Holiday Homes in Chestertown

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Our top choices for Chestertown holiday homes

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

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Grasonville
9.6 out of 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
Joe C.
The price is NZ$689
includes taxes & fees
3 Mar - 4 Mar
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

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

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.6 out of 10, Exceptional, (34 reviews)
"Great stay, would do it again."
United States
Brandon D.
The price is NZ$417
includes taxes & fees
4 Mar - 5 Mar
Charming Coastal/Country Home w/3 Acres & Sauna!

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

Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Stevensville
9.8 out of 10, Exceptional, (43 reviews)
"We had a great stay! The property has everything we needed and host was easy to communicate with "
United States
Stephanie S.
The price is NZ$405
includes taxes & fees
3 Mar - 4 Mar
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Amazing Modern house with a full kitchen and parking

Amazing Modern house with a full kitchen and parking
Smyrna
9.2 out of 10, Wonderful, (9 reviews)
"The house is a beautiful place to stay. The location was ideal for going to attractions and stores. "
United States
Laurie S.
The price is NZ$580
includes taxes & fees
3 Mar - 4 Mar
Amazing Modern house with a full kitchen and parking

Large 2 bedroom house with private parking in a nice neighborhood

Large 2 bedroom house with private parking in a nice neighborhood
Arnold
9.4 out of 10, Exceptional, (36 reviews)
"Super clean place, great communication from the host, and home is exactly as described and shown in pictures. "
United States
Traci L.
The price is NZ$527
includes taxes & fees
3 Mar - 4 Mar
Large 2 bedroom house with private parking in a nice neighborhood

Charming 2-bedroom house in Aberdeen with WiFi and AC

Charming 2-bedroom house in Aberdeen with WiFi and AC
Aberdeen
8.0 out of 10, Very good, (12 reviews)
"Pleasant stay"
United States
Yommali G.
The price is NZ$155
includes taxes & fees
15 Mar - 16 Mar
Charming 2-bedroom house in Aberdeen with WiFi and AC

Historic Row Home | Hot Tub - 1 Block from Gate 1!

Historic Row Home | Hot Tub - 1 Block from Gate 1!
Historic District
10.0 out of 10, Exceptional, (5 reviews)
"Perfect location. Very clean. Had everything we needed and front porch swing was a nice bonus. Would stay here every visit! "
United States
Tracie B.
The price is NZ$1,163
includes taxes & fees
3 Mar - 4 Mar
Historic Row Home | Hot Tub - 1 Block from Gate 1!

Hidden Fells Point Gem / Private Courtyard Patio

Hidden Fells Point Gem / Private Courtyard Patio
Fells Point
9.6 out of 10, Exceptional, (94 reviews)
"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
Edward J.
The price is NZ$356
includes taxes & fees
3 Mar - 4 Mar
Hidden Fells Point Gem / Private Courtyard Patio

5-bedroom vacation home 5 minutes from historic Charlestown

5-bedroom vacation home 5 minutes from historic Charlestown
Perryville
9.8 out of 10, Exceptional, (148 reviews)
"Magical and made tons of family wedding memories. What a perfect house on the river!! We will be booking again"
United States
Mary D.
The price is NZ$867
includes taxes & fees
3 Mar - 4 Mar
5-bedroom vacation home 5 minutes from historic Charlestown

Boho Oasis 2 Bed 1 Bath home in Baltimore City!

Boho Oasis 2 Bed 1 Bath home in Baltimore City!
Berea
10.0 out of 10, Exceptional, (3 reviews)
"House kept very clean and neighborhood was really quiet at night! Will be staying again."
United States
Pai’Syn
The price is NZ$441
includes taxes & fees
10 Mar - 11 Mar
Boho Oasis 2 Bed 1 Bath home in Baltimore City!

