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Chester Vacation Rentals
1-24 of 28 rentals

Winchester Creek Estate

$899 avg / night (excludes fees and taxes)
Grasonville, MD
5.0 (1)
4 Bedrooms | 4.5 Bath | Sleeps 8

The Little House

$395 avg / night (excludes fees and taxes)
Annapolis, MD
4.67 (30)
2 Bedrooms | 2 Bath | Sleeps 4

Harrison Hall

$830 avg / night (excludes fees and taxes)
Annapolis, MD
4.91 (22)
4 Bedrooms | 3 Bath | Sleeps 8

Anchors Aweigh

$946 avg / night (excludes fees and taxes)
Annapolis, MD
4.94 (32)
4 Bedrooms | 2.5 Bath | Sleeps 8

USNA Getaway

$189 avg / night (excludes fees and taxes)
Annapolis, MD
4.91 (11)
1 Bedrooms | 1 Bath | Sleeps 6

Skyline Sanctuary

$421 avg / night (excludes fees and taxes)
Annapolis, MD
5.0 (4)
2 Bedrooms | 1.5 Bath | Sleeps 6

The Master Shipwright

$1,299 avg / night (excludes fees and taxes)
Annapolis, MD
5.0 (11)
4 Bed | 4.5 Bath | Sleeps 10 (6 Adults Max)

Anchors Away Abode

$451 avg / night (excludes fees and taxes)
Annapolis, MD
4.93 (14)
3 Bedrooms | 2.5 Bath | Sleeps 8

The Corner Courtyard

$630 avg / night (excludes fees and taxes)
NEW!
Annapolis, MD
4.0 (1)
3 Bedrooms | 2.5 Bath | Sleeps 6

The Ship's Bridge

$976 avg / night (excludes fees and taxes)
Annapolis, MD
4.93 (56)
4 Bedrooms | 3.5 Bath | Sleeps 10

Porter Point

$907 avg / night (excludes fees and taxes)
NEW!
Annapolis, MD
5.0 (1)
4 Bedrooms | 4 Bath | Sleeps 12

Bella Chateau

$1,185 avg / night (excludes fees and taxes)
Annapolis, MD
4.9 (21)
6 Bedrooms | 4.5 Bath | Sleeps 15

Seas The Bay

$888 avg / night (excludes fees and taxes)
Annapolis, MD
4.88 (8)
4 Bedrooms | 2 Bath | Sleeps 10

Blue Angel's Nest

$754 avg / night (excludes fees and taxes)
Annapolis, MD
4.92 (37)
4 Bedrooms | 3.5 Bath | Sleeps 10

The Admiral's Retreat

$1,606 avg / night (excludes fees and taxes)
Annapolis, MD
4.78 (9)
6 Bedrooms | 4.5 Bath | Sleeps 12

The Salty Crab

$838 avg / night (excludes fees and taxes)
Annapolis, MD
4.83 (6)
3 Bedrooms | 3.5 Bath | Sleeps 10

Base Camp on the Lake

$2,309 avg / night (excludes fees and taxes)
Annapolis, MD
4.86 (7)
6 Bedrooms | 4.5 Bath | Sleeps 16

St Johns Adjacent

$2,318 avg / night (excludes fees and taxes)
Annapolis, MD
5.0 (1)
4 Bedrooms | 5.5 Bath | Sleeps 8

Ensign's Ridge

$1,525 avg / night (excludes fees and taxes)
NEW!
Annapolis, MD
6 Bedrooms | 6.5 Bath | Sleeps 12

Annapolis Bay Ridge Retreat

$1,143 avg / night (excludes fees and taxes)
Annapolis, MD
5.0 (4)
5 Bedrooms | 3.5 Bath | Sleeps 10

Thomas Point Tranquility

$1,161 avg / night (excludes fees and taxes)
Annapolis, MD
4.89 (9)
4 Bed | 3 Bath | Sleeps 10 (8 Adults Max)

Cardinal's Retreat

$830 avg / night (excludes fees and taxes)
NEW!
Annapolis, MD
5.0 (1)
4 Bedrooms | 3 Bath | Sleeps 8

The Morning Watch

$1,228 avg / night (excludes fees and taxes)
Annapolis, MD
5.0 (15)
5 Bedrooms | 3.5 Bath | Sleeps 10

The Herons Nest

$1,700 avg / night (excludes fees and taxes)
Annapolis, MD
5.0 (2)
4 Bedrooms | 4 Bath | Sleeps 11
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