Title: Chester Vacation Home Rentals from CA $356: Search Top Private Vacation Homes for Rent | Expedia.ca

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![Kent Narrows Maryland, USA, the narrows are just north of the Chesapeake bay and about an hour from Washington DC. Here the crabs are abundant and we had a great pick and peel crab dinner and Harrah's Crab house. Boats along this area go out each morning and pick the crabs out of the crab cages and get the catch of the day out in the Chesapeake bay . The Route 50 bridge is directly straight ahead, it the route into the Chesapeake bay bridge which is  at least 3 miles long.](https://images.trvl-media.com/place/3000440455/ea96dd54-4b86-4885-83c9-585f6f8e1fb2.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

Photo by Patricia Knorr

![](https://images.trvl-media.com/place/3000440455/ea96dd54-4b86-4885-83c9-585f6f8e1fb2.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check prices for these dates

Next weekend

[Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=3000440455&startDate=2026-01-23&endDate=2026-01-25&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=3000440455&startDate=2026-01-30&endDate=2026-02-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In one month

[Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=3000440455&startDate=2026-02-13&endDate=2026-02-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=3000440455&startDate=2026-03-13&endDate=2026-03-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Chester vacation homes

![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)

![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)

![Smart TV](https://images.trvl-media.com/lodging/85000000/84070000/84063700/84063656/80cf0fdf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Stevensville

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

9.8/10

Exceptional

(43 reviews)

"We had a great stay! The property has everything we needed and host was easy to communicate with "

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

Stephanie S.

CA $105

CA $356 total

includes taxes & fees

Jan 19 - Jan 20

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

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

![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.ca/Stevensville-Hotels-Charming-CoastalCountry-Home-W3-Acres-Sauna.h84063895.Hotel-Information)

9.6/10

Exceptional

(32 reviews)

"Very nice house! We had 3 people in our party and didn't want to rent 2 hotel rooms, this is a great way to save money and enjoy time together. "

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

Pamela

CA $112

CA $359 total

includes taxes & fees

Jan 18 - Jan 19

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

![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)

### Vacation Home in North Beach

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

10/10

Exceptional

(17 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.

CA $113

CA $448 total

includes taxes & fees

Jan 19 - Jan 20

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

![Fridge, microwave, dishwasher, coffee/tea maker](https://images.trvl-media.com/lodging/103000000/102640000/102631200/102631144/3bbc0763.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books, stereo](https://images.trvl-media.com/lodging/103000000/102640000/102631200/102631144/274adae6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/103000000/102640000/102631200/102631144/ee0975c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/103000000/102640000/102631200/102631144/3c8498e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Centreville

[](https://www.expedia.ca/Centreville-Hotels-Private.h102631144.Hotel-Information)

10/10

Exceptional

(8 reviews)

"Such a great property. Second time coming and planning to come back next summer as well! Highly recommend! Amazing host!"

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

Renee P.

CA $274

CA $620 total

includes taxes & fees

Jan 19 - Jan 20

[](https://www.expedia.ca/Centreville-Hotels-Private.h102631144.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)

![Exterior](https://images.trvl-media.com/lodging/100000000/99840000/99830400/99830322/737f2153.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)

### Vacation Home in Grasonville

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

CA $347

CA $586 total

includes taxes & fees

Jan 16 - Jan 17

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

![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/84000000/83970000/83966500/83966408/c0808af9.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)

![Smart TV](https://images.trvl-media.com/lodging/84000000/83970000/83966500/83966408/993af54b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in North Beach

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

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.

CA $139

CA $568 total

includes taxes & fees

Jan 21 - Jan 22

[](https://www.expedia.ca/North-Beach-Hotels-Huge-Beach-Bungalow-WYard.h83966408.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)

![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)

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

### Vacation Home in Cape Saint Claire

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

9.8/10

Exceptional

(11 reviews)

"Very nice home, location, close to our family and activities. Enjoyed our stay and would recommend to other renters looking for spaciousness and holiness that a hotel cannot provide! "

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

Lisa S.

