Holiday rentals near St. Michaels Winery
We found 602 holiday rentals — enter your dates for availability
If you want to to stay within easy reach of St. Michaels Winery, scroll through and discover private holiday rentals to choose your home away from home. Whether you’re staying in a holiday home with family or friends, you'll find the amenities that you need and want, which might include parking and a washer and dryer. Whatever you're looking for, you'll be able to choose a property to rent for everyone's needs, including accessible or non-smoking choices.
Holiday rentals with weekly discounts - St. Michaels Winery
Showing deals for:25 Jul - 1 Aug
Image gallery for 4 KING Bedrooms on the Waterfront- FREE Kent Island Sunsets- Near Wedding Venues
1010 out of 10 rating
Exceptional
(33 reviews)
4 KING Bedrooms on the Waterfront- FREE Kent Island Sunsets- Near Wedding Venues
Stevensville, MD
8% off
Price is £5,151
£5,151
£736 per night
includes taxes & fees
Image gallery for Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!
1010 out of 10 rating
Exceptional
(118 reviews)
Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!
Chester, MD
8% off
Price is £2,432
£2,432
£347 per night
includes taxes & fees
Image gallery for A Luxury Home located in Easton with Water VIEWS! Close to Oxford/St. Michaels
1010 out of 10 rating
Exceptional
(18 reviews)
A Luxury Home located in Easton with Water VIEWS! Close to Oxford/St. Michaels
Easton, MD
8% off
Price is £2,561
£2,561
£366 per night
includes taxes & fees
Image gallery for Waterfront, Private Saltwater Pool & Dock, Near Cambridge, Sleeps 10, Kayaks
9.89.8 out of 10 rating
Exceptional
(7 reviews)
Waterfront, Private Saltwater Pool & Dock, Near Cambridge, Sleeps 10, Kayaks
East New Market, MD
5% off
Price is £6,110
£6,110
£873 per night
includes taxes & fees
Image gallery for Accessible, Screened-in porch, Water Access, Sauna, Fire Pit, Dog Friendly
1010 out of 10 rating
Exceptional
(40 reviews)
Accessible, Screened-in porch, Water Access, Sauna, Fire Pit, Dog Friendly
Stevensville, MD
8% off
Price is £3,819
£3,819
£546 per night
includes taxes & fees
Image gallery for Chesapeake Bay Waterfront ARTectural Home
1010 out of 10 rating
Exceptional
(27 reviews)
Chesapeake Bay Waterfront ARTectural Home
Stevensville, MD
8% off
Price is £5,966
£5,966
£852 per night
includes taxes & fees
Image gallery for Annapolis Cozy Beachfront/Waterfront w/Chesapeake Bay Bridge view
9.89.8 out of 10 rating
Exceptional
(13 reviews)
Annapolis Cozy Beachfront/Waterfront w/Chesapeake Bay Bridge view
Annapolis, MD
8% off
Price is £3,900
£3,900
£557 per night
includes taxes & fees
Image gallery for Huge Beach Bungalow w/Yard, Beach Passes, 2 King Bds near Boardwalk, Restaurants
1010 out of 10 rating
Exceptional
(24 reviews)
Huge Beach Bungalow w/Yard, Beach Passes, 2 King Bds near Boardwalk, Restaurants
North Beach, MD
8% off
Price is £2,912
£2,912
£416 per night
includes taxes & fees
Image gallery for 25-50% Off~Private Beach~Hot Tub~Fire Table~
1010 out of 10 rating
Exceptional
(22 reviews)
25-50% Off~Private Beach~Hot Tub~Fire Table~
Stevensville, MD
8% off
Price is £4,128
£4,128
£590 per night
includes taxes & fees
Image gallery for Waterview Home by Kentmorr Marina, Beach Bar & Grill. Close to wedding venues.
1010 out of 10 rating
Exceptional
(38 reviews)
Waterview Home by Kentmorr Marina, Beach Bar & Grill. Close to wedding venues.
