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Centreville Holiday Rentals

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50 rentals in Centreville.
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Secluded Waterfront Cottage on 200 acre farm near Queenstown, holiday rental in Centreville

Secluded Waterfront Cottage on 200 acre farm near Queenstown

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Water Front Retreat - Sunrise and Sunset Water Views, holiday rental in Centreville

Water Front Retreat - Sunrise and Sunset Water Views

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Eastern Shore beach cottage get-away, holiday rental in Centreville

Eastern Shore beach cottage get-away

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Eastern Shore Get Away, holiday rental in Centreville

Eastern Shore Get Away

1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
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240' Private Beachfront *Kent Island Love Point-Reunions/Rehearsal Dinners, holiday rental in Centreville

240' Private Beachfront *Kent Island Love Point-Reunions/Rehearsal Dinners

5 bedrooms
5 bathrooms
Sleeps 26
Match: Sleeps
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Private Waterfront Retreat, holiday rental in Centreville

Private Waterfront Retreat

3 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Beautiful Retreat Located in Rock Hall - walk to everything!, holiday rental in Centreville

Beautiful Retreat Located in Rock Hall - walk to everything!

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Enhanced Cleaning & Disinfecting. Private Beach Volleyball Court. Walk to Beach., holiday rental in Centreville

Enhanced Cleaning & Disinfecting. Private Beach Volleyball Court. Walk to Beach.

4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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ADULT ONLY! Magnificent Waterfront Cottage on 5 Acres, holiday rental in Centreville

ADULT ONLY! Magnificent Waterfront Cottage on 5 Acres

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Peaceful getaway convenient to local amenities including beach, boating & food, holiday rental in Centreville

Peaceful getaway convenient to local amenities including beach, boating & food

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Stay in the landmark Lighthouse!, holiday rental in Centreville

Stay in the landmark Lighthouse!

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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rancher a half block from the bay, holiday rental in Centreville

rancher a half block from the bay

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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The Winehouse at Love Point Vineyards and Winery, holiday rental in Centreville

The Winehouse at Love Point Vineyards and Winery

6 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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200 steps to the beach!, holiday rental in Centreville

200 steps to the beach!

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Chestertown's Pet-Friendly Little Red Cottage, holiday rental in Centreville

Chestertown's Pet-Friendly Little Red Cottage

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Blissful Retreat In Rock Hall, holiday rental in Centreville

Blissful Retreat In Rock Hall

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Stunning Waterfront Hideaway on Michener's Choptank River.  Special Rates*, holiday rental in Centreville

Stunning Waterfront Hideaway on Michener's Choptank River. Special Rates*

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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5 acre estate with deep water dock and 1,700 feet of coastline, holiday rental in Centreville

5 acre estate with deep water dock and 1,700 feet of coastline

5 bedrooms
3 bathrooms
Sleeps 15
Match: Sleeps
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Victorian on Main Street, Rock Hall MD. Walk to everything! Sleeps 2-4, holiday rental in Centreville

Victorian on Main Street, Rock Hall MD. Walk to everything! Sleeps 2-4

1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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River Lodge, Casual Riverfront setting, holiday rental in Centreville

River Lodge, Casual Riverfront setting

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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In Town Beautiful Studio Cottage with Sauna, Lawton Avenue, holiday rental in Centreville

In Town Beautiful Studio Cottage with Sauna, Lawton Avenue

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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The Lodge on Main Street, a Victorian Apartment, walk to everything!, holiday rental in Centreville

The Lodge on Main Street, a Victorian Apartment, walk to everything!

3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Cape Cod Bed and Bath, holiday rental in Centreville

Cape Cod Bed and Bath

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Enhanced Cleaning and Disinfecting. Million$ Chesapeake Bay Sunsets by the Bay., holiday rental in Centreville

Enhanced Cleaning and Disinfecting. Million$ Chesapeake Bay Sunsets by the Bay.

