Title: Holiday Rentals Chesapeake Beach : 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

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

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## Check prices for these dates

In two weeks

[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 two months

[3 Apr - 5 Apr](https://www.expedia.co.uk/Hotel-Search?regionId=88967&startDate=2026-04-03&endDate=2026-04-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[1 May - 3 May](https://www.expedia.co.uk/Hotel-Search?regionId=88967&startDate=2026-05-01&endDate=2026-05-03&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[29 May - 31 May](https://www.expedia.co.uk/Hotel-Search?regionId=88967&startDate=2026-05-29&endDate=2026-05-31&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

![Exterior](https://images.trvl-media.com/lodging/85000000/84070000/84063700/84063656/57f188cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/85000000/84070000/84063700/84063656/12356e9c.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)

### Relax on Kent Island in a 4 Bedroom Home w/Waterview!

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

Stevensville

9.8/10

Exceptional

(43 reviews)

"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.

£208

includes taxes & fees

22 Feb - 23 Feb

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

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

![Smart TV, offices](https://images.trvl-media.com/lodging/70000000/69550000/69541400/69541327/28005d62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, offices](https://images.trvl-media.com/lodging/70000000/69550000/69541400/69541327/42bbbfcb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Walk to Beach! King Bed & Free Beach Passes

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

North Beach

10/10

Exceptional

(18 reviews)

"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.

£246

includes taxes & fees

16 Feb - 17 Feb

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

![Outdoor dining](https://images.trvl-media.com/lodging/84000000/83970000/83966500/83966408/d0edf916.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach nearby, sun-loungers, beach towels](https://images.trvl-media.com/lodging/84000000/83970000/83966500/83966408/c0808af9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/84000000/83970000/83966500/83966408/e5b3706d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/84000000/83970000/83966500/83966408/b40492dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

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

North Beach

10/10

Exceptional

(31 reviews)

"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.

£317

includes taxes & fees

12 Feb - 13 Feb

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

![Dining](https://images.trvl-media.com/lodging/125000000/124300000/124296100/124296028/d8734741.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/125000000/124300000/124296100/124296028/074a6cf6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Room, Non Smoking](https://images.trvl-media.com/lodging/125000000/124300000/124296100/124296028/3fb2d4e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/125000000/124300000/124296100/124296028/202cb189.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Haven 2 

[](https://www.expedia.co.uk/Waldorf-Hotels-Haven-2.h124296028.Hotel-Information)

Waldorf

£75

includes taxes & fees

12 Feb - 13 Feb

[](https://www.expedia.co.uk/Waldorf-Hotels-Haven-2.h124296028.Hotel-Information)

![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)

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

![Exterior](https://images.trvl-media.com/lodging/97000000/96120000/96117900/96117871/57a1dbf6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/97000000/96120000/96117900/96117871/eab3107c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Beautiful Waterfront Retreat in Cambridge!

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

Cambridge

10/10

Exceptional

(50 reviews)

"The house was completely spotless - the location was perfect! And the host included a s'mores kit, and baited crab traps and had them waiting with crabs in them when we arrived! This was an excellent weekend - we would recommend Hudson House to anyone!"

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

Elizabeth G.

£357

includes taxes & fees

8 Feb - 9 Feb

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

![Sun-loungers](https://images.trvl-media.com/lodging/38000000/37270000/37269100/37269068/9371a02d.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/w2046h1366x0y0-bfbcfcf3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/38000000/37270000/37269100/37269068/f7c493ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage Located on the Patuxent River!

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

Prince Frederick

10/10

Exceptional

(42 reviews)

"The accommodations were superb and being on the water was amazing!"

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

Daniel P.

£236

includes taxes & fees

7 Feb - 8 Feb

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

![Marina](https://images.trvl-media.com/lodging/102000000/101090000/101083600/101083507/0cad4612.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/102000000/101090000/101083600/101083507/3334515c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/102000000/101090000/101083600/101083507/f2ba56b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/102000000/101090000/101083600/101083507/0cab7732.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Bay Ridge unit by Downtown Annapolis and Quiet Waters Park 

[](https://www.expedia.co.uk/Annapolis-Hotels-Bay-Ridge-Unit-By-Downtown-Annapolis-And-Quiet-Waters-Park.h101083507.Hotel-Information)

Annapolis

8.8/10

Excellent

(3 reviews)

"The place is very nice and comfortable inside. Quiet. Great place to sleep - no noise."

