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Location Location! St Michaels-- In Town Cottage!
St. Michaels house
- 2 bedrooms
- 2 bathrooms
- sleeps 5
Price per night from
$352
Waterfront Property, Kayaks, Private Dock, Near Town
St. Michaels house
- 3 bedrooms
- 3 bathrooms
- sleeps 6
Price per night from
$860
Price per night from
$382
St. Michael's Premier in Town Summer Cottage now with private pool!
St. Michaels house
- 2 bedrooms
- 2 bathrooms
- sleeps 4
Price per night from
$717
Responds fast! avg. 38 minutes
Price per night from
$2,293
RANCH AT ROYAL OAK- Exclusive waterfront pool pier
St. Michaels house
- 6 bedrooms
- 6 bathrooms
- sleeps 12
Responds fast! avg. 38 minutes
Price per night from
$2,293
Price per night from
$1,890
Great rentals within 20 miles that match your search
“Love Point Retreat” I stayed at Paula's property 3 times so far. We stayed once in October 2014 and twice in April 2015. Here is how I would break it up: Owner: Paula is very nice, accommodating and extremely responsive. She was easy to deal with, answered all of our questions and concerns timely. Property (Interior): The property is really clean and very well maintained considering its age. I also feel that it is properly stocked with all the necessities. Property (Outdoor Space / View): We spend the majority of our time there outside. The deck / backyard area is very well maintained and stocked with adequate furniture. We used the gas grill every day of our stay. The dock is set up nicely for fishing including rod holders and a light for night fishing. The view from the dock is to die for, the Bay is so wide and the Bay Bridge is a nice backdrop to the view specially during sunset. Fishing: Fishing is the best I have ever experienced (compared to all other rentals I tried). I caught numerous species from the dock including Spot, White Perch and of course Striped Bass (Rockfish). I caught my biggest Rockfish ever from the dock there (39 inch fish, roughly 30 pounds) in April. Overall, I love the property, the view and the peaceful surroundings. A great bonus for me is the short one hour commute to get there. We will definitely be back to Love Point for an encore.
Price per night from
$459
“Comfortable and secure in a great home - almost as good as at ho” The house is set is a terrific neighborhood of annapolis within easy walking distance to two small parks on the water and to town. We all found the house a delight - the design, decorating, furnishings are tasteful and match the age and the imagery of the house. It is well equipped with comfortable bedrooms, adequate bathrooms and linens, utensils and staple supplies. We certainly will attempt to stay at this house again if we ever return to annapolis.
Price per night from
$488
Peaceful, Waterfront Home on 3 Acres (pier + western view w/gorgeous sunsets)
Chester house
- 4 bedrooms
- 2 bathrooms
- sleeps 8
“Unbelievable value” We were a family group of 3 couples plus an infant traveling to a wedding at the Usna chapel. The home was just wonderful, had a great view, was very clean, and was well equipped for the cooking being planned. Stores, restaurants, and liquor store were close by. Easy on and off the freeway into annapolis. Scott was very personable and worked with us to make our visit just right from the moment we first contacted him about renting.
Price per night from
$453
Vintage Bungalow-cozy, walk to shops, water, free pkg.
Annapolis house
- 3 bedrooms
- 2 bathrooms
- sleeps 6
Price per night from
$476
Responds fast! avg. 34 minutes
Price per night from
$258
KENT ISLAND-OCEAN VIEW Home for rent-4 bedrooms EASTERN SHORE sleeps 10-12
Kent Island house
- 4 bedrooms
- 2 bathrooms
- sleeps 12
Price per night from
$1,949
DOLCE VIDA AT Kent Island- 4 bedrooms House for rent-SLEEPS 10-12
Chester house
- 4 bedrooms
- 3 bathrooms
- sleeps 10
Price per night from
$1,949
Eat..Sleep..Fish..Repeat! Who needs a desk (there is one upstairs) when you can
Stevensville house
- 4 bedrooms
- 2 bathrooms
- sleeps 12
Price per night from
$803
Price per night from
$1,147
Price per night from
$400
CHESAPEAKE MANSION - NEW POOL/12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND
Sherwood house
- 8 bedrooms
- 10 bathrooms
- sleeps 12
Responds fast! avg. 38 minutes
Price per night from
$2,866
Price per night from
$1,261
Price per night from
$442
Price per night from
$228
Price per night from
$631
Beautiful Waterfront Home, Private Pool and Water Amenities- Sleeps 16
Cambridge house
- 5 bedrooms
- 3 bathrooms
- sleeps 18
Price per night from
$860
Price per night from
$226
Price per night from
$343
Price per night from
$572
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Annapolis apartment
- 2 bedrooms
- 1 bathroom
- sleeps 6
Price per night from
$224
Price per night from
$682
Price per night from
$670
Price per night from
$401
Price per night from
$248
Indoor pool and spa located in beautiful Southern Maryland woodlands
Chesapeake Beach house
- 3 bedrooms
- 3 bathrooms
- sleeps 8
Price per night from
$1,105
Annapolis Charm™ Waterfront Chesapeake Bay Getaway - Private Pier - Near USNA
Cape Saint Claire house
- 2 bedrooms
- 1 bathroom
- sleeps 6
Price per night from
$401
Price per night from
$189
Viewing 38 of 92
rentals in St. Michaels
About St. Michaels
St. Michaels has been a popular vacation destination for years – find out why by booking your vacation rental with FlipKey, today!
About St. Michaels, Maryland
This small town in Talbot County is famous throughout the east coast for being the perfect getaway spot.
It's slightly unusual, as it wasn't built in a grid form like so many other American towns. Instead, it centers around the town square and progresses outwards in layers.
Way back in the past, it was a tobacco growing and shipbuilding town. A real taste of old-time Americana. But, now its trade focuses on tourism and oysters – the latter are always delicious and well worth trying during your stay.
Plans to improve the town have been underway since the 60s. There's now a museum, waterfront restaurants and tour boats that make it a much more exciting place to stay. Check them out for yourself when you come here.
You may recognize this small town as it's starred in a few movies. Clara's Heart (starring Whoopi Goldberg and Neil Patrick Harris), and The Wedding Crashers (with Owen Wilson and Vince Vaughn) were both filmed here – how about that for a bit of Hollywood glitz and glamour?
What to do
FIrst stop, go to the Chesapeake Bay Maritime Museum. It's a really interesting place for sailing enthusiasts and history nuts. The exhibits are mostly historic bay vessels, including the ‘Chesapeake Bay bugeye’ named Edna E. Lockwood – ask the guide about that one!
For a little more history, go to the St. Michael's Mill. It’s a grist mill that dates back to the 19th century, and was a major part of the town life for the locals of yesteryear.
If you want some culture, there are three art galleries to choose from. The Clark Gallery, Hopkins and Gregario – all with something a little different for you to explore.
If you're looking for some fun activities to try during your stay, there are plenty. Take a boat out on the water and explore the area. Or, try stand up paddleboarding – it's hard work but great fun!
There are several running and kayaking trails for you to discover. Or, you could spend a day fishing in the shallow waters.
Top St. Michaels, Maryland travel tips
Most of St. Michaels is dog-friendly, so bring your pooch along on vacation and let them explore someplace new.
You'll have your pick of riverfront restaurants during your stay. Make sure to try the fresh seafood, but remember to tip as gratuity is not included.
For a peaceful trip away by the water, choose St. Michaels as your next vacation destination. Pick your St. Michaels vacation rental on FlipKey and let the adventure begin!
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