Title: Holiday Rentals St. Michaels from £956: Find Short-Term Rentals & Holiday Accommodations | Expedia.co.uk

[St. Michaels Travel Guide](https://expedia.co.uk/St-Michaels.dx5940)[Hotels in St. Michaels](https://expedia.co.uk/St-Michaels-Hotels.d5940.Travel-Guide-Hotels)[Flights to St. Michaels](https://expedia.co.uk/Cheap-Flights-To-St-Michaels.d5940.Travel-Guide-Flights)[St. Michaels Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-St-Michaels.d5940.Car-Hire-Guide)[St. Michaels Holidays](https://expedia.co.uk/St-Michaels.d5940.Holidays-City-Breaks)

![The Chesapeake Bay Maritime Museum in Saint Michaels, Maryland, features  the Hooper Strait Lighthouse, built in 1879](https://images.trvl-media.com/place/5940/6d454cf3-0755-44c6-999f-dfbbe160658d.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

![](https://images.trvl-media.com/place/5940/6d454cf3-0755-44c6-999f-dfbbe160658d.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=5940&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=5940&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=5940&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=5940&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 St. Michaels holiday rentals

![Marina](https://images.trvl-media.com/lodging/120000000/119340000/119331500/119331473/61e8c463.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/120000000/119340000/119331500/119331473/2ff1f3ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/120000000/119340000/119331500/119331473/108896ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119340000/119331500/119331473/4db5aa56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Station House East: Upscale Loft in the Historic District Cambridge, MD

[](https://www.expedia.co.uk/Cambridge-Hotels-Station-House-East-Upscale-Loft-In-The-Historic-District-Cambridge.h119331473.Hotel-Information)

Downtown Cambridge

10/10

Exceptional

(7 reviews)

"The apartment was exceptionally clean and comfortable."

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

Beth T.

£263

includes taxes & fees

11 Feb - 12 Feb

[](https://www.expedia.co.uk/Cambridge-Hotels-Station-House-East-Upscale-Loft-In-The-Historic-District-Cambridge.h119331473.Hotel-Information)

![Private kitchen](https://images.trvl-media.com/lodging/82000000/81260000/81259300/81259255/b3fc30c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/82000000/81260000/81259300/81259255/c9589eb6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/82000000/81260000/81259300/81259255/0251fd8c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/82000000/81260000/81259300/81259255/706f23d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sailwinds Loft at Cambridge Creek

[](https://www.expedia.co.uk/Cambridge-Hotels-Sailwinds-Loft-At-Cambridge-Creek.h81259255.Hotel-Information)

Cambridge

10/10

Exceptional

(24 reviews)

"What a great place to relax after exploring and enjoying the area. Definitely will visit again "

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

Chris S.

£189

includes taxes & fees

9 Feb - 10 Feb

[](https://www.expedia.co.uk/Cambridge-Hotels-Sailwinds-Loft-At-Cambridge-Creek.h81259255.Hotel-Information)

![Marina](https://images.trvl-media.com/lodging/107000000/106750000/106747700/106747609/5d73c26c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/107000000/106750000/106747700/106747609/e16941d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/107000000/106750000/106747700/106747609/bb311693.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/107000000/106750000/106747700/106747609/86a08fa5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

[](https://www.expedia.co.uk/Cambridge-Hotels-The-Drinking-Gourd-Stunning-Penthouse-In-Historic-Downtown-Cambridge.h106747609.Hotel-Information)

Downtown Cambridge

9.8/10

Exceptional

(12 reviews)

"This was such a cozy, comfortable space for a girls weekend away. We loved the charm of the old building paired with thoughtful amenities. "

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

Lauren V.

