Title: Holiday Rentals Chesapeake Beach from £285: Find Short-Term Rentals & Holiday Accommodations | Expedia.co.uk

[Chesapeake Beach Travel Guide](https://expedia.co.uk/Chesapeake-Beach.dx88967)[Hotels in Chesapeake Beach](https://expedia.co.uk/Chesapeake-Beach-Hotels.d88967.Travel-Guide-Hotels)[Flights to Chesapeake Beach](https://expedia.co.uk/Cheap-Flights-To-Chesapeake-Beach.d88967.Travel-Guide-Flights)[Chesapeake Beach Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Chesapeake-Beach.d88967.Car-Hire-Guide)[Chesapeake Beach Holidays](https://expedia.co.uk/Chesapeake-Beach.d88967.Holidays-City-Breaks)

![Boardwalk along the Chesapeake Bay.](https://images.trvl-media.com/place/88967/e2079c3a-0245-4a90-abab-4255f259a6e7.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

Photo by Ronanne Vinson

# Search Holiday Rentals in Chesapeake Beach

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## Check prices for these dates

In two weeks

[9 Jan - 11 Jan](https://www.expedia.co.uk/Hotel-Search?regionId=88967&startDate=2026-01-09&endDate=2026-01-11&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[20 Feb - 22 Feb](https://www.expedia.co.uk/Hotel-Search?regionId=88967&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 three months

[20 Mar - 22 Mar](https://www.expedia.co.uk/Hotel-Search?regionId=88967&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)

In four months

[17 Apr - 19 Apr](https://www.expedia.co.uk/Hotel-Search?regionId=88967&startDate=2026-04-17&endDate=2026-04-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Chesapeake Beach holiday rentals

![Pool](https://images.trvl-media.com/lodging/97000000/96350000/96341600/96341595/w952h953x0y0-b52c439e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/97000000/96350000/96341600/96341595/081bdf14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/97000000/96350000/96341600/96341595/ae401628.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/97000000/96350000/96341600/96341595/c5240202.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Holiday Home in Chesapeake Beach

[](https://www.expedia.co.uk/Chesapeake-Beach-Hotels-Beach-Front-Chesapeake-Views-Family-Getaway.h96341595.Hotel-Information)

9.0/10

Wonderful

(6)

"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."

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

Bryan P.

£329

includes taxes & fees

20 Jan - 21 Jan 2026

[](https://www.expedia.co.uk/Chesapeake-Beach-Hotels-Beach-Front-Chesapeake-Views-Family-Getaway.h96341595.Hotel-Information)

![Beach nearby](https://images.trvl-media.com/lodging/70000000/69550000/69541400/69541327/3f3bd4d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/70000000/69550000/69541400/69541327/07d26e78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, iron/ironing board, travel cot](https://images.trvl-media.com/lodging/70000000/69550000/69541400/69541327/0e96ebfa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/70000000/69550000/69541400/69541327/bf60932b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Holiday Home in North Beach

[](https://www.expedia.co.uk/North-Beach-Hotels-Plant-Filled-Oasis-Near-Beach-Town-With-Passes-Tips.h69541327.Hotel-Information)

10/10

Exceptional

(17)

"We loved our stay! The property was just as advertised and had everything we needed. Quiet area and felt very safe. The owners provided excellent communication as well!"

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

Jennifer B.

£249

includes taxes & fees

12 Jan - 13 Jan 2026

[](https://www.expedia.co.uk/North-Beach-Hotels-Plant-Filled-Oasis-Near-Beach-Town-With-Passes-Tips.h69541327.Hotel-Information)

![Outdoor pool](https://images.trvl-media.com/lodging/72000000/71120000/71116900/71116837/aabd7b99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/72000000/71120000/71116900/71116837/a336c972.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, offices](https://images.trvl-media.com/lodging/72000000/71120000/71116900/71116837/117e79aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, offices](https://images.trvl-media.com/lodging/72000000/71120000/71116900/71116837/10bef897.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Owings

[](https://www.expedia.co.uk/Close-To-North-Chesapeake-Beach.h71116837.Hotel-Information)

10/10

Exceptional

(48)

"We love this place!"

