Title: Chestertown Vacation Home Rentals from CA $175: Search Top Private Vacation Homes for Rent | Expedia.ca

 

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![Aerial summer view of colonial Chestertown on the Chesapeake Bay in Maryland USA](https://images.trvl-media.com/place/7215/2810851e-b7cc-4dfb-bf7e-dc0611ab1b49.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

# Chestertown Vacation Rentals

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## Check prices for these dates

Next weekend

[Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2025-12-12&endDate=2025-12-14&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2025-12-19&endDate=2025-12-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In one month

[Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2026-01-02&endDate=2026-01-04&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=7215&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)

## Browse Select Chestertown Vacation Homes

![Marina](https://images.trvl-media.com/lodging/85000000/84070000/84063900/84063895/c53ddff2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/85000000/84070000/84063900/84063895/aea8e7bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/85000000/84070000/84063900/84063895/89a58d5e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/85000000/84070000/84063900/84063895/da0262a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

Stevensville

9.6/10

Exceptional

(32)

"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 $131

CA $392 total

includes taxes & fees

Dec 4 - Dec 5

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

![Marina](https://images.trvl-media.com/lodging/85000000/84070000/84063700/84063656/c77382da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/85000000/84070000/84063700/84063656/b482bb5d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

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

Stevensville

9.8/10

Exceptional

(42)

"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 $110

CA $368 total

includes taxes & fees

Dec 4 - Dec 5

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

![Dining](https://images.trvl-media.com/lodging/102000000/101540000/101539300/101539294/cf034cb3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/102000000/101540000/101539300/101539294/76b495fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, stovetop, cookware/dishes/utensils](https://images.trvl-media.com/lodging/102000000/101540000/101539300/101539294/a9ce192e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/102000000/101540000/101539300/101539294/7a387636.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Amazing Modern house with a full kitchen and parking

Smyrna

9.8/10

Exceptional

(8)

"The house is a beautiful place to stay. The location was ideal for going to attractions and stores. "

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

Laurie S.

CA $251

CA $499 total

includes taxes & fees

Dec 5 - Dec 6

[](https://www.expedia.ca/Smyrna-Hotels-Amazing-Modern-House-With-A-Full-Kitchen-And-Parking.h101539294.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/113000000/112910000/112909100/112909050/cfc4be94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, in-room safe, desk, iron/ironing board](https://images.trvl-media.com/lodging/113000000/112910000/112909100/112909050/1055da7a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool](https://images.trvl-media.com/lodging/113000000/112910000/112909100/112909050/7c4173a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/113000000/112910000/112909100/112909050/3addbd27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Modern New Suite Close to US Capital and BWI Airport

Pasadena

7.0/10

Good

(2)

"Check in was super easy and he was very nice and accommodating. Location was easy enough to find and his instructions were very clear. Thank you! "

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

Brittnie A.

[](https://www.expedia.ca/Pasadena-Hotels-Modern-New-Townhouse-Close-To-US-Capital-And-BWI-Airport.h112909050.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/123000000/122710000/122706300/122706236/55c38442.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, towels, soap, toilet paper](https://images.trvl-media.com/lodging/123000000/122710000/122706300/122706236/bc0c7d40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/123000000/122710000/122706300/122706236/7a4b679d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/123000000/122710000/122706300/122706236/790b072e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Townhouse Room A

Belair - Edison

[](https://www.expedia.ca/Baltimore-Hotels-Townhouse-Room-A.h122706236.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/96000000/95980000/95979600/95979564/98344c73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/96000000/95980000/95979600/95979564/502fa10e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/96000000/95980000/95979600/95979564/8af0ae73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/96000000/95980000/95979600/95979564/a4e1c9eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hobbit House one of a kind home

Bel Air

10/10

Exceptional

(8)

"We had a great stay! "

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

Courtney H.

CA $159

CA $425 total

includes taxes & fees

Dec 8 - Dec 9

[](https://www.expedia.ca/Bel-Air-Hotels-Hobbit-House-One-Of-A-Kind-Home.h95979564.Hotel-Information)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/115000000/114590000/114588800/114588703/708da323.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/115000000/114590000/114588800/114588703/97debd4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/115000000/114590000/114588800/114588703/68e8f274.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/115000000/114590000/114588800/114588703/e33942cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Private Suite Gated Entry, Driveway Parking & Quiet Stay

Glen Burnie

8.0/10

Very good

(2)

"No problems close to everything, only gripe was it being a basement and little feet upstairs tend to be a bit lohd. However, just the bathroom alone made this property worth another stay"

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

James D.