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

William

£354

includes taxes & fees

9 Feb - 10 Feb

[](https://www.expedia.co.uk/Annapolis-Hotels-Bay-Ridge-Unit-By-Downtown-Annapolis-And-Quiet-Waters-Park.h101083507.Hotel-Information)

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

![Microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116010000/116005700/116005601/8aaef683.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/117000000/116010000/116005700/116005601/1bc5d356.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)

### Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene 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)

Shady Side

10/10

Exceptional

(4 reviews)

"Would stay here again "

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

Thomas D.

£322

includes taxes & fees

8 Feb - 9 Feb

[](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)

![Property grounds](https://images.trvl-media.com/lodging/97000000/96640000/96637800/96637704/df7451da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![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)

![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)

![Miscellaneous](https://images.trvl-media.com/lodging/97000000/96640000/96637800/96637704/3150e656.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

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

Benedict

9.0/10

Wonderful

(8 reviews)

"Just the perfect place I needed for a personal retreat. It is quiet, peaceful and serene. I would definitely visit again. "

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

Berenice N.

£222

includes taxes & fees

7 Feb - 8 Feb

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

![Beach nearby, sun-loungers, beach towels](https://images.trvl-media.com/lodging/92000000/91040000/91033700/91033683/8a8d7f46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/92000000/91040000/91033700/91033683/8a80c02f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/92000000/91040000/91033700/91033683/5c5b72be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor spa tub](https://images.trvl-media.com/lodging/92000000/91040000/91033700/91033683/825e8c03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

[](https://www.expedia.co.uk/Annapolis-Hotels-Charming-Cottage-With-Hot-Tub-1-Block-From-The-Bay.h91033683.Hotel-Information)

Arundel on the Bay

9.8/10

Exceptional

(11 reviews)

"Great communication with the host, easy check in.. nice property. "

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

Henry P.

£370

includes taxes & fees

9 Feb - 10 Feb

[](https://www.expedia.co.uk/Annapolis-Hotels-Charming-Cottage-With-Hot-Tub-1-Block-From-The-Bay.h91033683.Hotel-Information)

![Beach](https://images.trvl-media.com/lodging/104000000/103640000/103638100/103638094/5aeb926e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/104000000/103640000/103638100/103638094/dd4e694d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/104000000/103640000/103638100/103638094/b10c421b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/104000000/103640000/103638100/103638094/7d735d64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!

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

Prince Frederick

10/10

Exceptional

(8 reviews)

"Such a cool neighborhood! Easy walk to an amazing private beach. Would love to stay again. "

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

Olivia M.

£285

includes taxes & fees

9 Feb - 10 Feb

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

![Beach](https://images.trvl-media.com/lodging/118000000/117290000/117289400/117289332/bb0aa611.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/118000000/117290000/117289400/117289332/03302009.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117290000/117289400/117289332/a76a3d53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/118000000/117290000/117289400/117289332/42a552d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming 3-bedroom house with AC, WiFi in tranquil Edgewater on the bay .

[](https://www.expedia.co.uk/Edgewater-Hotels-Charming-3-Bedroom-House-With-AC.h117289332.Hotel-Information)

Edgewater

10/10

Exceptional

(4 reviews)

"Great location, easy check in/out. Everything we needed was available! Very comfortable bed, super cute property. "

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

MJ S.

£259

includes taxes & fees

7 Feb - 8 Feb

[](https://www.expedia.co.uk/Edgewater-Hotels-Charming-3-Bedroom-House-With-AC.h117289332.Hotel-Information)

![Outdoor spa tub](https://images.trvl-media.com/lodging/97000000/96310000/96305200/96305193/8bc5c09a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/97000000/96310000/96305200/96305193/6e5a14cc.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/97000000/96310000/96305200/96305193/28989db9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/97000000/96310000/96305200/96305193/bff50623.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### London Towne Bungalow w/Loft - Walk to the Beach!

[](https://www.expedia.co.uk/Edgewater-Hotels-London-Towne-Bungalow-WLoft-Walk-To-The-Beach.h96305193.Hotel-Information)

Edgewater

8.8/10

Excellent

(3 reviews)

"Very cute house. It was exactly what I was looking for. "

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

Collin G.

