Chestertown Rentals

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38 Houses

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Vintage Bungalow-cozy, walk to shops, water, free pkg.

Annapolis house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Balcony or terrace

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Price per night from

$476

Perfect Annapolis with Lots of Parking & Hot Tub

Annapolis townhouse

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Match: Balcony or terrace

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Price per night from

$796

Cozy & Quiet - Open Concept living - Near Hopkins Hospital

Baltimore house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Balcony or terrace

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Price per night from

$75

The Heart of Historic Cool in Annapolis

Annapolis house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

Match: Balcony or terrace

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Price per night from

$1,145

Charming Annapolis Waterview home

Annapolis house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Balcony or terrace

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Price per night from

$801

KENT ISLAND-OCEAN VIEW Home for rent-4 bedrooms EASTERN SHORE sleeps 10-12

Kent Island house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 12

Match: Balcony or terrace

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Price per night from

$1,947

Eat..Sleep..Fish..Repeat! Who needs a desk (there is one upstairs) when you can

Stevensville house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 12

Match: Balcony or terrace

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Price per night from

$802

Match: Balcony or terrace

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Price per night from

$403

Match: Balcony or terrace

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Price per night from

$407

Match: Balcony or terrace

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Price per night from

$785

Waterfront home with private pier is A Shore Thing

Chester house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 9

Match: Balcony or terrace

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Price per night from

$429

Match: Balcony or terrace

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Price per night from

$247

Eastport Gem - Popular house walk to Downtown & USNA

Annapolis house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Balcony or terrace

All filters match

Price per night from

$400

Take your Leave of Absence around gardens with driveway parking

Annapolis house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

Match: Balcony or terrace

All filters match

Price per night from

$426

Sprawling Family home on a Cul De Sac sleeps 10-14!

Severna Park house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

Match: Balcony or terrace

All filters match

Price per night from

$382

Waterfront pier, putting green just minutes from downtown Annapolis

Riva house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Balcony or terrace

All filters match

Price per night from

$725

Stunning Waterfront Home in Round Bay

Severna Park house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Balcony or terrace

All filters match

Price per night from

$1,451

Hanover House across from USNA Gate 3 with private back patio

Annapolis house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Balcony or terrace

All filters match

Price per night from

$465

Pool and Bay Views on wrap around deck in Kent Island

Stevensville house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 12

Match: Balcony or terrace

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Price per night from

$321

Match: Balcony or terrace

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Price per night from

$355

Match: Balcony or terrace

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Price per night from

$500

Waterfront Views and a Sandy Beach

Betterton condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Balcony or terrace

All filters match

Price per night from

$401

Ruby’s Sea Glass Cottage

Betterton house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 8

Match: Balcony or terrace

All filters match

Price per night from

$273

Parking at Stunning On Cloud 9 with private patio pet-friendly

Annapolis house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Balcony or terrace

All filters match

Price per night from

$500

Walk to Main Street from Waterfront Condo with pool and parking

Annapolis condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

Match: Balcony or terrace

All filters match

Price per night from

$407

Captain Quarters - Eastport!

Annapolis house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Match: Balcony or terrace

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Price per night from

$571

Still Available for 2024 Commissioning Week! Historic gem steps to USNA

Annapolis house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Balcony or terrace

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Price per night from

$465

Free Parking at Randall House in Downtown Annapolis

Annapolis house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 11

Match: Balcony or terrace

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Price per night from

$729

The Fritz

Edgewater house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Balcony or terrace

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Price per night from

$1,545

Match: Balcony or terrace

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Price per night from

$114

History & Charm Near the Annapolis City Dock

Annapolis house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

Match: Balcony or terrace

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Price per night from

$394

Luxury Waterfront home with private pier and guest house

Annapolis house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

Match: Balcony or terrace

All filters match

Price per night from

$907

APARTMENT-1 BEDROOM, 1 BATHROOM, FULL KITCHEN, DECK, LARGE CLOSET

Parkville apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Match: Balcony or terrace

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Price per night from

$102

Edgewater/Mayo Getaway!

Edgewater house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Balcony or terrace

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Price per night from

$457

Popular Historic Firehouse fully renovated with Parking and Pet Friendly

Annapolis house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Balcony or terrace

All filters match

Price per night from

$465

Private pier by Kurtz Beach pet-friendly Dock of the Bay

Riviera Beach house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

Match: Balcony or terrace

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Price per night from

$424

DOLCE VIDA AT Kent Island- 4 bedrooms House for rent-SLEEPS 10-12

Chester house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Match: Balcony or terrace

All filters match

Price per night from

$1,947

Match: Balcony or terrace

All filters match

Price per night from

$359

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