CA $126

CA $175 total

includes taxes & fees

Dec 9 - Dec 10

[](https://www.expedia.ca/Cozy-Private-Suite-Gated-Entry.h114588703.Hotel-Information)

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

![Fridge, microwave, dishwasher, coffee/tea maker](https://images.trvl-media.com/lodging/103000000/102640000/102631200/102631144/9eb7ac3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/103000000/102640000/102631200/102631144/25541a3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/103000000/102640000/102631200/102631144/259066d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### HGTV quality, private guest suite, country getaway with hot tub & fire pit

Centreville

10/10

Exceptional

(8)

"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 $275

CA $622 total

includes taxes & fees

Dec 15 - Dec 16

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

![Interior](https://images.trvl-media.com/lodging/114000000/113280000/113272300/113272210/cc3df3d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/114000000/113280000/113272300/113272210/733d81ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/114000000/113280000/113272300/113272210/85376bca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/114000000/113280000/113272300/113272210/f9a89b51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming Pet-Friendly Stay - Near Bay & Beaches.

Annapolis

10/10

Exceptional

(6)

"The property provided the space I needed for my family. It is located in a cute neighborhood. The property was clean and the owner was very responsive to any questions that I had. I really enjoyed staying here."

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

Kristina

CA $328

CA $791 total

includes taxes & fees

Dec 8 - Dec 9

[](https://www.expedia.ca/Annapolis-Hotels-Cozy-Retreat-Near-The-Bay.h113272210.Hotel-Information)

![Marina](https://images.trvl-media.com/lodging/20000000/19010000/19008100/19008016/226d6f82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/20000000/19010000/19008100/19008016/1f4387ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/20000000/19010000/19008100/19008016/76c1b6db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, DVD player, offices](https://images.trvl-media.com/lodging/20000000/19010000/19008100/19008016/7fa2b473.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hidden Fells Point Gem / Private Courtyard Patio

Fells Point

9.6/10

Exceptional

(91)

"Lenny & his housekeeper Elviea were exceptionally helpful, funny and a delight to be with! I spent two weeks here & it was the best place I've ever stayed compared to my stays in Korea, Ireland & several other US cities. Highly recommend!"

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

Edward J.

CA $82

CA $281 total

includes taxes & fees

Dec 7 - Dec 8

[](https://www.expedia.ca/Baltimore-Hotels-At-Fells-Point-Courtyard-Your-Historically-Restored-Apartment.h19008016.Hotel-Information)

![Smart TV, books](https://images.trvl-media.com/lodging/90000000/89060000/89057700/89057630/06a8a8c9.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)

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

![Exterior](https://images.trvl-media.com/lodging/90000000/89060000/89057700/89057630/762da084.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Large 2 bedroom house with private parking in a nice neighborhood

Arnold

9.4/10

Exceptional

(34)

"This place was perfect place to stay while visiting the area. Everything was clean and the location was great for visiting Annapolis. Will stay again when we are back out this way."

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

Jim G.

CA $182

CA $456 total

includes taxes & fees

Dec 8 - Dec 9

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

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

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

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

### Neptune by the Water - Pet Friendly Fenced Yard

Cape Saint Claire

9.8/10

Exceptional

(11)

"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 $221

CA $713 total

includes taxes & fees

Dec 4 - Dec 5

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

![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)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/93000000/92310000/92309300/92309210/w1100h489x0y146-b417c676.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Hideaway Spot- Waterfront w/ Dock on Long Cove

Glen Burnie

8.6/10

Excellent

(8)

"This place had everything we needed for a great family Christmas. Responsive host. Fun times! "

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

Tammy A.

CA $152

CA $486 total

includes taxes & fees

Dec 8 - Dec 9

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

![Marina](https://images.trvl-media.com/lodging/101000000/100140000/100139800/100139799/d79202ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/101000000/100140000/100139800/100139799/a439d4f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100140000/100139800/100139799/0ad77d89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/101000000/100140000/100139800/100139799/d109a1f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Johns Hopkins Historic Renovated home - Location!

Upper Fells Point

9.4/10

Exceptional

(14)

"Location was perfect and the place was great"

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

Sharon P.

