St. Michaels Houses | FlipKey Vacation Rentals

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Wireless Internet
Air conditioning
Swimming pool
Private pool

Heated pool
Private indoor pool
Balcony or terrace
Washing machine
Jacuzzi or hot tub
Garden
Internet access
Grill
Fireplace
Cot available
High chair
Sea view
Safe
Dishwasher
Children's pool
Shared indoor pool
Private outdoor pool (heated)
Private outdoor pool (unheated)
Pool or snooker table
Shared outdoor pool (heated)
Cribs
Ceiling Fans
Clothes dryer
Games room
Table tennis
Shared outdoor pool (unheated)
Trampoline
Fax machine
Microwave
Kettle
Toaster
Iron
Hair dryer
Stove
Fridge
Freezer
Linen provided
Video player
Towels provided
Bicycles available
Climbing frame
Swing set or jungle gym
Private fishing lake or river
Staffed property
Boat available
Housekeeping Included

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Pets
Pets allowed
Parking
Car not required

Children under 5
Smoking allowed
Non-Smoking property
Smoking - Ask
Elevator access
Wheelchair adapted
Wheelchair accessible
Secure parking

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Beach or lakeside relaxation
City breaks
Skiing – property near ski resort
Walking trips

Tennis in town
Nightlife
Water sports
Horse riding
Fishing
Cycling trips
Golf course on site or within 15 min walk
Waterfront
Beach or lakeside relaxation
Golf within 30mins drive
Lakefront

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28 houses

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Luxury Waterfront home with private pier and guest house

Annapolis house

5 bedrooms
4 bathrooms

sleeps 12

Match: Rental types Shared outdoor pool (unheated)

All filters match

Price per night from

$907

Private Waterfront Retreat with Pool, Hot Tub and Game Room

Tracys Landing house

5 bedrooms
4 bathrooms

sleeps 14

Match: Rental types Shared outdoor pool (unheated)

All filters match

Price per night from

$727

Pool and Bay Views on wrap around deck in Kent Island

Stevensville house

3 bedrooms
3 bathrooms

sleeps 12

Match: Rental types Shared outdoor pool (unheated)

All filters match

Price per night from

$321

St. Michael's Premier in Town Summer Cottage now with private pool!

St. Michaels house

2 bedrooms
2 bathrooms

sleeps 4

1 of 2 match: Shared outdoor pool (unheated), Rental types

1 of 2 filters match

Price per night from

$716

Waterfront Property, Kayaks, Private Dock, Near Town

St. Michaels house

3 bedrooms
3 bathrooms

sleeps 6

1 of 2 match: Shared outdoor pool (unheated), Rental types

1 of 2 filters match

Price per night from

$859

KENT ISLAND-OCEAN VIEW Home for rent-4 bedrooms EASTERN SHORE sleeps 10-12

Kent Island house

4 bedrooms
2 bathrooms

sleeps 12

1 of 2 match: Shared outdoor pool (unheated), Rental types

1 of 2 filters match

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

1 of 2 match: Shared outdoor pool (unheated), Rental types

1 of 2 filters match

Price per night from

$1,947

Eat..Sleep..Fish..Repeat! Who needs a desk (there is one upstairs) when you can

Stevensville house

4 bedrooms
2 bathrooms

sleeps 12

1 of 2 match: Shared outdoor pool (unheated), Rental types

1 of 2 filters match

Price per night from

$802

TRUE ST MICHAELS 6 ACRE WATERFRONT

St. Michaels house

5 bedrooms
3 bathrooms

sleeps 8

Responds fast! avg. 38 minutes

1 of 2 match: Shared outdoor pool (unheated), Rental types

1 of 2 filters match

Price per night from

$2,290

Gourmet Kitchen, Family and Pet Friendly Residence!

Mayo house

3 bedrooms
2 bathrooms

sleeps 8

1 of 2 match: Shared outdoor pool (unheated), Rental types

1 of 2 filters match

Price per night from

$401

Warwick River Retreat

East New Market house

5 bedrooms
3 bathrooms

sleeps 8

1 of 2 match: Shared outdoor pool (unheated), Rental types

1 of 2 filters match

Price per night from

$1,260

Ferry Bridge House

Easton house

3 bedrooms
5 bathrooms

sleeps 6

1 of 2 match: Shared outdoor pool (unheated), Rental types

1 of 2 filters match

Price per night from

$796

RANCH AT ROYAL OAK- Exclusive waterfront pool pier

St. Michaels house

6 bedrooms
6 bathrooms

sleeps 12

Responds fast! avg. 38 minutes

1 of 2 match: Shared outdoor pool (unheated), Rental types

1 of 2 filters match

Price per night from

$2,290

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

1 of 2 match: Shared outdoor pool (unheated), Rental types

1 of 2 filters match

Price per night from

$2,863

Huge Beach Bungalow- Yard, Beach Pass, King Beds

North Beach house

4 bedrooms
3 bathrooms

sleeps 8

1 of 2 match: Shared outdoor pool (unheated), Rental types

1 of 2 filters match

Price per night from

$630

Ship's Cove Inn and Resort in St. Michaels, MD

St. Michaels house

6 bedrooms
6 bathrooms

sleeps 12

1 of 2 match: Shared outdoor pool (unheated), Rental types

1 of 2 filters match

Price per night from

$1,890

Edgewater/Mayo Getaway!