CA $253

CA $842 total

includes taxes & fees

Jan 16 - Jan 17

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

![TV, books, offices](https://images.trvl-media.com/lodging/106000000/105400000/105392900/105392845/5550ff75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/106000000/105400000/105392900/105392845/24eb74b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, books, offices](https://images.trvl-media.com/lodging/106000000/105400000/105392900/105392845/a507208b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, books, offices](https://images.trvl-media.com/lodging/106000000/105400000/105392900/105392845/98da8700.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Edgewater

[](https://www.expedia.ca/Edgewater-Hotels-Escape-To-Our-Beautifully-Renovated-Home-In-The-Heart-Of-The-Scenic-Mayo-Peninsula.h105392845.Hotel-Information)

10/10

Exceptional

(3 reviews)

"House was clean and comfortable. Great layout. "

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

Kristin G.

CA $206

CA $777 total

includes taxes & fees

Feb 9 - Feb 10

[](https://www.expedia.ca/Edgewater-Hotels-Escape-To-Our-Beautifully-Renovated-Home-In-The-Heart-Of-The-Scenic-Mayo-Peninsula.h105392845.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/93000000/92090000/92080200/92080111/w4000h1746x0y0-fc1adaf1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/93000000/92090000/92080200/92080111/0017edf6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/93000000/92090000/92080200/92080111/2b0352ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/93000000/92090000/92080200/92080111/w4000h1729x0y0-ae4201db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Rock Hall

[](https://www.expedia.ca/Rock-Hall-Hotels-BAYSIDE-BUNGALOW.h92080111.Hotel-Information)

10/10

Exceptional

(52 reviews)

"Very quaint and quiet place to stay. Very relaxing."

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

Roger

CA $250

CA $384 total

includes taxes & fees

Jan 21 - Jan 22

[](https://www.expedia.ca/Rock-Hall-Hotels-BAYSIDE-BUNGALOW.h92080111.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/90000000/89060000/89057700/89057630/e5c30638.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89060000/89057700/89057630/a70d4b32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/90000000/89060000/89057700/89057630/86c425c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/90000000/89060000/89057700/89057630/3a482076.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Arnold

[](https://www.expedia.ca/Arnold-Hotels-Large-2-Bedroom-House-Private-Parking-Nice-Neighborhood.h89057630.Hotel-Information)

9.4/10

Exceptional

(36 reviews)

"Just as advertised. Clean and quiet."

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

Robert B.

CA $175

CA $445 total

includes taxes & fees

Jan 18 - Jan 19

[](https://www.expedia.ca/Arnold-Hotels-Large-2-Bedroom-House-Private-Parking-Nice-Neighborhood.h89057630.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/102000000/101090000/101083600/101083507/3334515c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/102000000/101090000/101083600/101083507/0cab7732.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Annapolis

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

CA $239

CA $673 total

includes taxes & fees

Jan 21 - Jan 22

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

![Smart TV, fireplace](https://images.trvl-media.com/lodging/100000000/99480000/99470800/99470706/8156a7b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Hillsmere

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

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.

CA $235

CA $738 total

includes taxes & fees

Jan 18 - Jan 19

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

![Outdoor spa tub](https://images.trvl-media.com/lodging/97000000/96310000/96305200/96305193/8bc5c09a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/97000000/96310000/96305200/96305193/28989db9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/97000000/96310000/96305200/96305193/6e5a14cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/97000000/96310000/96305200/96305193/75c4ec47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Edgewater

[](https://www.expedia.ca/Edgewater-Hotels-London-Towne-Bungalow-WLoft-Walk-To-The-Beach.h96305193.Hotel-Information)

8.8/10

Excellent

(3 reviews)

"Very cute house. It was exactly what I was looking for. "

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

Collin G.

CA $222

CA $697 total

includes taxes & fees

Feb 5 - Feb 6

[](https://www.expedia.ca/Edgewater-Hotels-London-Towne-Bungalow-WLoft-Walk-To-The-Beach.h96305193.Hotel-Information)

![Smart TV](https://images.trvl-media.com/lodging/93000000/92310000/92309300/92309210/w1100h506x0y137-5f725067.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/93000000/92310000/92309300/92309210/w642h780x229y0-93850baa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/93000000/92310000/92309300/92309210/w1100h508x0y136-4ba3382c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/93000000/92310000/92309300/92309210/w1100h506x0y137-97b0328a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Glen Burnie

[](https://www.expedia.ca/Glen-Burnie-Hotels-The-Hideaway-Spot-Waterfront-W-Dock-On-Long-Cove.h92309210.Hotel-Information)

8.6/10

Excellent

(8 reviews)

"The property is lovely and the home is truly beautiful and comfortable. I highly recommend staying here; beautiful, peaceful--perfect."

