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Chester Vacation Rentals
1-24 of 28 rentals

Winchester Creek Estate

$771 avg / night (excludes fees and taxes)
Grasonville, MD
5.0 (1)
4 Bedrooms | 4.5 Bath | Sleeps 8

The Admiral's Retreat

$1,546 avg / night (excludes fees and taxes)
Annapolis, MD
4.78 (9)
6 Bedrooms | 4.5 Bath | Sleeps 12

The Little House

$382 avg / night (excludes fees and taxes)
Annapolis, MD
4.66 (32)
2 Bedrooms | 2 Bath | Sleeps 4

The Morning Watch

$1,239 avg / night (excludes fees and taxes)
Annapolis, MD
5.0 (15)
5 Bedrooms | 3.5 Bath | Sleeps 10

The Ship's Bridge

$900 avg / night (excludes fees and taxes)
Annapolis, MD
4.93 (56)
4 Bedrooms | 3.5 Bath | Sleeps 10

The Salty Crab

$910 avg / night (excludes fees and taxes)
Annapolis, MD
4.86 (7)
3 Bedrooms | 3.5 Bath | Sleeps 10

Cardinal's Retreat

$735 avg / night (excludes fees and taxes)
NEW!
Annapolis, MD
5.0 (1)
4 Bedrooms | 3 Bath | Sleeps 8

The Master Shipwright

$1,269 avg / night (excludes fees and taxes)
Annapolis, MD
5.0 (11)
4 Bed | 4.5 Bath | Sleeps 10 (6 Adults Max)

USNA Getaway

$175 avg / night (excludes fees and taxes)
Annapolis, MD
4.91 (11)
1 Bedrooms | 1 Bath | Sleeps 6

Annapolis Bay Ridge Retreat

$1,099 avg / night (excludes fees and taxes)
Annapolis, MD
5.0 (4)
5 Bedrooms | 3.5 Bath | Sleeps 10

Porter Point

$825 avg / night (excludes fees and taxes)
Annapolis, MD
4.0 (3)
4 Bedrooms | 4 Bath | Sleeps 12

Bella Chateau

$1,074 avg / night (excludes fees and taxes)
Annapolis, MD
4.9 (21)
6 Bedrooms | 4.5 Bath | Sleeps 15

Anchors Away Abode

$406 avg / night (excludes fees and taxes)
Annapolis, MD
4.93 (15)
3 Bedrooms | 2.5 Bath | Sleeps 8

Anchors Aweigh

$858 avg / night (excludes fees and taxes)
Annapolis, MD
4.94 (32)
4 Bedrooms | 2.5 Bath | Sleeps 8

Skyline Sanctuary

$397 avg / night (excludes fees and taxes)
Annapolis, MD
5.0 (4)
2 Bedrooms | 1.5 Bath | Sleeps 6

The Herons Nest

$829 avg / night (excludes fees and taxes)
Annapolis, MD
5.0 (2)
4 Bedrooms | 4 Bath | Sleeps 11

Seas The Bay

$816 avg / night (excludes fees and taxes)
Annapolis, MD
4.88 (8)
4 Bedrooms | 2 Bath | Sleeps 10

Harrison Hall

$726 avg / night (excludes fees and taxes)
Annapolis, MD
4.91 (22)
4 Bedrooms | 3 Bath | Sleeps 8

Blue Angel's Nest

$959 avg / night (excludes fees and taxes)
Annapolis, MD
4.92 (37)
4 Bedrooms | 3.5 Bath | Sleeps 10

The Corner Courtyard

$595 avg / night (excludes fees and taxes)
Annapolis, MD
4.0 (1)
3 Bedrooms | 2.5 Bath | Sleeps 6

Base Camp on the Lake

$3,840 avg / night (excludes fees and taxes)
Annapolis, MD
4.86 (7)
6 Bedrooms | 4.5 Bath | Sleeps 16

Ensign's Ridge

$1,454 avg / night (excludes fees and taxes)
NEW!
Annapolis, MD
6 Bedrooms | 6.5 Bath | Sleeps 12

Thomas Point Tranquility

$988 avg / night (excludes fees and taxes)
Annapolis, MD
4.89 (9)
4 Bed | 3 Bath | Sleeps 10 (8 Adults Max)

St Johns Adjacent

$2,685 avg / night (excludes fees and taxes)
Annapolis, MD
5.0 (1)
4 Bedrooms | 5.5 Bath | Sleeps 8
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