Edgewater house

4 bedrooms
3 bathrooms

sleeps 8

1 of 2 match: Shared outdoor pool (unheated), Rental types

1 of 2 filters match

Price per night from

$457

Private setting, enjoy nature, kayaking and total relaxation

Bethlehem house

3 bedrooms
2 bathrooms

sleeps 8

1 of 2 match: Shared outdoor pool (unheated), Rental types

1 of 2 filters match

Price per night from

$344

Tranquil Easton Waterfront Property

Easton house

3 bedrooms
4 bathrooms

sleeps 6

1 of 2 match: Shared outdoor pool (unheated), Rental types

1 of 2 filters match

Price per night from

$6,870

Location Location! St Michaels-- In Town Cottage!

St. Michaels house

2 bedrooms
2 bathrooms

sleeps 5

1 of 2 match: Shared outdoor pool (unheated), Rental types

1 of 2 filters match

Price per night from

$352

Charming Annapolis Waterview home

Annapolis house

4 bedrooms
4 bathrooms

sleeps 10

1 of 2 match: Shared outdoor pool (unheated), Rental types

1 of 2 filters match

Price per night from

$801

Chesapeake Bay Getaway™ | Waterfront Experience with Pier!

Edgewater house

2 bedrooms
1 bathroom

sleeps 8

1 of 2 match: Shared outdoor pool (unheated), Rental types

1 of 2 filters match

Price per night from

$573

Indoor pool and spa located in beautiful Southern Maryland woodlands

Chesapeake Beach house

3 bedrooms
3 bathrooms

sleeps 8

1 of 2 match: Shared outdoor pool (unheated), Rental types

1 of 2 filters match

Price per night from

$1,105

Cottage by the Bay on one level in family-friendly community

Annapolis house

3 bedrooms
2 bathrooms

sleeps 8

1 of 2 match: Shared outdoor pool (unheated), Rental types

1 of 2 filters match

Price per night from

$367

Private Waterview Estate with 4 bedroom Suites & Hot Tub

Shady Side house

6 bedrooms
7 bathrooms

sleeps 14

1 of 2 match: Shared outdoor pool (unheated), Rental types

1 of 2 filters match

Price per night from

$429

Breathtaking Waterfront Cambridge Getaway

Cambridge house

3 bedrooms
2 bathrooms

sleeps 12

1 of 2 match: Shared outdoor pool (unheated), Rental types

1 of 2 filters match

Price per night from

$682

180-degree water views at unique round house

Shady Side house

3 bedrooms
2 bathrooms

sleeps 8

1 of 2 match: Shared outdoor pool (unheated), Rental types

1 of 2 filters match

Price per night from

$367

Private pier at Waterfront Kent Island home with Hot Tub (Open!)

Stevensville house

4 bedrooms
4 bathrooms

sleeps 8

1 of 2 match: Shared outdoor pool (unheated), Rental types

1 of 2 filters match

Price per night from

$416

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Houses St. Michaels

Per night

28 houses

Luxury Waterfront home with private pier and guest house

Private Waterfront Retreat with Pool, Hot Tub and Game Room

Pool and Bay Views on wrap around deck in Kent Island

St. Michael's Premier in Town Summer Cottage now with private pool!

Waterfront Property, Kayaks, Private Dock, Near Town

KENT ISLAND-OCEAN VIEW Home for rent-4 bedrooms EASTERN SHORE sleeps 10-12

DOLCE VIDA AT Kent Island- 4 bedrooms House for rent-SLEEPS 10-12

Eat..Sleep..Fish..Repeat! Who needs a desk (there is one upstairs) when you can

TRUE ST MICHAELS 6 ACRE WATERFRONT

Gourmet Kitchen, Family and Pet Friendly Residence!

Warwick River Retreat

Ferry Bridge House

RANCH AT ROYAL OAK- Exclusive waterfront pool pier

CHESAPEAKE MANSION - NEW POOL/12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND

Huge Beach Bungalow- Yard, Beach Pass, King Beds

Ship's Cove Inn and Resort in St. Michaels, MD

Edgewater/Mayo Getaway!

Private setting, enjoy nature, kayaking and total relaxation

Tranquil Easton Waterfront Property

Location Location! St Michaels-- In Town Cottage!

Charming Annapolis Waterview home

Chesapeake Bay Getaway™ | Waterfront Experience with Pier!

Indoor pool and spa located in beautiful Southern Maryland woodlands

Cottage by the Bay on one level in family-friendly community

Private Waterview Estate with 4 bedroom Suites & Hot Tub

Breathtaking Waterfront Cambridge Getaway

180-degree water views at unique round house

Private pier at Waterfront Kent Island home with Hot Tub (Open!)

Viewing 28 of 28
rentals in St. Michaels

Also consider

Houses St. Michaels

Per night

28 houses

Viewing 28 of 28rentals in St. Michaels

Also consider

Viewing 28 of 28
rentals in St. Michaels