Vacation Rentals & House Rentals in Chestertown

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Wireless Internet
Air conditioning
Swimming pool
Private pool

Heated pool
Private indoor pool
Balcony or terrace
Washing machine
Garden
Internet access
DVD player
Grill
Fireplace
Cot available
High chair
Sea view
Safe
Dishwasher
Children's pool
Shared outdoor pool (unheated)
Shared indoor pool
Private outdoor pool (heated)
Private outdoor pool (unheated)
Pool or snooker table
Cribs
Ceiling Fans
Clothes dryer
Games room
Table tennis
Shared outdoor pool (heated)
Swing set or jungle gym
Fax machine
Microwave
Toaster
Iron
Hair dryer
Stove
Fridge
Freezer
Linen provided
Video player
Towels provided
Bicycles available
Climbing frame
Trampoline
Private fishing lake or river
Staffed property
Boat available
Housekeeping Included

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Pets allowed
Parking
Car not required
Children under 5

Smoking allowed
Non-Smoking property
Smoking - Ask
Wheelchair adapted
Wheelchair accessible

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Horse riding
Beach or lakeside relaxation
City breaks
Walking trips

Tennis in town
Water sports
Fishing
Cycling trips
Golf course on site or within 15 min walk
Golf within 30mins drive
Waterfront
Mountain Views

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6 Houses

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Vintage Bungalow-cozy, walk to shops, water, free pkg.

Annapolis house

3 bedrooms
2 bathrooms

sleeps 6

Match: Horse riding

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Price per night from

$475

Eat..Sleep..Fish..Repeat! Who needs a desk (there is one upstairs) when you can

Stevensville house

4 bedrooms
2 bathrooms

sleeps 12

Match: Horse riding

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Price per night from

$801

Chesapeake Bay Getaway™ | Waterfront Experience with Pier!

Edgewater house

2 bedrooms
1 bathroom

sleeps 8

Match: Horse riding

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Price per night from

$572

DOLCE VIDA AT Kent Island- 4 bedrooms House for rent-SLEEPS 10-12

Chester house

4 bedrooms
3 bathrooms

sleeps 10

Match: Horse riding

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Price per night from

$1,944

Annapolis Charm™ Waterfront Chesapeake Bay Getaway - Private Pier - Near USNA

Cape Saint Claire house

2 bedrooms
1 bathroom

sleeps 6

Match: Horse riding

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Price per night from

$401

Beautiful Historical Home with a Private Studio for 2 in Baltimore/ Parkville

Parkville house

4 bedrooms
1 bathroom

sleeps 2

Match: Horse riding

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Price per night from

$114

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Ocean City 145 properties
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Florida 19,951 properties
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Chestertown Rentals

Per night

6 Houses

Vintage Bungalow-cozy, walk to shops, water, free pkg.

Eat..Sleep..Fish..Repeat! Who needs a desk (there is one upstairs) when you can

Chesapeake Bay Getaway™ | Waterfront Experience with Pier!

DOLCE VIDA AT Kent Island- 4 bedrooms House for rent-SLEEPS 10-12

Annapolis Charm™ Waterfront Chesapeake Bay Getaway - Private Pier - Near USNA

Beautiful Historical Home with a Private Studio for 2 in Baltimore/ Parkville

Viewing 6 of 6
rentals in Chestertown

Also consider

Chestertown Rentals

Per night

6 Houses

Vintage Bungalow-cozy, walk to shops, water, free pkg.

Eat..Sleep..Fish..Repeat! Who needs a desk (there is one upstairs) when you can

Chesapeake Bay Getaway™ | Waterfront Experience with Pier!

DOLCE VIDA AT Kent Island- 4 bedrooms House for rent-SLEEPS 10-12

Annapolis Charm™ Waterfront Chesapeake Bay Getaway - Private Pier - Near USNA

Beautiful Historical Home with a Private Studio for 2 in Baltimore/ Parkville

Viewing 6 of 6rentals in Chestertown

Also consider

Viewing 6 of 6
rentals in Chestertown