£262

includes taxes & fees

9 Feb - 10 Feb

[](https://www.expedia.co.uk/Cambridge-Hotels-The-Drinking-Gourd-Stunning-Penthouse-In-Historic-Downtown-Cambridge.h106747609.Hotel-Information)

![Marina](https://images.trvl-media.com/lodging/100000000/99690000/99684200/99684191/69bef312.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/100000000/99690000/99684200/99684191/7f132b5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/100000000/99690000/99684200/99684191/3651a7b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/100000000/99690000/99684200/99684191/7cf0d433.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

[](https://www.expedia.co.uk/Cambridge-Hotels-Cozy-2-Bedroom.h99684191.Hotel-Information)

Cambridge

9.6/10

Exceptional

(20 reviews)

"Very clean, and very comfortable beds."

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

Edward R.

£258

includes taxes & fees

16 Feb - 17 Feb

[](https://www.expedia.co.uk/Cambridge-Hotels-Cozy-2-Bedroom.h99684191.Hotel-Information)

![Marina](https://images.trvl-media.com/lodging/106000000/105950000/105946100/105946058/65fc84d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/106000000/105950000/105946100/105946058/013c787c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bar (on property)](https://images.trvl-media.com/lodging/106000000/105950000/105946100/105946058/ee3b6008.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/106000000/105950000/105946100/105946058/167fd0dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland

[](https://www.expedia.co.uk/Cambridge-Hotels-Conductors-Rest-Beautiful-2-Bedroom-Loft-In-Historic-Cambridge.h105946058.Hotel-Information)

Downtown Cambridge

10/10

Exceptional

(10 reviews)

"Just a beautiful place. I would stay here again. Everything was walking distance. "

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

Sylvie G.

£271

includes taxes & fees

12 Feb - 13 Feb

[](https://www.expedia.co.uk/Cambridge-Hotels-Conductors-Rest-Beautiful-2-Bedroom-Loft-In-Historic-Cambridge.h105946058.Hotel-Information)

![Beach](https://images.trvl-media.com/lodging/105000000/104010000/104005300/104005223/b4e88275.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/105000000/104010000/104005300/104005223/daf32ef4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/105000000/104010000/104005300/104005223/5a5ec3f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/105000000/104010000/104005300/104005223/b0be7e2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

[](https://www.expedia.co.uk/Rock-Hall-Hotels-Walk-To-Everything-Rock-Hall-From-This-1st-Floor-Apartment-Sleeps-4.h104005223.Hotel-Information)

Rock Hall

10/10

Exceptional

(17 reviews)

"Close to Main Street. Very nice and spacious accommodations."

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

Michael D.

£213

includes taxes & fees

9 Feb - 10 Feb

[](https://www.expedia.co.uk/Rock-Hall-Hotels-Walk-To-Everything-Rock-Hall-From-This-1st-Floor-Apartment-Sleeps-4.h104005223.Hotel-Information)

![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/c77382da.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)

![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.

£203

includes taxes & fees

17 Feb - 18 Feb

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

![Exterior](https://images.trvl-media.com/lodging/85000000/84070000/84063900/84063895/a71c8e39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/85000000/84070000/84063900/84063895/c53ddff2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/85000000/84070000/84063900/84063895/w1024h678x0y5-f3e384c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/85000000/84070000/84063900/84063895/7d796cd2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming Coastal/Country Home w/3 Acres & Sauna!

[](https://www.expedia.co.uk/Stevensville-Hotels-Charming-CoastalCountry-Home-W3-Acres-Sauna.h84063895.Hotel-Information)

Stevensville

9.6/10

Exceptional

(32 reviews)

"Great stay, would do it again."

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

Brandon D.

£209

includes taxes & fees

17 Feb - 18 Feb

[](https://www.expedia.co.uk/Stevensville-Hotels-Charming-CoastalCountry-Home-W3-Acres-Sauna.h84063895.Hotel-Information)

![Marina](https://images.trvl-media.com/lodging/104000000/103590000/103584900/103584811/756cfb64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/104000000/103590000/103584900/103584811/aece230b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach](https://images.trvl-media.com/lodging/104000000/103590000/103584900/103584811/e14723bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/104000000/103590000/103584900/103584811/57f74d8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland

[](https://www.expedia.co.uk/Cambridge-Hotels-Upscale-Condo-In-Historic-Downtown-Cambridge.h103584811.Hotel-Information)

Downtown Cambridge

8.4/10

Very good

(6 reviews)

"Perfectly located in town and well appointed, comfortable quarters. We would stay again."

