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Vacation Rentals in St Michaels, Maryland

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about St Michaels

St Michaels, Maryland Vacation Rentals and Tourism

Golfing, swimming, biking, plenty of good eating and St Michaels vacation rentals should make the prospect of your upcoming trip an exciting one. It’s a trip that’s meant to refresh everyone, right? Then be sure to take a few basic steps now in order to ensure that all goes well later…the first should be to secure a solid foundation in the form of a St. Michaels Maryland rental. 

It’s not the most talked about New England vacation destination but that doesn’t mean it’s not worth embracing. By the end of the trip you’ll feel that you’ve discovered something great – meaning your St Michaels MD rental as well as the city itself. Spending a few days doing nothing but sailing, biking and lounging on the beach could do wonders for family morale, so it’s imperative to check out St. Michaels beach rentals as soon as you have the chance.

Once you’ve laid a solid foundation for the trip the rest will easily fall into place. St. Michaels house rentals plus a sunny array of diversions equals a winning equation. Adventures can take all kinds of forms, including visiting a semi-quiet Maryland town. As long as St Michaels vacation home rentals make an appearance, then odds are that all will be well.

St Michaels Vacation Rental Deals

The Chesepeake Bay is one of the most beautiful places on the East Coast, and you can enjoy the area with one of our amazing St Michaels discounted vacation rentals. We provide cheap St Michael’s vacation homes that won’t hurt your wallet. Save money on a St Michaels getaway that will have you within driving distance of Washington DC, Baltimore, and Philadelphia. We offer St Michaels last minute deals that will allow you to spend a great weekend on a majestic peninsula. Not only can we make your trip affordable, but we can make it a vacation your will remember. So, book a low-cost St Michaels vacation rental today!

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Check out more areas which feature homes, villas, cabins, cottages, or condos.

St Michaels things to do

 

Sail Selina II

We decided to do our wedding ceremony aboard the Salina II on our anniversary. Capt. Iris and crew were amazing! Despite the bleak weather and diminishing...read more

 

Carpenter Street Saloon

We tried the: pancakes - standard, came with three large pancakes crab omelette - nice lump pieces of crab with lots of boursin cheese YMCA (yogurt,...read more

 

Chesapeake Bay Maritime Museum

YES! This is a fabulous museum for any age group, with plenty of hands-on activities to keep people interested and really enhance the learning. I hadn't...read more

 

St. Michaels Winery

I've been here twice. The more recent visit took place just two days ago. We had the dry red tasting, and unfortunately I did not find most of the wines to...read more

 

Tricycle and Run

My wife and I were biking around St. Michael's on Memorial Day, and my wife's bike seat broke. I called Tricycle and Run to see if they were open and could...read more

 

Calico Toys and Games

Wow. This is like the BEST toy store I've ever seen. And it's not a chi-chi, "we're all wood and German-made and you're all Very Involved in Your...read more

 

The Big Owl Tiki Bar

Great place to relax on the water instead of waiting in the traffic on bay bridge. Great seafood for a great price.read more

 

Lady Patty Classic Yacht Charters

Worth every minute, captain Jeff and first mate pj were very friendly and knowledgable . Great margaritas and the boat is beautiful. Can't wait to go again.read more

 

Shore Pedal & Paddle

Friendly and locally owned shop with great water and bike options. Got recommendations on water trails as well as restaurants to try. Will definitely rent...read more

 

St. Michaels Concours d'Elegance

With the help of Cole Porter: It's delightful, it's delicious, it's d'Elegance You can tell at a glance what a swell event this is for romance You can...read more

 

Feelin' Good Studio

I recently made the trip to St. Michael's for a workshop in Reflexology with Lara. The studio was lovely, clean and quiet. Lara was a great teacher and made...read more

 

Tilghman Island Marina

Spouse rented a boat with a cousin while on vacation in July 2014.Captain Ron gave them a thorough lesson in regards to the area, where to avoid and how to...read more

 

Dockside Express

As the Maid of Honor it's my responsibility to ensure a good time is had by all! I was planning this bachelorette weekend from 640 miles away, having never...read more

 

Riverhouse at Easton Club Golf Course

My cousin just had her wedding here last weekend and everything went very smoothly (minus the weather which didn't cooperate till the VERY last minute)....read more

 

