10 Best St. Michaels Vacation rentals on Holiday Lettings - Apartments

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St. Michaels

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14 Vacation rentals

(13) Excellent 

24

Vacation home in St. Michaels

Talbot County / St. Michaels

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
The historic and recently restored Thomas Blades House is a 2 bedroom, 1.5 bathroom vacation cottage that is a short walk from the harbor, all museums, parks, restaurants, town pool, library, churches and shops in St. Michaels. The house was built around 1850 by …see more

from $150 / night

$975 - $1810 / week

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from $150 / night

(21) Excellent 

27

Vacation home in St. Michaels

Talbot County / St. Michaels

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary
The recently restored historic Washington Melson House is a 2 bedroom, 1.5 bathroom vacation cottage that is a short walk from the harbor, all museums, town pool, parks, restaurants, library, churches and shops in St. Michaels. The house was built around 1840 by …see more

from $150 / night

$975 - $1750 / week

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from $150 / night

(4) Excellent 

23

St. Michaels Vacation cottage rental

Talbot County / St. Michaels

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
The recently renovated Carpenter St. Cottage is centrally located in village of St. Michaels. The Cottage is just steps to the harbor and to museums, shops, restaurants, parks etc. The house is a 2 bedroom 2 full bathroom house with plenty of living space and a large …see more

from $160 / night

$1195 - $1910 / week

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from $160 / night

38

Vacation villa in St. Michaels

Talbot County / St. Michaels

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 7 mi
  • Swimming pool
A St. Michaels 3.5-acre waterfront vacation rental property with 500' shoreline, private pier, deep-water boat slips, dinghy dock, waterside pool, fire pit, and sundeck. We offer the warmest hospitality and the finest comfort. Walk to St. Michaels, MD attractions - sho …see more

from $780 / night

$4100 - $6400 / week

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Responds fast!
avg. 1 hour 13 minutes

from $780 / night

18

Vacation home in St. Michaels

Talbot County / St. Michaels

3 8 2 nights min

  • 3 bedrooms
  • Sleeps 8
  • 2 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Cranford on the Miles is a waterfront home located on 3+ acres, in St. Michaels. Fully renovated, with Wi-Fi, there is a Master Bedroom with king bed, sitting room, and private balcony; Second Bedroom with a double bed; Third Bedroom with both a double and twin bed; and …see more

from $750 / night

$3500 / week

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Responds fast!
avg. 2 hours 5 minutes

from $750 / night

(2) Excellent 

12

Vacation home in St. Michaels

Talbot County / St. Michaels

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Air conditioning
Pot Pie House - Newly Renovated Historic Cottage Located Close to St. Michaels MD Welcome to Pot Pie House! Immerse yourself in Eastern Shore culture in this newly renovated historic cottage located in the quaint waterfront village of Wittman, just minutes from St. Mich …see more

from $225 / night

$1500 / week

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from $225 / night

(11) Very Good 

30

Vacation home in St. Michaels

Talbot County / St. Michaels

7 9 Min stay varies

  • 7 bedrooms
  • Sleeps 9
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
The historic Thomas Harrison House is located on the harbor in the center of the town of St. Michaels. This Eastern Shore/Chesapeake Bay vacation rental has magnificent water VIEWS and can accomodate up to 12 people. The house is a short walk from all the museums, parks …see more

from $290 / night

$1550 - $2950 / week

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from $290 / night

15

Vacation home in St. Michaels

Talbot County / St. Michaels

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Ask about pets
Charming waterfront 2-story cottage on Oak Creek is just off the Miles River, minutes from the historic village of St. Michaels, spectacular water view with a 75' long, deep water (6") private dock with bench seating. Canoes and kayaks can be launched off the sandy bea …see more

from $350 / night

$2400 / week

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from $350 / night

(4) Excellent 

22

St. Michaels Vacation home rental

Talbot County / St. Michaels

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Sandy Pines, with its own waterfront, dock, and swimming pool, offers a peaceful retreat within the quiet natural beauty of the Chesapeake Bay region. The very private home, sited on broad Harris Creek, enjoys stunning sunset views across the Chesapeake tributary, and i …see more

from $375 / night

$2300 - $4800 / week

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from $375 / night

14

Vacation home with swimming pool in McDaniel

St. Michaels / McDaniel

5 10 2 nights min

  • 5 bedrooms
  • Sleeps 10
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Halo's Haven is a true piece of Heaven!! Bring your boat and your bathing suit. Twenty picturesque acres on a beautiful point of land off of the Chesapeake Bay near historic St. Michael's, Maryland. This property is beautifully landscaped, has a waterfront pool, pool ho …see more

from $700 / night

$4200 / week

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from $700 / night

6

St. Michaels Vacation home rental

Talbot County / St. Michaels

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Private garden
This beautiful 2,000 sq foot fenced in spacious home is the guest quarters for Halo's Haven Horse Rescue in gorgeous historic downtown St. Michaels. 1.25 green acres with fenced in backyard located on a quite street. Located just under a mile to the parks, shops, harbor …see more

from $325 / night

$2275 / week

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from $325 / night

(3) Very Good 

35

Vacation log cabin with swimming pool in St. Michaels

Talbot County / St. Michaels

5 10 3 nights min

  • 5 bedrooms
  • Sleeps 10
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Pool, Shoreline, Small Private Beach, Acreage, Lawn, Barbecue, and Nature. Spacious 6000+ square foot home. Up-to-date Gourmet Kitchen. Large and Open Common Spaces. Wall of Glass Overlooking the Chesapeake. 4 Master Suites with Attached Bathrooms and Each with Ki …see more

from $1000 / night

$6501 / week

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from $1000 / night

(3) Very Good 

25

Cottage rental in St. Michaels

Talbot County / St. Michaels

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
The fully restored historic John Bruff House, located on the Town park, has magnificent St. Michaels harbor and Miles River water views. The house is 2 bedroom, 3 bathroom cottage with plenty of living space and a rear screened porch. It is a short walk from all museum …see more

from $160 / night

$1195 - $1910 / week

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from $160 / night

(2) Excellent 

6

St. Michaels Vacation home rental

Talbot County / St. Michaels

1 6 2 nights min

  • 1 bedroom
  • Sleeps 6
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Private garden
Near the water, near the town. Steps to shopping, winery, brewery and more. Enjoy the former renowned painters studio remade into a loft for sleeping, chilling out. You're close to everything at Long Lane Lodge - no need to drive! Enjoy grilling out or building a firepi …see more

from $229 / night

$1603 / week

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from $229 / night