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Chester Rentals

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Price range

Per night

$10 - $500

Rental types

Chester Rentals

77 Houses

Peaceful, Waterfront Home on 3 Acres (pier + western view w/gorgeous sunsets)

Chester house

4 bedrooms / 2 bathrooms / sleeps 8

“Unbelievable value” We were a family group of 3 couples plus an infant traveling to a wedding at the Usna chapel. The home was just wonderful, had a great view, was very clean, and was well equipped for the cooking being planned. Stores, restaurants,

Price per night from

$285

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

Chester house

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$750

1 / 32

Price per night from

$300

1 / 12

Luxury vacation condominum with private beach

Chester house

4 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$440

1 / 35

Great rentals within 20 miles that match your search

Summer House

Rock Hall bungalow

3 bedrooms / 1 bathroom / sleeps 8

Price per night from

$285

1 / 10

St. Michaels Waterfront Home W/Dock for 2 boats

Neavitt house

2 bedrooms / 1 bathroom / sleeps 5

Price per night from

$225

1 / 18

Annapolis Crows Nest Cottage: Chesapeake Bay View

Annapolis villa

5 bedrooms / 3 bathrooms / sleeps 20

Price per night from

$695

1 / 26

Love Point Luxury Waterfront in Stevensville

Stevensville house

3 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$1,399

1 / 26

Charming Annapolis home with stunning water views

Annapolis house

4 bedrooms / 4 bathrooms / sleeps 11

Price per night from

$500

1 / 55

Huge Stevensville House Overlooking Eastern Shore!

Stevensville house

3 bedrooms / 5 bathrooms / sleeps 10

Responds fast! avg. 55 minutes

Price per night from

$400

1 / 26

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

Tilghman cottage

3 bedrooms / 2 bathrooms / sleeps 6

“We loved it!” We had a great (albeit too short!) family getaway at the Roost! The cottage is extremely clean, comfortable, well-maintained, and spacious. The kids (ages 6 and 20 months) loved it -- especially the bunk beds and the nice backyard, and t

Price per night from

$200

1 / 20

Serene Waterfront Apartment on Kent Island

Stevensville apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$150

1 / 17

Luxury Apartment with Private Entrance

Centreville apartment

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$117

1 / 13

Large Historic Thomas Harrison House on Harbor in St. Michaels Town

St. Michaels house

7 bedrooms / 4 bathrooms / sleeps 9

“Perfect in every way!” I stayed at the Thomas Harrison house a few weeks ago and all I can say is..."if you are planning on coming to St. Michael's you need to stay at this house." This house is perfect in every way. It has all the accommodations that

Responds fast! avg. 3 hours 32 minutes

Price per night from

$290

1 / 30

Cottage 1a at Grandview Pleasure Point

Bozman house

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$245

1 / 8

Contemporary Pasadena Apt w/Fireplace -Near River!

Pasadena apartment

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 55 minutes

Price per night from

$88

1 / 24

St. Michaels Area Cottage - Walk to Water & Marina

Neavitt house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 55 minutes

Price per night from

$175

1 / 28

Premier Cottage in St. Michaels- In Town Location!

St. Michaels house

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 3 hours 32 minutes

Price per night from

$150

1 / 24

C/ean & Cozy

Annapolis room

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$59

1 / 10

Retreat at a quiet, water front cottage

Chestertown house

3 bedrooms / 3 bathrooms / sleeps 8

“A best kept secret!” I have had the pleasure of staying at Cliff Point many times. The view cannot be matched, water views more than 180 degrees, sunsets are stunning. But on top of that the house is so comfortable and charming, spacious and cozy. Ch

Price per night from

$295

1 / 14

Love Point Waterfront

Kent Island house

3 bedrooms / 3 bathrooms / sleeps 12

“Love Point Retreat” I stayed at Paula's property 3 times so far. We stayed once in October 2014 and twice in April 2015. Here is how I would break it up: Owner: Paula is very nice, accommodating and extremely responsive. She was easy to deal with, ans

Price per night from

$250

1 / 19

Annapolis Area Waterfront Home

Annapolis house

5 bedrooms / 4 bathrooms / sleeps 11

Price per night from

$550

1 / 21

Chester River House with Views

Chestertown house

3 bedrooms / 1 bathroom / sleeps 7

Responds fast! avg. 1 hour 40 minutes

Price per night from

$155

1 / 11

Love Point Bay Vacation Home

Stevensville apartment

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$329

1 / 11

Cottage 2 at Grandview Pleasure Point

Bozman house

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$386

1 / 9

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

Annapolis apartment

2 bedrooms / 1 bathroom / sleeps 5

Price per night from

$180

1 / 15

Clean & Spacious

Cape Saint Claire house

4 bedrooms / 2 bathrooms / sleeps 9

Price per night from

$350

1 / 12

Walk to Shops/Eateries Charming Cottage. Dogs Wel.

Annapolis house

3 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 1 hour 49 minutes

Price per night from

$250

1 / 52

Cottage 1b at Grandview Pleasure Point

Bozman cottage

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$245

1 / 6

Custom Annapolis Home w/ Private Pool & Hot Tub!

Riva house

3 bedrooms / 4 bathrooms / sleeps 8

Responds fast! avg. 19 minutes

Price per night from

$291

1 / 29

St. Michael's Premier in Town Summer Cottage!

St. Michaels house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$285

1 / 7

Beautiful Murray Hill Home (Annapolis)

Annapolis house

4 bedrooms / 3 bathrooms / sleeps 9

“Comfortable and secure in a great home - almost as good as at ho” The house is set is a terrific neighborhood of annapolis within easy walking distance to two small parks on the water and to town. We all found the house a delight - the design, decor

Price per night from

$425

1 / 30

Lochhaven house for rent

Edgewater house

3 bedrooms / 1 bathroom / sleeps 2

Price per night from

$100

1 / 4

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

St. Michaels villa

6 bedrooms / 6 bathrooms / sleeps 12

Responds fast! avg. 1 hour 1 minutes

Price per night from

$850

1 / 38

The Yellow House- Gorgeous Southern Colonial

Annapolis house

6 bedrooms / 6 bathrooms / sleeps 14

Responds fast! avg. 1 hour 30 minutes

Price per night from

$995

1 / 43

3BR Annapolis Home on Oyster Creek w/Amazing Views

Annapolis house

3 bedrooms / 4 bathrooms / sleeps 9

Responds fast! avg. 8 minutes

Price per night from

$350

1 / 26

KI Golf House-A PAR for the Course & Mile to Beach

Kent Island house

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$600

1 / 17

Charming Home close to historic district

Annapolis house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 59 minutes

Price per night from

$250

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