Top 50 Chestertown Vacation Rentals

Houses (44)
Beachfront (26)
Golf rental (25)

Explore a selection of Chestertown vacation rentals

Historic Retreat With River, Garden And Marina Views
Guests6
Bedrooms3
Bathrooms2
Wonderful 5 / 5
$220 avg/night
3 beds
2 Bathrooms
Guests 6
9 reviews
Waterfront w/Deepwater Pier Walking Distance to Downtown...
Guests8
Bedrooms4
Bathrooms3
Wonderful 5 / 5
$500 avg/night
4 beds
3 Bathrooms
Guests 8
6 reviews
Victorian Hideaway: Beautiful Exterior, Modern interior
Guests8
Bedrooms4
Bathrooms2
Wonderful 5 / 5
$174 avg/night
4 beds
2 Bathrooms
Guests 8
4 reviews
New Listing! Chestertown's Pet-Friendly Little Red Cottage
Guests4
Bedrooms2
Bathroom1
Wonderful 0 / 5
$225 avg/night
2 beds
1 Bathroom
Guests 4
Bed & Breakfast: Brampton Bed and Breakfast Inn - Simone's Retreat
Guests2
Bedroom1
Bathroom1
Wonderful 0 / 5
$205 avg/night
1 bed
1 Bathroom
Guests 2
Water Front Retreat - Sunrise and Sunset Water Views
Guests8
Bedrooms3
Bathrooms3
Wonderful 5 / 5
$295 avg/night
3 beds
3 Bathrooms
Guests 8
66 reviews
Eastern Shore River Retreat with Dock, Jon Boat, Kayaks, Fishing...
Guests8
Bedrooms3
Bathrooms2
Wonderful 5 / 5
$225 avg/night
3 beds
2 Bathrooms
Guests 8
15 reviews
Victorian on Main Street, Rock Hall MD. Walk to everything! Sleeps...
Guests4
Bedroom1
Bathroom1
Wonderful 4.9 / 5
$75 avg/night
1 bed
1 Bathroom
Guests 4
15 reviews
Chesapeake Bay Waterfront Home, Huge Deck, Spectacular Sunsets, 2...
Guests12
Bedrooms4
Bathrooms3
Wonderful 4.8 / 5
$307 avg/night
4 beds
3 Bathrooms
Guests 12
24 reviews
Stunning 7-Acre Chesapeake Bay Estate
Guests10
Bedrooms5
Bathrooms5
Wonderful 4.9 / 5
$652 avg/night
5 beds
5 Bathrooms
Guests 10
26 reviews
Private Lakefront Home on 17 acres in historic town, w/ a Canoe...
Guests18
Bedrooms5
Bathrooms4
Wonderful 4.9 / 5
$417 avg/night
5 beds
4 Bathrooms
Guests 18
21 reviews
Eastern Shore Getaway: Sleeps 10, Large Yard, Close To Beach
Guests10
Bedrooms4
Bathrooms2
Wonderful 4.7 / 5
$167 avg/night
4 beds
2 Bathrooms
Guests 10
24 reviews
Eastern Shore beach cottage get-away
Guests5
Bedrooms2
Bathrooms2
Wonderful 5 / 5
$196 avg/night
2 beds
2 Bathrooms
Guests 5
27 reviews
Chester River House with Views
Guests7
Bedrooms3
Bathroom1
Wonderful 4.6 / 5
$150 avg/night
3 beds
1 Bathroom
Guests 7
36 reviews
Love Point Waterfront
Guests12
Bedrooms3
Bathrooms3
Wonderful 4.6 / 5
$290 avg/night
3 beds
3 Bathrooms
Guests 12
42 reviews
The Lodge on Main Street, a Victorian Apartment, walk to...
Guests9
Bedrooms3
Bathrooms2
Wonderful 4.9 / 5
$103 avg/night
3 beds
2 Bathrooms
Guests 9
16 reviews
Beautiful Retreat Located in Rock Hall - walk to everything!
Guests10
Bedrooms4
Bathrooms2
Wonderful 5 / 5
$131 avg/night
4 beds
2 Bathrooms
Guests 10
21 reviews
Beautiful Cottage On Maryland's Eastern Shore
Guests8
Bedrooms3
Bathrooms2
Wonderful 5 / 5
$233 avg/night
3 beds
2 Bathrooms
Guests 8
26 reviews
EASTERN SHORE Maryland --2 minute walk to beach; Quintessential...
Guests11
Bedrooms6
Bathrooms2
Wonderful 4.8 / 5
$286 avg/night
6 beds
2 Bathrooms
Guests 11
17 reviews
Quiet Peaceful Country Home With Water Front Views of Swan Creek
Guests8
Bedrooms4
Bathrooms2
Wonderful 4.9 / 5
$279 avg/night
4 beds
2 Bathrooms
Guests 8
19 reviews
Eastern Shore Get Away
Guests5
Bedroom1
Bathroom1
Wonderful 4.9 / 5
$117 avg/night
1 bed
1 Bathroom
Guests 5
35 reviews
Waterfront Cottage With Pier, Pool And Amazing Sunsets
Guests8
Bedrooms3
Bathroom1
Wonderful 4 / 5
$271 avg/night
3 beds
1 Bathroom
Guests 8
5 reviews
Lakefront Private Apartment
Guests5
Bedroom1
Bathroom1
Wonderful 4.9 / 5
$140 avg/night
1 bed
1 Bathroom
Guests 5
8 reviews
rancher a half block from the bay
Guests8
Bedrooms3
Bathroom1
Wonderful 4.8 / 5
$150 avg/night
3 beds
1 Bathroom
Guests 8
13 reviews
Secluded Waterfront Cottage on 200 acre farm near Queenstown
Guests8
Bedrooms4
Bathrooms2
Wonderful 4.9 / 5
