Title: St. Michaels Vacation Rentals : Search Short-Term Rentals | Expedia.com

[St. Michaels Travel Guide](https://expedia.com/St-Michaels.dx5940)[Hotels in St. Michaels](https://expedia.com/St-Michaels-Hotels.d5940.Travel-Guide-Hotels)[Flights to St. Michaels](https://expedia.com/Cheap-Flights-To-St-Michaels.d5940.Travel-Guide-Flights)[Car Rentals in St. Michaels](https://expedia.com/Car-Rentals-In-St-Michaels.d5940.Car-Rental-Guide)[St. Michaels Vacation Packages](https://expedia.com/St-Michaels.d5940.Destination-Travel-Guides)

![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

[Mar 20 - Mar 22](https://www.expedia.com/Hotel-Search?regionId=5940&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 two months

[May 1 - May 3](https://www.expedia.com/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 three months

[May 29 - May 31](https://www.expedia.com/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)

In four months

[Jun 26 - Jun 28](https://www.expedia.com/Hotel-Search?regionId=5940&startDate=2026-06-26&endDate=2026-06-28&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 vacation rentals

![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)

![Bar (on property)](https://images.trvl-media.com/lodging/100000000/99690000/99684200/99684191/c7785aa6.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)

### Vacation Home in Cambridge

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

9.6/10

Exceptional

(20 reviews)

"Very nice place in a great location. We would definitely stay there again "

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

Traci C.

$345 nightly

$366 total

Mar 5 - Mar 6

Total with taxes and fees

[](https://www.expedia.com/Cambridge-Hotels-Cozy-2-Bedroom.h99684191.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)

![Interior](https://images.trvl-media.com/lodging/107000000/106750000/106747700/106747609/f35d159c.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)

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

### Condo in Downtown Cambridge

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

9.8/10

Exceptional

(12 reviews)

"Host was personally accessible during stay, responded quickly, and went the extra mile with wonderful touches left around the place."

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

John S.

$347 nightly

$368 total

Mar 23 - Mar 24

Total with taxes and fees

[](https://www.expedia.com/Cambridge-Hotels-The-Drinking-Gourd-Stunning-Penthouse-In-Historic-Downtown-Cambridge.h106747609.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/dea9ce41.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)

### Condo in Downtown Cambridge

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

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.

$294 nightly

$312 total

Mar 5 - Mar 6

Total with taxes and fees

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

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119340000/119331500/119331473/868b127d.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)

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

### Condo in Downtown Cambridge

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

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.

$338 nightly

$358 total

Mar 5 - Mar 6

Total with taxes and fees

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

![Interior](https://images.trvl-media.com/lodging/106000000/105950000/105946100/105946058/3840464a.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)

### Condo in Downtown Cambridge

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

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.

$368 nightly

$390 total

Mar 17 - Mar 18

Total with taxes and fees

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

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

![Exterior](https://images.trvl-media.com/lodging/100000000/99840000/99830400/99830322/737f2153.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Grasonville

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

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.

$397 nightly

$421 total

Mar 5 - Mar 6

Total with taxes and fees

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

![Interior](https://images.trvl-media.com/lodging/82000000/81260000/81259300/81259255/706f23d9.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)

### Apartment in Cambridge

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

10/10

Exceptional

(24 reviews)

"Lovely place, huge rooms, definitely recommend it. "

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

Lee P.

$240 nightly

$254 total

Mar 6 - Mar 7

Total with taxes and fees

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

![Smart TV](https://images.trvl-media.com/lodging/104000000/103760000/103759100/103759056/9ec17f2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/104000000/103760000/103759100/103759056/a01170f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/104000000/103760000/103759100/103759056/7a6a8ebd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/104000000/103760000/103759100/103759056/4239f612.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Cambridge

[](https://www.expedia.com/Cambridge-Hotels-WATERFRONT-HOT-TUB-4-BED4-BATH-CHARMING-HOME-IN-THE-HEART-OF-CAMBRIDGE.h103759056.Hotel-Information)

8.8/10

Excellent

(10 reviews)

"Clean, cozy, and lovely - a winter cabin stay to remember. Kids already wanted to go back 5 days later. 10 out of 10 stars! "

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

Mr.

