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Centreville Rentals

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Price range

Per night

$10 - $500

Centreville Rentals

38 Houses

Luxury Apartment with Private Entrance

Centreville apartment

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$117

1 / 13

Waterfront House, Eastern Shore Chesapeake Bay

Centreville house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$400

1 / 34

Great rentals within 20 miles that match your search

Love Point Luxury Waterfront in Stevensville

Stevensville house

3 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$1,391

1 / 26

Summer House

Rock Hall bungalow

3 bedrooms / 1 bathroom / sleeps 8

Price per night from

$285

1 / 10

St. Michaels Area Waterfront Retreat with pier, pool, kayaks and bikes

Royal Oak house

5 bedrooms / 4 bathrooms / sleeps 11

Price per night from

$595

1 / 4

Cozy & Spacious Chestertown Home

Chestertown house

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 2 hours 43 minutes

Price per night from

$250

1 / 28

Waterfront Stevensville House w/ Pier & 2 Decks!

Stevensville house

5 bedrooms / 2 bathrooms / sleeps 12

Responds fast! avg. 9 minutes

Price per night from

$375

1 / 25

Cottage On Kent

Chestertown cottage

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$195

1 / 7

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

$289

1 / 30

Serene Waterfront Apartment on Kent Island

Stevensville apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$150

1 / 17

Big BD in Civil War House starting at 55$/night

Still Pond house

1 bedroom / 1 bathroom / sleeps 3

Responds fast! avg. 2 hours 9 minutes

Price per night from

$55

1 / 39

Bay Cottage

Rock Hall house

2 bedrooms / 1 bathroom / sleeps 5

Responds fast! avg. 3 hours 15 minutes

Price per night from

$250

1 / 8

Carpenter St. Cottage in the Heart of St. Michaels - Walk To Everything!

St. Michaels cottage

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 3 hours 32 minutes

Price per night from

$160

1 / 23

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

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

$284

1 / 21

Sailors Crossing

Rock Hall house

3 bedrooms / 2 bathrooms / sleeps 10

Responds fast! avg. 3 hours 15 minutes

Price per night from

$340

1 / 12

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

$294

1 / 14

Great BD in Civil War House starting at 55$/night

Still Pond house

2 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 2 hours 9 minutes

Price per night from

$55

1 / 58

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

$746

1 / 32

Belle Rose Cottage at Victory Farm (Pet Friendly!)

Chestertown house

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$135

1 / 17

Love Point Bay Vacation Home

Stevensville apartment

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$329

1 / 11

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

$249

1 / 19

Phenomenal Vacation Rental by Water in St Michaels - Walk to Town! 4 ADULTS MAX

St. Michaels house

1 bedroom / 1 bathroom / sleeps 6

Price per night from

$229

1 / 18

Location Location! St Michaels-- In Town Cottage!

St. Michaels house

2 bedrooms / 2 bathrooms / sleeps 5

“Crabtastic Great Escape” This cottage is the perfect great escape. Conveniently located in the middle of quaint St Michael's close to the harbor, restaurants, and shops. The property is clean and well-maintained with beautiful landscaping. The buildin

Responds fast! avg. 3 hours 32 minutes

Price per night from

$150

1 / 27

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

Waterview Cottage In St. Michaels!

St. Michaels cottage

2 bedrooms / 3 bathrooms / sleeps 5

Responds fast! avg. 3 hours 32 minutes

Price per night from

$160

1 / 25

Tranquil Easton Waterfront Property

Easton house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$597

1 / 15

Lakeside Private Apartment

Wye Mills apartment

1 bedroom / 1 bathroom / sleeps 5

Price per night from

$139

1 / 15

Sunview Cottage on Chesapeake Bay

Chestertown house

2 bedrooms / 1 bathroom / sleeps 5

Responds fast! avg. 2 hours 19 minutes

Price per night from

$145

1 / 22

Annapolis Townhome w/Deck by Nature Trails & River

Annapolis house

1 bedroom / 2 bathrooms / sleeps 4

Responds fast! avg. 9 minutes

Price per night from

$89

1 / 24

Cozy Apartment in Chestertown

Chestertown apartment

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 2 hours 19 minutes

Price per night from

$88

1 / 7

Price per night from

$299

1 / 12

Charming Apartment in Historic Chestertown, MD

Chestertown apartment

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 2 hours 19 minutes

Price per night from

$99

1 / 10

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

$846

1 / 38

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

Kent Island house

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$1,500

1 / 32

Luxury vacation condominum with private beach

Chester house

4 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$440

1 / 35

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

Kent Island house

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$597

1 / 17

Kent Island Beach House II:Chesapeake Bay Fisherman's Village at Kentmorr Marina

Stevensville house

4 bedrooms / 2 bathrooms / sleeps 12

Price per night from

$650

1 / 9
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