St. Michaels Marina

Funny time to write about a marina, but hey I forgot to do it in the summer. Although this place gets "props" for friendliness and proximity to town,...read more

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Restored Waterfront Cottage near St Michaels
St Michaels House Rental Picture
  • bedrooms 3
  • community
  • rental type House
  • sleeps 6
  • baths 3
  • rates (USD) $280 - $455 /nt
    $1,908 - $2,556 /wk
 
 
 
 
 

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St. Michaels Waterfront Cottage, Spa & Fireplace
St Michaels House Rental Picture
  • bedrooms 3
  • community
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths
  • rates (USD) $250 - $350 /nt
    $1,800 - $2,000 /wk
 
 
 
 
 

2 reviews write a review

Miles River Guest House
St Michaels House Rental Picture
  • bedrooms 2
  • community
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $250 - $450 /nt
    $1,800 - $2,975 /wk
    $7,200 - $9,000 /mth
 
 
 
 
 

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Prestigious Waterfront
St Michaels House Rental Picture
  • bedrooms 5
  • community
  • rental type House
  • sleeps 10
  • baths 4
  • rates (USD) $2,000 - $6,500 /wk
 
 
 
 
 

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Waterfront Home in Historic St. Michaels
St Michaels Farmhouse Rental Picture
  • bedrooms 4
  • rental type Farmhouse
  • owner badgeowner badge
  • sleeps 8
  • baths
  • rates (USD) $550 /nt
    $3,500 /wk
 
 
 
 
 

11 reviews write a review

20% off stays of 3 nights or more during August 2014
St Michaels Estate Rental Picture
  • bedrooms 3
  • rental type Estate
  • owner badgeowner badge
  • sleeps 9
  • baths
  • rates (USD) $350 - $600 /nt
    $2,405 - $3,750 /wk
    $9,720 - $16,020 /mth
 
 
 
 
 

11 reviews write a review

Breezy Point Waterfront Home-Pool-Dock/Pier-Recreation Pavilion
St Michaels House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 3
  • rates (USD) $325 - $472 /nt
    $3,300 /wk
 
 
 
 
 

3 reviews write a review

Charmer - Perfect for Quick Retreat on the Water, 2 Paddleboards Included
St Michaels Cottage Rental Picture
  • bedrooms 3
  • rental type Cottage
  • sleeps 5
  • baths 2
  • rates (USD) $386 - $425 /nt
    $1,495 - $1,712 /wk
 
 
 
 
 

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Tucked Away - Guests Love Waterfront Screen Porch & Sunning on Dock
St Michaels Cottage Rental Picture
  • bedrooms 4
  • rental type Cottage
  • sleeps 8
  • baths 3
  • rates (USD) $511 - $581 /nt
    $1,880 - $2,233 /wk
 
 
 
 
 

2 reviews write a review

Book your September Getaway - 3 Night Specials - Email Today!!
St Michaels House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths
  • rates (USD) $275 - $450 /nt
    $1,600 - $3,000 /wk
    $6,000 /mth
 
 
 
 
 

12 reviews write a review

**** $750/night on stays of 3 nights or more in September ****
St Michaels Estate Rental Picture
  • bedrooms 4
  • rental type Estate
  • sleeps 10
  • baths 5
  • rates (USD) $650 - $1,000 /nt
    $4,000 - $6,300 /wk
    $14,000 - $22,000 /mth
 
 
 
 
 

2 reviews write a review

St. Michael's premier in town summer vacation cottage!
St Michaels Cottage Rental Picture
  • bedrooms 2
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 4
  • baths 2
  • rates (USD) $257 - $400 /nt
    $1,700 - $1,800 /wk
    $7,200 /mth
 
 
 
 
 

39 reviews write a review

Estate Privacy Secs from St Mikes - Shoreline, Acreage, Pool, Decor, Hot Tub.
St Michaels House Rental Picture
  • bedrooms 6
  • rental type House
  • sleeps 12
  • baths
  • rates (USD) $1,232 - $2,183 /nt
    $6,428 - $10,738 /wk
 
 
 
 
 

5 reviews write a review

Quaint renovated 1910 hideaway - Guests Love Waterfront Screened Porch
St Michaels Cottage Rental Picture
  • bedrooms 3
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 6
  • baths
  • rates (USD) $515 - $720 /nt
    $2,000 - $3,195 /wk
 