$583 nightly

$618 total

Mar 5 - Mar 6

Total with taxes and fees

[](https://www.expedia.com/Cambridge-Hotels-WATERFRONT-HOT-TUB-4-BED4-BATH-CHARMING-HOME-IN-THE-HEART-OF-CAMBRIDGE.h103759056.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)

![Smart TV](https://images.trvl-media.com/lodging/85000000/84070000/84063900/84063895/e9f923a1.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)

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

### Vacation Home in Stevensville

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

9.6/10

Exceptional

(34 reviews)

"Great stay, would do it again."

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

Brandon D.

$243 nightly

$258 total

Mar 8 - Mar 9

Total with taxes and fees

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

![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)

![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/69000000/68990000/68986300/68986275/8e1aa433.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Annapolis

[](https://www.expedia.com/Annapolis-Hotels-Comfy-Oasis.h68986275.Hotel-Information)

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

$361 nightly

$412 total

Mar 5 - Mar 6

Total with taxes and fees

[](https://www.expedia.com/Annapolis-Hotels-Comfy-Oasis.h68986275.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)

![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)

![Marina](https://images.trvl-media.com/lodging/85000000/84070000/84063700/84063656/12356e9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Stevensville

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

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.

$231 nightly

$245 total

Mar 5 - Mar 6

Total with taxes and fees

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

![Interior](https://images.trvl-media.com/lodging/102000000/101090000/101083600/101083507/f79dd58b.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)

### Vacation Home in Annapolis

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

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

$423 nightly

$483 total

Mar 5 - Mar 6

Total with taxes and fees

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

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

![Property grounds](https://images.trvl-media.com/lodging/105000000/104010000/104005300/104005223/ee75c514.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Rock Hall

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

10/10

Exceptional

(18 reviews)

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

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

Michael D.

$259 nightly

$286 total

Mar 5 - Mar 6

Total with taxes and fees

[](https://www.expedia.com/Rock-Hall-Hotels-Walk-To-Everything-Rock-Hall-From-This-1st-Floor-Apartment-Sleeps-4.h104005223.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/70000000/69550000/69541400/69541327/457a4a48.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)

### Vacation Home in North Beach

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

10/10

Exceptional

(19 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.

$293 nightly

$323 total

Mar 9 - Mar 10

Total with taxes and fees

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100210000/100202700/100202663/f3add354.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100210000/100202700/100202663/ab2cfa42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/101000000/100210000/100202700/100202663/7efcfe99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/101000000/100210000/100202700/100202663/465f6a52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Admiral Heights

[](https://www.expedia.com/Annapolis-Hotels-Cute-Bungalow-Blocks-To-Stadium.h100202663.Hotel-Information)

9.8/10

Exceptional

(8 reviews)

"Great property. Third time staying at property while visiting Annapolis. "

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

Holly W.

$454 nightly

$513 total

Mar 5 - Mar 6

Total with taxes and fees

[](https://www.expedia.com/Annapolis-Hotels-Cute-Bungalow-Blocks-To-Stadium.h100202663.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)

![TV, offices](https://images.trvl-media.com/lodging/106000000/105550000/105549100/105549011/f0fc07ee.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)

![Interior](https://images.trvl-media.com/lodging/106000000/105550000/105549100/105549011/91738a72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Annapolis

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

9.2/10

Wonderful

(16 reviews)

"Nice little spot, very quiet "

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

Susan S.

$321 nightly

$367 total

Mar 9 - Mar 10

Total with taxes and fees

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

![Dining](https://images.trvl-media.com/lodging/81000000/80030000/80024200/80024112/w508h683x258y0-7ad5c2e6.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)

### Vacation Home in Woolford

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

10/10

Exceptional

(53 reviews)

"Great place, will stay again"

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

Matt S.

$255 nightly

$270 total

Mar 5 - Mar 6

Total with taxes and fees

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

![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/abb760b6.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)

### Vacation Home in Chesapeak beach

[](https://www.expedia.com/Chesapeake-Beach-Hotels-Family-Beach-House-Spacious-Deck.h96341595.Hotel-Information)

9.0/10

Wonderful

(6 reviews)

"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.

