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Talbot County
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Talbot County, MD Holiday Rentals, Homes and Villas
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Talbot County, MD Holiday Rentals, Homes and Villas
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Kid friendly (85)
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Holiday Rental House (95)
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Boat Available (19)
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96 rentals
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Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
114 reviews
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
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Large Luxury Waterfront Home with pool...... 2 1/2 miles from the center of town
69 reviews
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 8
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TRUE IN-TOWN SAINT MICHAELS 6 ACRE WATERFRONT w/POOL!!!
44 reviews
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 8
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New St. Michaels estate -Pier,Pool, Gas fire pit, Bikes & Kayaks
110 reviews
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
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Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
104 reviews
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
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Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
79 reviews
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 5
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Waterfront Property, kayaks, private dock, near town
130 reviews
Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
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Luxurious and Extremely Private Waterfront Estate (SORRY - NO WEDDINGS)
96 reviews
Holiday Rental House
7 bedrooms
9 bathrooms
Sleeps 12
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Beautiful Tidewater home between Easton & ST Michaels!
42 reviews
Holiday Rental House
4 bedrooms
7 bathrooms
Sleeps 8
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Fully remodel 2 bedroom country cottage.
88 reviews
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
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Waterfront Cottage, Private Hot Tub, Fire Pit - perfect Romantic Getaway
53 reviews
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
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Simplicity Cottage - Renovated Waterman's Home Circa 1920, Relax in the Hammock!
79 reviews
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
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Comfy home on beautiful Leadenham Creek. Book now for summer!
44 reviews
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
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Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac
55 reviews
Holiday Rental House
6 bedrooms
5 bathrooms
Sleeps 10
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Cottage downtown on a quiet street
56 reviews
Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 2
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BREATHTAKING WATERFRONT ESTATE
52 reviews
Holiday Rental House
6 bedrooms
5 bathrooms
Sleeps 12
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Walk to Everything House
28 reviews
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
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�Tuckaway Cove�Relaxing Private Getaway, St Michaels, MD
31 reviews
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
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*****Waterfront home w/ pool in St. Michaels
43 reviews
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
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Looking to get away this September? Gorgeous waterfront property awaits.
62 reviews
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
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Location Location! St Michaels-- In Town Cottage!
24 reviews
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
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Relax in Tilghman Island
40 reviews
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
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Historic Oxford Waterfront Estate
49 reviews
Holiday Rental House
6 bedrooms
6 bathrooms
Sleeps 12
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Premier Cottage in St. Michaels- In Town Location!
15 reviews
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
16 reviews
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
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BEAUTIFUL WATERFRONT HOME AVAILABLE NOW!!!
35 reviews
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
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Perfect Waterview Cottage - St. Michaels Getaway
77 reviews
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
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Travelers Rest! Dock, Pool Eastern Shore Private Retreat St. Micheals / Easton
45 reviews
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
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Time to book your 2020 Sunset vacation!
40 reviews
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
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John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
72 reviews
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 5
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Tilghman Island Cottage - Across from Marina and Knapps Narrows
40 reviews
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
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Comfortable Relaxing Spacious & Fun! 6+ Acres Pool+Bay Waterfront by St Michaels
60 reviews
Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 10
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St. Michaels Area Cottage - Walk to Water & Marina
45 reviews
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
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Charming 3 Bedroom 3 Bath Beach Front Property
42 reviews
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
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Large -IN TOWN- Historic House on Harbor in St Michaels - Walk to Everything!
96 reviews
Holiday Rental House
6 bedrooms
4 bathrooms
Sleeps 9
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Eastern Shore Getaway Near St. Michaels
82 reviews
Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 2
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FANTASTIC WATERFRONT HOME WITH BEACH AWAITS!
69 reviews
Holiday Rental House
2 bedrooms
4 bathrooms
Sleeps 4
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Waterfront Getaway on the Choptank River
61 reviews
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
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Caulk's Cove - Waterfront Near St. Michaels, Bikes, Kayaks!
42 reviews
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
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Pride and Joy - Charming Pet-Friendly Home in Historic Oxford!
31 reviews
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
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Osprey Point - Tranquil Waterfront Cottage w/ Pool & Kayaks - Pets Welcome!
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
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Holidays at the Cove - plenty of space to gather while making memories
34 reviews
Holiday Rental House
5 bedrooms
7 bathrooms
Sleeps 10
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Large Historic Thomas Harrison House on Harbor in St. Michaels Town
15 reviews
Holiday Rental House
7 bedrooms
4 bathrooms
Sleeps 9
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Luxury Waterfront with pool and deep water dock, minutes from St Michaels.
10 reviews
Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 8
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Main House at Grandview at Pleasure Point
13 reviews
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 9
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New Modern Waterfront Farmhouse Built 2018
21 reviews
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
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Waterfront Home with Magnificent Views
39 reviews
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
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Crabber's Cove - Charming Waterfront Cottage Near St. Michaels, Kayaks & Bikes!
12 reviews
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
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Riverview Retreat - Charming Waterfront Cottage in St Michaels!
11 reviews
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
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Large waterfront estate with breathtaking sunset views
37 reviews
Holiday Rental House
8 bedrooms
5 bathrooms
Sleeps 12
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Frequently Asked Questions about Talbot County
Do any holiday rentals in Talbot County have a pool?
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
\n
See all holiday rentals with a pool in Talbot County on Tripadvisor
Do any holiday rentals in Talbot County have internet access?
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
\n
See all holiday rentals in Talbot County on Tripadvisor
What are the best pet friendly rentals in Talbot County?
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
\n
See all pet friendly holiday rentals in Talbot County on Tripadvisor
What are some great rentals in Talbot County that are kid friendly?
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
\n
See all kid friendly holiday rentals in Talbot County on Tripadvisor