$250 avg/night
4 beds
2 Bathrooms
Guests 8
22 reviews
Wow! Secluded waterfront home on Maryland's Charming Eastern Shore
Guests8
Bedrooms4
Bathrooms3
Wonderful 4.9 / 5
$600 avg/night
4 beds
3 Bathrooms
Guests 8
10 reviews
Quiet peaceful Home with Water Front Views of Swan Creek
Guests4
Bedrooms2
Bathroom1
Wonderful 5 / 5
$242 avg/night
2 beds
1 Bathroom
Guests 4
7 reviews
Rock Hall Home With Pond, Only 6 Minutes to Town Center, Nicely...
Guests8
Bedrooms3
Bathrooms2
Wonderful 4.9 / 5
$160 avg/night
3 beds
2 Bathrooms
Guests 8
10 reviews
- Farmhouse On Wye Lake- Totally Remodeled in 2015 -Perfect...
Guests10
Bedrooms5
Bathrooms2
Wonderful 4.2 / 5
$333 avg/night
5 beds
2 Bathrooms
Guests 10
5 reviews
New Listing! Peaceful and relaxing two story apartment in...
Guests4
Bedrooms2
Bathroom1
Wonderful 5 / 5
$177 avg/night
2 beds
1 Bathroom
Guests 4
9 reviews
Apartment with private Entrance located at Wye Branch Manor House
Guests3
Bedroom1
Bathroom1
Wonderful 4.8 / 5
$129 avg/night
1 bed
1 Bathroom
Guests 3
5 reviews
10 Acre Estate - Suite with Water Front View
Guests2
Bedroom1
Bathroom1
Wonderful 5 / 5
$235 avg/night
1 bed
1 Bathroom
Guests 2
1 reviews
Spacious Waterfront Property
Guests10
Bedrooms5
Bathrooms4
Wonderful 5 / 5
$450 avg/night
5 beds
4 Bathrooms
Guests 10
2 reviews
Stunning Home on a 25-acre Private Woodland Estate
Guests10
Bedrooms4
Bathrooms4
Wonderful 4.8 / 5
$510 avg/night
4 beds
4 Bathrooms
Guests 10
21 reviews
Waterfront house, private pool & dock, free WiFi, Eastern Shore of...
Guests8
Bedrooms4
Bathrooms2
Wonderful 4.5 / 5
$286 avg/night
4 beds
2 Bathrooms
Guests 8
8 reviews
Private Eastern Shore Retreat
Guests13
Bedrooms7
Bathrooms4
Wonderful 5 / 5
$1,599 avg/night
7 beds
4 Bathrooms
Guests 13
8 reviews
Completely Restored Family and Pet Friendly Home on 300 acres near...
Guests10
Bedrooms4
Bathrooms2
Wonderful 4.3 / 5
$300 avg/night
4 beds
2 Bathrooms
Guests 10
3 reviews
PET FRIENDLY Updated Farmhouse w/organic garden- Let The Kids...
Guests10
Bedrooms5
Bathrooms2
Wonderful 4.9 / 5
$300 avg/night
5 beds
2 Bathrooms
Guests 10
12 reviews
Cottage with Harbor and Chesapeake Bay View in Rock Hall, MD
Guests6
Bedrooms2
Bathroom1
Wonderful 4.9 / 5
$214 avg/night
2 beds
1 Bathroom
Guests 6
20 reviews
Chester River Waterfront, Magnificent Views, Dock, Beach
Guests6
Bedrooms2
Bathroom1
Wonderful 4.8 / 5
$286 avg/night
2 beds
1 Bathroom
Guests 6
32 reviews
Chester River Gorgeous Home. 5 BR, 5.5 baths
Guests10
Bedrooms5
Bathrooms5
Wonderful 5 / 5
$602 avg/night
5 beds
5 Bathrooms
Guests 10
3 reviews
Hillside Motel in historic Centreville
Guests4
Bedrooms8
Bathrooms8
Wonderful 0 / 5
$59 avg/night
8 beds
8 Bathrooms
Guests 4
400 Acre Waterfront Farm with Private Dock, Pool, Canoe, Kayaks...
Guests8
Bedrooms4
Bathrooms4
Wonderful 4.9 / 5
$600 avg/night
4 beds
4 Bathrooms
Guests 8
29 reviews
Sunview Cottage - Modern, Cozy Cottage for Relaxing Getaway on...
Guests5
Bedrooms2
Bathroom1
Wonderful 5 / 5
$107 avg/night
2 beds
1 Bathroom
Guests 5
2 reviews
WATERFRONT 3 BR/1 ba country cottage w/ gameroomdeep water,dock, 2...
Guests6
Bedrooms3
Bathroom1
Wonderful 4.8 / 5
$240 avg/night
3 beds
1 Bathroom
Guests 6
27 reviews
Summer House - Walk to town
Guests8
Bedrooms3
Bathroom1
Wonderful 4 / 5
$217 avg/night
3 beds
1 Bathroom
Guests 8
1 reviews
Peaceful getaway convenient to local amenities including beach...
Guests4
Bedrooms2
Bathroom1
Wonderful 5 / 5
$275 avg/night
2 beds
1 Bathroom
Guests 4
2 reviews
Welcome to Sailors Crossing..
Guests10
Bedrooms5
Bathrooms2
Wonderful 5 / 5
$330 avg/night
5 beds
2 Bathrooms
Guests 10
1 reviews
Guest cottage on working farm
Guests2
Bedroom1
Bathroom1
Wonderful 0 / 5
$114 avg/night
1 bed
1 Bathroom
Guests 2
Chestertown Tranquil Waterfront with Pool and Kayaks
Guests11
Bedrooms4
Bathrooms3
Wonderful 0 / 5
$983 avg/night
4 beds
3 Bathrooms
Guests 11
3 reviews

