We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Holiday Apartments in Chestertown

List your property
Owner log in
Check-in
— / — / —
Check-out
— / — / —
Guests
0 rooms, 2+ guests
Distance from
1 km
Suitability
Show more
Bathrooms
Any
Amenities
Show more
Property type
Show more
Distinctive Features
Show more
Neighbourhood
32 rentals in Chestertown.
Sort by:
Tripadvisor Sort
Chestertown's Pet-Friendly Little Red Cottage, holiday rental in Chestertown

Chestertown's Pet-Friendly Little Red Cottage

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out

Carriage House Hideaway in Middle of Chestertown

0 bedrooms
0 bathrooms
Sleeps 0
Match: Sleeps
More info
Check-in
Check-out
Cottage within walking distance to the Bay!, holiday rental in Chestertown

Cottage within walking distance to the Bay!

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Beautiful Waterfront Estate - Special Summer Rates, holiday rental in Chestertown

Beautiful Waterfront Estate - Special Summer Rates

11 bedrooms
9 bathrooms
Sleeps 27
Match: Sleeps
More info
Check-in
Check-out
Eastern Shore beach cottage get-away, holiday rental in Chestertown

Eastern Shore beach cottage get-away

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
240' Private Beachfront *Kent Island Love Point-Reunions/Rehearsal Dinners, holiday rental in Chestertown

240' Private Beachfront *Kent Island Love Point-Reunions/Rehearsal Dinners

5 bedrooms
5 bathrooms
Sleeps 26
Match: Sleeps
More info
Check-in
Check-out
Secluded Waterfront Cottage on 200 acre farm near Queenstown, holiday rental in Chestertown

Secluded Waterfront Cottage on 200 acre farm near Queenstown

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Peaceful getaway convenient to local amenities including beach, boating & food, holiday rental in Chestertown

Peaceful getaway convenient to local amenities including beach, boating & food

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Life is better at the RIVER!--Cozy waterfront cottage, holiday rental in Chestertown

Life is better at the RIVER!--Cozy waterfront cottage

3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
Blissful Retreat In Rock Hall, holiday rental in Chestertown

Blissful Retreat In Rock Hall

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Save time - get the best Chestertown rentals sent straight to your email!
Waterfront with Chesapeake Sunsets, holiday rental in Chestertown

Waterfront with Chesapeake Sunsets

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Stay in the landmark Lighthouse!, holiday rental in Chestertown

Stay in the landmark Lighthouse!

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
BEAUTIFUL BAY FRONT VIEW, holiday rental in Chestertown

BEAUTIFUL BAY FRONT VIEW

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
200 steps to the beach!, holiday rental in Chestertown

200 steps to the beach!

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
rancher a half block from the bay, holiday rental in Chestertown

rancher a half block from the bay

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
5 acre estate with deep water dock and 1,700 feet of coastline, holiday rental in Chestertown

5 acre estate with deep water dock and 1,700 feet of coastline

5 bedrooms
3 bathrooms
Sleeps 15
Match: Sleeps
More info
Check-in
Check-out
Waterfront House, pier, close to Betterton Chestertown & Rockhall, holiday rental in Chestertown

Waterfront House, pier, close to Betterton Chestertown & Rockhall

4 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
More info
Check-in
Check-out
The Winehouse at Love Point Vineyards and Winery, holiday rental in Chestertown

The Winehouse at Love Point Vineyards and Winery

6 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
More info
Check-in
Check-out
Eastern Shore Getaway: Sleeps 10, Large Yard, Close To Beach, holiday rental in Chestertown

Eastern Shore Getaway: Sleeps 10, Large Yard, Close To Beach

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
A European styled retreat on Marylands Eastern Shore with Private pool, holiday rental in Chestertown

A European styled retreat on Marylands Eastern Shore with Private pool

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Victorian on Main Street, Rock Hall MD. Walk to everything! Sleeps 2-4, holiday rental in Chestertown

Victorian on Main Street, Rock Hall MD. Walk to everything! Sleeps 2-4

1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
Luxurious Home on the Chesapeake Bay, Fantastic Views, W/ Pool, holiday rental in Chestertown

Luxurious Home on the Chesapeake Bay, Fantastic Views, W/ Pool

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Overton Farm Cottage, holiday rental in Chestertown

Overton Farm Cottage

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
The Lodge on Main Street, a Victorian Apartment, walk to everything!, holiday rental in Chestertown

The Lodge on Main Street, a Victorian Apartment, walk to everything!

3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
More info
Check-in
Check-out
Love Point Waterfront, holiday rental in Chestertown

Love Point Waterfront

3 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
This is truly a Baydream!, holiday rental in Chestertown

This is truly a Baydream!

2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Serene Waterfront Cottage with dock and gorgeous views., holiday rental in Chestertown

Serene Waterfront Cottage with dock and gorgeous views.

1 bedroom
2 bathrooms
Sleeps 7
Match: Sleeps
More info
Check-in
Check-out
3BR 1BA Private Beach / Pool / Boat Launch / Pier / Golf Cart and much more!, holiday rental in Chestertown

3BR 1BA Private Beach / Pool / Boat Launch / Pier / Golf Cart and much more!

3 bedrooms
1 bathroom
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
The Cottage at Broken Spoke Winery, holiday rental in Chestertown

The Cottage at Broken Spoke Winery

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Abay Palace of Kent Narrows in a King Bed, holiday rental in Chestertown

Abay Palace of Kent Narrows in a King Bed

1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Waterfront Views and a Sandy Beach, holiday rental in Chestertown

Waterfront Views and a Sandy Beach

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Big house w/ big backyard! Everything you need in a house & stay is right here., holiday rental in Chestertown

Big house w/ big backyard! Everything you need in a house & stay is right here.

3 bedrooms
1 bathroom
Sleeps 12
Match: Sleeps
More info
Check-in
Check-out
PreviousNext
1
Frequently Asked Questions about Chestertown