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

Jeffrey S.

CA $151

CA $486 total

includes taxes & fees

Jan 20 - Jan 21

[](https://www.expedia.ca/Glen-Burnie-Hotels-The-Hideaway-Spot-Waterfront-W-Dock-On-Long-Cove.h92309210.Hotel-Information)

![Smart TV](https://images.trvl-media.com/lodging/117000000/116010000/116005700/116005601/0100abcb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116010000/116005700/116005601/8aaef683.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/117000000/116010000/116005700/116005601/681a375c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/117000000/116010000/116005700/116005601/10e31f36_edited_f301.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Shady Side

[](https://www.expedia.ca/Shady-Side-Hotels-Peaceful-2-Bedroom-2-Bathroom-House-With-WiFi-And-AC-In-Serene-Shady-Side.h116005601.Hotel-Information)

10/10

Exceptional

(4 reviews)

"Would stay here again "

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

Thomas D.

CA $225

CA $628 total

includes taxes & fees

Jan 21 - Jan 22

[](https://www.expedia.ca/Shady-Side-Hotels-Peaceful-2-Bedroom-2-Bathroom-House-With-WiFi-And-AC-In-Serene-Shady-Side.h116005601.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/125000000/124830000/124829800/124829757/f552eabe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/125000000/124830000/124829800/124829757/c9619fa9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, internet, bed sheets](https://images.trvl-media.com/lodging/125000000/124830000/124829800/124829757/4d8e2703.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, towels, soap](https://images.trvl-media.com/lodging/125000000/124830000/124829800/124829757/28adc57c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Herald Harbor

[](https://www.expedia.ca/Crownsville-Hotels-Cute.h124829757.Hotel-Information)

CA $113

CA $327 total

includes taxes & fees

Jan 16 - Jan 17

[](https://www.expedia.ca/Crownsville-Hotels-Cute.h124829757.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/111000000/110590000/110587800/110587715/dab63ee1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/111000000/110590000/110587800/110587715/d0b78f7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach](https://images.trvl-media.com/lodging/111000000/110590000/110587800/110587715/76eea0ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/111000000/110590000/110587800/110587715/99c8bbb0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Edgewater

[](https://www.expedia.ca/Edgewater-Hotels-New-Golden-Anchor-Retreat-Lux-Living.h110587715.Hotel-Information)

10/10

Exceptional

(2 reviews)

"The property was beautiful with plenty of space to have a getaway with friends. The host was super communicative when we had issues with check in. Would highly recommend staying here!"

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

Sam A.

CA $285

CA $904 total

includes taxes & fees

Jan 19 - Jan 20

[](https://www.expedia.ca/Edgewater-Hotels-New-Golden-Anchor-Retreat-Lux-Living.h110587715.Hotel-Information)

![Smart TV, fireplace, foosball, table tennis](https://images.trvl-media.com/lodging/76000000/75720000/75710800/75710733/084c9639.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/76000000/75720000/75710800/75710733/0431981f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/76000000/75720000/75710800/75710733/ce9756b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/76000000/75720000/75710800/75710733/8f3dc26a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Homewood

[](https://www.expedia.ca/Annapolis-Hotels-Charming-Historic-Home-15-Miles-To-USNA-And-1-Mile-To-Marine-Corps-Stadium.h75710733.Hotel-Information)

9.8/10

Exceptional

(8 reviews)

"Our family gathered for a special celebration and loved the home! It was roomy and had everything we needed for our stay. The location was perfect for getting around."

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

Jeanie W.

CA $262

CA $659 total

includes taxes & fees

Jan 21 - Jan 22

[](https://www.expedia.ca/Annapolis-Hotels-Charming-Historic-Home-15-Miles-To-USNA-And-1-Mile-To-Marine-Corps-Stadium.h75710733.Hotel-Information)

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

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

![Outdoor dining](https://images.trvl-media.com/lodging/101000000/100210000/100202700/100202663/98bec3d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

### Vacation Home in Admiral Heights

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

9.8/10

Exceptional

(8 reviews)

"We loved the layout, location, and porch- quality time with family with plenty to do and close USNA. We will stay here again!"

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

Tammy L.

