Title: Sherwood Vacation Rentals from CA $366: Short-Term Rentals for 2026 | Expedia.ca

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![Gardens and large home at Sherwood Gardens Park, in Baltimore, M](https://images.trvl-media.com/place/6034722/0bcbb682-8042-4738-8664-a432e128f170.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

![](https://images.trvl-media.com/place/6034722/0bcbb682-8042-4738-8664-a432e128f170.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check prices for these dates

In two weeks

[Apr 24 - Apr 26](https://www.expedia.ca/Hotel-Search?regionId=6034722&startDate=2026-04-24&endDate=2026-04-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Jun 5 - Jun 7](https://www.expedia.ca/Hotel-Search?regionId=6034722&startDate=2026-06-05&endDate=2026-06-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Jul 3 - Jul 5](https://www.expedia.ca/Hotel-Search?regionId=6034722&startDate=2026-07-03&endDate=2026-07-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jul 31 - Aug 2](https://www.expedia.ca/Hotel-Search?regionId=6034722&startDate=2026-07-31&endDate=2026-08-02&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Sherwood vacation rentals

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

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

![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)

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

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

Stevensville

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.

CA $108

CA $366 total

includes taxes & fees

Apr 8 - Apr 9

[](https://www.expedia.ca/Stevensville-Hotels-Charming-CoastalCountry-Home-W3-Acres-Sauna.h84063895.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/82000000/81260000/81259300/81259255/6d418f2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

### Sailwinds Loft at Cambridge Creek

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

Cambridge

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.

CA $216

CA $355 total

includes taxes & fees

Apr 7 - Apr 8

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

![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)

![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)

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

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

CA $349

CA $588 total

includes taxes & fees

Apr 7 - Apr 8

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

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

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

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

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

Cambridge

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.

CA $272

CA $576 total

includes taxes & fees

Apr 14 - Apr 15

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

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

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

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

Downtown Cambridge

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.

CA $258

CA $567 total

includes taxes & fees

Apr 20 - Apr 21

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

![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)

![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)

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

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

Downtown Cambridge

10/10

Exceptional

(11 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.

CA $286

CA $594 total

includes taxes & fees

Apr 14 - Apr 15

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

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

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

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

Stevensville

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.

CA $108

CA $366 total

includes taxes & fees

Apr 12 - Apr 13

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

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

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

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

CA $223

CA $482 total

includes taxes & fees

Apr 20 - Apr 21

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

![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/102000000/101090000/101083600/101083507/3334515c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

CA $240

CA $673 total

includes taxes & fees

Apr 7 - Apr 8

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

![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/ae401628.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)

### Family Beach House: Spacious Deck, Grill & Views

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

Chesapeak beach

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.

CA $237

CA $620 total

includes taxes & fees

Apr 7 - Apr 8

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

![Outdoor dining](https://images.trvl-media.com/lodging/64000000/63650000/63641700/63641659/a9c3170d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/64000000/63650000/63641700/63641659/2b76d904.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, DVD player, stereo](https://images.trvl-media.com/lodging/64000000/63650000/63641700/63641659/ba3c3f81.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/64000000/63650000/63641700/63641659/f39074a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sunset Breezes - quiet waterfront retreat

[](https://www.expedia.ca/Cambridge-Hotels-Sunset-Breezes-Quiet-Waterfront-Retreat.h63641659.Hotel-Information)

Dorchester County

10/10

Exceptional

(43 reviews)

"Clean, quiet, comfy"

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

Deborah V.

CA $420

CA $529 total

includes taxes & fees

Apr 12 - Apr 13

[](https://www.expedia.ca/Cambridge-Hotels-Sunset-Breezes-Quiet-Waterfront-Retreat.h63641659.Hotel-Information)

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

![4 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/104000000/103640000/103638100/103638094/f8f86577.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

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

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

Prince Frederick

10/10

Exceptional

(10 reviews)

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

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

Olivia M.

CA $370

CA $698 total

includes taxes & fees

Apr 7 - Apr 8

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

![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)

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

### Waterfront Oasis of Annapolis Star

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

Annapolis

10/10

Exceptional

(81 reviews)

"Owners were great hosts. Loved this property!"

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

Thomas

CA $345

CA $646 total

includes taxes & fees

Apr 7 - Apr 8

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

![Iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/127000000/126960000/126959900/126959889/bfd2d8bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/127000000/126960000/126959900/126959889/2fa8c51f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/127000000/126960000/126959900/126959889/9dc11bbc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/127000000/126960000/126959900/126959889/19325de4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Pint-Sized on Poplar - Contemporary Cambridge Apartment Across from RAR Brewing

[](https://www.expedia.ca/Cambridge-Hotels-Pint-Sized-On-Poplar-Contemporary-Cambridge-Apartment-Across-From-RAR-Brewing.h126959889.Hotel-Information)

Downtown Cambridge

CA $156

CA $316 total

includes taxes & fees

Apr 13 - Apr 14

[](https://www.expedia.ca/Cambridge-Hotels-Pint-Sized-On-Poplar-Contemporary-Cambridge-Apartment-Across-From-RAR-Brewing.h126959889.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/70000000/69550000/69541400/69541327/42bbbfcb.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.ca/North-Beach-Hotels-Plant-Filled-Oasis-Near-Beach-Town-With-Passes-Tips.h69541327.Hotel-Information)

North Beach

10/10

Exceptional

(19 reviews)

"Delightful one-night stay! Place was clean, quiet, convenient and very comfortable. Especially grateful that our beloved dog was welcomed"

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

Elaine D.