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Serene Waterfront Cottage with dock and gorgeous views., holiday rental in Centreville

Serene Waterfront Cottage with dock and gorgeous views.

1 bedroom
2 bathrooms
Sleeps 7
Match: Sleeps
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Overton Farm Cottage, holiday rental in Centreville

Overton Farm Cottage

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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This is truly a Baydream!, holiday rental in Centreville

This is truly a Baydream!

2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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KI Golf House-A PAR for the Course & Mile to Beach, holiday rental in Centreville

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

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Cozy & Spacious Chestertown Home, holiday rental in Centreville

Cozy & Spacious Chestertown Home

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Peaceful, Waterfront Home on 3 Acres (pier + western view w/gorgeous sunsets), holiday rental in Centreville

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

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Cottage On Kent, holiday rental in Centreville

Cottage On Kent

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Beatiful Waterfront Home with Large Deck, Pool and Spa close to Bay Bridge, holiday rental in Centreville

Beatiful Waterfront Home with Large Deck, Pool and Spa close to Bay Bridge

3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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First time VRBO Offering!, holiday rental in Centreville

First time VRBO Offering!

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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KENT ISLAND-OCEAN VIEW Home for rent  -4 bedrooms EASTERN SHORE sleeps 10-12, holiday rental in Centreville

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

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Beautiful Kent Island 4BR, Perfect Location, Close to Chesapeake Bay Beach Club!, holiday rental in Centreville

Beautiful Kent Island 4BR, Perfect Location, Close to Chesapeake Bay Beach Club!

4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Bay Cottage, holiday rental in Centreville

Bay Cottage

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Kent Island Beach House II:Chesapeake Bay Fisherman's Village at Kentmorr Marina, holiday rental in Centreville

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

4 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Serene Waterfront Apartment on Kent Island, holiday rental in Centreville

Serene Waterfront Apartment on Kent Island

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Bayside Retreat, holiday rental in Centreville

Bayside Retreat

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful Waterfront Estate - Special Summer Rates, holiday rental in Centreville

Beautiful Waterfront Estate - Special Summer Rates

11 bedrooms
9 bathrooms
Sleeps 27
Match: Sleeps
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Cottage within walking distance to the Bay!, holiday rental in Centreville

Cottage within walking distance to the Bay!

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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The Rose Cottage - Next to Washington College, holiday rental in Centreville

The Rose Cottage - Next to Washington College

3 bedrooms
2 bathrooms
Sleeps 3
Match: Sleeps
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Luxurious Home on the Chesapeake Bay, Fantastic Views, W/ Pool, holiday rental in Centreville

Luxurious Home on the Chesapeake Bay, Fantastic Views, W/ Pool

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Chesapeake Bay Waterfront ARTectural Home, holiday rental in Centreville

Chesapeake Bay Waterfront ARTectural Home

3 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Private waterfront estate with pool, convenient to Easton and St. Michaels, holiday rental in Centreville

Private waterfront estate with pool, convenient to Easton and St. Michaels

5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Wren Retweet-Country Estate in the Center of Chestertown, holiday rental in Centreville

Wren Retweet-Country Estate in the Center of Chestertown

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Carriage House Hideaway in Middle of Chestertown, holiday rental in Centreville

Carriage House Hideaway in Middle of Chestertown

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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3BR 1BA Private Beach / Pool / Boat Launch / Pier / Golf Cart and much more!, holiday rental in Centreville

3BR 1BA Private Beach / Pool / Boat Launch / Pier / Golf Cart and much more!

3 bedrooms
1 bathroom
Sleeps 10
Match: Sleeps
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Newly Listed - Charming Farmhouse in the heart of Stevensville Historic Village, holiday rental in Centreville

Newly Listed - Charming Farmhouse in the heart of Stevensville Historic Village

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Carriage House Hideaway in Middle of Chestertown

0 bedrooms
0 bathrooms
Sleeps 0
Match: Sleeps
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