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73 villas
Halos'Haven Vacation Rental
St. Michaels / McDaniel
5 10 2 nights min
- 5 bedrooms
- sleeps 10
- 2 nights min
- Swimming pool
- Child Friendly
- Air conditioning
Map
Price per night from
$700
Price per night from
$700
Carpenter St. Cottage in the Heart of St. Michaels - Walk To Everything!
Talbot County / St. Michaels
2 5 min stay varies
- 2 bedrooms
- sleeps 5
- min stay varies
- Child Friendly
- Air conditioning
- Pet Friendly
Map
Price per night from
$160
Responds fast!
avg. 3 hours 32 minutes
Price per night from
$160
Large Historic Thomas Harrison House on Harbor in St. Michaels Town
Talbot County / St. Michaels
7 9 min stay varies
- 7 bedrooms
- sleeps 9
- min stay varies
- Beach / lakeside relaxation
- Child Friendly
- Air conditioning
Map
Price per night from
$290
Responds fast!
avg. 3 hours 32 minutes
Price per night from
$290
Location Location! St Michaels-- In Town Cottage!
Talbot County / St. Michaels
2 5 min stay varies
- 2 bedrooms
- sleeps 5
- min stay varies
- Beach / lakeside relaxation
- Child Friendly
- Car not necessary
Map
Price per night from
$148
Responds fast!
avg. 3 hours 32 minutes
Price per night from
$148
Phenomenal Vacation Rental by Water in St Michaels - Walk to Town! 4 ADULTS MAX
Talbot County / St. Michaels
1 6 2 nights min
- 1 bedroom
- sleeps 6
- 2 nights min
- Child Friendly
- Air conditioning
- Private garden
Map
Price per night from
$229
Price per night from
$229
Pot Pie House
Talbot County / St. Michaels
3 6 3 nights min
- 3 bedrooms
- sleeps 6
- 3 nights min
- Air conditioning
Price per night from
$225
Price per night from
$225
Best sunrise in St. Michaels....Broadview Bay House
Talbot County / St. Michaels
6 12 min stay varies
- 6 bedrooms
- sleeps 12
- min stay varies
- Swimming pool
- Child Friendly
- Air conditioning
Map
Price per night from
$596
Price per night from
$596
Premier Cottage in St. Michaels- In Town Location!
Talbot County / St. Michaels
2 5 min stay varies
- 2 bedrooms
- sleeps 5
- min stay varies
- Child Friendly
- Air conditioning
- Pet Friendly
Map
Price per night from
$150
Responds fast!
avg. 3 hours 32 minutes
Price per night from
$150
Historic Waterfront Property with Wi-Fi and Dock
Talbot County / St. Michaels
3 8 2 nights min
- 3 bedrooms
- sleeps 8
- 2 nights min
- Beach / lakeside relaxation
- Child Friendly
- Air conditioning
Map
Price per night from
$745
Responds fast!
avg. 3 hours 21 minutes
Price per night from
$745
Waterview Cottage 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
Map
Price per night from
$160
Responds fast!
avg. 3 hours 32 minutes
Price per night from
$160
Sandy Pines: Enjoy Harris Creek w/Pool and Boats
Talbot County / St. Michaels
4 10 min stay varies
- 4 bedrooms
- sleeps 10
- min stay varies
- Beach / lakeside relaxation
- Swimming pool
- Child Friendly
Map
Price per night from
$373
Price per night from
$373
Harris Cove Cottages LLC
Talbot County / St. Michaels
1 4 1 night min
- 1 bedroom
- sleeps 4
- 1 night min
- Child Friendly
- Air conditioning
Map
Price per night from
$199
Price per night from
$199
Halo's Haven Guest Quarters
Talbot County / St. Michaels
3 6 1 night min
- 3 bedrooms
- sleeps 6
- 1 night min
- Child Friendly
- Air conditioning
- Private garden
Map
Price per night from
$325
Price per night from
$325
St. Michael's Premier in Town Summer Cottage!