Chestertown, MD, USA Vacation Rentals

Historic Retreat With River, Garden And Marina Views

Waterfront w/Deepwater Pier Walking Distance to Downtown...

Victorian Hideaway: Beautiful Exterior, Modern interior

New Listing! Chestertown's Pet-Friendly Little Red Cottage

Bed & Breakfast: Brampton Bed and Breakfast Inn - Simone's Retreat

Water Front Retreat - Sunrise and Sunset Water Views

Eastern Shore River Retreat with Dock, Jon Boat, Kayaks, Fishing...

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

Chesapeake Bay Waterfront Home, Huge Deck, Spectacular Sunsets, 2...

Stunning 7-Acre Chesapeake Bay Estate

Private Lakefront Home on 17 acres in historic town, w/ a Canoe...

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

Eastern Shore beach cottage get-away

Chester River House with Views

Love Point Waterfront

The Lodge on Main Street, a Victorian Apartment, walk to...

Beautiful Retreat Located in Rock Hall - walk to everything!

Beautiful Cottage On Maryland's Eastern Shore

EASTERN SHORE Maryland --2 minute walk to beach; Quintessential...

Quiet Peaceful Country Home With Water Front Views of Swan Creek

Eastern Shore Get Away

Waterfront Cottage With Pier, Pool And Amazing Sunsets

Lakefront Private Apartment

rancher a half block from the bay

Secluded Waterfront Cottage on 200 acre farm near Queenstown

Wow! Secluded waterfront home on Maryland's Charming Eastern Shore

Quiet peaceful Home with Water Front Views of Swan Creek

Rock Hall Home With Pond, Only 6 Minutes to Town Center, Nicely...

- Farmhouse On Wye Lake- Totally Remodeled in 2015 -Perfect...

New Listing! Peaceful and relaxing two story apartment in...

Apartment with private Entrance located at Wye Branch Manor House

10 Acre Estate - Suite with Water Front View

Spacious Waterfront Property

Stunning Home on a 25-acre Private Woodland Estate

Waterfront house, private pool & dock, free WiFi, Eastern Shore of...

Private Eastern Shore Retreat

Completely Restored Family and Pet Friendly Home on 300 acres near...

PET FRIENDLY Updated Farmhouse w/organic garden- Let The Kids...

Cottage with Harbor and Chesapeake Bay View in Rock Hall, MD

Chester River Waterfront, Magnificent Views, Dock, Beach

Chester River Gorgeous Home. 5 BR, 5.5 baths

Hillside Motel in historic Centreville

400 Acre Waterfront Farm with Private Dock, Pool, Canoe, Kayaks...

Sunview Cottage - Modern, Cozy Cottage for Relaxing Getaway on...

WATERFRONT 3 BR/1 ba country cottage w/ gameroomdeep water,dock, 2...

Summer House - Walk to town

Peaceful getaway convenient to local amenities including beach...

Welcome to Sailors Crossing..

Guest cottage on working farm

Chestertown Tranquil Waterfront with Pool and Kayaks