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

Joan K.

£223

includes taxes & fees

28 Dec - 29 Dec

[](https://www.expedia.co.uk/Close-To-North-Chesapeake-Beach.h71116837.Hotel-Information)

![Marina](https://images.trvl-media.com/lodging/85000000/84070000/84063700/84063656/c77382da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/85000000/84070000/84063700/84063656/b482bb5d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/85000000/84070000/84063700/84063656/99582f9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/85000000/84070000/84063700/84063656/80cf0fdf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Holiday Home in Stevensville

[](https://www.expedia.co.uk/Stevensville-Hotels-Relax-On-Kent-Island-In-3-Bedroom-Home-WWaterview.h84063656.Hotel-Information)

9.8/10

Exceptional

(42)

"We had a great stay! The property has everything we needed and host was easy to communicate with "

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

Stephanie S.

£211

includes taxes & fees

5 Jan - 6 Jan 2026

[](https://www.expedia.co.uk/Stevensville-Hotels-Relax-On-Kent-Island-In-3-Bedroom-Home-WWaterview.h84063656.Hotel-Information)

![Beach nearby, sun-loungers, beach towels](https://images.trvl-media.com/lodging/84000000/83970000/83966500/83966408/aaa820d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, desk, iron/ironing board, travel cot](https://images.trvl-media.com/lodging/84000000/83970000/83966500/83966408/67700a38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83970000/83966500/83966408/520df554.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/84000000/83970000/83966500/83966408/d4e67bdb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Holiday Home in North Beach

[](https://www.expedia.co.uk/North-Beach-Hotels-Huge-Beach-Bungalow-WYard.h83966408.Hotel-Information)

10/10

Exceptional

(31)

"Perfect place to spend quality time with our three adult children and their significant others. "

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

Malarkey F.

£311

includes taxes & fees

4 Jan - 5 Jan 2026

[](https://www.expedia.co.uk/North-Beach-Hotels-Huge-Beach-Bungalow-WYard.h83966408.Hotel-Information)

![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/115000000/114310000/114310000/114309947/w1179h1552x0y10-4ae4c675.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/115000000/114310000/114310000/114309947/6b784e97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/115000000/114310000/114310000/114309947/a52717e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/115000000/114310000/114310000/114309947/d32606e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in North Beach

[](https://www.expedia.co.uk/North-Beach-Hotels-Charming-2-Bedroom-1-Bath-Cottage-With-AC.h114309947.Hotel-Information)

9.6/10

Exceptional

(4)

"Great place in a wonderful area! So cozy & well situated! A perfect weekend getaway!"

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

Jana S.

£211

includes taxes & fees

1 Jan - 2 Jan 2026

[](https://www.expedia.co.uk/North-Beach-Hotels-Charming-2-Bedroom-1-Bath-Cottage-With-AC.h114309947.Hotel-Information)

![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/110000000/109450000/109441700/109441651/3d607d41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/110000000/109450000/109441700/109441651/798bc57a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/110000000/109450000/109441700/109441651/b413d45b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/110000000/109450000/109441700/109441651/c8581751.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Port Republic

[](https://www.expedia.co.uk/Cozy-Centrally-Located-Studio-With-WiFi-And-AC-In-Delightful-Port-Republic.h109441651.Hotel-Information)

9.4/10

Exceptional

(6)

"Very friendly and convenient!"

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

Robin B.

£132

includes taxes & fees

5 Jan - 6 Jan 2026

[](https://www.expedia.co.uk/Cozy-Centrally-Located-Studio-With-WiFi-And-AC-In-Delightful-Port-Republic.h109441651.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/97000000/96120000/96117900/96117871/e7ff4058.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/97000000/96120000/96117900/96117871/5ae97cc8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/97000000/96120000/96117900/96117871/49fd9b22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, ping pong](https://images.trvl-media.com/lodging/97000000/96120000/96117900/96117871/4d65add6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Holiday Home in Cambridge

[](https://www.expedia.co.uk/Cambridge-Hotels-Beautiful-Waterfront-Retreat-In-Cambridge.h96117871.Hotel-Information)

10/10

Exceptional

(50)

"Beautiful place! Loved all the activities, will return in the future! Our family and friends had a blast! Thank you so much!!"

