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Preston Vacation Rentals

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42 rentals in Preston.
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Peaceful Cambridge Home on Jenkins Creek, vacation rental in Preston

Peaceful Cambridge Home on Jenkins Creek

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Luxurious and Extremely Private Waterfront Estate (SORRY - NO WEDDINGS), vacation rental in Preston

Luxurious and Extremely Private Waterfront Estate (SORRY - NO WEDDINGS)

7 bedrooms
9 bathrooms
Sleeps 20
Match: Sleeps
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New St. Michaels estate -Pier,Pool, Gas fire pit, Bikes & Kayaks, vacation rental in Preston

New St. Michaels estate -Pier,Pool, Gas fire pit, Bikes & Kayaks

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Charming Waterfront Cottage Outside St. Michaels Close to the Oaks, vacation rental in Preston

Charming Waterfront Cottage Outside St. Michaels Close to the Oaks

3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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TRUE IN-TOWN SAINT MICHAELS 6 ACRE WATERFRONT w/POOL!!!, vacation rental in Preston

TRUE IN-TOWN SAINT MICHAELS 6 ACRE WATERFRONT w/POOL!!!

5 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Escape To This Oxford, Md Waterfront Home - Kayaking, Canoeing & Relaxing, vacation rental in Preston

Escape To This Oxford, Md Waterfront Home - Kayaking, Canoeing & Relaxing

4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful Tidewater home between Easton & ST Michaels!, vacation rental in Preston

Beautiful Tidewater home between Easton & ST Michaels!

4 bedrooms
7 bathrooms
Sleeps 8
Match: Sleeps
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Waterfront Cottage, Private Hot Tub, Fire Pit - perfect Romantic Getaway, vacation rental in Preston

Waterfront Cottage, Private Hot Tub, Fire Pit - perfect Romantic Getaway

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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St. Michael's Waterfront Vacation Home, vacation rental in Preston

St. Michael's Waterfront Vacation Home

5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Waterfront, 23 Private Acres, Dock  & Pool, vacation rental in Preston

Waterfront, 23 Private Acres, Dock & Pool

4 bedrooms
5 bathrooms
Sleeps 17
Match: Sleeps
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My Chesapeake Retreat Cambridge, Maryland, vacation rental in Preston

My Chesapeake Retreat Cambridge, Maryland

5 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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Vintage Eastern Shore Retreat, vacation rental in Preston

Vintage Eastern Shore Retreat

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Waterfront Rental on Fishing Creek, Cambridge, MD, vacation rental in Preston

Waterfront Rental on Fishing Creek, Cambridge, MD

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Travelers Rest! Dock, Pool Eastern Shore Private Retreat St. Micheals / Easton, vacation rental in Preston

Travelers Rest! Dock, Pool Eastern Shore Private Retreat St. Micheals / Easton

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Victorian Home In Historic West End, vacation rental in Preston

Victorian Home In Historic West End

6 bedrooms
3 bathrooms
Sleeps 13
Match: Sleeps
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Stunning Waterfront Hideaway on Michener's Choptank River.  Special Rates*, vacation rental in Preston

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

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Location Location! St Michaels-- In Town Cottage!, vacation rental in Preston

Location Location! St Michaels-- In Town Cottage!

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Premier Cottage in St. Michaels- In Town Location!, vacation rental in Preston

Premier Cottage in St. Michaels- In Town Location!

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Cottage at Heron Cove, Chesapeake Bay, Cambridge, vacation rental in Preston

Cottage at Heron Cove, Chesapeake Bay, Cambridge

3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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*****Waterfront home w/ pool in St. Michaels, vacation rental in Preston

*****Waterfront home w/ pool in St. Michaels

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Year Round Estate on Bay / Fam. Reunions / Slps 28, vacation rental in Preston

Year Round Estate on Bay / Fam. Reunions / Slps 28

7 bedrooms
7 bathrooms
Sleeps 28
Match: Sleeps
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Waterfront Retreat on the Chesapeake, vacation rental in Preston

Waterfront Retreat on the Chesapeake

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Oxford Waterfront Cottage-Walk to Town, Kayak, Dock, and Bikes, vacation rental in Preston

Oxford Waterfront Cottage-Walk to Town, Kayak, Dock, and Bikes

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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RESTORED WATERFRONT COTTAGE, vacation rental in Preston

RESTORED WATERFRONT COTTAGE

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Large Historic Thomas Harrison House on Harbor in St. Michaels Town, vacation rental in Preston

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

7 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
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Carpenter St. Cottage in the Heart of St. Michaels - Walk To Everything!, vacation rental in Preston

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

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Waterview Cottage In St. Michaels!, vacation rental in Preston

Waterview Cottage In St. Michaels!

2 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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Phenomenal Vacation Rental by Water in St Michaels - Walk to Town! 4 ADULTS MAX, vacation rental in Preston

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

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Cambridge Waterfront Home, vacation rental in Preston

Cambridge Waterfront Home

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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St. Michael's Premier in Town Summer Cottage!, vacation rental in Preston

St. Michael's Premier in Town Summer Cottage!

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Waterfront Property, Kayaks, Private Dock, Near Town, vacation rental in Preston

Waterfront Property, Kayaks, Private Dock, Near Town

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Tranquil Easton Waterfront Property, vacation rental in Preston

Tranquil Easton Waterfront Property

3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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6 Bdrm, 3.5 Bath, Cambridge Md Vacation Home, vacation rental in Preston

6 Bdrm, 3.5 Bath, Cambridge Md Vacation Home

6 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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St. Michaels Waterfront Retreat with pier, pool, kayaks, gas fire pit and bikes, vacation rental in Preston

St. Michaels Waterfront Retreat with pier, pool, kayaks, gas fire pit and bikes

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Cambridge Colonial Home, Walk to Town & Waterfront, vacation rental in Preston

Cambridge Colonial Home, Walk to Town & Waterfront

3 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Private setting, enjoy nature, kayaking and total relaxation, vacation rental in Preston

Private setting, enjoy nature, kayaking and total relaxation

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Waterfront Home on the Choptank River in Cambridge MD 3 bed room 2 bath and pool, vacation rental in Preston

Waterfront Home on the Choptank River in Cambridge MD 3 bed room 2 bath and pool

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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6942 Travelers Rest, vacation rental in Preston

6942 Travelers Rest

4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Private waterfront estate with pool, convenient to Easton and St. Michaels, vacation rental in Preston

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

5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Bay Cottage Resort, vacation rental in Preston

Bay Cottage Resort

6 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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