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72 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
$802
Price per night from
$802
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
$401
Responds fast!
avg. 2 hours 48 minutes
Price per night from
$401
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
$859
Responds fast!
avg. 3 hours 23 minutes
Price per night from
$859
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
$207
Responds fast!
avg. 2 hours 48 minutes
Price per night from
$207
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
$207
Responds fast!
avg. 2 hours 48 minutes
Price per night from
$207
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
$600
Price per night from
$600
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
$263
Price per night from
$263
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
$258
Price per night from
$258
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
$218
Responds fast!
avg. 2 hours 48 minutes
Price per night from
$218
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
$218
Responds fast!
avg. 2 hours 48 minutes
Price per night from
$218
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
$430
Price per night from
$430
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
$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
$229
Price per night from
$229
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
$327
Price per night from
$327
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
$1,145
Responds fast!
avg. 3 hours 35 minutes
Price per night from
$1,145
Great rentals within 20 miles that match your search
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
$1,602
Price per night from
$1,602
Distance approx 16.12 km from St. Michaels
Waterfront Room Rentals 2 with Private Beach
Talbot County / Trappe
1 2 min stay varies
- 1 bedroom
- sleeps 2
- min stay varies
- Child Friendly
- Air conditioning
- Pet Friendly
Price per night from
$115
Responds fast!
avg. 1 hour 34 minutes
Price per night from
$115
Distance approx 16.12 km from St. Michaels
Waterfront Room Rentals 3 with Private Beach
Talbot County / Trappe
1 2 min stay varies
- 1 bedroom
- sleeps 2
- min stay varies
- Child Friendly
- Air conditioning
- Pet Friendly
Price per night from
$115
Responds fast!
avg. 1 hour 34 minutes
Price per night from
$115
Distance approx 3.11 km from St. Michaels Show on Map
St. Michaels Waterfront Retreat with pier, pool, kayaks, gas fire pit and bikes
Talbot County / Royal Oak
5 10 min stay varies
- 5 bedrooms
- sleeps 10
- min stay varies
- Swimming pool
- Child Friendly
- Air conditioning
Map
Price per night from
$572
Price per night from
$572
Distance approx 19.23 km from St. Michaels
NEW! Annapolis Home w/ Deck & Whitehall Bay Access
Maryland / Cape Saint Claire
4 8 min stay varies
- 4 bedrooms
- sleeps 8
- min stay varies
- Child Friendly
- Air conditioning
Price per night from
$251
Responds fast!
avg. 9 minutes
Price per night from
$251
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
$487
Responds fast!
avg. 9 minutes
Price per night from
$487
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
$796
Price per night from
$796
Distance approx 17.89 km from St. Michaels
6 Bdrm, 3.5 Bath, Cambridge Md Vacation Home
Maryland / Cambridge
6 12 3 nights min
- 6 bedrooms
- sleeps 12
- 3 nights min
- Child Friendly
- Air conditioning
- Pet Friendly
Price per night from
$995
Price per night from
$995
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
$212
Responds fast!
avg. 9 minutes
Price per night from
$212
Distance approx 17.55 km from St. Michaels
Panoramic Views of Herrington Harbour on the Bay.
Calvert County / North Beach
3 8 1 night min
- 3 bedrooms
- sleeps 8
- 1 night min
- Child Friendly
- Air conditioning
- Pet Friendly
Price per night from
$573
Price per night from
$573
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
$442
Price per night from
$442
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
$572
Price per night from
$572
Distance approx 16.55 km from St. Michaels
Love Point Bay Vacation Home
Kent Island / Stevensville
2 6 2 nights min
- 2 bedrooms
- sleeps 6
- 2 nights min
- Child Friendly
Price per night from
$377
Price per night from
$377
Distance approx 17.96 km from St. Michaels
Love Point Waterfront
Maryland / Kent Island
3 12 3 nights min
- 3 bedrooms
- sleeps 12
- 3 nights min
- Beach / lakeside relaxation
- Nearest beach 5 mi
- Child Friendly
Price per night from
$287
Price per night from
$287
Distance approx 18.91 km from St. Michaels
Location,location,location,walk to city dock,free
Maryland / Annapolis
2 5 min stay varies
- 2 bedrooms
- sleeps 5
- min stay varies
- Car not necessary
- Air conditioning
- Private garden
Price per night from
$287
Price per night from
$287
Distance approx 17.32 km from St. Michaels
Deerpond Carriage House
Maryland / Woolford
1 2 3 nights min
- 1 bedroom
- sleeps 2
- 3 nights min
- Swimming pool
- Air conditioning
- Private garden
Price per night from
$207
Price per night from
$207
Distance approx 19.67 km from St. Michaels
Stunning Home in the Heart of Downtown Annapolis
Maryland / Annapolis
3 11 2 nights min
- 3 bedrooms
- sleeps 11
- 2 nights min
- Ask about children
- Air conditioning
- Private garden
Price per night from
$796
Price per night from
$796
Distance approx 16.33 km from St. Michaels
Annapolis Home w/ Bay Views - Near Naval Academy!
Maryland / Annapolis
5 11 min stay varies
- 5 bedrooms
- sleeps 11
- min stay varies
- Swimming pool
- Child Friendly
- Air conditioning
Price per night from
$819
Responds fast!
avg. 9 minutes
Price per night from
$819
Distance approx 16.31 km from St. Michaels
3BR Annapolis Home on Oyster Creek w/Amazing Views
Maryland / Annapolis
3 9 2 nights min
- 3 bedrooms
- sleeps 9
- 2 nights min
- Child Friendly
- Air conditioning
Price per night from
$401
Responds fast!
avg. 9 minutes
Price per night from
$401
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
$1,718
Price per night from
$1,718
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
$440
Price per night from
$440
Distance approx 3.66 km from St. Michaels Show on Map
RESTORED WATERFRONT COTTAGE
Talbot County / Royal Oak
3 6 2 nights min
- 3 bedrooms
- sleeps 6
- 2 nights min
- Beach / lakeside relaxation
- Child Friendly
- Air conditioning
Map
Price per night from
$344
Price per night from
$344
Distance approx 11.36 km from St. Michaels
KI Golf House-A PAR for the Course & Mile to Beach
Maryland / Kent Island
4 10 min stay varies
- 4 bedrooms
- sleeps 10
- min stay varies
- Nearest beach 1 mi
- Child Friendly
- Air conditioning
Price per night from
$458
Responds fast!
avg. 1 hour 7 minutes
Price per night from
$458
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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