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

Richard D.

£221

includes taxes & fees

10 Feb - 11 Feb

[](https://www.expedia.co.uk/Cambridge-Hotels-Upscale-Condo-In-Historic-Downtown-Cambridge.h103584811.Hotel-Information)

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/69000000/68990000/68986300/68986275/b2a36b22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/69000000/68990000/68986300/68986275/8c6112e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/69000000/68990000/68986300/68986275/95f44d8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, in-room safe, free WiFi, bed sheets](https://images.trvl-media.com/lodging/69000000/68990000/68986300/68986275/d5668d89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Waterfront Oasis of Annapolis Star

[](https://www.expedia.co.uk/Annapolis-Hotels-Waterfront-Oasis-Sleep-4-Close-To-Downtown.h68986275.Hotel-Information)

Annapolis

10/10

Exceptional

(81 reviews)

"Owners were great hosts. Loved this property!"

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

Thomas

£298

includes taxes & fees

9 Feb - 10 Feb

[](https://www.expedia.co.uk/Annapolis-Hotels-Waterfront-Oasis-Sleep-4-Close-To-Downtown.h68986275.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117370000/117360200/117360157/8d73bbbc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/118000000/117370000/117360200/117360157/a19fc40c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach](https://images.trvl-media.com/lodging/118000000/117370000/117360200/117360157/491acaae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/118000000/117370000/117360200/117360157/45c5363e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Luxury Pool Loft sleeps 4

[](https://www.expedia.co.uk/Annapolis-Hotels-New-The-Pool-Loft-At-Poplar-Hill.h117360157.Hotel-Information)

Cape Saint Claire

10/10

Exceptional

(4 reviews)

"This place has a fantastic location and an incredibly welcoming host! The area also features wonderful walking trails."

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

Ana S.

£282

includes taxes & fees

9 Feb - 10 Feb

[](https://www.expedia.co.uk/Annapolis-Hotels-New-The-Pool-Loft-At-Poplar-Hill.h117360157.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/81000000/80030000/80024200/80024112/w507h683x258y0-d94bdb39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/81000000/80030000/80024200/80024112/w904h683x60y0-e98964a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/81000000/80030000/80024200/80024112/w506h683x259y0-9b301d23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/81000000/80030000/80024200/80024112/w509h683x258y0-2cb187b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Waterfront Getaway with Dock

[](https://www.expedia.co.uk/Woolford-Hotels-Waterfront-Getaway-With-Dock.h80024112.Hotel-Information)

Woolford

10/10

Exceptional

(52 reviews)

"Great place, will stay again"

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

Matt S.

£206

includes taxes & fees

9 Feb - 10 Feb

[](https://www.expedia.co.uk/Woolford-Hotels-Waterfront-Getaway-With-Dock.h80024112.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)

![Smart TV](https://images.trvl-media.com/lodging/84000000/83970000/83966500/83966408/993af54b.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.

£302

includes taxes & fees

11 Feb - 12 Feb

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

![Dining](https://images.trvl-media.com/lodging/100000000/99840000/99830400/99830322/2a64ee56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/100000000/99840000/99830400/99830322/23f1d475.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, table football](https://images.trvl-media.com/lodging/100000000/99840000/99830400/99830322/44a64359.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/100000000/99840000/99830400/99830322/30ebd57e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Spacious 2 bedroom duplex located conveniently near Route 50 East and West. 

[](https://www.expedia.co.uk/Spacious-2-Bedroom-Duplex-Located-Conveniently-Near-Route-50-East-And-West.h99830322.Hotel-Information)

Grasonville

9.6/10

Exceptional

(12 reviews)

"Had a short getaway for a couple this location was perfect for our visit to Chestertown and the local establishments in Grasonville. Will definitely book this again. "

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

Joe C.

