Chester Vacation Rentals, Houses & More


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Areas near Chester

Great rentals within 20 miles that match your search

1 / 19

Annapolis Waterfront very near USNA

  • 3
  • 6
  • Min stay varies

$285

Details

1 / 26

Annapolis Crows Nest Cottage: Chesapeake Bay View

  • 5
  • 20
  • 2 nights min

$696

Details

1 / 18

Family home one minute work away from Navy Stadium

  • 3
  • 6
  • 5 nights min

$551

Details

1 / 38

St. Michaels award-winning waterfront BayCottage, pool, docks, sundeck, grounds

  • 6
  • 12
  • Min stay varies

$780

Details

1 / 43

The Yellow House- Gorgeous Southern Colonial

  • 6
  • 14
  • 4 nights min

$996

Details

1 / 24

RESTORED WATERFRONT COTTAGE

  • 3
  • 6
  • Min stay varies

$100

Details

1 / 7

Charming Townhouse - Steps to City Dock and USNA

  • 3
  • 8
  • 3 nights min

$450

Details

1 / 16

Neat & Clean 1BR Apartment in Historic Annapolis w/Wifi - Prime Location

  • 1
  • 4
  • 2 nights min

$176

Details

1 / 18

Historic Waterfront Property with Wi-Fi and Dock

  • 3
  • 8
  • 2 nights min

$750

Details

1 / 15

Location,location,location,walk to city dock,free

  • 2
  • 5
  • Min stay varies

$181

Details

1 / 21

Annapolis Area Waterfront Home

  • 5
  • 11
  • Min stay varies

$551

Details

1 / 11

Love Point Bay Vacation Home

  • 2
  • 6
  • 2 nights min

$210

Details

1 / 24

Amazing Waterfront Annapolis & easy walk downtown

  • 4
  • 14
  • 2 nights min

Inquire for Rates

Details

1 / 6

Halo's Haven Guest Quarters

  • 3
  • 6
  • 2 nights min

$326

Details

1 / 20

Tilghman Island Cottage for Six - Near Marina and Knapps Narrows Drawbridge

  • 3
  • 6
  • 3 nights min

$201

Details

1 / 4

LOCATION,LOCATION,,LUXURY,WALK TO CITY ,PARKING. Annapolis, MD

  • 2
  • 5
  • 3 nights min

$250

Details

1 / 7

2. Private 20 acre waterfront estate - studio apt

  • 1
  • 2
  • 1 night min

$300

Details

1 / 35

Comfortable, Spacious & Fun! 6 Acres Pool & Shore

  • 5
  • 10
  • 3 nights min

$1001

Details

1 / 12

Sailors Crossing

  • 3
  • 10
  • 1 night min

$336

Details

1 / 17

Excellent Location in Downtown Annapolis- walk to everything !

  • 3
  • 7
  • 2 nights min

$300

Details

1 / 34

Waterfront House, Eastern Shore Chesapeake Bay

  • 4
  • 8
  • Min stay varies

$351

Details

1 / 24

Charming and Spacious Annapolis Victorian

  • 6
  • 12
  • Min stay varies

$750

Details

1 / 30

Beautiful Murray Hill Home (Annapolis)

  • 4
  • 9
  • Min stay varies

$425

Details

1 / 22

Sandy Pines: Enjoy Harris Creek w/Pool and Boats

  • 4
  • 10
  • Min stay varies

$376

Details

1 / 34

Grandview at Pleasure Point

  • 8
  • 27
  • 7 nights min

$902

Details

1 / 25

*BOOK NOW* Beautiful Cottage in historic Annapolis

  • 3
  • 6
  • 2 nights min

$351

Details

1 / 39

Love Point Bay Vacation Home

  • 2
  • 6
  • 2 nights min

$300

Details

1 / 10

C/ean & Cozy

  • 1
  • 2
  • 1 night min

$59

Details

1 / 10

Condo Laval/Montreal 3mths or L/T: Pool,Tennis,Gym

  • 2
  • 4
  • 90 nights min

$91

Details

1 / 14

Retreat at a quiet, water front cottage

  • 3
  • 8
  • 2 nights min

$295

Details

1 / 17

* 3 Bedroom Rental House in Historic Rock Hall MD

  • 3
  • 7
  • 2 nights min

$250

Details

1 / 24

Charming Artists Home in Eastport/Annapolis

  • 3
  • 6
  • 3 nights min

$376

Details

1 / 20

Love Point Waterfront

  • 3
  • 12
  • 3 nights min

$201

Details

1 / 12

Captain's Quarters, a waterfront couples retreat

  • 1
  • 4
  • 2 nights min

$181

Details

1 / 24

Relaxing, Fun, Dog-Friendly Waterfront Cottage

  • 3
  • 8
  • Min stay varies

$170

Details

1 / 11

ENDLESS SUNSETS - The perfect getaway!

  • 3
  • 8
  • Min stay varies

Inquire for Rates

Details

1 / 35

Luxury vacation condominum with private beach

  • 4
  • 10
  • 2 nights min

$440

Details

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