We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Holiday Apartments in St. Michaels

List your property
Owner log in
Check-in
— / — / —
Check-out
— / — / —
Guests
0+ rooms, 2+ guests
Distance from
1 km
Price per night
RM 0
RM 1,000+
Suitability
Show more
Bathrooms
Any
Amenities
Show more
Property type
Show more
Distinctive Features
Show more
Neighbourhood
51 rentals in St. Michaels.
Sort by:
Tripadvisor Sort
TRUE IN-TOWN SAINT MICHAELS 6 ACRE WATERFRONT w/POOL!!!
5 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Premier Cottage in St. Michaels- In Town Location!
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Location Location! St Michaels-- In Town Cottage!
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Large Historic Thomas Harrison House on Harbor in St. Michaels Town
7 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
*****Waterfront home w/ pool in St. Michaels
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Carpenter St. Cottage in the Heart of St. Michaels - Walk To Everything!
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Sandy Pines: Enjoy Harris Creek w/Pool and Boats
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Waterview Cottage In St. Michaels!
2 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Phenomenal Vacation Rental by Water in St Michaels - Walk to Town! 4 ADULTS MAX
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Pot Pie House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Save time - get the best St. Michaels rentals sent straight to your email!
St. Michael's Premier in Town Summer Cottage!
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Waterfront Property, Kayaks, Private Dock, Near Town
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Bay Cottage Resort
6 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Luxurious and Extremely Private Waterfront Estate (SORRY - NO WEDDINGS)
7 bedrooms
9 bathrooms
Sleeps 20
Match: Sleeps
More info
Check-in
Check-out
New St. Michaels estate -Pier,Pool, Gas fire pit, Bikes & Kayaks
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Charming Waterfront Cottage Outside St. Michaels Close to the Oaks
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
More info
Check-in
Check-out
Stunning Views of the Bay - Waterfront
3 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Comfy home on beautiful Leadenham Creek. Book now for summer!
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Beautiful Tidewater home between Easton & ST Michaels!
4 bedrooms
7 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Escape To This Oxford, Md Waterfront Home - Kayaking, Canoeing & Relaxing
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Newly available rental: Relaxing Waterfront Cottage Near St Michaels, Maryland
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Fully remodel 2 bedroom country cottage.
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Waterfront Cottage, Private Hot Tub, Fire Pit - perfect Romantic Getaway
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Gorgeous Sunsets and Chesapeake Charm
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Holidays at the Cove - plenty of space to gather while making memories
5 bedrooms
7 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Charming 3 Bedroom 3 Bath Beach Front Property
3 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
Check-in
Check-out
Eastern Shore Getaway Near St. Michaels
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
Travelers Rest! Dock, Pool Eastern Shore Private Retreat St. Micheals / Easton
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Relax in Tilghman Island
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
St. Michael's Waterfront Vacation Home
5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
More info
Check-in
Check-out
Luxurious Waterfront Kent Island Home 30 miles from Annapolis
4 bedrooms
5 bathrooms
Sleeps 7
Match: Sleeps
More info
Check-in
Check-out
Main House at Grandview at Pleasure Point
5 bedrooms
3 bathrooms
Sleeps 13
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Oxford Waterfront Cottage-Walk to Town, Kayak, Dock, and Bikes
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Holiday on the Bay, Kent Island Beach House
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
RESTORED WATERFRONT COTTAGE
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
New Modern Waterfront Farmhouse Built 2018
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
KI Golf House-A PAR for the Course & Mile to Beach
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Beatiful Waterfront Home with Large Deck, Pool and Spa close to Bay Bridge
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Not to early to think about joining us this Spring and Summer.
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Comfortable 5 Bedroom Waterfront Home on Chesapeake Bay
5 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
More info
Check-in
Check-out
Comfortable, Spacious & Fun! 6+ Acres Pool & Shore. 4 Master Suites Waterview
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Cottage 2 at Grandview Pleasure Point
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
KENT ISLAND-OCEAN VIEW Home for rent -4 bedrooms EASTERN SHORE sleeps 10-12
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
BEST Exposure on the Bay for SUNSETS with Pool, Dock & Spa
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Cottage 1a at Grandview Pleasure Point
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Cottage 1b at Grandview Pleasure Point
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Tranquil Easton Waterfront Property
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
St. Michaels Area Cottage - Walk to Water & Marina
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
St. Michaels Waterfront Retreat with pier, pool, kayaks, gas fire pit and bikes
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
6942 Travelers Rest
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Previous
12