$417 nightly

$439 total

Mar 17 - Mar 18

Total with taxes and fees

[](https://www.expedia.com/Chesapeake-Beach-Hotels-Family-Beach-House-Spacious-Deck.h96341595.Hotel-Information)

![Smart TV](https://images.trvl-media.com/lodging/84000000/83930000/83922000/83921931/a2c7c68e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/84000000/83930000/83922000/83921931/ce9b7709.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83930000/83922000/83921931/8ae0a25a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/84000000/83930000/83922000/83921931/21befbf7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Rock Hall

[](https://www.expedia.com/Rock-Hall-Hotels-Bayside-Cottage-Steps-From-Rock-Hall-Harbor.h83921931.Hotel-Information)

10/10

Exceptional

(2 reviews)

"Property was nicely refurbished and furnished and well equipped. The younger set especially enjoyed the 5 bikes in good condition and the large yard to play sports. All in all, a great weekend stay!"

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

Dorothy R.

$354 nightly

$375 total

Apr 1 - Apr 2

Total with taxes and fees

[](https://www.expedia.com/Rock-Hall-Hotels-Bayside-Cottage-Steps-From-Rock-Hall-Harbor.h83921931.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101900000/101897400/101897342/dc0187f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101900000/101897400/101897342/3f9288e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/102000000/101900000/101897400/101897342/ea596829.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/102000000/101900000/101897400/101897342/bb91d7f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Cape Saint Claire

[](https://www.expedia.com/Annapolis-Hotels-Neptune-By-The-Water.h101897342.Hotel-Information)

9.8/10

Exceptional

(11 reviews)

"The house had everything we needed for a comfortable stay. We would definitely recommend this place."

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

Kelly D.

$492 nightly

$561 total

Mar 5 - Mar 6

Total with taxes and fees

[](https://www.expedia.com/Annapolis-Hotels-Neptune-By-The-Water.h101897342.Hotel-Information)

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

[View all properties](https://expedia.com/Hotel-Search?startDate=2026-03-18&endDate=2026-03-19&regionId=5940&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

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## 

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## Find vacation rentals that suit your style

Private vacation homes

[](https://www.expedia.com/Hotel-Search?destination=St.+Michaels%2C+Maryland%2C+United+States+of+America&regionId=5940&latLong=38.78656%2C-76.224365&adults=2&startDate=2026-06-02&d1=2026-06-02&endDate=2026-06-05&d2=2026-06-05&lodging=VACATION_HOME)

Cottages

[](https://www.expedia.com/Hotel-Search?destination=St.+Michaels%2C+Maryland%2C+United+States+of+America&regionId=5940&latLong=38.78656%2C-76.224365&adults=2&startDate=2026-06-02&d1=2026-06-02&endDate=2026-06-05&d2=2026-06-05&lodging=COTTAGE)

Condos

[](https://www.expedia.com/Hotel-Search?destination=St.+Michaels%2C+Maryland%2C+United+States+of+America&regionId=5940&latLong=38.78656%2C-76.224365&adults=2&startDate=2026-06-02&d1=2026-06-02&endDate=2026-06-05&d2=2026-06-05&lodging=CONDO)

Houseboats

[](https://www.expedia.com/Hotel-Search?destination=St.+Michaels%2C+Maryland%2C+United+States+of+America&regionId=5940&latLong=38.78656%2C-76.224365&adults=2&startDate=2026-06-02&d1=2026-06-02&endDate=2026-06-05&d2=2026-06-05&lodging=HOUSE_BOAT)

Apartments

[](https://www.expedia.com/Hotel-Search?destination=St.+Michaels%2C+Maryland%2C+United+States+of+America&regionId=5940&latLong=38.78656%2C-76.224365&adults=2&startDate=2026-06-02&d1=2026-06-02&endDate=2026-06-05&d2=2026-06-05&lodging=APARTMENT)

Villas

[](https://www.expedia.com/Hotel-Search?destination=St.+Michaels%2C+Maryland%2C+United+States+of+America&regionId=5940&latLong=38.78656%2C-76.224365&adults=2&startDate=2026-06-02&d1=2026-06-02&endDate=2026-06-05&d2=2026-06-05&lodging=VILLA)

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## Top St. Michaels Hotel Reviews

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

### The Westin Annapolis

10/10 Excellent

"Great property"

[](https://expedia.com/Annapolis-Hotels-The-Westin-Annapolis.h1678710.Hotel-Information)

![Courtyard by Marriott Annapolis](https://images.trvl-media.com/lodging/1000000/20000/11100/11049/f531cd56_y.jpg)

### Courtyard by Marriott Annapolis

10/10 Excellent

"The room was immaculate and all the staff were friendly, professional, and able to help me with any questions I asked. "

[](https://expedia.com/Annapolis-Hotels-Courtyard-By-Marriott-Annapolis.h11049.Hotel-Information)

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

### St Michaels Inn

10/10 Excellent

"Everyone was friendly, the room was great, and even though the Inn was going through some renovations i did not find my stay impacted by them at all. Breakfast was still delicious and I never wanted for anything."