Talbot County / St. Michaels
2 4 2 nights min
- 2 bedrooms
- sleeps 4
- 2 nights min
- Child Friendly
- Air conditioning
- Private garden
Map
Price per night from
$283
Price per night from
$283
St. Michaels award-winning waterfront BayCottage, pool, docks, sundeck, grounds
Talbot County / St. Michaels
6 12 2 nights min
- 6 bedrooms
- sleeps 12
- 2 nights min
- Beach / lakeside relaxation
- Nearest beach 7 mi
- Swimming pool
Map
Price per night from
$839
Responds fast!
avg. 1 hour 1 minutes
Price per night from
$839
Great rentals within 20 miles that match your search
Distance approx 16.31 km from St. Michaels
NEW! Colonial Home in Cambridge w/Wraparound Porch
Maryland / Cambridge
3 7 min stay varies
- 3 bedrooms
- sleeps 7
- min stay varies
- Child Friendly
- Air conditioning
Price per night from
$220
Responds fast!
avg. 12 minutes
Price per night from
$220
Distance approx 16.12 km from St. Michaels
Waterfront Vacation Home with Private Beach
Talbot County / Trappe
3 6 2 nights min
- 3 bedrooms
- sleeps 6
- 2 nights min
- Beach / lakeside relaxation
- Nearest beach 97 mi
- Child Friendly
Price per night from
$326
Responds fast!
avg. 1 hour 34 minutes
Price per night from
$326
Distance approx 15.86 km from St. Michaels
Choptank River View House
Maryland / Cambridge
6 14 3 nights min
- 6 bedrooms
- sleeps 14
- 3 nights min
- Beach / lakeside relaxation
- Nearest beach 0 mi
- Air conditioning
Price per night from
$993
Price per night from
$993
Distance approx 17.7 km from St. Michaels
Seahorse Guest Cottage near the Bay, dog friendly
Calvert County / North Beach
1 5 2 nights min
- 1 bedroom
- sleeps 5
- 2 nights min
- Beach / lakeside relaxation
- Nearest beach 0.2 mi
- Child Friendly
Price per night from
$159
Responds fast!
avg. 12 minutes
Price per night from
$159
Distance approx 15.75 km from St. Michaels
Annapolis Crows Nest Cottage: Chesapeake Bay View
Maryland / Annapolis
5 20 min stay varies
- 5 bedrooms
- sleeps 20
- min stay varies
- Beach / lakeside relaxation
- Nearest beach 0.2 mi
- Child Friendly
Price per night from
$686
Price per night from
$686
Distance approx 16.58 km from St. Michaels
Love Point Luxury Waterfront in Stevensville
Kent Island / Stevensville
3 10 3 nights min
- 3 bedrooms
- sleeps 10
- 3 nights min
- Beach / lakeside relaxation
- Child Friendly
- Air conditioning
Price per night from
$1,389
Price per night from
$1,389
Distance approx 8.9 km from St. Michaels Show on Map
Huge Stevensville House Overlooking Eastern Shore!
Kent Island / Stevensville
3 10 min stay varies
- 3 bedrooms
- sleeps 10
- min stay varies
- Swimming pool
- Child Friendly
- Air conditioning
Map
Price per night from
$397
Responds fast!
avg. 9 minutes
Price per night from
$397
Distance approx 10.43 km from St. Michaels
Waterfront Stevensville House w/ Pier & 2 Decks!
Kent Island / Stevensville
5 12 min stay varies
- 5 bedrooms
- sleeps 12
- min stay varies
- Child Friendly
- Air conditioning
- Pet Friendly
Price per night from
$373
Responds fast!
avg. 10 minutes
Price per night from
$373
Distance approx 15.05 km from St. Michaels
Shady Side House on Chesapeake Bay Near Marina!
Maryland / Shady Side
2 5 min stay varies
- 2 bedrooms
- sleeps 5
- min stay varies
- Child Friendly
- Air conditioning
Price per night from
$184
Responds fast!
avg. 9 minutes
Price per night from
$184
Distance approx 5.32 km from St. Michaels Show on Map
St. Michaels Area Cottage - Walk to Water & Marina
Talbot County / Neavitt
2 4 2 nights min
- 2 bedrooms
- sleeps 4
- 2 nights min
- Child Friendly
- Air conditioning
- Pet Friendly
Map
Price per night from
$174
Responds fast!