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

Karen L.

£285

includes taxes & fees

4 Jan - 5 Jan 2026

[](https://www.expedia.co.uk/Cambridge-Hotels-Beautiful-Waterfront-Retreat-In-Cambridge.h96117871.Hotel-Information)

![On the beach](https://images.trvl-media.com/lodging/97000000/96640000/96637800/96637704/b3cbb2b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Miscellaneous](https://images.trvl-media.com/lodging/97000000/96640000/96637800/96637704/35851591.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/97000000/96640000/96637800/96637704/89e18a15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/97000000/96640000/96637800/96637704/d31a8fd6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Benedict

[](https://www.expedia.co.uk/Benedict-Hotels-Peaceful-Suite-On-The-Water-Osprey-Sunrise-Over-The-River-From-Your-Porch.h96637704.Hotel-Information)

9.0/10

Wonderful

(8)

"The owner was very nice "

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

karen

£228

includes taxes & fees

23 Dec - 24 Dec

[](https://www.expedia.co.uk/Benedict-Hotels-Peaceful-Suite-On-The-Water-Osprey-Sunrise-Over-The-River-From-Your-Porch.h96637704.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/124000000/124000000/123993900/123993858/9c5012e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/124000000/124000000/123993900/123993858/b2896f67.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/124000000/124000000/123993900/123993858/e356022f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/124000000/124000000/123993900/123993858/26713e5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Waldorf

[](https://www.expedia.co.uk/Waldorf-Hotels-Commute-To-Alexandria-DC-Home-W-Shared-Yard.h123993858.Hotel-Information)

£391

includes taxes & fees

23 Dec - 24 Dec

[](https://www.expedia.co.uk/Waldorf-Hotels-Commute-To-Alexandria-DC-Home-W-Shared-Yard.h123993858.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/124000000/123990000/123980400/123980361/20652ce7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Desk, Internet, bed sheets](https://images.trvl-media.com/lodging/124000000/123990000/123980400/123980361/e9085c2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/124000000/123990000/123980400/123980361/2f6e181b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/124000000/123990000/123980400/123980361/b2c4ecf8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Waldorf

[](https://www.expedia.co.uk/Waldorf-Hotels-Commuter-Friendly-Studio-Near-DC-Alexandria.h123980361.Hotel-Information)

£347

includes taxes & fees

23 Dec - 24 Dec

[](https://www.expedia.co.uk/Waldorf-Hotels-Commuter-Friendly-Studio-Near-DC-Alexandria.h123980361.Hotel-Information)

![Sun-loungers](https://images.trvl-media.com/lodging/38000000/37270000/37269100/37269068/b6a8273a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/38000000/37270000/37269100/37269068/573d8c0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/38000000/37270000/37269100/37269068/42c55f30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/38000000/37270000/37269100/37269068/46d28537.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Prince Frederick

[](https://www.expedia.co.uk/Prince-Frederick-Hotels-Cottage-Located-On-The-Patuxent-River.h37269068.Hotel-Information)

10/10

Exceptional

(42)

"This place was very lovely. Beautiful atmosphere and very spacious cottage. Didn’t get to see the owners but really enjoyed their property. Loved having the coffee maker, comfy bed and awesome tub! I will definitely be back. "

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

RACHEL S.

£242

includes taxes & fees

23 Dec - 24 Dec

[](https://www.expedia.co.uk/Prince-Frederick-Hotels-Cottage-Located-On-The-Patuxent-River.h37269068.Hotel-Information)

![3 bedrooms, iron/ironing board, travel cot, free WiFi](https://images.trvl-media.com/lodging/114000000/113530000/113522300/113522263/9a42128d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach nearby](https://images.trvl-media.com/lodging/114000000/113530000/113522300/113522263/4429fbeb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/114000000/113530000/113522300/113522263/a1c3089f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/114000000/113530000/113522300/113522263/287cc71d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Holiday Home in Prince Frederick

[](https://www.expedia.co.uk/Prince-Frederick-Hotels-Kick-Back-And-Enjoy-The-Chesapeake-This-3-Bedroom.h113522263.Hotel-Information)

9.6/10

Exceptional

(5)

"We had a short stay after a sporting event in DC, it was a little less than an hour away. Convenient location and a very clean house. Kitchen was well stocked. There was little communication with the owner, which was nice vs a long list of rules, but we would have liked to know any of their local specific favorite spots or more detailed check in/check out. Worked out nicely for our family. "

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

Carrie K.