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

![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

"Perfect location, comfortable bed, clean and spacious room, cheap parking around the corner that was recommended by the staff. "

[](https://expedia.com/Annapolis-Hotels-Hilton-Garden-Inn-Annapolis-Downtown.h892213.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

"The staff was very helpful. The room was nice and there were shops & restaurants nearby."

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

"Such a cool place to stay! Water pressure wasn’t great but it’s a very old building. "

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

![Sonesta ES Suites Annapolis](https://images.trvl-media.com/lodging/1000000/10000/3000/2982/eac8c079_y.jpg)

### Sonesta ES Suites Annapolis

10/10 Excellent

"We had a great time here. The room was bright, clean, warm and fully stocked with everything we needed! The fireplace was a bonus! Close to all types of activities and food, but really serene and quiet. I will stay here again. "

[](https://expedia.com/Annapolis-Hotels-Sonesta-ES-Suites-Annapolis.h2982.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

"Cleaness,staff was welcoming,great over all well put together "

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

![Rod 'N' Reel Resort](https://images.trvl-media.com/lodging/2000000/1060000/1050500/1050433/43373394_y.jpg)

### Rod 'N' Reel Resort

10/10 Excellent

"Rooms were clean, our request to have rooms close to each other was honored. Staff were very friendly. John, bartender at the restaurant was very accommodating to our gift exchange, DJ was fun and took requests. Front desk staff were friendly and helpful with our needs, checked that our rooms were ready when we arrived early even! Two of us live in this town, but we will be back for another staycation! "

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

## Find out more about St. Michaels

**Everything you need to know about St. Michaels vacation rentals**

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the St. Michaels vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect St. Michaels vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

**St. Michaels vacation 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 low season months. For more hustle and bustle, you may prefer to visit St. Michaels in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

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

At Expedia, we put the best St. Michaels vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top 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 vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around 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.

## Explore a world of travel with Expedia

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- [Michigan Vacation Rentals ](https://www.expedia.com/Destinations-In-Michigan.d224.Vacation-Rental-Destinations)

- [Vacation Homes in St. Michaels ](https://expedia.com/St-Michaels-Private-Vacation-Homes.d5940-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Cottages in St. Michaels ](https://expedia.com/St-Michaels-Cottages.d5940-aaCottages.Travel-Guide-Accommodation)
- [Apartments in St. Michaels ](https://expedia.com/St-Michaels-Apartments.d5940-aaApartments.Travel-Guide-Accommodation)
- [B&B in St. Michaels ](https://expedia.com/St-Michaels-Bed-And-Breakfast.d5940-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Condo Rentals in St. Michaels ](https://expedia.com/St-Michaels-Condos.d5940-aaCondos.Travel-Guide-Accommodation)
- [Houseboats in St. Michaels ](https://expedia.com/St-Michaels-Houseboats.d5940-aaHouseboats.Travel-Guide-Accommodation)
- [Motels in St. Michaels ](https://expedia.com/St-Michaels-Motels.d5940-aaMotels.Travel-Guide-Accommodation)
- [Farmstay in St. Michaels ](https://expedia.com/St-Michaels-Agritourism.d5940-aaAgritourism.Travel-Guide-Accommodation)
- [Inns in St. Michaels ](https://expedia.com/St-Michaels-Inns.d5940-aaInns.Travel-Guide-Accommodation)
- [Guest Houses in St. Michaels ](https://expedia.com/St-Michaels-Guest-Houses.d5940-aaGuestHouses.Travel-Guide-Accommodation)
- [Villas in St. Michaels ](https://expedia.com/St-Michaels-Villas.d5940-aaVillas.Travel-Guide-Accommodation)
- [Cabin Rentals in St. Michaels ](https://expedia.com/St-Michaels-Cabins.d5940-aaCabins.Travel-Guide-Accommodation)
- [Lodges in St. Michaels ](https://expedia.com/St-Michaels-Lodges.d5940-aaLodges.Travel-Guide-Accommodation)
- [Resorts in St. Michaels ](https://expedia.com/St-Michaels-Resorts.d5940-aaResorts.Travel-Guide-Accommodation)

