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Bozman Vacation Rentals

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50 rentals in Bozman.
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Comfy home on beautiful Leadenham Creek. Book now for summer!, vacation rental in Bozman

Comfy home on beautiful Leadenham Creek. Book now for summer!

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Main House at Grandview at Pleasure Point, vacation rental in Bozman

Main House at Grandview at Pleasure Point

5 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Eastern Shore Getaway Near St. Michaels, vacation rental in Bozman

Eastern Shore Getaway Near St. Michaels

1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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Cottage 2 at Grandview Pleasure Point, vacation rental in Bozman

Cottage 2 at Grandview Pleasure Point

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Cottage 1a at Grandview Pleasure Point, vacation rental in Bozman

Cottage 1a at Grandview Pleasure Point

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Cottage 1b at Grandview Pleasure Point, vacation rental in Bozman

Cottage 1b at Grandview Pleasure Point

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Luxurious and Extremely Private Waterfront Estate (SORRY - NO WEDDINGS), vacation rental in Bozman

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

7 bedrooms
9 bathrooms
Sleeps 12
Match: Sleeps
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New St. Michaels estate -Pier,Pool, Gas fire pit, Bikes & Kayaks, vacation rental in Bozman

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

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Waterfront Cottage, Private Hot Tub, Fire Pit - perfect Romantic Getaway, vacation rental in Bozman

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

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Private Waterfront Retreat, vacation rental in Bozman

Private Waterfront Retreat

3 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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TRUE IN-TOWN SAINT MICHAELS 6 ACRE WATERFRONT w/POOL!!!, vacation rental in Bozman

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

5 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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ADULT ONLY! Magnificent Waterfront Cottage on 5 Acres, vacation rental in Bozman

ADULT ONLY! Magnificent Waterfront Cottage on 5 Acres

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful Tidewater home between Easton & ST Michaels!, vacation rental in Bozman

Beautiful Tidewater home between Easton & ST Michaels!

4 bedrooms
7 bathrooms
Sleeps 8
Match: Sleeps
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Chesapeake Bay Cottage, vacation rental in Bozman

Chesapeake Bay Cottage

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Enhanced Cleaning & Disinfecting. Private Beach Volleyball Court. Walk to Beach., vacation rental in Bozman

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

4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Fully remodel 2 bedroom country cottage., vacation rental in Bozman

Fully remodel 2 bedroom country cottage.

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Charming 3 Bedroom 3 Bath Beach Front Property, vacation rental in Bozman

Charming 3 Bedroom 3 Bath Beach Front Property

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Stunning Views of the Bay - Waterfront, vacation rental in Bozman

Stunning Views of the Bay - Waterfront

3 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Waterfront Family Retreat with Deepwater Dock, vacation rental in Bozman

Waterfront Family Retreat with Deepwater Dock

4 bedrooms
2 bathrooms
Sleeps 15
Match: Sleeps
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Relax in Tilghman Island, vacation rental in Bozman

Relax in Tilghman Island

4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Holidays at the Cove  - plenty of space to gather while making memories, vacation rental in Bozman

Holidays at the Cove - plenty of space to gather while making memories

5 bedrooms
7 bathrooms
Sleeps 10
Match: Sleeps
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Enhanced Cleaning and Disinfecting. Million$ Chesapeake Bay Sunsets by the Bay., vacation rental in Bozman

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

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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New Modern Waterfront Farmhouse Built 2018, vacation rental in Bozman

New Modern Waterfront Farmhouse Built 2018

4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Travelers Rest! Dock, Pool Eastern Shore Private Retreat St. Micheals / Easton, vacation rental in Bozman

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

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Waterfront Getaway on the Choptank River, vacation rental in Bozman

Waterfront Getaway on the Choptank River

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Location Location! St Michaels-- In Town Cottage!, vacation rental in Bozman

Location Location! St Michaels-- In Town Cottage!

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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*****Waterfront home w/ pool in St. Michaels, vacation rental in Bozman

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

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Premier Cottage in St. Michaels- In Town Location!, vacation rental in Bozman

Premier Cottage in St. Michaels- In Town Location!

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Not to early to think about joining us this Spring and Summer., vacation rental in Bozman

Not to early to think about joining us this Spring and Summer.

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Large Historic Thomas Harrison House on Harbor in St. Michaels Town, vacation rental in Bozman

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

7 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
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BEST Exposure on the Bay for SUNSETS with Pool, Dock & Spa, vacation rental in Bozman

BEST Exposure on the Bay for SUNSETS with Pool, Dock & Spa

3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Private waterfront estate with pool, convenient to Easton and St. Michaels, vacation rental in Bozman

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

5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Chesapeake Bay Waterfront ARTectural Home, vacation rental in Bozman

Chesapeake Bay Waterfront ARTectural Home

3 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Carpenter St. Cottage in the Heart of St. Michaels - Walk To Everything!, vacation rental in Bozman

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

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Sandy Pines:  Enjoy Harris Creek w/Pool and Boats, vacation rental in Bozman

Sandy Pines: Enjoy Harris Creek w/Pool and Boats

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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KI Golf House-A PAR for the Course & Mile to Beach, vacation rental in Bozman

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

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Waterview Cottage In St. Michaels!, vacation rental in Bozman

Waterview Cottage In St. Michaels!

2 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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Peaceful, Waterfront Home on 3 Acres (pier + western view w/gorgeous sunsets), vacation rental in Bozman

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

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Phenomenal Vacation Rental by Water in St Michaels - Walk to Town! 4 ADULTS MAX, vacation rental in Bozman

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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St. Michael's Premier in Town Summer Cottage now with private pool!, vacation rental in Bozman

St. Michael's Premier in Town Summer Cottage now with private pool!

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Beautiful Kent Island 4BR, Perfect Location, Close to Chesapeake Bay Beach Club!, vacation rental in Bozman

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

4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Comfortable, Spacious & Fun! 6+ Acres Pool & Shore. 4 Master Suites Waterview, vacation rental in Bozman

Comfortable, Spacious & Fun! 6+ Acres Pool & Shore. 4 Master Suites Waterview

5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Waterfront Property, Kayaks, Private Dock, Near Town, vacation rental in Bozman

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 Bozman

Tranquil Easton Waterfront Property

3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Kent Island Beach House II:Chesapeake Bay Fisherman's Village at Kentmorr Marina, vacation rental in Bozman

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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Ship's Cove Inn and Resort, vacation rental in Bozman

Ship's Cove Inn and Resort

6 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
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Kent Island House with Pool and Bay Views!, vacation rental in Bozman

Kent Island House with Pool and Bay Views!

3 bedrooms
3 bathrooms
Sleeps 13
Match: Sleeps
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Tentrr Signature Site - Wye Island View, vacation rental in Bozman

Tentrr Signature Site - Wye Island View

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Newly-managed Waterfront Kent Island home, vacation rental in Bozman

Newly-managed Waterfront Kent Island home

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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New! Stunning Waterfront with pool for Naval Academy families!, vacation rental in Bozman

New! Stunning Waterfront with pool for Naval Academy families!

4 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
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