£300

includes taxes & fees

5 Jan - 6 Jan 2026

[](https://www.expedia.co.uk/Prince-Frederick-Hotels-Kick-Back-And-Enjoy-The-Chesapeake-This-3-Bedroom.h113522263.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/97000000/96310000/96305200/96305191/be87237c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/97000000/96310000/96305200/96305191/1f3bb03b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/97000000/96310000/96305200/96305191/4b2ae259.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, iron/ironing board, travel cot, WiFi](https://images.trvl-media.com/lodging/97000000/96310000/96305200/96305191/12965aa6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Holiday Home in Edgewater

[](https://www.expedia.co.uk/Edgewater-Hotels-EdgewaterMayo-Getaway.h96305191.Hotel-Information)

9.8/10

Exceptional

(25)

"Very clean, had everything we needed for our stay!"

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

Jackie R.

[](https://www.expedia.co.uk/Edgewater-Hotels-EdgewaterMayo-Getaway.h96305191.Hotel-Information)

![Beach](https://images.trvl-media.com/lodging/104000000/103640000/103638100/103638094/624fee99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/104000000/103640000/103638100/103638094/598c5e4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/104000000/103640000/103638100/103638094/9a1b795e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/104000000/103640000/103638100/103638094/fcc30818.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Holiday Home in Prince Frederick

[](https://www.expedia.co.uk/Prince-Frederick-Hotels-2-Blocks-From-Dares-Beach-On-The-Chesapeake-Bay-Beach-And-Boat-Access.h103638094.Hotel-Information)

10/10

Exceptional

(8)

"Everything was amazing. "

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

Lorie S.

£298

includes taxes & fees

14 Jan - 15 Jan 2026

[](https://www.expedia.co.uk/Prince-Frederick-Hotels-2-Blocks-From-Dares-Beach-On-The-Chesapeake-Bay-Beach-And-Boat-Access.h103638094.Hotel-Information)

![Smart TV](https://images.trvl-media.com/lodging/84000000/83070000/83066200/83066154/3f6b4c84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83070000/83066200/83066154/0b964f44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/84000000/83070000/83066200/83066154/c86d900d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, travel cot, free WiFi, bed sheets](https://images.trvl-media.com/lodging/84000000/83070000/83066200/83066154/d811e5a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Holiday Home in Cambridge

[](https://www.expedia.co.uk/Cambridge-Hotels-WATERFRONT-3-Bed-Oasis-On-2-Acres-Sleeps-8.h83066154.Hotel-Information)

10/10

Exceptional

(14)

"Second time staying at this lovely, serene home/property. It’s the perfect getaway if you’re looking to escape into some peace! Highly recommend "

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

Jill C.

£406

includes taxes & fees

2 Jan - 3 Jan 2026

[](https://www.expedia.co.uk/Cambridge-Hotels-WATERFRONT-3-Bed-Oasis-On-2-Acres-Sleeps-8.h83066154.Hotel-Information)

![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/100000000/99480000/99470800/99470706/f08880e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/100000000/99480000/99470800/99470706/f8485bcb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/100000000/99480000/99470800/99470706/w2047h1365x0y0-070a1442.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/100000000/99480000/99470800/99470706/c9912697.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Holiday Home in Hillsmere

[](https://www.expedia.co.uk/Annapolis-Hotels-Annapolis-Retreat-7-Mins-From-Downtown-Annapolis.h99470706.Hotel-Information)

10/10

Exceptional

(4)

"Great house in cute neighborhood. Thanks for a very comfortable stay!"

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

Paul C.

