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Holiday Homes in Chestertown

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Check prices for these dates

Next weekend
10 Oct - 12 Oct
In two weeks
17 Oct - 19 Oct
In one month
31 Oct - 2 Nov
In two months
28 Nov - 30 Nov

Featured Holiday Homes in Chestertown

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, (36)
"Fabulous place. We’ll be booking again next year. "
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Luxury Waterfront Executive Family Home Annapolis with All Amenities
Outdoor dining

Luxury Waterfront Executive Family Home Annapolis with All Amenities

7.4 out of 10, Good, (3)
"Very beautiful, uniquely designed home on the water. There were 2 bedrooms on the first floor making in it easy for our elderly quests. The main suite was great for our young adults to stay in together with 2 kings, sectional and multiple love sacs. Plenty of seating throughout the home both inside and out. "
Luxury Waterfront Executive Family Home Annapolis with All Amenities
Charming Historic Townhouse Steps From USNA
Fridge, microwave, oven, stovetop

Charming Historic Townhouse Steps From USNA

10.0 out of 10, Exceptional, (30)
"It was great!"
Charming Historic Townhouse Steps From USNA
BAYSIDE BUNGALOW
Outdoor dining

BAYSIDE BUNGALOW

10.0 out of 10, Exceptional, (50)
"Wonderful quiet night in Rock Hall. Quick walk to Blue Heron Oyster for dinner. "
The price is NZ$525
includes taxes & fees
30 Sept - 1 Oct
BAYSIDE BUNGALOW
Large 2 bedroom house with private parking in a nice neighborhood
Smart TV, books

Large 2 bedroom house with private parking in a nice neighborhood

9.4 out of 10, Exceptional, (28)
"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."
The price is NZ$565
includes taxes & fees
30 Sept - 1 Oct
Large 2 bedroom house with private parking in a nice neighborhood
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Marina

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

10.0 out of 10, Exceptional, (233)
"This was a wonderful historic home to vacation in"
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Cozy home with fenced in yard-Dog Friendly . 2 block walk to historic downtown!
Outdoor dining

Cozy home with fenced in yard-Dog Friendly . 2 block walk to historic downtown!

9.6 out of 10, Exceptional, (62)
"The wife and myself agreed this was a great place to stay with 2 French bulldogs fenced in yard and nice and cool and nice and clean"
Cozy home with fenced in yard-Dog Friendly . 2 block walk to historic downtown!
Sailor's Sunrise Cottage - Chesapeake Bay
Outdoor spa tub

Sailor's Sunrise Cottage - Chesapeake Bay

9.4 out of 10, Exceptional, (53)
"It was represented very well. I would definitely recommend for getting away from crowds. NEAT place,yes you are at the water! Would give it a 4.7 overall.! "
Sailor's Sunrise Cottage - Chesapeake Bay
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, (8)
"Terrific location. Enough bedrooms to comfortably accommodate 3 generations worth of relatives. Wonderful roof deck."
Beautiful Luxury waterfront Property,clean,Fully sterilized,Family oriented.
Cozy 2br home w/ parking in downtown Annapolis
Marina

Cozy 2br home w/ parking in downtown Annapolis

10.0 out of 10, Exceptional, (71)
"The house was clean and all amenities were provided. It was also very walkable to many restuarants and the dock street location in town. Would highly recomment this house for your next stay"
The price is NZ$824
includes taxes & fees
27 Oct - 28 Oct
Cozy 2br home w/ parking in downtown Annapolis
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, (29)
"Great location for our team to stay during Annapolis sail show. "
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA
NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.
Fridge, microwave, oven, stovetop

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

9.4 out of 10, Exceptional, (14)
"Our group had a great time! This house was super convenient location and easily walkable to Main Street. Thank you!"
The price is NZ$2,149
includes taxes & fees
13 Oct - 14 Oct
NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.
Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !
Property grounds

Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !

9.4 out of 10, Exceptional, (89)
"This property was a great place for a family to all relax together, play games, and enjoy the water!"
Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !
25-50% Off~Private Beach~Hot Tub~Fire Table~
Terrace/patio

25-50% Off~Private Beach~Hot Tub~Fire Table~

10.0 out of 10, Exceptional, (29)
"Excellent property, great communication with the hosts. Quite and relaxing"
25-50% Off~Private Beach~Hot Tub~Fire Table~
Charming garden row home, easy 4 block walk to the heart of Annapolis.
Exterior

Charming garden row home, easy 4 block walk to the heart of Annapolis.

10.0 out of 10, Exceptional, (119)
"We felt so comfortable and relaxed in this home away from home - it was beautiful and the location was perfect - so close to downtown - we were able to walk everywhere! "
Charming garden row home, easy 4 block walk to the heart of Annapolis.
Circa 1900 Home in the Heart of Historic Downtown Chestertown
Property grounds

Circa 1900 Home in the Heart of Historic Downtown Chestertown

10.0 out of 10, Exceptional, (74)
"Great house, will stay again in the future. "
Circa 1900 Home in the Heart of Historic Downtown Chestertown
Entire Townhouse in Rock Hall
Fridge, microwave, oven, stovetop

Entire Townhouse in Rock Hall

10.0 out of 10, Exceptional, (31)
"House was exactly as advertised. Quite community. Close to shopping, dining and beach! "
Entire Townhouse in Rock Hall
Parkside Comfort & Spaciousness-Family Friendly
Fridge, microwave, oven, stovetop

Parkside Comfort & Spaciousness-Family Friendly

9.8 out of 10, Exceptional, (57)
"Seven of us slept and prepared food comfortably while visiting sites in Baltimore, Phiadelphia, and DC. Teens are tall but managed the low ceilings in basement with really nice blow up mattress. Everything was clean and owner was very responsive and kind. Well provided for supporting kids (younger particularlly with stroller, games. etc). Enjoyed stay!"
Parkside Comfort & Spaciousness-Family Friendly
421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!
Fridge, microwave, oven, stovetop

421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!

10.0 out of 10, Exceptional, (122)
"Early summer stay and the house, especially the pool, was very clean and tidy. Relaxing and secluded outdoor area with a larger than expected pool for the kids to enjoy. About 0.5 miles to the center of town with excellent restaurants less than 0.25 miles away in Eastport. "
421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!
Stunning, Large Historic Annapolis Home, Steps to Downtown, Private Driveway!
Fridge, microwave, oven, stovetop

Stunning, Large Historic Annapolis Home, Steps to Downtown, Private Driveway!

10.0 out of 10, Exceptional, (29)
"We came to Annapolis from FL and CA for a family reunion to celebrate my mom’s 90th … the property is perfectly located and very well maintained… can’t wait to return! "
Stunning, Large Historic Annapolis Home, Steps to Downtown, Private Driveway!
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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Top Chestertown Hotel Reviews

Fairfield Inn & Suites by Marriott White Marsh

Fairfield Inn & Suites by Marriott White Marsh

10/10 Excellent
"As is my usual review and stay at Fairfield Inn and Suites by Marriott, in White Marsh, MD was excellent: friendly staff always with a smile on their face, along with the cleaning crew during the day: very friendly and helpful. Everyone was willing to "go the extra yard" in order to make one's stay memorable.... and a desirable destination to lodge again. "
Joe 4-night trip
Posted 3 days ago
Fairfield Inn & Suites by Marriott White Marsh

Find out more about Chestertown

Find out more about Chestertown

Chestertown Holiday Homes information

Number of reviews
1,125
Accommodation
483 Holiday Homes
Lowest Price
NZ$525
Highest Price
NZ$2,149

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