 
 
 
 

31 reviews write a review

1900 Circa Quirky Cottage - Nothing Cookie Cutter About This One-Country Fun
St Michaels Cottage Rental Picture
  • bedrooms 3
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 5
  • baths 3
  • rates (USD) $521 - $680 /nt
    $1,810 - $2,746 /wk
 
 
 
 
 

10 reviews write a review

Got family? Pool, hot tub, canoe, grilling deck all minutes to town
St Michaels House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 3
  • rates (USD) $578 - $783 /nt
    $2,125 - $3,275 /wk
 
 
 
 
 

27 reviews write a review

Soothing getaway cottage with waterside hot tub for relaxation
St Michaels Cottage Rental Picture
  • bedrooms 3
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $458 - $520 /nt
    $1,660 - $1,975 /wk
 
 
 
 
 

47 reviews write a review

Pool open until October 15! Fall weeks available at discounted rate.
St Michaels House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD) $521 - $742 /nt
    $2,035 - $3,316 /wk
 
 
 
 
 

32 reviews write a review

Single family cottage with pool, kayaks, play gym & dock
St Michaels Cottage Rental Picture
  • bedrooms 3
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 6
  • baths
  • rates (USD) $496 - $655 /nt
    $1,760 - $2,696 /wk
 
 
 
 
 

36 reviews write a review

Every possible amenity for a dream family vacation and only 1/2 mile to town!
St Michaels House Rental Picture
  • bedrooms 5
  • rental type House
  • owner badgeowner badge
  • sleeps 10
  • baths 4
  • rates (USD) $860 - $1,324 /nt
    $5,756 - $6,778 /wk
 
 
 
 
 

23 reviews write a review

Firepit and Waterside BBQ for cool fall evenings
St Michaels Cottage Rental Picture
  • bedrooms 3
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $430 - $493 /nt
    $1,605 - $1,920 /wk
 
 
 
 
 

29 reviews write a review

Fall foliage! Beautiful colors and waterfowl abound on this 90 acre farm
St Michaels House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD) $493 - $698 /nt
    $1,955 - $3,105 /wk
 
 
 
 
 

40 reviews write a review

Private hideaway just a 1/2 mile from historic district. Great for biking.
St Michaels Cottage Rental Picture
  • bedrooms 3
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 6
  • baths 3
  • rates (USD) $536 - $619 /nt
    $2,155 - $2,583 /wk
 
 
 
 
 

21 reviews write a review

Elegant, Waterfront Cottage on Six Acres in Historic Area
St Michaels Cottage Rental Picture
  • bedrooms 3
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD)
 
 
 
 
 

7 reviews write a review

Elegant Ralph Lauren Waterfront Cottage Nr St Michaels
St Michaels Cottage Rental Picture
  • bedrooms 3
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $350 - $450 /nt
    $1,500 - $1,990 /wk
    $4,000 - $6,000 /mth
 
 
 
 
 

7 reviews write a review

Charming English Country Apartment On The Chesapeake
St Michaels Apartment Rental Picture
  • bedrooms 2
  • rental type Apartment
  • sleeps 6
  • baths 2
  • rates (USD) $400 /nt
    $2,500 /wk
    $9,000 /mth
 
 
 
 
 

3 reviews write a review

Luxurious and Extremely Private Waterfront Estate
St Michaels Estate Rental Picture
  • bedrooms 8
  • rental type Estate
  • owner badgeowner badge
  • sleeps 20
  • baths 8
  • rates (USD) $1,200 - $2,000 /nt
    $7,450 - $13,500 /wk
 
 
 
 
 

13 reviews write a review

Bay Cottage, St. Michaels, Md Waterfront Vacation Retreat: Pool, Dock,Farm, Bike
St Michaels Estate Rental Picture
  • bedrooms 6
  • rental type Estate
  • sleeps 12
  • baths
  • rates (USD) $759 - $1,419 /nt
    $4,050 - $6,350 /wk
    $12,150 - $19,050 /mth
 
 
 
 
 

1 reviews write a review

Classic Eastern Shore Cottage with all the best amenities!
St Michaels Cottage Rental Picture
  • bedrooms 3
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $448 - $576 /nt
    $1,932 - $2,445 /wk
 
 
 
 
 

8 reviews write a review