Stevensville, MD
8% off
Price is £5,151
£5,151
£736 per night
includes taxes & fees
Image gallery for "PIER JOY!" - 3BR WATERFRONT HOME W/PRIVATE DOCK
9.69.6 out of 10 rating
Exceptional
(30 reviews)
"PIER JOY!" - 3BR WATERFRONT HOME W/PRIVATE DOCK
Shady Side, MD
8% off
Price is £3,246
£3,246
£464 per night
includes taxes & fees
Image gallery for Private+Cozy-3br+2ba-1mile to Historic Downtown Saint Michaels
1010 out of 10 rating
Exceptional
(6 reviews)
Private+Cozy-3br+2ba-1mile to Historic Downtown Saint Michaels
St. Michaels, MD
17% off
Price is £2,394
£2,394
£342 per night
includes taxes & fees
Image gallery for Kent Island Waterfront Cottage
9.49.4 out of 10 rating
Exceptional
(8 reviews)
Kent Island Waterfront Cottage
Stevensville, MD
16% off
Price is £1,899
£1,899
£271 per night
includes taxes & fees
Image gallery for Beach Home with King Bed and Beach Passes in a Cute Town
1010 out of 10 rating
Exceptional
(11 reviews)
Beach Home with King Bed and Beach Passes in a Cute Town
North Beach, MD
8% off
Price is £2,317
£2,317
£331 per night
includes taxes & fees
Image gallery for Spacious house, great deck & grill, close to boardwalk, shops, and restaurants.
1010 out of 10 rating
Exceptional
(89 reviews)
Spacious house, great deck & grill, close to boardwalk, shops, and restaurants.
North Beach, MD
7% off
Price is £1,589
£1,589
£227 per night
includes taxes & fees
Image gallery for Water Views - Close to Downtown Annapolis
1010 out of 10 rating
Exceptional
(43 reviews)
Water Views - Close to Downtown Annapolis
Annapolis, MD
11% off
Price is £2,982
£2,982
£426 per night
includes taxes & fees
Image gallery for Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.
9.89.8 out of 10 rating
Exceptional
(34 reviews)
Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.
West River, MD
11% off
Price is £999
£999
£143 per night
includes taxes & fees
Image gallery for Large -IN TOWN- Historic House on Harbor in St Michaels - Walk to Everything!
9.49.4 out of 10 rating
Exceptional
(126 reviews)
Large -IN TOWN- Historic House on Harbor in St Michaels - Walk to Everything!
St. Michaels, MD
8% off
Price is £4,169
£4,169
£596 per night
includes taxes & fees
Image gallery for Well-appointed 1 bedroom, 1 bath in Annapolis / Eastport
1010 out of 10 rating
Exceptional
(48 reviews)
Well-appointed 1 bedroom, 1 bath in Annapolis / Eastport
Annapolis, MD
11% off
Price is £1,327
£1,327
£190 per night
includes taxes & fees
Image gallery for Crabby Casa; Waterfront with pool and dock on the Choptank River in Cambridge MD
9.49.4 out of 10 rating
Exceptional
(6 reviews)
Crabby Casa; Waterfront with pool and dock on the Choptank River in Cambridge MD
Cambridge, MD
8% off
Price is £3,751
£3,751
£536 per night
includes taxes & fees
Image gallery for Charming cottage along water with private pier, near St. Michaels Winery
9.69.6 out of 10 rating
Exceptional
(132 reviews)
Charming cottage along water with private pier, near St. Michaels Winery
Bozman, MD
12% off
Price is £1,609
£1,609
£230 per night
includes taxes & fees
Image gallery for Cheerful three-bedroom Cottage
9.69.6 out of 10 rating
Exceptional
(5 reviews)
Cheerful three-bedroom Cottage
Cambridge, MD
8% off
Price is £1,406
£1,406
£201 per night
includes taxes & fees
Image gallery for Perfect Waterview Cottage - St. Michaels Getaway
9.89.8 out of 10 rating
Exceptional
(110 reviews)
Perfect Waterview Cottage - St. Michaels Getaway
Wittman, MD
8% off
Price is £1,464
£1,464
£209 per night
includes taxes & fees
Image gallery for Edgewater/Mayo Getaway!
9.89.8 out of 10 rating
Exceptional
(14 reviews)
Edgewater/Mayo Getaway!
Edgewater, MD
7% off
Price is £2,255
£2,255
£322 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - St. Michaels Winery
Waterfront Retreat with a New in ground pool! The Eastern Shore at it's best!
Sleeps 12 · 5 bedrooms · 5+ bathrooms
9.89.8 out of 10
Exceptionalexceptional
9 reviews(9 reviews)
Rising Sun Bay View Cottage
Sleeps 6 · 3 bedrooms · 3+ bathrooms
Luxury Waterfront Retreat with in ground pool and close to town
Sleeps 14 · 4 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
34 reviews(34 reviews)
Grasonville Home w/ Private Pool on the Water
Sleeps 8 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
21 reviews(21 reviews)
The Blue Crab Beach House - Free beach passes
Sleeps 6 · 2 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
52 reviews(52 reviews)
Sunset Breezes - quiet waterfront retreat
Sleeps 8 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
36 reviews(36 reviews)
Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value