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Search Vacation Homes in Chestertown

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Check prices for these dates

Next weekend
27 Jun - 29 Jun
In two weeks
4 Jul - 6 Jul
In one month
18 Jul - 20 Jul
In two months
15 Aug - 17 Aug

Vacation Homes in Chestertown

Captivating Chesapeake experience
Beach

Captivating Chesapeake experience

10.0 out of 10, Exceptional, (261)
"Such a hidden gem of a spot! Pictures were exactly like the house and the owners were super responsive!"
Captivating Chesapeake experience
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Miscellaneous

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

10.0 out of 10, Exceptional, (220)
"Perfect Location - Easy Process - Comfortable Home!"
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Serene 3-bedroom waterfront newly renovated house, AC, Fast WiFi, Patio
Property grounds

Serene 3-bedroom waterfront newly renovated house, AC, Fast WiFi, Patio

10.0 out of 10, Exceptional, (1)
"We absolutely loved this place. Location and home are perfect. So relaxing! The deck was just great for a morning cup of coffee and all the birds and sounds were so peaceful! We were literally blown away by this home. The house was stocked with everything you could need. This is one of my favorite places I have stayed yet! Great job!"
Serene 3-bedroom waterfront newly renovated house, AC, Fast WiFi, Patio
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Fridge, microwave, oven, stovetop

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

10.0 out of 10, Exceptional, (28)
"Great place for gathering. Plenty of space to hang out. Kitchen is big, well stocked and great for a large crowd. "
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Luxury Waterfront Home Built for Entertaining!
6 bedrooms, iron/ironing board, WiFi, bed sheets

Luxury Waterfront Home Built for Entertaining!

2.0 out of 10, (1)
The price is SAR 2,101
SAR 3,408 total
includes taxes & fees
24 Jun - 25 Jun
Luxury Waterfront Home Built for Entertaining!
*** NEWLY RENOVATED**** Escape to a Beautiful Getaway on the Chesapeake Bay
Interior

*** NEWLY RENOVATED**** Escape to a Beautiful Getaway on the Chesapeake Bay

9.2 out of 10, Wonderful, (173)
"We throughly enjoyed our stay here! The house was absolutely spotless, check in was easy, and kitchen is well appointed. The views are beautiful too. Brian was super responsive and answered all of my questions. Can’t wait to go back! "
*** NEWLY RENOVATED**** Escape to a Beautiful Getaway on the Chesapeake Bay
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA
Fridge, microwave, oven, stovetop

Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA

10.0 out of 10, Exceptional, (25)
"Great location for our team to stay during Annapolis sail show. "
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA
5 Mi to Downtown Baltimore: Quiet Home w/ Porch
Fridge, microwave, stovetop, dishwasher

5 Mi to Downtown Baltimore: Quiet Home w/ Porch

9.6 out of 10, Exceptional, (4)
"Nice house in a quiet, safe, residential neighborhood. Clean and comfortable. Easy access to all the attractions in Baltimore. "
The price is SAR 567
SAR 1,876 total
includes taxes & fees
25 Jun - 26 Jun
5 Mi to Downtown Baltimore: Quiet Home w/ Porch
Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything
Fridge, microwave, oven, stovetop

Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything

9.8 out of 10, Exceptional, (20)
"Loved the stay, easy and functional for a larger group to get together in Annapolis. "
Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything
PERFECT LOCATION in the heart of history
Exterior

PERFECT LOCATION in the heart of history

10.0 out of 10, Exceptional, (201)
"Great weekend at this property in Annapolis! Location is within walking distance to restaurants and shopping!"
PERFECT LOCATION in the heart of history
Waterfront at "The Landing" in Historic Rock Hall, overlooking marina and pool.
Marina

Waterfront at "The Landing" in Historic Rock Hall, overlooking marina and pool.

10.0 out of 10, Exceptional, (7)
"Property was extremely well kempt. It was beautiful. We enjoyed ourselves there and would recommend it to others."
Waterfront at "The Landing" in Historic Rock Hall, overlooking marina and pool.
NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.
Parking

NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.