£404

includes taxes & fees

12 Jan - 13 Jan 2026

[](https://www.expedia.co.uk/Annapolis-Hotels-Annapolis-Retreat-7-Mins-From-Downtown-Annapolis.h99470706.Hotel-Information)

![TV, offices](https://images.trvl-media.com/lodging/106000000/105550000/105549100/105549011/b24c0f35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/106000000/105550000/105549100/105549011/f3fa7d0e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/106000000/105550000/105549100/105549011/756b8e7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/106000000/105550000/105549100/105549011/b705d36c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Holiday Home in Annapolis

[](https://www.expedia.co.uk/Annapolis-Hotels-Wrights-Cottage-Pets-Welcome-EV-Charging.h105549011.Hotel-Information)

9.2/10

Wonderful

(16)

"Nice little spot, very quiet "

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

Susan S.

£291

includes taxes & fees

4 Jan - 5 Jan 2026

[](https://www.expedia.co.uk/Annapolis-Hotels-Wrights-Cottage-Pets-Welcome-EV-Charging.h105549011.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/117000000/116010000/116005700/116005601/5eca3b46_edited_e784.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/117000000/116010000/116005700/116005601/0100abcb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/117000000/116010000/116005700/116005601/10e31f36_edited_f301.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/117000000/116010000/116005700/116005601/681a375c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Holiday Home in Shady Side

[](https://www.expedia.co.uk/Shady-Side-Hotels-Peaceful-2-Bedroom-2-Bathroom-House-With-WiFi-And-AC-In-Serene-Shady-Side.h116005601.Hotel-Information)

10/10

Exceptional

(4)

"Would stay here again "

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

Thomas D.

£357

includes taxes & fees

4 Jan - 5 Jan 2026

[](https://www.expedia.co.uk/Shady-Side-Hotels-Peaceful-2-Bedroom-2-Bathroom-House-With-WiFi-And-AC-In-Serene-Shady-Side.h116005601.Hotel-Information)

![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/121000000/120840000/120836100/120836005/8d105af0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/121000000/120840000/120836100/120836005/ed18b7e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/121000000/120840000/120836100/120836005/2f8e6449.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/121000000/120840000/120836100/120836005/3e37b615.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Lusby

[](https://www.expedia.co.uk/Lusby-Hotels-Hot-Tub-Beach-Access-Lakefront-Getaway-In-Lusby.h120836005.Hotel-Information)

£676

includes taxes & fees

30 Dec - 31 Dec

[](https://www.expedia.co.uk/Lusby-Hotels-Hot-Tub-Beach-Access-Lakefront-Getaway-In-Lusby.h120836005.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.co.uk/Hotel-Search?startDate=2026-01-05&endDate=2026-01-06&regionId=88967&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find holiday rentals that suit your style

Cottages

[](https://www.expedia.co.uk/Hotel-Search?destination=Chesapeake+Beach%2C+Maryland%2C+United+States+of+America&regionId=88967&latLong=38.694%2C-76.53376&adults=2&startDate=2026-03-22&d1=2026-03-22&endDate=2026-03-25&d2=2026-03-25&lodging=COTTAGE)

Private holiday homes

[](https://www.expedia.co.uk/Hotel-Search?destination=Chesapeake+Beach%2C+Maryland%2C+United+States+of+America&regionId=88967&latLong=38.694%2C-76.53376&adults=2&startDate=2026-03-22&d1=2026-03-22&endDate=2026-03-25&d2=2026-03-25&lodging=VACATION_HOME)

Apartments

[](https://www.expedia.co.uk/Hotel-Search?destination=Chesapeake+Beach%2C+Maryland%2C+United+States+of+America&regionId=88967&latLong=38.694%2C-76.53376&adults=2&startDate=2026-03-22&d1=2026-03-22&endDate=2026-03-25&d2=2026-03-25&lodging=APARTMENT)

Condos

[](https://www.expedia.co.uk/Hotel-Search?destination=Chesapeake+Beach%2C+Maryland%2C+United+States+of+America&regionId=88967&latLong=38.694%2C-76.53376&adults=2&startDate=2026-03-22&d1=2026-03-22&endDate=2026-03-25&d2=2026-03-25&lodging=CONDO)