Bayside Cottage steps from Rock Hall Harbor

Bayside Cottage steps from Rock Hall Harbor
Rock Hall
10.0 out of 10, Exceptional, (2 reviews)
"Property was nicely refurbished and furnished and well equipped. The younger set especially enjoyed the 5 bikes in good condition and the large yard to play sports. All in all, a great weekend stay!"
United States
Dorothy R.
The price is NZ$631
includes taxes & fees
1 Apr - 2 Apr
Bayside Cottage steps from Rock Hall Harbor

Cozy 2br home w/ parking in downtown Annapolis

Cozy 2br home w/ parking in downtown Annapolis
Historic District
10.0 out of 10, Exceptional, (75 reviews)
"Welcoming host, great location and easy parking "
United States
Chris B.
The price is NZ$540
includes taxes & fees
24 Mar - 25 Mar
Cozy 2br home w/ parking in downtown Annapolis

Neptune by the Water - Pet Friendly Fenced Yard

Neptune by the Water - Pet Friendly Fenced Yard
Cape Saint Claire
9.8 out of 10, Exceptional, (11 reviews)
"The house had everything we needed for a comfortable stay. We would definitely recommend this place."
United States
Kelly D.
The price is NZ$918
includes taxes & fees
3 Mar - 4 Mar
Neptune by the Water - Pet Friendly Fenced Yard

Glen Burnie Hideaway - Pet friendly with easy access to multiple attractions.

Glen Burnie Hideaway - Pet friendly with easy access to multiple attractions.
Glen Burnie
10.0 out of 10, Exceptional, (7 reviews)
"This home had everything we needed and more. I say home because it felt like home when we walked in. Super cozy and comfortable. The basement was perfect for our family playing card games. Kitchen had everything we needed. We'll definitely see if this place is avaliable on our next visit. "
United States
Jena F.
The price is NZ$527
includes taxes & fees
4 Mar - 5 Mar
Glen Burnie Hideaway - Pet friendly with easy access to multiple attractions.

Glen Burnie Escape - Pet friendly with easy access to multiple attractions.

Glen Burnie Escape - Pet friendly with easy access to multiple attractions.
Glen Burnie
10.0 out of 10, Exceptional, (23 reviews)
"We enjoyed this property so much that we stayed here again just 4 months later."
United States
Kim C.
The price is NZ$635
includes taxes & fees
3 Mar - 4 Mar
Glen Burnie Escape - Pet friendly with easy access to multiple attractions.

Cozy Private Family Palace near BWI, Pet-Friendly

Cozy Private Family Palace near BWI, Pet-Friendly
Glen Burnie
9.8 out of 10, Exceptional, (23 reviews)
"Nice place and good location "
United States
FRANKLIN S.
The price is NZ$787
includes taxes & fees
10 Mar - 11 Mar
Cozy Private Family Palace near BWI, Pet-Friendly

Luxury Waterfront Home Built for Entertaining!

Luxury Waterfront Home Built for Entertaining!
Abingdon
9.0 out of 10, Wonderful, (9 reviews)
"Excellent communication with host, we had everything we needed"
United States
Kelly W.
The price is NZ$1,928
includes taxes & fees
3 Mar - 4 Mar
Luxury Waterfront Home Built for Entertaining!

Charming 1-bedroom basement in enjoyable Aberdeen with WiFi, AC

Charming 1-bedroom basement in enjoyable Aberdeen with WiFi, AC
Aberdeen
The price is NZ$380
includes taxes & fees
7 Mar - 8 Mar
Charming 1-bedroom basement in enjoyable Aberdeen with WiFi, AC

Abingdon Haven Hideaway

Abingdon Haven Hideaway
Abingdon
7.0 out of 10, Good, (2 reviews)
"We made good use of this rental, it was convenient to all our family & activities. Host is very kind & quickly helpful on request. The main problem with a basement apt is that the thermostat is usually upstairs in the main house, but host was most accommodating about temperature control. We rested well here and had a nice week."
United States
Pam L.
The price is NZ$624
includes taxes & fees
3 Mar - 4 Mar
Abingdon Haven Hideaway

The Hideaway Spot- Waterfront w/ Dock on Long Cove

The Hideaway Spot- Waterfront w/ Dock on Long Cove
Glen Burnie
8.8 out of 10, Excellent, (9 reviews)
"The property is lovely and the home is truly beautiful and comfortable. I highly recommend staying here; beautiful, peaceful--perfect."
United States
Jeffrey S.
The price is NZ$646
includes taxes & fees
11 Mar - 12 Mar
The Hideaway Spot- Waterfront w/ Dock on Long Cove
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

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Chestertown Holiday Homes information

Number of reviews
509
Accommodation
486 Holiday Homes
Lowest Price
NZ$155
Highest Price
NZ$1,928