CA $166

CA $523 total

includes taxes & fees

Apr 12 - Apr 13

[](https://www.expedia.ca/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/101000000/100210000/100202700/100202663/841d93b3.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/b6d125f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/101000000/100210000/100202700/100202663/e8979b62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/101000000/100210000/100202700/100202663/b3be55ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cute bungalow blocks to Stadium

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

Admiral Heights

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.

CA $276

CA $724 total

includes taxes & fees

Apr 7 - Apr 8

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

![Smart TV, books](https://images.trvl-media.com/lodging/114000000/113530000/113522300/113522263/0806f7bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach nearby](https://images.trvl-media.com/lodging/114000000/113530000/113522300/113522263/4429fbeb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/114000000/113530000/113522300/113522263/a1c3089f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/114000000/113530000/113522300/113522263/9a42128d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

[](https://www.expedia.ca/Prince-Frederick-Hotels-Kick-Back-And-Enjoy-The-Chesapeake-This-3-Bedroom.h113522263.Hotel-Information)

Prince Frederick

9.8/10

Exceptional

(6 reviews)

"Our family had a great stay. Thank you!"

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

Colleen G.

CA $286

CA $597 total

includes taxes & fees

Apr 14 - Apr 15

[](https://www.expedia.ca/Prince-Frederick-Hotels-Kick-Back-And-Enjoy-The-Chesapeake-This-3-Bedroom.h113522263.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)

![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.ca/Woolford-Hotels-Waterfront-Getaway-With-Dock.h80024112.Hotel-Information)

Woolford

10/10

Exceptional

(54 reviews)

"Great place, will stay again"

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

Matt S.

CA $321

CA $387 total

includes taxes & fees

Apr 29 - Apr 30

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

![Oven, stovetop](https://images.trvl-media.com/lodging/121000000/120860000/120855800/120855751/009658d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/121000000/120860000/120855800/120855751/1e2f03eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/121000000/120860000/120855800/120855751/f21ef3f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Miscellaneous](https://images.trvl-media.com/lodging/121000000/120860000/120855800/120855751/f5323c3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 40' Bristol sailboat with spectacular views

[](https://www.expedia.ca/Stevensville-Hotels-40-Bristol-Sailboat-With-Spectacular-Views.h120855751.Hotel-Information)

Stevensville

CA $418

CA $602 total

includes taxes & fees

Apr 7 - Apr 8

[](https://www.expedia.ca/Stevensville-Hotels-40-Bristol-Sailboat-With-Spectacular-Views.h120855751.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)

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

![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)

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

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

Cambridge

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.

CA $466

CA $867 total

includes taxes & fees

Apr 21 - Apr 22

[](https://www.expedia.ca/Cambridge-Hotels-WATERFRONT-3-Bed-Oasis-On-2-Acres-Sleeps-8.h83066154.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.ca/Hotel-Search?startDate=2026-04-20&endDate=2026-04-21&regionId=6034722&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.ca/Hotel-Search?destination=Sherwood%2C+Maryland%2C+United+States+of+America&regionId=6034722&latLong=38.761505%2C-76.31884&adults=2&startDate=2026-07-05&d1=2026-07-05&endDate=2026-07-08&d2=2026-07-08&lodging=VACATION_HOME)

Condos

[](https://www.expedia.ca/Hotel-Search?destination=Sherwood%2C+Maryland%2C+United+States+of+America&regionId=6034722&latLong=38.761505%2C-76.31884&adults=2&startDate=2026-07-05&d1=2026-07-05&endDate=2026-07-08&d2=2026-07-08&lodging=CONDO)

Apartments

[](https://www.expedia.ca/Hotel-Search?destination=Sherwood%2C+Maryland%2C+United+States+of+America&regionId=6034722&latLong=38.761505%2C-76.31884&adults=2&startDate=2026-07-05&d1=2026-07-05&endDate=2026-07-08&d2=2026-07-08&lodging=APARTMENT)

Houseboats

[](https://www.expedia.ca/Hotel-Search?destination=Sherwood%2C+Maryland%2C+United+States+of+America&regionId=6034722&latLong=38.761505%2C-76.31884&adults=2&startDate=2026-07-05&d1=2026-07-05&endDate=2026-07-08&d2=2026-07-08&lodging=HOUSE_BOAT)

Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Sherwood%2C+Maryland%2C+United+States+of+America&regionId=6034722&latLong=38.761505%2C-76.31884&adults=2&startDate=2026-07-05&d1=2026-07-05&endDate=2026-07-08&d2=2026-07-08&lodging=COTTAGE)

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## Top Sherwood 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

"The Crowne Plaza is absolutely beautiful and clean. The staff, amenities and room were top notch. The area is phenomenal and close to everything! I will definitely stay at this location again."