£347

includes taxes & fees

7 Feb - 8 Feb

[](https://www.expedia.co.uk/Edgewater-Hotels-London-Towne-Bungalow-WLoft-Walk-To-The-Beach.h96305193.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/100000000/99480000/99470800/99470706/d00ee2e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/100000000/99480000/99470800/99470706/a72fcd9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/100000000/99480000/99470800/99470706/8156a7b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/100000000/99480000/99470800/99470706/48c7542a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Annapolis Retreat - 7 mins from downtown Annapolis!

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

Hillsmere

10/10

Exceptional

(5 reviews)

"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.

£377

includes taxes & fees

9 Feb - 10 Feb

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

![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/121000000/120840000/120836100/120836005/6d192d96.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)

![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)

### Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!

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

Lusby

£385

includes taxes & fees

15 Feb - 16 Feb

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117640000/117630300/117630212/c38145a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/118000000/117640000/117630300/117630212/2d43a6e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/118000000/117640000/117630300/117630212/a1d0efa5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/118000000/117640000/117630300/117630212/8fb2f231.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Annapolis Gem: Stylish and Cozy

[](https://www.expedia.co.uk/Annapolis-Hotels-Annapolis-Gem-Stylish-And-Cozy.h117630212.Hotel-Information)

Eastport

10/10

Exceptional

(3 reviews)

"Great spot"

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

Brian F.

£350

includes taxes & fees

7 Feb - 8 Feb

[](https://www.expedia.co.uk/Annapolis-Hotels-Annapolis-Gem-Stylish-And-Cozy.h117630212.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/118000000/117740000/117737300/117737253/a948ba3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/118000000/117740000/117737300/117737253/08f434f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool](https://images.trvl-media.com/lodging/118000000/117740000/117737300/117737253/4e78dd69.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117740000/117737300/117737253/e8e7a98b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming 3-bedroom in Upper Marlboro - Minutes from Washington, DC

[](https://www.expedia.co.uk/Upper-Marlboro-Hotels-Charming-3-Bedroom-In-Upper-Marlboro-Minutes-From-Washington.h117737253.Hotel-Information)

Upper Marlboro

£101

includes taxes & fees

9 Feb - 10 Feb

[](https://www.expedia.co.uk/Upper-Marlboro-Hotels-Charming-3-Bedroom-In-Upper-Marlboro-Minutes-From-Washington.h117737253.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)

![Smart TV](https://images.trvl-media.com/lodging/84000000/83070000/83066200/83066154/960e2739.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)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83070000/83066200/83066154/fcc4baa2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### WATERFRONT!! \*\*HOT TUB\*\* 3 bedroom Oasis on 2+ acres - Sleeps 8

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

Cambridge

10/10

Exceptional

(14 reviews)

"Amazing news out of the back.Great for kayaking.We brought our own kayaksAnd also use yoursThere were four of usWe also took a nice trip over to Saint Michael’s"

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

Sandy S.

£380

includes taxes & fees

8 Feb - 9 Feb

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/111000000/110590000/110587800/110587715/dab63ee1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach](https://images.trvl-media.com/lodging/111000000/110590000/110587800/110587715/76eea0ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/111000000/110590000/110587800/110587715/4fa5385d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/111000000/110590000/110587800/110587715/d0b78f7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Golden Anchor Retreat; Lux Living! - Sleeps 7

[](https://www.expedia.co.uk/Edgewater-Hotels-New-Golden-Anchor-Retreat-Lux-Living.h110587715.Hotel-Information)

Edgewater

10/10

Exceptional

(2 reviews)

"The property was beautiful with plenty of space to have a getaway with friends. The host was super communicative when we had issues with check in. Would highly recommend staying here!"

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

Sam A.

£484

includes taxes & fees

9 Feb - 10 Feb

[](https://www.expedia.co.uk/Edgewater-Hotels-New-Golden-Anchor-Retreat-Lux-Living.h110587715.Hotel-Information)

![TV, books, offices](https://images.trvl-media.com/lodging/106000000/105400000/105392900/105392845/5550ff75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, books, offices](https://images.trvl-media.com/lodging/106000000/105400000/105392900/105392845/98da8700.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/106000000/105400000/105392900/105392845/cf100abd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, books, offices](https://images.trvl-media.com/lodging/106000000/105400000/105392900/105392845/a507208b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Holly Hill Haven - Sleeps 10

[](https://www.expedia.co.uk/Edgewater-Hotels-Escape-To-Our-Beautifully-Renovated-Home-In-The-Heart-Of-The-Scenic-Mayo-Peninsula.h105392845.Hotel-Information)

Edgewater

10/10

Exceptional

(3 reviews)

"House was clean and comfortable. Great layout. "

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

Kristin G.