[](https://www.expedia.ca/Baltimore-Hotels-Johns-Hopkins-Historic-Renovated-Home-Location.h100139799.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/82000000/81770000/81762800/81762790/0e962c4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/82000000/81770000/81762800/81762790/c7f2698d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/82000000/81770000/81762800/81762790/0417cf18.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/82000000/81770000/81762800/81762790/9fea4520.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Exclusive Sunken Living Room Soaring Exposed Brick

Patterson Place

10/10

Exceptional

(7)

"Place was amazing. So many amenities. So close to all the tourist attractions as well. Tons of street parking even at late night. Neighborhood is nice and secure. Would certainly stay again! Communication was excellent. "

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

Mike J.

CA $214

CA $497 total

includes taxes & fees

Dec 9 - Dec 10

[](https://www.expedia.ca/Baltimore-Hotels-Exclusive-Sunken-Living-Room-Soaring-Exposed-Brick.h81762790.Hotel-Information)

![1 bedroom, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/23000000/22730000/22720500/22720424/250c9a49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/23000000/22730000/22720500/22720424/7214dd06.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/23000000/22730000/22720500/22720424/1751c2b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor spa tub](https://images.trvl-media.com/lodging/23000000/22730000/22720500/22720424/6c38888f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Romantic Hot Tub Getaway, Walking Distance to Fells Point

Upper Fells Point

10/10

Exceptional

(33)

"Awesome place.. take advice on parking when offered "

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

Steven B.

CA $101

CA $255 total

includes taxes & fees

Dec 10 - Dec 11

[](https://www.expedia.ca/Baltimore-Hotels-Romantic-Hot-Tub-Getaway.h22720424.Hotel-Information)

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

![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)

![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/100000000/99840000/99830400/99830322/23f1d475.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

Grasonville

9.6/10

Exceptional

(12)

"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 $585 total

includes taxes & fees

Dec 15 - Dec 16

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/24000000/23930000/23927100/23927080/3fe6d96d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/24000000/23930000/23927100/23927080/2ec17b55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/24000000/23930000/23927100/23927080/62f27275.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, video games](https://images.trvl-media.com/lodging/24000000/23930000/23927100/23927080/0085cedc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Luxury Parkfront Haven with Hot Tub - Beloved by Families & their Dogs

Canton

9.8/10

Exceptional

(65)

"Brandon was a thoughtful host and responded quickly. The property was lovely and so convenient. "

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

andrea s.

CA $217

CA $443 total

includes taxes & fees

Dec 21 - Dec 22

[](https://www.expedia.ca/Baltimore-Hotels-Luxury-Parkfront-Haven-With-Hot-Tub-Beloved-By-Families-Their-Dogs.h23927080.Hotel-Information)

![A heated pool](https://images.trvl-media.com/lodging/123000000/122590000/122582500/122582410/6d809621.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/123000000/122590000/122582500/122582410/5e630db3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/123000000/122590000/122582500/122582410/dc2f3672.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/123000000/122590000/122582500/122582410/e9849d32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Heated Pool • Private Backyard • Home Theater

Middletown

CA $260

CA $755 total

includes taxes & fees

Dec 15 - Dec 16

[](https://www.expedia.ca/Middletown-Hotels-Heated-Pool-Private-Backyard-Home-Theater.h122582410.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/122000000/121090000/121084800/121084764/952fef86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/122000000/121090000/121084800/121084764/a1db5475.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool](https://images.trvl-media.com/lodging/122000000/121090000/121084800/121084764/13d9abf3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/122000000/121090000/121084800/121084764/bf6c1b68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chesapeake Bay Harbor View in a central location to events/restaurants

Rock Hall

10/10

Exceptional

(2)

"House was clean, great location. Furniture needs a little updating but overall our stay was great! Would definitely stay here again."

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

Todd W.

CA $314

CA $381 total

includes taxes & fees

Dec 9 - Dec 10

[](https://www.expedia.ca/Rock-Hall-Hotels-Chesapeake-Bay-Harbor-View-In-A-Central-Location-To-Eventsrestaurants.h121084764.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.