## Frequently asked questions

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

### What are some of the best vacation rentals in St. Michaels?

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

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

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

### Expedia's Latest Trends

Hotels

- [Waldorf Hotels](https://expedia.com/Waldorf-Hotels.d6057464.Travel-Guide-Hotels)
- [Ocean City Pet-friendly Hotels](https://expedia.com/Ocean-City-Hotels-Pet-Friendly-Hotel.0-0-d9151-tPetfriendlyHotel.Travel-Guide-Filter-Hotels)
- [Hagerstown Hotels](https://expedia.com/Hagerstown-Hotels.d6057475.Travel-Guide-Hotels)
- [Silver Spring Hotels](https://expedia.com/Silver-Spring-Hotels.d6891.Travel-Guide-Hotels)
- [Ocean City Hotels](https://expedia.com/Ocean-City-Hotels.d9151.Travel-Guide-Hotels)
- [Ocean City Oceanfront Hotels](https://expedia.com/Ocean-City-Hotels-Oceanfront-Hotels.0-0-d9151-tOceanfrontHotels.Travel-Guide-Filter-Hotels)
- [Ocean City Cheap Hotels](https://expedia.com/Ocean-City-Hotels-Cheap-Hotels.0-0-d9151-tCheapHotels.Travel-Guide-Filter-Hotels)
- [Bowie Hotels](https://expedia.com/Bowie-Hotels.d6278.Travel-Guide-Hotels)
- [Upper Marlboro Hotels](https://expedia.com/Upper-Marlboro-Hotels.d168650.Travel-Guide-Hotels)
- [Rockville Hotels](https://expedia.com/Rockville-Hotels.d6353.Travel-Guide-Hotels)
- [Salisbury Hotels](https://expedia.com/Salisbury-Hotels.d6057491.Travel-Guide-Hotels)
- [Aberdeen Hotels](https://expedia.com/Aberdeen-Hotels.d6044.Travel-Guide-Hotels)
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- [Frederick Hotels](https://expedia.com/Frederick-Hotels.d6057476.Travel-Guide-Hotels)
- [Annapolis Oceanfront Hotels](https://expedia.com/Annapolis-Hotels-Oceanfront-Hotels.0-0-d6034082-tOceanfrontHotels.Travel-Guide-Filter-Hotels)
- [Bel Air Hotels](https://expedia.com/Bel-Air-Hotels.d6023736.Travel-Guide-Hotels)
- [Ocean City Luxury Hotels](https://expedia.com/Ocean-City-Hotels-Luxury-Hotel.0-0-d9151-tLuxuryHotel.Travel-Guide-Filter-Hotels)
- [Gaithersburg Hotels](https://expedia.com/Gaithersburg-Hotels.d7427.Travel-Guide-Hotels)

Flights

- [Flights to Ocean City](https://expedia.com/Cheap-Flights-To-Ocean-City.d9151.Travel-Guide-Flights)

Cars

- [Car rentals in Rockville](https://expedia.com/Car-Rentals-In-Rockville.d6353.Car-Rental-Guide)
- [Car rentals in Silver Spring](https://expedia.com/Car-Rentals-In-Silver-Spring.d6891.Car-Rental-Guide)
- [Car rentals in Frederick](https://expedia.com/Car-Rentals-In-Frederick.d6057476.Car-Rental-Guide)

Activities

- [Things to do in Annapolis](https://expedia.com/Things-To-Do-In-Annapolis.d6034082.Travel-Guide-Activities)
- [Things to do in Ocean City](https://expedia.com/Things-To-Do-In-Ocean-City.d9151.Travel-Guide-Activities)

Packages

- [Ocean City Vacation Packages](https://expedia.com/Ocean-City.d9151.Destination-Travel-Guides)

Vacation Rentals

- [Vacation Rentals Ocean City](https://expedia.com/Ocean-City-Vacation-Rentals.d9151.Travel-Guide-VacationRentals)

General

- [Visit Ocean City](https://expedia.com/Ocean-City.dx9151)
- [Visit Chesapeake City](https://expedia.com/Chesapeake-City.dx177517)

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