Title: St. Michaels Vacation Rentals from $249: 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

[Apr 3 - Apr 5](https://www.expedia.com/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 two months

[May 15 - May 17](https://www.expedia.com/Hotel-Search?regionId=5940&startDate=2026-05-15&endDate=2026-05-17&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Jun 12 - Jun 14](https://www.expedia.com/Hotel-Search?regionId=5940&startDate=2026-06-12&endDate=2026-06-14&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jul 10 - Jul 12](https://www.expedia.com/Hotel-Search?regionId=5940&startDate=2026-07-10&endDate=2026-07-12&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)

![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)

![Exterior](https://images.trvl-media.com/lodging/100000000/99690000/99684200/99684191/7f132b5b.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.

$362 nightly

$384 total

Mar 23 - Mar 24

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/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)

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

$373 nightly

$395 total

Mar 23 - Mar 24

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)

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

![Smart TV, foosball](https://images.trvl-media.com/lodging/100000000/99840000/99830400/99830322/44a64359.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 23 - Mar 24

Total with taxes and fees

[](https://www.expedia.com/Spacious-2-Bedroom-Duplex-Located-Conveniently-Near-Route-50-East-And-West.h99830322.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/120000000/119340000/119331500/119331473/4db5aa56.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)

![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)

### 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 property was clean, accurate to the listing and to prior feedback from other visitors. We loved the area; very quaint and cute. We enjoyed our stay and would recommend it to anyone looking for a cozy place to stay. "

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

Amanda S.

$336 nightly

$356 total

Mar 22 - Mar 23

Total with taxes and fees

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

![Smart TV](https://images.trvl-media.com/lodging/104000000/103760000/103759100/103759056/4239f612.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)

![Smart TV](https://images.trvl-media.com/lodging/104000000/103760000/103759100/103759056/62242b9c.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 21 - Mar 22

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)

![Private kitchen](https://images.trvl-media.com/lodging/82000000/81260000/81259300/81259255/b3fc30c5.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)

![Interior](https://images.trvl-media.com/lodging/82000000/81260000/81259300/81259255/6d418f2b.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 21 - Mar 22

Total with taxes and fees

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

![Exterior](https://images.trvl-media.com/lodging/104000000/103590000/103584900/103584811/57f74d8a.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)

### 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.

$296 nightly

$314 total

Mar 25 - Mar 26

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/102000000/101090000/101083600/101083507/0cad4612.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)

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

### 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

$425 nightly

$485 total

Mar 22 - Mar 23

Total with taxes and fees

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

![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)

![Terrace/patio](https://images.trvl-media.com/lodging/69000000/68990000/68986300/68986275/95f44d8a.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 21 - Mar 22

Total with taxes and fees

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

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

![Dining](https://images.trvl-media.com/lodging/85000000/84070000/84063900/84063895/7d796cd2.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)

### Vacation Home in Stevensville

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

9.6/10

Exceptional

(35 reviews)

"Great stay, would do it again."

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

Brandon D.

$235 nightly

$249 total

Mar 23 - Mar 24

Total with taxes and fees

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

![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 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)

### 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.

$257 nightly

$284 total

Mar 22 - Mar 23

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, 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)

![Dining](https://images.trvl-media.com/lodging/92000000/91040000/91033700/91033683/5c5b72be.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)

![Smart TV, fireplace, books, printers](https://images.trvl-media.com/lodging/92000000/91040000/91033700/91033683/c2958ab0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Arundel on the Bay

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

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.

$478 nightly

$545 total

Mar 24 - Mar 25

Total with taxes and fees

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

![Smart TV](https://images.trvl-media.com/lodging/85000000/84070000/84063700/84063656/80cf0fdf.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)

### 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 wonderful stay! The host was incredibly kind, responsive, and helpful throughout, making everything smooth and stress-free. The house itself was a great place to stay. It is clean, comfortable, and exactly as described. We really appreciated the thoughtful touches and would happily stay here again. Highly recommended!"

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

Supriya V.

$296 nightly

$313 total

Mar 21 - Mar 22

Total with taxes and fees

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

![Exterior](https://images.trvl-media.com/lodging/97000000/96350000/96341600/96341595/b3688b5d.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)

### 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.

$419 nightly

$441 total

Mar 22 - Mar 23

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)

![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/84000000/83930000/83922000/83921931/4cfce214.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.

$341 nightly

$361 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)

![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/d0df96b9.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 crib, 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)

### Vacation Home in Cambridge

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

10/10

Exceptional

(14 reviews)

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

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

Jill C.

$497 nightly

$527 total

Mar 22 - Mar 23

Total with taxes and fees

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

![Exterior](https://images.trvl-media.com/lodging/101000000/100210000/100202700/100202663/12f61ea1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/101000000/100210000/100202700/100202663/2489f9da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/101000000/100210000/100202700/100202663/1b88ca60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100210000/100202700/100202663/6da23d79.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.

