Virginia Beach with the Shamrock Half and full marathons. I’m sure staff were working quickly to accommodate everyone. Valet - so easy and professional! The pool was nice! The rooftop bar, outside pool and hot tub were closed (out of season). Indoor one was nice, warm and relaxing! The restaurant attached to the hotel is also very nice. Staff were friendly in both places. We did learn a lesson. If you book another night, do so directly with the hotel front desk staff. We were told to do it online but the online rooms from the hotel website redirects you to a 3rd party w/o telling you then charges additional hidden fees, again without telling you - $140 worth. We got our money back at the hotel rate. It looks like you are booking through the Hilton website when in fact, you are not. They apparently do this to try to quickly sell off unbooked rooms. Race weekend prices are highly inflated $750 vs $180\. Book early. We are looking forward to another visit! "

[](https://expedia.com/Virginia-Beach-Hotels-Hilton-Virginia-Beach-Oceanfront.h1155964.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

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- [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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