avg. 12 minutes
Price per night from
$174
Distance approx 5.18 km from St. Michaels Show on Map
Cottage 1a at Grandview Pleasure Point
Talbot County / Bozman
1 4 2 nights min
- 1 bedroom
- sleeps 4
- 2 nights min
- Swimming pool
- Ask about children
- Ask about pets
Map
Price per night from
$244
Price per night from
$244
Distance approx 12.34 km from St. Michaels
Peaceful, Waterfront Home on 3 Acres (pier + western view w/gorgeous sunsets)
Kent Island / Chester
4 8 3 nights min
- 4 bedrooms
- sleeps 8
- 3 nights min
- Beach / lakeside relaxation
- Nearest beach 14 mi
- Child Friendly
Price per night from
$283
Price per night from
$283
Distance approx 17.37 km from St. Michaels
Renovated Luxury Waterview House
Calvert County / North Beach
3 6 2 nights min
- 3 bedrooms
- sleeps 6
- 2 nights min
- Child Friendly
Price per night from
$296
Price per night from
$296
Distance approx 5.19 km from St. Michaels Show on Map
Cottage 2 at Grandview Pleasure Point
Talbot County / Bozman
2 6 2 nights min
- 2 bedrooms
- sleeps 6
- 2 nights min
- Beach / lakeside relaxation
- Swimming pool
- Child Friendly
Map
Price per night from
$383
Price per night from
$383
Distance approx 17.41 km from St. Michaels
Stunning, Newer Chesapeake Waterfront Estate, Pool - 6/7 Bedrms 5 Baths
Maryland / Cambridge
6 20 min stay varies
- 6 bedrooms
- sleeps 20
- min stay varies
- Beach / lakeside relaxation
- Nearest beach 0.1 mi
- Swimming pool
Price per night from
$493
Responds fast!
avg. 3 hours 27 minutes
Price per night from
$493
Distance approx 19.12 km from St. Michaels
Walk to Shops/Eateries Charming Cottage. Dogs Wel.
Maryland / Annapolis
3 6 min stay varies
- 3 bedrooms
- sleeps 6
- min stay varies
- Nearest beach 6 mi
- Child Friendly
- Car not necessary
Price per night from
$249
Responds fast!
avg. 1 hour 49 minutes
Price per night from
$249
Distance approx 16.68 km from St. Michaels
The Yellow House- Gorgeous Southern Colonial
Maryland / Annapolis
6 14 4 nights min
- 6 bedrooms
- sleeps 14
- 4 nights min
- Beach / lakeside relaxation
- Nearest beach 1 mi
- Child Friendly
Price per night from
$982
Responds fast!
avg. 1 hour 30 minutes
Price per night from
$982
Distance approx 11.05 km from St. Michaels
KENT ISLAND-OCEAN VIEW Home for rent -4 bedrooms EASTERN SHORE sleeps 10-12
Maryland / Kent Island
4 10 2 nights min
- 4 bedrooms
- sleeps 10
- 2 nights min
- Nearest beach 5 mi
- Swimming pool
- Air conditioning
Price per night from
$1,489
Price per night from
$1,489
Distance approx 13.2 km from St. Michaels
Luxury vacation condominum with private beach
Kent Island / Chester
4 10 2 nights min
- 4 bedrooms
- sleeps 10
- 2 nights min
- Beach / lakeside relaxation
- Nearest beach 0.2 mi
- Child Friendly
Price per night from
$437
Price per night from
$437
Distance approx 11.36 km from St. Michaels
KI Golf House-A PAR for the Course & Mile to Beach
Maryland / Kent Island
4 10 2 nights min
- 4 bedrooms
- sleeps 10
- 2 nights min
- Nearest beach 1 mi
- Child Friendly
- Air conditioning
Price per night from
$596
Price per night from
$596
Distance approx 11.74 km from St. Michaels
Kent Island Beach House II:Chesapeake Bay Fisherman's Village at Kentmorr Marina
Kent Island / Stevensville
4 12 3 nights min
- 4 bedrooms
- sleeps 12
- 3 nights min
- Nearest beach 0 mi
- Child Friendly
- Air conditioning
Price per night from
$645
Price per night from
$645
Distance approx 14.3 km from St. Michaels
Cottage at Heron Cove, Chesapeake Bay, Cambridge
Maryland / Cambridge
3 5 min stay varies
- 3 bedrooms
- sleeps 5
- min stay varies
- Beach / lakeside relaxation
- Child Friendly
- Air conditioning
Price per night from
$166
Price per night from
$166
Distance approx 16.39 km from St. Michaels
EASTERN SHORE MARYLAND WELCOMES YOU
Maryland / Preston
1 2 1 night min
- 1 bedroom
- sleeps 2
- 1 night min
- Swimming pool
- Child Friendly
- Air conditioning
Price per night from
$74
Price per night from
$74
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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