Houseboats

[](https://www.expedia.co.uk/Hotel-Search?destination=Chesapeake+Beach%2C+Maryland%2C+United+States+of+America&regionId=88967&latLong=38.694%2C-76.53376&adults=2&startDate=2026-03-22&d1=2026-03-22&endDate=2026-03-25&d2=2026-03-25&lodging=HOUSE_BOAT)

Villas

[](https://www.expedia.co.uk/Hotel-Search?destination=Chesapeake+Beach%2C+Maryland%2C+United+States+of+America&regionId=88967&latLong=38.694%2C-76.53376&adults=2&startDate=2026-03-22&d1=2026-03-22&endDate=2026-03-25&d2=2026-03-25&lodging=VILLA)

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## Top Chesapeake Beach Hotel Reviews

![Holiday Inn Express Waldorf by IHG](https://images.trvl-media.com/lodging/1000000/30000/25500/25493/9a1d7d08_y.jpg)

### Holiday Inn Express Waldorf by IHG

10/10 Excellent

"The breakfast was very good. Rooms were very clean "

[](https://expedia.co.uk/Waldorf-Hotels-Holiday-Inn-Express-Waldorf.h25493.Hotel-Information)

![SpringHill Suites by Marriott Annapolis](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364028/80b99d82_y.jpg)

### SpringHill Suites by Marriott Annapolis

10/10 Excellent

"Good breakfast and easy parking. "

[](https://expedia.co.uk/Annapolis-Hotels-SpringHill-Suites-By-Marriott-Annapolis.h1364028.Hotel-Information)

![Residence Inn by Marriott Waldorf](https://images.trvl-media.com/lodging/3000000/2680000/2675800/2675705/7669562a_y.jpg)

### Residence Inn by Marriott Waldorf

10/10 Excellent

"Great experience. Friendly staff. Loved it"

[](https://expedia.co.uk/Waldorf-Hotels-Residence-Inn-By-Marriott-Waldorf.h2675705.Hotel-Information)

![The Wildset](https://images.trvl-media.com/lodging/65000000/64420000/64410600/64410566/38a42051_y.jpg)

### The Wildset

10/10 Excellent

"Well decorated inn w spacious and clean rooms, walking distance to shops, great restaurant with bar & breakfast included. Would absolutely come back. "

[](https://expedia.co.uk/St-Michaels-Hotels-The-Wildset.h64410566.Hotel-Information)

![Econo Lodge Andrews Air Force Base](https://images.trvl-media.com/lodging/1000000/30000/20400/20372/c9584ffd_y.jpg)

### Econo Lodge Andrews Air Force Base

10/10 Excellent

"Good for price"

[](https://expedia.co.uk/Waldorf-Hotels-Econo-Lodge-Andrews-Air-Force-Base.h20372.Hotel-Information)

![St Michaels Inn](https://images.trvl-media.com/lodging/1000000/20000/10300/10281/6601016b_y.jpg)

### St Michaels Inn

10/10 Excellent

"Everything was great! The desk receptionists were especially awesome. Loved the restaurants they recommended, spot on."

[](https://expedia.co.uk/St-Michaels-Hotels-St-Michaels-Inn.h10281.Hotel-Information)

![Towneplace Suites by Marriott Clinton at Joint Base Andrews](https://images.trvl-media.com/lodging/3000000/2310000/2308600/2308579/eb7a3f7b_y.jpg)

### Towneplace Suites by Marriott Clinton at Joint Base Andrews

10/10 Excellent

"The room was very clean and had all items we needed. The staff was helpful and considerate with any questions we had making our stay comfortable, safe, and enjoyable. "

[](https://expedia.co.uk/Waldorf-Hotels-Towneplace-Suites-By-Marriott-Clinton-At-Joint-Base-Andrews.h2308579.Hotel-Information)

![Candlewood Suites Annapolis by IHG](https://images.trvl-media.com/lodging/2000000/1170000/1160800/1160798/f27fb62d_y.jpg)