CA $237

CA $770 total

includes taxes & fees

Jan 19 - Jan 20

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

![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)

![Outdoor spa tub](https://images.trvl-media.com/lodging/92000000/91040000/91033700/91033683/825e8c03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Arundel on the Bay

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

CA $312

CA $723 total

includes taxes & fees

Jan 27 - Jan 28

[](https://www.expedia.ca/Annapolis-Hotels-Charming-Cottage-With-Hot-Tub-1-Block-From-The-Bay.h91033683.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=2026-01-29&endDate=2026-01-30&regionId=3000440455&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=Chester%2C+Maryland%2C+United+States+of+America&regionId=3000440455&latLong=38.975391%2C-76.289398&adults=2&startDate=2026-04-15&d1=2026-04-15&endDate=2026-04-18&d2=2026-04-18&lodging=VACATION_HOME)

Apartments

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Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Maryland%2C+United+States+of+America&regionId=3000440455&latLong=38.975391%2C-76.289398&adults=2&startDate=2026-04-15&d1=2026-04-15&endDate=2026-04-18&d2=2026-04-18&lodging=COTTAGE)

Houseboats

[](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Maryland%2C+United+States+of+America&regionId=3000440455&latLong=38.975391%2C-76.289398&adults=2&startDate=2026-04-15&d1=2026-04-15&endDate=2026-04-18&d2=2026-04-18&lodging=HOUSE_BOAT)

Condos

[](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Maryland%2C+United+States+of+America&regionId=3000440455&latLong=38.975391%2C-76.289398&adults=2&startDate=2026-04-15&d1=2026-04-15&endDate=2026-04-18&d2=2026-04-18&lodging=CONDO)

Villas

[](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Maryland%2C+United+States+of+America&regionId=3000440455&latLong=38.975391%2C-76.289398&adults=2&startDate=2026-04-15&d1=2026-04-15&endDate=2026-04-18&d2=2026-04-18&lodging=VILLA)

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## Top Chester Hotel Reviews

![Country Inn & Suites by Radisson, Annapolis, MD](https://images.trvl-media.com/lodging/1000000/150000/140400/140359/d2b7f950_y.jpg)

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

10/10 Excellent

"Wonderful staff, great options for breakfast, room is perfect and quiet and clean. The amenities work nicely, gym is great and Thai is where I would stay again in the future. "

[](https://expedia.ca/Annapolis-Hotels-Country-Inn-Suites-By-Radisson.h140359.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 great and the staff was super nice. "

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

"Great "

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

"Kind staff, clean room, and nice accommodations!"

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

![Hyatt Place Kent Narrows & Marina](https://images.trvl-media.com/lodging/78000000/77980000/77974900/77974873/35e0cb86_y.jpg)

### Hyatt Place Kent Narrows & Marina

10/10 Excellent

"The room is clean and staff was courteous "

[](https://expedia.ca/Grasonville-Hotels-Hyatt-Place-Kent-Narrows-Marina.h77974873.Hotel-Information)

![SpringHill Suites by Marriott Annapolis](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364028/80b99d82_y.jpg)

### SpringHill Suites by Marriott Annapolis

10/10 Excellent

"We use this property for business travel .Good clean property, nice location. Good breakfast and coffee. Reasonably priced (except parking fee)"

[](https://expedia.ca/Annapolis-Hotels-SpringHill-Suites-By-Marriott-Annapolis.h1364028.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

"Very nice and neat hotel in good location. Staff are wonderful"

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

![Hampton Inn & Suites Annapolis](https://images.trvl-media.com/lodging/1000000/70000/64200/64115/23865424_y.jpg)

### Hampton Inn & Suites Annapolis

10/10 Excellent

"Everything was great about my stay. From checking in to checking out! The front desk staff as well as housekeeping were extremely helpful and kind! I look forward to my next visit!"

[](https://expedia.ca/Annapolis-Hotels-Hampton-Inn-Suites-Annapolis.h64115.Hotel-Information)

![Annapolis Waterfront Hotel, Autograph Collection](https://images.trvl-media.com/lodging/1000000/10000/5100/5075/2011e31d_y.jpg)

### Annapolis Waterfront Hotel, Autograph Collection

10/10 Excellent

"Very welcoming and room very clean."

[](https://expedia.ca/Annapolis-Hotels-Annapolis-Waterfront-Hotel.h5075.Hotel-Information)

## Find out more about Chester

## Chester Vacation Homes information

| Number of reviews | 284                |
| ----------------- | ------------------ |
| Accommodation     | 659 Vacation Homes |
| Lowest Price      | CA $356            |
| Highest Price     | CA $904            |

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