[](https://expedia.ca/Annapolis-Hotels-Crowne-Plaza-Annapolis.h7668.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

"It was the perfect location for our activities "

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

![The Westin Annapolis](https://images.trvl-media.com/lodging/2000000/1680000/1678800/1678710/73550aaf_y.jpg)

### The Westin Annapolis

10/10 Excellent

"Excellent experience. "

[](https://expedia.ca/Annapolis-Hotels-The-Westin-Annapolis.h1678710.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

"Hotel was nice. The rooms were very clean and nice. The only thing was the outside was a little dirty people throwing trash on the ground. But my overall experience was very good. Staff was excellent."

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

![Inn at Perry Cabin](https://images.trvl-media.com/lodging/1000000/20000/14600/14576/12b2f8fd_y.jpg)

### Inn at Perry Cabin

8/10 Good

"Disappointing. The hotel is lovely but the staff are in training mode and don’t get things quite right. They didn’t tell us there was an Easter brunch so we missed breakfast on Sunday as they had booked out the dining room and everything in town was already full. The food was nice but relatively expensive. When it rains there is nowhere to sit that is not the room or the pub. The pool despite being advertised was not yet open for the season which was of the main reasons we chose the hotel. "

[](https://expedia.ca/St-Michaels-Hotels-Inn-At-Perry-Cabin.h14576.Hotel-Information)

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

### Courtyard by Marriott Annapolis

4/10 Poor

"Front of the building looks new but the inside looks very very old , like a hotel in the middle of nowhere."

[](https://expedia.ca/Annapolis-Hotels-Courtyard-By-Marriott-Annapolis.h11049.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

10/10 Excellent

"Convenient and easy to get to from Veterans Highway!!!"

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

![The Inn at Chesapeake Bay Beach Club](https://images.trvl-media.com/lodging/13000000/12410000/12402300/12402244/986ce82e_y.jpg)

### The Inn at Chesapeake Bay Beach Club

10/10 Excellent

"Beautiful Boutique Hotel on the eastern shore right over the Bay bridge great restaurant Little market that’s amazing nice spa and very pretty and accommodating hotel would highly recommend it! "

[](https://expedia.ca/Annapolis-Hotels-The-Inn-At-Chesapeake-Bay-Beach-Club.h12402244.Hotel-Information)

![Historic Inns of Annapolis](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/e84869d1_y.jpg)

### Historic Inns of Annapolis

10/10 Excellent

"Great historic building… felt like home away from home."

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

## Find out more about Sherwood

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.  
  
As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Sherwood. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.   
  
It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.   

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- [Vacation Homes in Sherwood ](https://expedia.ca/Sherwood-Private-Vacation-Homes.d6034722-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Cottages in Sherwood ](https://expedia.ca/Sherwood-Cottages.d6034722-aaCottages.Travel-Guide-Accommodation)
- [Apartments in Sherwood ](https://expedia.ca/Sherwood-Apartments.d6034722-aaApartments.Travel-Guide-Accommodation)
- [Condo Rentals in Sherwood ](https://expedia.ca/Sherwood-Condos.d6034722-aaCondos.Travel-Guide-Accommodation)
- [B&B in Sherwood ](https://expedia.ca/Sherwood-Bed-And-Breakfast.d6034722-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Houseboats in Sherwood ](https://expedia.ca/Sherwood-Houseboats.d6034722-aaHouseboats.Travel-Guide-Accommodation)
- [Farmstay in Sherwood ](https://expedia.ca/Sherwood-Agritourism.d6034722-aaAgritourism.Travel-Guide-Accommodation)
- [Inns in Sherwood ](https://expedia.ca/Sherwood-Inns.d6034722-aaInns.Travel-Guide-Accommodation)
- [Guest Houses in Sherwood ](https://expedia.ca/Sherwood-Guest-Houses.d6034722-aaGuestHouses.Travel-Guide-Accommodation)
- [Cabin Rentals in Sherwood ](https://expedia.ca/Sherwood-Cabins.d6034722-aaCabins.Travel-Guide-Accommodation)
- [Villas in Sherwood ](https://expedia.ca/Sherwood-Villas.d6034722-aaVillas.Travel-Guide-Accommodation)
- [Motels in Sherwood ](https://expedia.ca/Sherwood-Motels.d6034722-aaMotels.Travel-Guide-Accommodation)
- [Resorts in Sherwood ](https://expedia.ca/Sherwood-Resort-Hotels.d6034722-aaResortHotels.Travel-Guide-Accommodation)

## Frequently asked questions

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