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Talbot County Holiday Rentals

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46 rentals in Talbot County.
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*****Waterfront home w/ pool in St. Michaels, holiday rental in Talbot County

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

33 reviews
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Carpenter St. Cottage in the Heart of St. Michaels - Walk To Everything!, holiday rental in Talbot County

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

11 reviews
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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New St. Michaels estate -Pier,Pool, Gas fire pit, Bikes & Kayaks, holiday rental in Talbot County

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

94 reviews
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Luxurious and Extremely Private Waterfront Estate (SORRY - NO WEDDINGS), holiday rental in Talbot County

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

84 reviews
7 bedrooms
9 bathrooms
Sleeps 20
Match: Sleeps
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St. Michaels Area Cottage - Walk to Water & Marina, holiday rental in Talbot County

St. Michaels Area Cottage - Walk to Water & Marina

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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TRUE IN-TOWN SAINT MICHAELS 6 ACRE WATERFRONT w/POOL!!!, holiday rental in Talbot County

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

33 reviews
5 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Newly available rental: Relaxing Waterfront Cottage Near St Michaels, Maryland, holiday rental in Talbot County

Newly available rental: Relaxing Waterfront Cottage Near St Michaels, Maryland

93 reviews
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Escape To This Oxford, Md Waterfront Home - Kayaking, Canoeing & Relaxing, holiday rental in Talbot County

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

46 reviews
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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Charming Waterfront Cottage Outside St. Michaels Close to the Oaks, holiday rental in Talbot County

Charming Waterfront Cottage Outside St. Michaels Close to the Oaks

44 reviews
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Fully remodel 2 bedroom country cottage., holiday rental in Talbot County

Fully remodel 2 bedroom country cottage.

52 reviews
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Beautiful Tidewater home between Easton & ST Michaels!, holiday rental in Talbot County

Beautiful Tidewater home between Easton & ST Michaels!

32 reviews
4 bedrooms
7 bathrooms
Sleeps 8
Match: Sleeps
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Comfy home on beautiful Leadenham Creek. Book now for summer!, holiday rental in Talbot County

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

31 reviews
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Premier Cottage in St. Michaels- In Town Location!, holiday rental in Talbot County

Premier Cottage in St. Michaels- In Town Location!

15 reviews
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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St. Michael's Waterfront Vacation Home, holiday rental in Talbot County

St. Michael's Waterfront Vacation Home

39 reviews
5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Waterfront Cottage, Private Hot Tub, Fire Pit - perfect Romantic Getaway, holiday rental in Talbot County

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

25 reviews
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Location Location! St Michaels-- In Town Cottage!, holiday rental in Talbot County

Location Location! St Michaels-- In Town Cottage!

24 reviews
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Gorgeous Sunsets and Chesapeake Charm, holiday rental in Talbot County

Gorgeous Sunsets and Chesapeake Charm

75 reviews
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Waterfront Getaway on the Choptank River, holiday rental in Talbot County

Waterfront Getaway on the Choptank River

41 reviews
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Eastern Shore Getaway Near St. Michaels, holiday rental in Talbot County

Eastern Shore Getaway Near St. Michaels

69 reviews
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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Travelers Rest! Dock, Pool Eastern Shore Private Retreat St. Micheals / Easton, holiday rental in Talbot County

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

33 reviews
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Main House at Grandview at Pleasure Point, holiday rental in Talbot County

Main House at Grandview at Pleasure Point

13 reviews
5 bedrooms
3 bathrooms
Sleeps 13
Match: Sleeps
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Large Historic Thomas Harrison House on Harbor in St. Michaels Town, holiday rental in Talbot County

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

14 reviews
7 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
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Holidays at the Cove - plenty of space to gather while making memories, holiday rental in Talbot County

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

30 reviews
5 bedrooms
7 bathrooms
Sleeps 10
Match: Sleeps
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Charming 3 Bedroom 3 Bath Beach Front Property, holiday rental in Talbot County

Charming 3 Bedroom 3 Bath Beach Front Property

23 reviews
3 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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New Modern Waterfront Farmhouse Built 2018, holiday rental in Talbot County

New Modern Waterfront Farmhouse Built 2018

12 reviews
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Relax in Tilghman Island, holiday rental in Talbot County

Relax in Tilghman Island

18 reviews
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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RESTORED WATERFRONT COTTAGE, holiday rental in Talbot County

RESTORED WATERFRONT COTTAGE

10 reviews
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Sandy Pines: Enjoy Harris Creek w/Pool and Boats, holiday rental in Talbot County

Sandy Pines: Enjoy Harris Creek w/Pool and Boats

5 reviews
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Luxurious Waterfront Kent Island Home 30 miles from Annapolis, holiday rental in Talbot County

Luxurious Waterfront Kent Island Home 30 miles from Annapolis

23 reviews
4 bedrooms
5 bathrooms
Sleeps 7
Match: Sleeps
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Oxford Waterfront Cottage-Walk to Town, Kayak, Dock, and Bikes, holiday rental in Talbot County

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

9 reviews
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Waterview Cottage In St. Michaels!, holiday rental in Talbot County

Waterview Cottage In St. Michaels!

5 reviews
2 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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Pot Pie House, holiday rental in Talbot County

Pot Pie House

2 reviews
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Phenomenal Vacation Rental by Water in St Michaels - Walk to Town! 4 ADULTS MAX, holiday rental in Talbot County

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

2 reviews
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Comfortable, Spacious & Fun! 6+ Acres Pool & Shore. 4 Master Suites Waterview, holiday rental in Talbot County

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

3 reviews
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Not to early to think about joining us this Spring and Summer., holiday rental in Talbot County

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

3 reviews
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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St. Michael's Premier in Town Summer Cottage!, holiday rental in Talbot County

St. Michael's Premier in Town Summer Cottage!

1 review
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Cottage 2 at Grandview Pleasure Point, holiday rental in Talbot County

Cottage 2 at Grandview Pleasure Point

1 review
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Waterfront Property, Kayaks, Private Dock, Near Town, holiday rental in Talbot County

Waterfront Property, Kayaks, Private Dock, Near Town

1 review
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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BEST Exposure on the Bay for SUNSETS with Pool, Dock & Spa, holiday rental in Talbot County

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

1 review
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Bay Cottage Resort, holiday rental in Talbot County

Bay Cottage Resort

6 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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St. Michaels Waterfront Retreat with pier, pool, kayaks, gas fire pit and bikes, holiday rental in Talbot County

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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Cottage 1a at Grandview Pleasure Point, holiday rental in Talbot County

Cottage 1a at Grandview Pleasure Point

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Cottage 1b at Grandview Pleasure Point, holiday rental in Talbot County

Cottage 1b at Grandview Pleasure Point

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Tranquil Easton Waterfront Property, holiday rental in Talbot County

Tranquil Easton Waterfront Property

3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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6942 Travelers Rest, holiday rental in Talbot County

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, holiday rental in Talbot County

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

5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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