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## Find vacation rentals that suit your style

Houseboats

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Cottages

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Private vacation homes

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Apartments

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Cabins

[](https://www.expedia.ca/Hotel-Search?destination=Chestertown%2C+Maryland%2C+United+States+of+America&regionId=7215&latLong=39.218864%2C-76.069&adults=2&startDate=2026-03-03&d1=2026-03-03&endDate=2026-03-06&d2=2026-03-06&lodging=CABIN)

Condos

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Villas

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Residences

[](https://www.expedia.ca/Hotel-Search?destination=Chestertown%2C+Maryland%2C+United+States+of+America&regionId=7215&latLong=39.218864%2C-76.069&adults=2&startDate=2026-03-03&d1=2026-03-03&endDate=2026-03-06&d2=2026-03-06&lodging=RESIDENCE)

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## Top Chestertown Hotel Reviews

![Pendry Baltimore](https://images.trvl-media.com/lodging/18000000/17400000/17395900/17395897/45fde7f6_y.jpg)

### Pendry Baltimore

10/10 Excellent

"Super nice hotel in the best part of downtown Baltimore. Will definitely stay again"

[](https://expedia.ca/Baltimore-Hotels-Sagamore-Pendry-Baltimore.h17395897.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

"Excellent hotel Really nice staff Love the valet guys "

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

![Hampton Inn Baltimore Bayview Campus](https://images.trvl-media.com/lodging/24000000/23840000/23830900/23830804/e92cee9e_y.jpg)

### Hampton Inn Baltimore Bayview Campus

10/10 Excellent

"The front desk staff was exceptional. On the first day November 26th it was a young man who was so pleasant and professional. Very friendly. Then on Thanksgiving there was a nice lady that was very accommodating to my needs traveling with 2 toddlers. Thank you for your hospitality during this holiday season. My family has stayed here every Thanksgiving for the past 5 years and will continue to do so."

[](https://expedia.ca/Baltimore-Hotels-Hampton-Inn-Baltimore-Bayview-Campus.h23830804.Hotel-Information)

![Courtyard by Marriott Baltimore Downtown/McHenry Row](https://images.trvl-media.com/lodging/43000000/42120000/42119100/42119031/fba8c798_y.jpg)

### Courtyard by Marriott Baltimore Downtown/McHenry Row

10/10 Excellent

"The staff was wonderful."

[](https://expedia.ca/Holabird-Industrial-Park-Hotels-Courtyard-By-Marriott-Baltimore-DowntownMcHenry-Row.h42119031.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

"clean and great location"

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

![Comfort Inn & Suites Chestertown](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/a1387f46_y.jpg)

### Comfort Inn & Suites Chestertown

10/10 Excellent

"Excellent hotel. Will stay there anytime I travel to the area."

[](https://expedia.ca/Chestertown-Hotels-Comfort-Inn-Suites.h1700736.Hotel-Information)

![Best Western Plus Hotel & Conference Center](https://images.trvl-media.com/lodging/1000000/20000/10300/10260/314defe9_y.jpg)

### Best Western Plus Hotel & Conference Center

10/10 Excellent

"Amazing hotel, staff was great. It was clean and I will be returning "

[](https://expedia.ca/Baltimore-Hotels-Best-Western-Plus-Hotel-Conference-Center.h10260.Hotel-Information)

![SpringHill Suites Baltimore White Marsh/Middle River](https://images.trvl-media.com/lodging/24000000/23690000/23686900/23686806/ac399738_y.jpg)

### SpringHill Suites Baltimore White Marsh/Middle River

10/10 Excellent

"Excellent stay and service "

[](https://expedia.ca/Baltimore-Hotels-SpringHill-Suites-Baltimore-White-MarshMiddle-River.h23686806.Hotel-Information)

![Quality Inn & Suites Bel Air I-95 Exit 77A](https://images.trvl-media.com/lodging/5000000/4870000/4862300/4862298/95fafc76_y.jpg)

### Quality Inn & Suites Bel Air I-95 Exit 77A

10/10 Excellent

"Yes "

[](https://expedia.ca/Edgewood-Hotels-Quality-Inn-Suites-Bel-Air-I-95-Exit-77A.h4862298.Hotel-Information)

## Find out more about Chestertown

## Chestertown Vacation Homes information

| Number of reviews | 323 |
| --- | --- |
| Accommodation | 483 Vacation Homes |
| Lowest Price | CA $175 |
| Highest Price | CA $793 |