£422

includes taxes & fees

7 Feb - 8 Feb

[](https://www.expedia.co.uk/Edgewater-Hotels-Escape-To-Our-Beautifully-Renovated-Home-In-The-Heart-Of-The-Scenic-Mayo-Peninsula.h105392845.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=2026-02-20&endDate=2026-02-21&regionId=88967&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find holiday rentals that suit your style

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=2026-05-07&d1=2026-05-07&endDate=2026-05-10&d2=2026-05-10&lodging=VACATION_HOME)

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=2026-05-07&d1=2026-05-07&endDate=2026-05-10&d2=2026-05-10&lodging=COTTAGE)

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=2026-05-07&d1=2026-05-07&endDate=2026-05-10&d2=2026-05-10&lodging=APARTMENT)

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=2026-05-07&d1=2026-05-07&endDate=2026-05-10&d2=2026-05-10&lodging=HOUSE_BOAT)

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=2026-05-07&d1=2026-05-07&endDate=2026-05-10&d2=2026-05-10&lodging=CONDO)

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=2026-05-07&d1=2026-05-07&endDate=2026-05-10&d2=2026-05-10&lodging=VILLA)

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## Top Chesapeake Beach Hotel Reviews

![Rod 'N' Reel Resort](https://images.trvl-media.com/lodging/2000000/1060000/1050500/1050433/4803b1f5_y.jpg)

### Rod 'N' Reel Resort

10/10 Excellent

"Staff was courteous "

[](https://expedia.co.uk/Chesapeake-Beach-Hotels-Rod-N-Reel-Resort.h1050433.Hotel-Information)

![Spark by Hilton Waldorf](https://images.trvl-media.com/lodging/1000000/30000/26400/26379/cbec5af3_y.jpg)

### Spark by Hilton Waldorf

10/10 Excellent

"Great stays."

[](https://expedia.co.uk/Waldorf-Hotels-Spark-By-Hilton-Waldorf.h26379.Hotel-Information)

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

### St Michaels Inn

10/10 Excellent

"Very good motel "

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

"Great front desk people. Great room"

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

![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 staff was accommodating and the room was very clean. The house keeper even helped me back in my room when locked out early. "

[](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

"Greer service "

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

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

### The Wildset

10/10 Excellent

"Clean rooms, great staff, awesome restaurant on site called Ruse & right in downtown. "

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

![Sleep Inn & Suites Near Joint Base Andrews - Washington Area](https://images.trvl-media.com/lodging/3000000/2010000/2001600/2001534/677b7b85_y.jpg)

### Sleep Inn & Suites Near Joint Base Andrews - Washington Area

10/10 Excellent

"Everything was great. The only problem was that the shower did not get very hot "

[](https://expedia.co.uk/Waldorf-Hotels-Sleep-Inn-Suites-Near-Joint-Base-Andrews-Washington-Area.h2001534.Hotel-Information)

![Sonesta ES Suites Annapolis](https://images.trvl-media.com/lodging/1000000/10000/3000/2982/e773fcbe_y.jpg)

### Sonesta ES Suites Annapolis

10/10 Excellent

"Room was bigger than i had expected,and well appointed the fire place was nice and the hot breakfast was very good for being an included meal. The staff was great!!!!"

[](https://expedia.co.uk/Annapolis-Hotels-Sonesta-ES-Suites-Annapolis.h2982.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 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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- [Cumbria Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-Cumbria.d6046194.Holiday-Rental-Destinations)
- [Yorkshire Holiday Rentals ](https://www.expedia.co.uk/Yorkshire-Holiday-Rentals.d6342462.Travel-Guide-HolidayRentals)
- [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?

### Expedia's Latest Trends

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General

- [Visit Snow Hill](https://expedia.co.uk/Snow-Hill.dx7604)
- [Visit Cumberland](https://expedia.co.uk/Cumberland.dx6057474)
- [Visit Chesapeake City](https://expedia.co.uk/Chesapeake-City.dx177517)
- [Visit Ocean City](https://expedia.co.uk/Ocean-City.dx9151)

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## Go further with the Expedia app

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