£311

includes taxes & fees

9 Feb - 10 Feb

[](https://www.expedia.co.uk/Spacious-2-Bedroom-Duplex-Located-Conveniently-Near-Route-50-East-And-West.h99830322.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/f79dd58b.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

£355

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)

![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/eab3107c.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)

### 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.

£358

includes taxes & fees

10 Feb - 11 Feb

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

£236

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)

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

![Exterior detail](https://images.trvl-media.com/lodging/100000000/99480000/99470800/99470706/9df6bc62.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)

![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)

### 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.

£378

includes taxes & fees

9 Feb - 10 Feb

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

![Marina](https://images.trvl-media.com/lodging/103000000/102760000/102759300/102759203/1b7ace28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/103000000/102760000/102759300/102759203/e1e4be63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, WiFi](https://images.trvl-media.com/lodging/103000000/102760000/102759300/102759203/9891f005.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/103000000/102760000/102759300/102759203/0c843e91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sailboat Experience in Annapolis

[](https://www.expedia.co.uk/Annapolis-Hotels-Sailboat-Experience-In-Annapolis.h102759203.Hotel-Information)

Parole

10/10

Exceptional

(1 review)

£158

includes taxes & fees

2 Mar - 3 Mar

[](https://www.expedia.co.uk/Annapolis-Hotels-Sailboat-Experience-In-Annapolis.h102759203.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102770000/102761900/102761818/f435d690.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/103000000/102770000/102761900/102761818/c718db9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, WiFi](https://images.trvl-media.com/lodging/103000000/102770000/102761900/102761818/ece96a3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/103000000/102770000/102761900/102761818/492a6deb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Annapolis Boat Life - Overnight Stays

[](https://www.expedia.co.uk/Annapolis-Hotels-Annapolis-Boat-Life-Overnight-Stays.h102761818.Hotel-Information)

ANNAPOLIS

10/10

Exceptional

(1 review)

"Great stay, host was super amazing and we had the best time!!"

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

Kirstyn I.

£195

includes taxes & fees

10 Mar - 11 Mar

[](https://www.expedia.co.uk/Annapolis-Hotels-Annapolis-Boat-Life-Overnight-Stays.h102761818.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=2026-02-22&endDate=2026-02-23&regionId=5940&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=St.+Michaels%2C+Maryland%2C+United+States+of+America&regionId=5940&latLong=38.78656%2C-76.224365&adults=2&startDate=2026-05-09&d1=2026-05-09&endDate=2026-05-12&d2=2026-05-12&lodging=VACATION_HOME)

Apartments

[](https://www.expedia.co.uk/Hotel-Search?destination=St.+Michaels%2C+Maryland%2C+United+States+of+America&regionId=5940&latLong=38.78656%2C-76.224365&adults=2&startDate=2026-05-09&d1=2026-05-09&endDate=2026-05-12&d2=2026-05-12&lodging=APARTMENT)

Cottages

[](https://www.expedia.co.uk/Hotel-Search?destination=St.+Michaels%2C+Maryland%2C+United+States+of+America&regionId=5940&latLong=38.78656%2C-76.224365&adults=2&startDate=2026-05-09&d1=2026-05-09&endDate=2026-05-12&d2=2026-05-12&lodging=COTTAGE)

Condos

[](https://www.expedia.co.uk/Hotel-Search?destination=St.+Michaels%2C+Maryland%2C+United+States+of+America&regionId=5940&latLong=38.78656%2C-76.224365&adults=2&startDate=2026-05-09&d1=2026-05-09&endDate=2026-05-12&d2=2026-05-12&lodging=CONDO)

Houseboats

[](https://www.expedia.co.uk/Hotel-Search?destination=St.+Michaels%2C+Maryland%2C+United+States+of+America&regionId=5940&latLong=38.78656%2C-76.224365&adults=2&startDate=2026-05-09&d1=2026-05-09&endDate=2026-05-12&d2=2026-05-12&lodging=HOUSE_BOAT)

