Title: St. Michaels Vacation Rentals from $1,324: 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

[Feb 20 - Feb 22](https://www.expedia.com/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

[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 three 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 four 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)

## Our top choices for St. Michaels vacation rentals

![Marina](https://images.trvl-media.com/lodging/120000000/119340000/119331500/119331473/61e8c463.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)

![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)

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

[](https://www.expedia.com/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.

$338 nightly

$358 total

Feb 11 - Feb 12

Total with taxes and fees

[](https://www.expedia.com/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)

![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)

![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/82000000/81260000/81259300/81259255/6d418f2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sailwinds Loft at Cambridge Creek

[](https://www.expedia.com/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.

$240 nightly

$254 total

Feb 9 - Feb 10

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/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)

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

[](https://www.expedia.com/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.

$328 nightly

$347 total

Feb 12 - Feb 13

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/100000000/99690000/99684200/99684191/69bef312.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)

![Property grounds](https://images.trvl-media.com/lodging/100000000/99690000/99684200/99684191/7cf0d433.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)

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

[](https://www.expedia.com/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.

$333 nightly

$353 total

Feb 16 - Feb 17

Total with taxes and fees

[](https://www.expedia.com/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)

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

$339 nightly

$359 total

Feb 9 - Feb 10

Total with taxes and fees

[](https://www.expedia.com/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)

![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)

![Property grounds](https://images.trvl-media.com/lodging/105000000/104010000/104005300/104005223/ee75c514.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.com/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.

$259 nightly

$286 total

Feb 9 - Feb 10

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)

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

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

![Marina](https://images.trvl-media.com/lodging/85000000/84070000/84063700/84063656/c77382da.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.com/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.

$263 nightly

$279 total

Feb 17 - Feb 18

Total with taxes and fees

[](https://www.expedia.com/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)

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

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

[](https://www.expedia.com/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.

$271 nightly

$287 total

Feb 17 - Feb 18

Total with taxes and fees

[](https://www.expedia.com/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)

![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)

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

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

[](https://www.expedia.com/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.

$283 nightly

$300 total

Feb 10 - Feb 11

Total with taxes and fees

[](https://www.expedia.com/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)

![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)

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

### Waterfront Oasis of Annapolis Star

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

$363 nightly

$414 total

Feb 9 - Feb 10

Total with taxes and fees

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

![Interior](https://images.trvl-media.com/lodging/118000000/117370000/117360200/117360157/28c9186e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Luxury Pool Loft sleeps 4

[](https://www.expedia.com/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.

$343 nightly

$391 total

Feb 9 - Feb 10

Total with taxes and fees

[](https://www.expedia.com/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)

![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)

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

### Waterfront Getaway with Dock

[](https://www.expedia.com/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.

$263 nightly

$279 total

Feb 9 - Feb 10

Total with taxes and fees

[](https://www.expedia.com/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.com/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.

$369 nightly

$408 total

Feb 11 - Feb 12

Total with taxes and fees

[](https://www.expedia.com/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)

![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)

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

[](https://www.expedia.com/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.

$396 nightly

$420 total

Feb 9 - Feb 10

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

![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)

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

[](https://www.expedia.com/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

$425 nightly

$485 total

Feb 9 - Feb 10

Total with taxes and fees

[](https://www.expedia.com/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)

![Smart TV, table tennis](https://images.trvl-media.com/lodging/97000000/96120000/96117900/96117871/4d65add6.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)

![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.com/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.

$455 nightly

$482 total

Feb 10 - Feb 11

Total with taxes and fees

[](https://www.expedia.com/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)

![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)

![Interior](https://images.trvl-media.com/lodging/70000000/69550000/69541400/69541327/bf60932b.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)

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

[](https://www.expedia.com/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.

$283 nightly

$313 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)

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

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

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

![Exterior detail](https://images.trvl-media.com/lodging/100000000/99480000/99470800/99470706/9df6bc62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.com/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.

$453 nightly

$516 total

Feb 9 - Feb 10

Total with taxes and fees

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

Parole

10/10

Exceptional

(1 review)

$209 nightly

$212 total

Mar 2 - Mar 3

Total with taxes and fees

[](https://www.expedia.com/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)

![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)

![Interior](https://images.trvl-media.com/lodging/103000000/102770000/102761900/102761818/7c9eec10.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)

### Annapolis Boat Life - Overnight Stays

[](https://www.expedia.com/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.

$257 nightly

$261 total

Mar 10 - Mar 11

Total with taxes and fees

[](https://www.expedia.com/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.com/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 vacation rentals that suit your style

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=2026-05-08&d1=2026-05-08&endDate=2026-05-11&d2=2026-05-11&lodging=COTTAGE)

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=2026-05-08&d1=2026-05-08&endDate=2026-05-11&d2=2026-05-11&lodging=VACATION_HOME)

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=2026-05-08&d1=2026-05-08&endDate=2026-05-11&d2=2026-05-11&lodging=APARTMENT)

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=2026-05-08&d1=2026-05-08&endDate=2026-05-11&d2=2026-05-11&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=2026-05-08&d1=2026-05-08&endDate=2026-05-11&d2=2026-05-11&lodging=HOUSE_BOAT)

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=2026-05-08&d1=2026-05-08&endDate=2026-05-11&d2=2026-05-11&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.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

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

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

"The room was very spacious. Staff were nice. Amenities were excellent. Good location for our stay."

[](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/e773fcbe_y.jpg)

### Sonesta ES Suites Annapolis

10/10 Excellent

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

[](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

"The room was wonderful, the venue wonderful and pillows wonderful! We were there for a bluegrass festival and it was WONDERFUL!"

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

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

### Rod 'N' Reel Resort

10/10 Excellent

"Staff was great & amazing views. The room was spacious and updated. "

[](https://expedia.com/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.com/Annapolis-Hotels-Historic-Inns-Of-Annapolis.h42068.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.com/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.com/St-Michaels-Hotels-St-Michaels-Inn.h10281.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 $1,324 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
- All accommodation types in St. Michaels

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- [Florida Vacation Rentals ](https://www.expedia.com/Destinations-In-Florida.d211.Vacation-Rental-Destinations)
- [Hawaii Vacation Rentals ](https://www.expedia.com/Destinations-In-Hawaii.d213.Vacation-Rental-Destinations)
- [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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