$470 nightly

$532 total

Mar 22 - Mar 23

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)

![Exterior detail](https://images.trvl-media.com/lodging/106000000/105550000/105549100/105549011/bc27c0ac.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.

$369 nightly

$421 total

Mar 21 - Mar 22

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/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)

![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/102000000/101900000/101897400/101897342/6b287c9b.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)

"Enjoyed our stay- thank you!"

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

KateriK

$504 nightly

$575 total

Mar 23 - Mar 24

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=2026-04-03&endDate=2026-04-04&regionId=5940&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## 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=2026-06-18&d1=2026-06-18&endDate=2026-06-21&d2=2026-06-21&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=2026-06-18&d1=2026-06-18&endDate=2026-06-21&d2=2026-06-21&lodging=COTTAGE)

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=2026-06-18&d1=2026-06-18&endDate=2026-06-21&d2=2026-06-21&lodging=HOUSE_BOAT)

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=2026-06-18&d1=2026-06-18&endDate=2026-06-21&d2=2026-06-21&lodging=CONDO)

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=2026-06-18&d1=2026-06-18&endDate=2026-06-21&d2=2026-06-21&lodging=APARTMENT)

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## Top St. Michaels Hotel Reviews

![Crowne Plaza Annapolis by IHG](https://images.trvl-media.com/lodging/1000000/10000/7700/7668/0f404f98_y.jpg)

### Crowne Plaza Annapolis by IHG

10/10 Excellent

"Great bar. "

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

![Hilton Garden Inn Annapolis Downtown](https://images.trvl-media.com/lodging/1000000/900000/892300/892213/8ee1610f_y.jpg)

### Hilton Garden Inn Annapolis Downtown

10/10 Excellent

"Great!"

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

![The Wildset](https://images.trvl-media.com/lodging/65000000/64420000/64410600/64410566/391fbabf_y.jpg)

### The Wildset

10/10 Excellent

"Best HOTEL EVER!!!"

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

![DoubleTree by Hilton Hotel Annapolis](https://images.trvl-media.com/lodging/1000000/10000/3100/3040/be920909_y.jpg)

### DoubleTree by Hilton Hotel Annapolis

6/10 Okay

"Yes"

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

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

### Rod 'N' Reel Resort

2/10 Terrible

"Bathroom door wouldn't close, laminate floor was popping up, no microwave in the room, fire alarm going off early in the morning, construction happening early in the morning. I've stayed at Super 8s and Motel 6s that have been better than this. It is a cheap hotel that is overpriced because you can see water from it and there are no other options nearby."

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

![Country Inn & Suites by Radisson, Annapolis, MD](https://images.trvl-media.com/lodging/1000000/150000/140400/140359/65a79802_y.jpg)

### Country Inn & Suites by Radisson, Annapolis, MD

8/10 Good

"It was wonderful having the suite on this visit, a separate room & chair for late night tv so as not to disturb my husband."

[](https://expedia.com/Annapolis-Hotels-Country-Inn-Suites-By-Radisson.h140359.Hotel-Information)

![Graduate by Hilton Annapolis](https://images.trvl-media.com/lodging/1000000/10000/900/846/ca081b22_y.jpg)

### Graduate by Hilton Annapolis

10/10 Excellent

"The hotel has cute and trendy decor. It’s located centrally nearby many restaurants and coffee shops around. Our room was clean and spacious. Check in was easy and on point. We had no issues with this hotel. This is my second Graduate hotel that I’m staying in and they are very efficient. "

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

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

### Sonesta ES Suites Annapolis

8/10 Good

"I have stayed here twice and this is a really great hotel to stay at. They also have breakfast which is great too. "

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

![Annapolis Waterfront Hotel, Autograph Collection](https://images.trvl-media.com/lodging/1000000/10000/5100/5075/76a0c2be_y.jpg)

### Annapolis Waterfront Hotel, Autograph Collection

10/10 Excellent

"Great waterfront room with roomy balcony. Gym was nice also. Can't wait for the var and restaurants to open."

[](https://expedia.com/Annapolis-Hotels-Annapolis-Waterfront-Hotel.h5075.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 $249 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

- Trending destinations on Expedia.com
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- [Florida Vacation Rentals ](https://www.expedia.com/Destinations-In-Florida.d211.Vacation-Rental-Destinations)
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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)
- [Annapolis Hotels](https://expedia.com/Annapolis-Hotels.d6034082.Travel-Guide-Hotels)
- [Cumberland Hotels](https://expedia.com/Cumberland-Hotels.d6057474.Travel-Guide-Hotels)
- [College Park Hotels](https://expedia.com/College-Park-Hotels.d6057494.Travel-Guide-Hotels)
- [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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