Talbot County Holiday Rentals
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96 rentals in Talbot County.
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Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Large Luxury Waterfront Home with pool...... 2 1/2 miles from the center of town
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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TRUE IN-TOWN SAINT MICHAELS 6 ACRE WATERFRONT w/POOL!!!
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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New St. Michaels estate -Pier,Pool, Gas fire pit, Bikes & Kayaks
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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Waterfront Property, kayaks, private dock, near town
Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Luxurious and Extremely Private Waterfront Estate (SORRY - NO WEDDINGS)
Holiday Rental House
7 bedrooms
9 bathrooms
Sleeps 12
Match: Sleeps
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Beautiful Tidewater home between Easton & ST Michaels!
Holiday Rental House
4 bedrooms
7 bathrooms
Sleeps 8
Match: Sleeps
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Fully remodel 2 bedroom country cottage.
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Waterfront Cottage, Private Hot Tub, Fire Pit - perfect Romantic Getaway
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Simplicity Cottage - Renovated Waterman's Home Circa 1920, Relax in the Hammock!
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Comfy home on beautiful Leadenham Creek. Book now for summer!
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac
Holiday Rental House
6 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Cottage downtown on a quiet street
Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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BREATHTAKING WATERFRONT ESTATE
Holiday Rental House
6 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Walk to Everything House
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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�Tuckaway Cove�Relaxing Private Getaway, St Michaels, MD
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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*****Waterfront home w/ pool in St. Michaels
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Looking to get away this September? Gorgeous waterfront property awaits.
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Location Location! St Michaels-- In Town Cottage!
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Relax in Tilghman Island
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
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Historic Oxford Waterfront Estate
Holiday Rental House
6 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
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Premier Cottage in St. Michaels- In Town Location!
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
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New-Gorgeous Private Waterfront Home, Dock, Huge Deck&Heated Swim Spa, 2 MBR
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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BEAUTIFUL WATERFRONT HOME AVAILABLE NOW!!!
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Perfect Waterview Cottage - St. Michaels Getaway
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
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Travelers Rest! Dock, Pool Eastern Shore Private Retreat St. Micheals / Easton
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Time to book your 2020 Sunset vacation!
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 5
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Tilghman Island Cottage - Across from Marina and Knapps Narrows
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Comfortable Relaxing Spacious & Fun! 6+ Acres Pool+Bay Waterfront by St Michaels
Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 10
Match: Sleeps
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St. Michaels Area Cottage - Walk to Water & Marina
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Charming 3 Bedroom 3 Bath Beach Front Property
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Large -IN TOWN- Historic House on Harbor in St Michaels - Walk to Everything!
Holiday Rental House
6 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
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Eastern Shore Getaway Near St. Michaels
Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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FANTASTIC WATERFRONT HOME WITH BEACH AWAITS!
Holiday Rental House
2 bedrooms
4 bathrooms
Sleeps 4
Match: Sleeps
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Waterfront Getaway on the Choptank River
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Caulk's Cove - Waterfront Near St. Michaels, Bikes, Kayaks!
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Pride and Joy - Charming Pet-Friendly Home in Historic Oxford!
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Osprey Point - Tranquil Waterfront Cottage w/ Pool & Kayaks - Pets Welcome!
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Holidays at the Cove - plenty of space to gather while making memories
Holiday Rental House
5 bedrooms
7 bathrooms
Sleeps 10
Match: Sleeps
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Large Historic Thomas Harrison House on Harbor in St. Michaels Town
Holiday Rental House
7 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
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Luxury Waterfront with pool and deep water dock, minutes from St Michaels.
Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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Main House at Grandview at Pleasure Point
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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New Modern Waterfront Farmhouse Built 2018
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Waterfront Home with Magnificent Views
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Crabber's Cove - Charming Waterfront Cottage Near St. Michaels, Kayaks & Bikes!
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Riverview Retreat - Charming Waterfront Cottage in St Michaels!
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Large waterfront estate with breathtaking sunset views
Holiday Rental House
8 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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12
Frequently Asked Questions about Talbot County
- Yes, here are some popular holiday rentals in Talbot County that have a pool:\n
- \n
- Main House at Grandview at Pleasure Point \n
- Cottage 1a at Grandview Pleasure Point \n
- Cottage 1b at Grandview Pleasure Point \n
- Yes, here are some popular holiday rentals in Talbot County that have internet access:\n
- \n
- Large Historic Thomas Harrison House on Harbor in St. Michaels Town \n
- Premier Cottage in St. Michaels- In Town Location! \n
- Location Location! St Michaels-- In Town Cottage! \n
- The best pet friendly rentals in Talbot County are:\n
- \n
- Large Historic Thomas Harrison House on Harbor in St. Michaels Town \n
- Premier Cottage in St. Michaels- In Town Location! \n
- Location Location! St Michaels-- In Town Cottage! \n
- Some of the most popular kid friendly rentals in Talbot County are:\n
- \n
- Large Historic Thomas Harrison House on Harbor in St. Michaels Town \n
- Premier Cottage in St. Michaels- In Town Location! \n
- Location Location! St Michaels-- In Town Cottage! \n