9.8 out of 10, Exceptional, (8)
"Three generations of family gathered here for a holiday together. The beautiful historic home is located in the heart of downtown Annapolis - activities for everyone within blocks. We opted for the chef-prepared breakfast,- a highlight!"
The price is SAR 4,237
SAR 6,259 total
includes taxes & fees
30 Jun - 1 Jul
NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.
Welcome to Bayside Breeze! One Block From Town Beach, Walk to Waterfront Dining
Outdoor dining

Welcome to Bayside Breeze! One Block From Town Beach, Walk to Waterfront Dining

10.0 out of 10, Exceptional, (44)
"Cool house within walking distance to beach, restaurant and marinas"
Welcome to Bayside Breeze! One Block From Town Beach, Walk to Waterfront Dining
Waterfront Home Private Dock, Boat,fish,Eastern shore, Betterton,Chestertown
Miscellaneous

Waterfront Home Private Dock, Boat,fish,Eastern shore, Betterton,Chestertown

9.8 out of 10, Exceptional, (87)
"In the area for a wedding. This was a great place for the family to gather in between events. Communication with the owners is top notch. We highly recommend it. "
Waterfront Home Private Dock, Boat,fish,Eastern shore, Betterton,Chestertown
5-bedroom vacation home 5 minutes from historic Charlestown
View from property

5-bedroom vacation home 5 minutes from historic Charlestown

9.8 out of 10, Exceptional, (138)
"Can’t wait to come back during warmer weather. It was a perfect over night stay. "
The price is SAR 1,347
SAR 2,430 total
includes taxes & fees
15 Jul - 16 Jul
5-bedroom vacation home 5 minutes from historic Charlestown
Beautiful Luxury waterfront Property,clean,Fully sterilized,Family oriented.
Terrace/patio

Beautiful Luxury waterfront Property,clean,Fully sterilized,Family oriented.

10.0 out of 10, Exceptional, (2)
"Terrific location. Enough bedrooms to comfortably accommodate 3 generations worth of relatives. Wonderful roof deck."
Beautiful Luxury waterfront Property,clean,Fully sterilized,Family oriented.
The Hideaway Spot- Waterfront w/ Dock on Long Cove
Smart TV

The Hideaway Spot- Waterfront w/ Dock on Long Cove

9.4 out of 10, Exceptional, (6)
"The property is lovely and the home is truly beautiful and comfortable. I highly recommend staying here; beautiful, peaceful--perfect."
The price is SAR 875
SAR 1,913 total
includes taxes & fees
15 Jul - 16 Jul
The Hideaway Spot- Waterfront w/ Dock on Long Cove
BEAUTIFULLY FURNISHED COZY ENSUITE 2BR3 BA IN UPPER FELLS POINT, BALTIMORE
Smart TV

BEAUTIFULLY FURNISHED COZY ENSUITE 2BR3 BA IN UPPER FELLS POINT, BALTIMORE

9.4 out of 10, Exceptional, (3)
"Great place, great location!"
BEAUTIFULLY FURNISHED COZY ENSUITE 2BR3 BA IN UPPER FELLS POINT, BALTIMORE
Pet-Friendly Home on Chester River w/ Dock!
Interior

Pet-Friendly Home on Chester River w/ Dock!

2.0 star property
9.8 out of 10, Exceptional, (8)
"This was a wonderful house for our family gathering. We enjoyed watching the birds, fish, and wildlife from the glassed-in porch. We cooked in the well appointed kitchen and we kayaked too. Evolve staff was top notch all around."
Pet-Friendly Home on Chester River w/ Dock!
Cozy Cape Cod nestled in the heart of Rock Hall, sleeps 8 with pond view!
Property grounds

Cozy Cape Cod nestled in the heart of Rock Hall, sleeps 8 with pond view!

10.0 out of 10, Exceptional, (21)
"Good location."
Cozy Cape Cod nestled in the heart of Rock Hall, sleeps 8 with pond view!
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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