Villas

[](https://www.expedia.co.uk/Hotel-Search?destination=St.+Michaels%2C+Maryland%2C+United+States+of+America&regionId=5940&latLong=38.78656%2C-76.224365&adults=2&startDate=2026-05-09&d1=2026-05-09&endDate=2026-05-12&d2=2026-05-12&lodging=VILLA)

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## Top St. Michaels Hotel Reviews

![Hilton Garden Inn Annapolis Downtown](https://images.trvl-media.com/lodging/1000000/900000/892300/892213/4fdee6d5_y.jpg)

### Hilton Garden Inn Annapolis Downtown

10/10 Excellent

"The room was ready early and very clean..staff was very friendly "

[](https://expedia.co.uk/Annapolis-Hotels-Hilton-Garden-Inn-Annapolis-Downtown.h892213.Hotel-Information)

![Crowne Plaza Annapolis by IHG](https://images.trvl-media.com/lodging/1000000/10000/7700/7668/6084a9f0_y.jpg)

### Crowne Plaza Annapolis by IHG

10/10 Excellent

"Wonderful stay! Automatic checkout 2pm. Thank you!!"

[](https://expedia.co.uk/Annapolis-Hotels-Crowne-Plaza-Annapolis.h7668.Hotel-Information)

![DoubleTree by Hilton Hotel Annapolis](https://images.trvl-media.com/lodging/1000000/10000/3100/3040/f77b4116_y.jpg)

### DoubleTree by Hilton Hotel Annapolis

10/10 Excellent

"Room was spotless. Staff was very courteous. Would highly recommended."

[](https://expedia.co.uk/Annapolis-Hotels-DoubleTree-By-Hilton-Hotel-Annapolis.h3040.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

"We were happy to stay at this place. Very beautiful, warm, comfortable ❤️❤️❤️"

[](https://expedia.co.uk/Annapolis-Hotels-Sonesta-ES-Suites-Annapolis.h2982.Hotel-Information)

![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)

![Historic Inns of Annapolis](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/bf4c0cc1_y.jpg)

### Historic Inns of Annapolis

10/10 Excellent

"Everything about this beautiful historic hotel was beautiful and perfect—I can’t wait to come back!"

[](https://expedia.co.uk/Annapolis-Hotels-Historic-Inns-Of-Annapolis.h42068.Hotel-Information)

![Graduate by Hilton Annapolis](https://images.trvl-media.com/lodging/1000000/10000/900/846/dcb23c20_y.jpg)

### Graduate by Hilton Annapolis

10/10 Excellent

"Everything! The hotel was clean, great location, and the front desk clerk was kind and helpful! "

[](https://expedia.co.uk/Annapolis-Hotels-Graduate-By-Hilton-Annapolis.h846.Hotel-Information)

![The Westin Annapolis](https://images.trvl-media.com/lodging/2000000/1680000/1678800/1678710/w3998h2667x0y0-54f847ff_y.jpg)

### The Westin Annapolis

10/10 Excellent

"Great!!"

[](https://expedia.co.uk/Annapolis-Hotels-The-Westin-Annapolis.h1678710.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)

## Find out more about St. Michaels

**Everything you need to know about** **St. Michaels** **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 St. Michaels 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 St. Michaels holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

**St. Michaels holiday rentals: An excellent choice for every season**

Whenever you want to travel, a warm welcome awaits you in St. Michaels. 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 St. Michaels 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 St. Michaels holiday rentals we have selected for you start as low as £956 per night. Entering your travel dates in the search wizard you might find even better deals!

**How to find incredible deals on St. Michaels rentals**

At Expedia, we put the best St. Michaels 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 St. Michaels 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 St. Michaels 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 St. Michaels. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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- [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

### Are there holiday rentals in St. Michaels?

### What are some of the best holiday rentals that St. Michaels has to offer?

### How many holiday rentals are there in St. Michaels?

### What’s there to see and do in St. Michaels?

### What’s a holiday rental in St. Michaels like?

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