### Candlewood Suites Annapolis by IHG

10/10 Excellent

"The staff was extremely pleasant and enjoyable to work with!! "

[](https://expedia.co.uk/Annapolis-Hotels-Homestyle-Suites.h1160798.Hotel-Information)

![Springhill Suites by Marriott Prince Frederick](https://images.trvl-media.com/lodging/2000000/1670000/1662000/1661950/39882431_y.jpg)

### Springhill Suites by Marriott Prince Frederick

10/10 Excellent

"The staff at the breakfast bar was very attentive, and detail oriented. She was very good about checking everything. She very friendly and helpful. "

[](https://expedia.co.uk/Prince-Frederick-Hotels-Springhill-Suites-By-Marriott-Prince-Frederick.h1661950.Hotel-Information)

## Find out more about Chesapeake Beach

**Everything you need to know about** **Chesapeake Beach** **holiday rentals**

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chesapeake Beach holiday rental for you. At Expedia, you can take your pick from private holiday homes, [apartments](https://www.expedia.co.uk/aa/Apartments), cottages, [apart-hotels](https://www.expedia.co.uk/aa/ApartHotels), cabins, [villas](https://www.expedia.co.uk/aa/Villas)... 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 Beach holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

**Chesapeake Beach holiday rentals: An excellent choice for every season**

Whenever you want to travel, a warm welcome awaits you in Chesapeake Beach. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chesapeake Beach holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in. The selection of Chesapeake Beach holiday rentals we have selected for you start as low as £285 per night. Entering your travel dates in the search wizard you might find even better deals!

**How to find incredible deals on Chesapeake Beach rentals**

At Expedia, we put the best Chesapeake Beach holiday 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 Beach 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 Beach holiday.

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 Beach. 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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- [South Wales Holiday Rentals ](https://www.expedia.co.uk/South-Wales-Holiday-Rentals.d6054274.Travel-Guide-HolidayRentals)
- [North Wales Holiday Rentals ](https://www.expedia.co.uk/North-Wales-Holiday-Rentals.d6054276.Travel-Guide-HolidayRentals)
- [London Holiday Rentals ](https://www.expedia.co.uk/London-Holiday-Rentals.d178279.Travel-Guide-HolidayRentals)
- [York Holiday Rentals ](https://www.expedia.co.uk/York-Holiday-Rentals.d5489.Travel-Guide-HolidayRentals)
- [Blackpool Holiday Rentals ](https://www.expedia.co.uk/Blackpool-Holiday-Rentals.d619.Travel-Guide-HolidayRentals)
- [Isle of Wight Holiday Rentals ](https://www.expedia.com/Destinations-In-Isle-Of-Wight.d6046218.Vacation-Rental-Destinations)
- [Scarborough Holiday Rentals ](https://www.expedia.co.uk/Scarborough-Holiday-Rentals.d5680.Travel-Guide-HolidayRentals)
- [Edinburgh Holiday Rentals ](https://www.expedia.co.uk/Edinburgh-Holiday-Rentals.d6069845.Travel-Guide-HolidayRentals)
- [Bath Holiday Rentals ](https://www.expedia.co.uk/Bath-Holiday-Rentals.d6084496.Travel-Guide-HolidayRentals)
- [Bournemouth Holiday Rentals ](https://www.expedia.co.uk/Bournemouth-Holiday-Rentals.d654.Travel-Guide-HolidayRentals)
- [England Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-England.d11218.Holiday-Rental-Destinations)
- [Scotland Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-Scotland.d11219.Holiday-Rental-Destinations)
- [Cornwall Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-Cornwall.d6046193.Holiday-Rental-Destinations)
- [Wales Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-Wales.d11220.Holiday-Rental-Destinations)
- [Northern Ireland Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-Northern-Ireland.d11221.Holiday-Rental-Destinations)

## Frequently asked questions

### Can I find a holiday rental in Chesapeake Beach?

### What are some of the best holiday rentals that Chesapeake Beach has to offer?

### How many holiday rentals will I find in Chesapeake Beach?

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

### What’s a holiday rental in Chesapeake Beach like?

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