Chestertown Holiday Homes from £71: Search Holiday Homes in Chestertown

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Our top choices for Chestertown holiday homes

3 bedrooms, iron/ironing board, free WiFi, bed sheets

Amazing Modern house with a full kitchen and parking

Smyrna

9.2 out of 10, Wonderful, (9 reviews)

9.2/10

Wonderful

(9 reviews)

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

Laurie S.

The price is £202

£202

includes taxes & fees

18 Feb - 19 Feb

Amazing Modern house with a full kitchen and parking

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

Stevensville

9.8 out of 10, Exceptional, (43 reviews)

9.8/10

Exceptional

(43 reviews)

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

Stephanie S.

The price is £197

£197

includes taxes & fees

18 Feb - 19 Feb

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

4 bedrooms, desk, iron/ironing board, free WiFi

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

Stevensville

9.6 out of 10, Exceptional, (32 reviews)

9.6/10

Exceptional

(32 reviews)

"Great stay, would do it again."

Brandon D.

The price is £197

£197

includes taxes & fees

17 Feb - 18 Feb

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

Charming 2-bedroom house in Aberdeen with WiFi and AC

Aberdeen

8.0 out of 10, Very good, (12 reviews)

8.0/10

Very good

(12 reviews)

"Pleasant stay"

Yommali G.

The price is £71

£71

includes taxes & fees

19 Feb - 20 Feb

Charming 2-bedroom house in Aberdeen with WiFi and AC

Boho Oasis 2 Bed 1 Bath home in Baltimore City!

Berea

10.0 out of 10, Exceptional, (2 reviews)

10/10

Exceptional

(2 reviews)

"House kept very clean and neighborhood was really quiet at night! Will be staying again."

Pai’Syn

The price is £198

£198

includes taxes & fees

18 Feb - 19 Feb

Boho Oasis 2 Bed 1 Bath home in Baltimore City!

Hobbit House one of a kind home

Bel Air

10.0 out of 10, Exceptional, (9 reviews)

10/10

Exceptional

(9 reviews)

"We had a great stay! "

Courtney H.

The price is £209

£209

includes taxes & fees

22 Feb - 23 Feb

Hobbit House one of a kind home

1 bedroom, desk, iron/ironing board, travel cot

Hidden Fells Point Gem / Private Courtyard Patio

Fells Point

9.6 out of 10, Exceptional, (94 reviews)

9.6/10

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!"

Edward J.

The price is £150

£150

includes taxes & fees

22 Feb - 23 Feb

Hidden Fells Point Gem / Private Courtyard Patio

1 bedroom, iron/ironing board, WiFi, bed sheets

High Tide Haven Suite

Kent County

The price is £150

£150

includes taxes & fees

4 Mar - 5 Mar

High Tide Haven Suite

The Hideaway Spot- Waterfront w/ Dock on Long Cove

Glen Burnie

8.6 out of 10, Excellent, (8 reviews)

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."

Jeffrey S.

The price is £254

£254

includes taxes & fees

18 Feb - 19 Feb

The Hideaway Spot- Waterfront w/ Dock on Long Cove

2 bedrooms, iron/ironing board, free WiFi, bed sheets

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

Grasonville

9.6 out of 10, Exceptional, (12 reviews)

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. "

Joe C.

The price is £310

£310

includes taxes & fees

13 Feb - 14 Feb

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

2 bedrooms, desk, iron/ironing board, free WiFi

Large 2 bedroom house with private parking in a nice neighborhood

Arnold

9.4 out of 10, Exceptional, (36 reviews)

9.4/10

Exceptional

(36 reviews)

"This house was perfect for my husband and I, plus two daughters! We loved the location and how clean the unit was. The beds were comfortable and there were plenty of towels and all the things we needed for our weekend. We will definitely stay here again!"

Emily B.

The price is £245

£245

includes taxes & fees

1 Mar - 2 Mar

Large 2 bedroom house with private parking in a nice neighborhood

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

Historic District

10.0 out of 10, Exceptional, (5 reviews)

10/10

Exceptional

(5 reviews)

"Perfect location. Very clean. Had everything we needed and front porch swing was a nice bonus. Would stay here every visit! "

Tracie B.

The price is £510

£510

includes taxes & fees

23 Feb - 24 Feb

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

3 bedrooms, iron/ironing board, WiFi, bed sheets

JVA LUXURY HOUSING

Smyrna

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

"The house was clean and wonderful. I highly recommend!"

Daryl C.

The price is £424

£424

includes taxes & fees

18 Feb - 19 Feb

JVA LUXURY HOUSING

Cozy Private Suite Gated Entry, Driveway Parking & Quiet Stay

Glen Burnie

8.0 out of 10, Very good, (2 reviews)

8.0/10

Very good

(2 reviews)

"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"

James D.

The price is £95

£95

includes taxes & fees

13 Feb - 14 Feb

Cozy Private Suite Gated Entry, Driveway Parking & Quiet Stay

5 bedrooms, iron/ironing board, free WiFi, bed sheets

Smart TV, DVD player, books, video library

5-bedroom vacation home 5 minutes from historic Charlestown

Perryville

9.8 out of 10, Exceptional, (147 reviews)

9.8/10

Exceptional

(147 reviews)

"Magical and made tons of family wedding memories. What a perfect house on the river!! We will be booking again"

Mary D.

The price is £388

£388

includes taxes & fees

18 Feb - 19 Feb

5-bedroom vacation home 5 minutes from historic Charlestown

1 bedroom, desk, iron/ironing board, free WiFi

Secluded Tiny Pool House -Private Pool -Self Check in

Glen Burnie

8.6 out of 10, Excellent, (10 reviews)

8.6/10

Excellent

(10 reviews)

"Absolutely loved it, very quiet and peaceful, Jordan is an excellent host"

Robert F.

The price is £82

£82

includes taxes & fees

17 Feb - 18 Feb

Secluded Tiny Pool House -Private Pool -Self Check in

family-friendly 2-bedroom home in Baltimore with WiFi, AC, Pool table, Poker

Berea

9.6 out of 10, Exceptional, (5 reviews)

9.6/10

Exceptional

(5 reviews)

"Everything was great, easy check in and simple and clean space!!! Amazing thank you"

michael t.

The price is £233

£233

includes taxes & fees

18 Feb - 19 Feb

family-friendly 2-bedroom home in Baltimore with WiFi, AC, Pool table, Poker

Luxury 3-bed Townhome W/Modern finishes & Easy access to Baltimore &Annapolis.

Ferndale

10.0 out of 10, Exceptional, (2 reviews)

10/10

Exceptional

(2 reviews)

"Nice place. Donald was accommodating. Good location. "

William D.

The price is £281

£281

includes taxes & fees

18 Feb - 19 Feb

Luxury 3-bed Townhome W/Modern finishes & Easy access to Baltimore &Annapolis.

Entire House by the Fells Point, JHU.

Upper Fells Point

9.4 out of 10, Exceptional, (34 reviews)

9.4/10

Exceptional

(34 reviews)

"Nice location, comfy beds"

Paul C.

The price is £215

£215

includes taxes & fees

18 Feb - 19 Feb

Entire House by the Fells Point, JHU.

Cute, Cozy 2-bedroom house in near Annapolis with water access

Herald Harbor

The price is £164

£164

includes taxes & fees

13 Feb - 14 Feb

Cute, Cozy 2-bedroom house in near Annapolis with water access

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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