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-   [Flights from Barclay](https://www.expedia.ca/lp/flights/553248634998993874/flights-from-barclay)
-   [Flights from Aberdeen Proving Ground](https://www.expedia.ca/lp/flights/553248634999428212/flights-from-aberdeen-proving-ground)
-   [Flights from Centreville](https://www.expedia.ca/lp/flights/88125/flights-from-centreville)
-   [Flights from Birmingham (BHX) to Aberdeen (APG)](https://www.expedia.ca/lp/flights/bhx/apg/birmingham-to-aberdeen)
-   [Flights from Boston (BOS) to Aberdeen (APG)](https://www.expedia.ca/lp/flights/bos/apg/boston-to-aberdeen)
-   [Flights from Brussels (BRU) to Aberdeen (APG)](https://www.expedia.ca/lp/flights/bru/apg/brussels-to-aberdeen)
-   [Flights from Cambridge (CGE) to Aberdeen (APG)](https://www.expedia.ca/lp/flights/cge/apg/cambridge-to-aberdeen)
-   [Flights from Charlotte (CLT) to Aberdeen (APG)](https://www.expedia.ca/lp/flights/clt/apg/charlotte-to-aberdeen)
-   [Flights from Copenhagen (CPH) to Aberdeen (APG)](https://www.expedia.ca/lp/flights/cph/apg/copenhagen-to-aberdeen)
-   [Flights from Dover (DOV) to Aberdeen (APG)](https://www.expedia.ca/lp/flights/dov/apg/dover-to-aberdeen)
-   [Flights from Detroit (DTW) to Aberdeen (APG)](https://www.expedia.ca/lp/flights/dtw/apg/detroit-to-aberdeen)
-   [Flights from Hamburg (HAM) to Aberdeen (APG)](https://www.expedia.ca/lp/flights/ham/apg/hamburg-to-aberdeen)
-   [Flights from Indianapolis (IND) to Aberdeen (APG)](https://www.expedia.ca/lp/flights/ind/apg/indianapolis-to-aberdeen)
-   [Flights from Kingston (KIN) to Aberdeen (APG)](https://www.expedia.ca/lp/flights/kin/apg/kingston-to-aberdeen)
-   [Flights from Minneapolis (MSP) to Aberdeen (APG)](https://www.expedia.ca/lp/flights/msp/apg/minneapolis-to-aberdeen)
-   [Flights from Princeton (PCT) to Aberdeen (APG)](https://www.expedia.ca/lp/flights/pct/apg/princeton-to-aberdeen)
-   [Flights from Philadelphia (PHL) to Aberdeen (APG)](https://www.expedia.ca/lp/flights/phl/apg/philadelphia-to-aberdeen)

-   [Historical Society of Kent County Maryland](https://www.expedia.ca/Historical-Society-Of-Kent-County-Maryland-Chestertown.d553248621561000400.Vacation-Attraction)
-   [Mount Harmon Plantation](https://www.expedia.ca/Mount-Harmon-Plantation-Earleville.d553248621561879694.Vacation-Attraction)
-   [Wilmer Park](https://www.expedia.ca/Wilmer-Park-Chestertown.d553248621561000402.Vacation-Attraction)

-   [Car rental Centreville](https://www.expedia.ca/Car-Rentals-In-Centreville.d88125.Car-Rental-Guide)
-   [Car rental Edgewood](https://www.expedia.ca/Car-Rentals-In-Edgewood.d10362.Car-Rental-Guide)
-   [Car rental Queenstown](https://www.expedia.ca/Car-Rentals-In-Queenstown.d56094.Car-Rental-Guide)
-   [Enterprise Rental Cars in Aberdeen Proving Ground](https://www.expedia.ca/Enterprise-Car-Rentals-In-Aberdeen-Proving-Ground.d553248634999428212-c15.Car-Rental-Guide-Suppliers)
-   [Enterprise Rental Cars in Edgewood](https://www.expedia.ca/Enterprise-Car-Rentals-In-Edgewood.d10362-c15.Car-Rental-Guide-Suppliers)

-   [Centreville Vacation Rentals](https://www.expedia.ca/Centreville-Vacation-Rentals.d88125.Travel-Guide-VacationRentals)
-   [Edgewood Vacation Rentals](https://www.expedia.ca/Edgewood-Vacation-Rentals.d10362.Travel-Guide-VacationRentals)

-   [Book Vacation Homes in Chestertown on Expedia.com](https://www.expedia.com/Chestertown-Private-Vacation-Homes.d7215-aaPrivateVacationHomes.Travel-Guide-Accommodation)