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66 villas
Large Historic Thomas Harrison House on Harbor in St. Michaels Town
St. Michaels house
7 bedrooms / 4 bathrooms / sleeps 9
“Perfect in every way!” I stayed at the Thomas Harrison house a few weeks ago and all I can say is..."if you are planning on coming to St. Michael's you need to stay at this house." This house is perfect in every way. It has all the accommodations that you could ever need and is very unique and quaint. The location is more than perfect (we literally were in walking distance of everything, shops, restaurants, etc.) and did not even have to get into the car to drive anywhere the entire time. The backyard has a wonderful porch where you can sit outside and converse with friends or even sip your coffee in the morning. The view is phenomenal! You have a wonderful panoramic view of the water from your bedroom window and the beds are very comfortable (which is a must for me). If you are planning on a trip to experience St. Michael's whether it is a romantic weekend getaway or a family (group) outing I would hands down recommend this house.
Price per night from
$516
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
Responds fast! avg. 2 hours 3 minutes
Price per night from
$859
Premier Cottage in St. Michaels- In Town Location!
St. Michaels house
2 bedrooms / 2 bathrooms / sleeps 5
Price per night from
$297
Carpenter St. Cottage in the Heart of St. Michaels - Walk To Everything!
St. Michaels cottage
2 bedrooms / 2 bathrooms / sleeps 5
Price per night from
$431
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$382
Sandy Pines: Enjoy Harris Creek w/Pool and Boats
St. Michaels house
4 bedrooms / 3 bathrooms / sleeps 8
Responds fast! avg. 34 minutes
Price per night from
$785
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
$716
Ship's Cove Inn and Resort in St. Michaels, MD
St. Michaels house
6 bedrooms / 6 bathrooms / sleeps 12
Price per night from
$1,890
Great rentals within 20 miles that match your search
“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.
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$487
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$218
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$218
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$321
“5 out of 5” I spent a long weekend at the main house, and it was easily the best weekend of the summer! The location is phenomenal. The house sits on large stretch of beautiful waterfront property. The views from the piers and the pool are exquisite. As for the house itself, we couldn't have asked for more. It is spacious, clean, and has all of the amenities you could want. I must also mention that it was a breeze and a pleasure working with the folks at Grandview. They are incredibly responsive, and make a great effort to ensure that you enjoy your stay.
Price per night from
$549
Stunning Home in the Heart of Downtown Annapolis
Annapolis house
3 bedrooms / 5 bathrooms / sleeps 11
Price per night from
$796
Stunning, Newer Chesapeake Waterfront Estate, Pool - 7 Bedrms 5 Baths
Cambridge house
6 bedrooms / 5 bathrooms / sleeps 18
“Outstanding Vacation Rental” Our extended family (22 people - 13A/9K) had a great week at Saddle Beach. The house was beautiful and in very good condition. The option of being in the pool or the river during the day was wonderful. The house was clean and well furnished. The dining room table and table on the porch provided plenty of seating for meals. There was plenty of hot water for showers and clean-up after meals. The pool was clean and the river was awesome, with a gradual slope that was perfect for kids and adults. We used the crab traps provided and caught 2 dozen crabs that made a great contribution to dinner on Friday. Crabbing was best by the dock. We caught all but 3 crabs there, rather than out closer to the middle of the river. The AC on the ground floor stopped working on Tuesday, but one call to the owner and the repair team was on-site in less than 2 hours. The issue was resolved before noon on Wednesday. We have been renting vacation properties for years and issues crop up from time to time. We appreciated the quick response and resolution. The one recommendation we will make is to bring bug spray (mosquitos and horse flies). We anticipated it being right on the river, but if you haven't had that experience, you need to be prepared.
Responds fast! avg. 3 hours 53 minutes
Price per night from
$686
Responds fast! avg. 33 minutes
Price per night from
$487
Cottage at Heron Cove, Chesapeake Bay, Cambridge
Cambridge cottage
3 bedrooms / 1 bathroom / sleeps 5
Responds fast! avg. 2 hours 34 minutes
Price per night from
$221
KI Golf House-A PAR for the Course & Mile to Beach
Kent Island house
4 bedrooms / 3 bathrooms / sleeps 10
Price per night from
$573
Responds fast! avg. 2 hours 53 minutes
Price per night from
$6,870
Comfortable, Spacious & Fun! 6+ Acres Pool & Shore. 4 Master Suites Waterview
Wittman log cabin
5 bedrooms / 5 bathrooms / sleeps 10
Price per night from
$1,117
Year Round Estate on Bay / Fam. Reunions / Slps 28
Cambridge house
7 bedrooms / 7 bathrooms / sleeps 28
“Unbelievable Home in an Unbelievable Setting!!!” Our family cant thank you enough for the memories made at captains quarters this summer. This was the first time getting away with the entire family (kids grandkids, grand parents, etc) and it was propabaly the most memorable week our family has ever spent together. The house was absolutely perfect! Clean, beautifully furnished, amenities for all ages and the most spectacular grounds and views for the entire family to enjoy. We are already planning our stay for next summer and hope to come back this winter as well for a long weekend. Thank you thank you thank you!
Price per night from
$1,890
Kent Island Beach House II:Chesapeake Bay Fisherman's Village at Kentmorr Marina
Stevensville house
4 bedrooms / 2 bathrooms / sleeps 12
Price per night from
$602
Beautiful Kent Island 4BR, Perfect Location, Close to Chesapeake Bay Beach Club!
Chester house
4 bedrooms / 3 bathrooms / sleeps 12
Responds fast! avg. 54 minutes
Price per night from
$458
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
$1,947
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
$1,718
Private setting, enjoy nature, kayaking and total relaxation
Bethlehem house
3 bedrooms / 2 bathrooms / sleeps 8
Price per night from
$344
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
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$1,145
Price per night from
$801
Responds fast! avg. 1 hour 11 minutes
Price per night from
$196
22 Fleet St. - Best Spot for Commissioning Week, Newly-Renovated & Historic!
Annapolis condo
3 bedrooms / 3 bathrooms / sleeps 6
Price per night from
$302
Price per night from
$189
Chesapeake Bay Getaway™ | Waterfront Experience with Pier!
Edgewater house
2 bedrooms / 1 bathroom / sleeps 8
Price per night from
$573
Price per night from
$229
Quiet Home Close to Downtown Annapolis and Parks
Annapolis house
4 bedrooms / 3 bathrooms / sleeps 7
Price per night from
$400
Cozy cottage with expansive backyard and firepit!
Tracys Landing house
2 bedrooms / 1 bathroom / sleeps 4
Price per night from
$287
Annapolis Charm™ Waterfront Chesapeake Bay Getaway - Private Pier - Near USNA
Cape Saint Claire house
2 bedrooms / 1 bathroom / sleeps 6
Price per night from
$573
Viewing 38 of 66
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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