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.

St. Michaels Vacation Rentals

List your property
Owner log in
Check in
— / — / —
Check out
— / — / —
Guests
0 rooms, 2+ guests
Distance from
1 mi
Suitability
Show more
Bathrooms
Any
Amenities
Show more
Property type
Show more
Distinctive Features
Show more
50 rentals in St. Michaels.
Sort by:
Tripadvisor Sort
TRUE IN-TOWN SAINT MICHAELS 6 ACRE WATERFRONT w/POOL!!!, vacation rental in St. Michaels

TRUE IN-TOWN SAINT MICHAELS 6 ACRE WATERFRONT w/POOL!!!

5 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Premier Cottage in St. Michaels- In Town Location!, vacation rental in St. Michaels

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!, vacation rental in St. Michaels

Location Location! St Michaels-- In Town Cottage!

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Check in
Check out
Payment Protection
*****Waterfront home w/ pool in St. Michaels, vacation rental in St. Michaels

*****Waterfront home w/ pool in St. Michaels

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Large Historic Thomas Harrison House on Harbor in St. Michaels Town, vacation rental in St. Michaels

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
Carpenter St. Cottage in the Heart of St. Michaels - Walk To Everything!, vacation rental in St. Michaels

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
Waterview Cottage In St. Michaels!, vacation rental in St. Michaels

Waterview Cottage In St. Michaels!

2 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
More info
Check in
Check out
Payment Protection
Sandy Pines:  Enjoy Harris Creek w/Pool and Boats, vacation rental in St. Michaels

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
Phenomenal Vacation Rental by Water in St Michaels - Walk to Town! 4 ADULTS MAX, vacation rental in St. Michaels

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
St. Michael's Premier in Town Summer Cottage now with private pool!, vacation rental in St. Michaels

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

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check in
Check out
Payment Protection
Save time - get the best St. Michaels rentals sent straight to your email!
Waterfront Property, Kayaks, Private Dock, Near Town, vacation rental in St. Michaels

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, vacation rental in St. Michaels

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), vacation rental in St. Michaels

Luxurious and Extremely Private Waterfront Estate (SORRY - NO WEDDINGS)

7 bedrooms
9 bathrooms
Sleeps 20
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
New St. Michaels estate -Pier,Pool, Gas fire pit, Bikes & Kayaks, vacation rental in St. Michaels

New St. Michaels estate -Pier,Pool, Gas fire pit, Bikes & Kayaks

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Waterfront Cottage, Private Hot Tub, Fire Pit - perfect Romantic Getaway, vacation rental in St. Michaels

Waterfront Cottage, Private Hot Tub, Fire Pit - perfect Romantic Getaway

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Comfy home on beautiful Leadenham Creek. Book now for summer!, vacation rental in St. Michaels

Comfy home on beautiful Leadenham Creek. Book now for summer!

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Beautiful Tidewater home between Easton & ST Michaels!, vacation rental in St. Michaels

Beautiful Tidewater home between Easton & ST Michaels!

4 bedrooms
7 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Enhanced Cleaning & Disinfecting. Private Beach Volleyball Court. Walk to Beach., vacation rental in St. Michaels

Enhanced Cleaning & Disinfecting. Private Beach Volleyball Court. Walk to Beach.

4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Fully remodel 2 bedroom country cottage., vacation rental in St. Michaels

Fully remodel 2 bedroom country cottage.

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Charming 3 Bedroom 3 Bath Beach Front Property, vacation rental in St. Michaels

Charming 3 Bedroom 3 Bath Beach Front Property

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Stunning Views of the Bay - Waterfront, vacation rental in St. Michaels

Stunning Views of the Bay - Waterfront

3 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Escape To This Oxford, Md Waterfront Home - Kayaking, Canoeing & Relaxing, vacation rental in St. Michaels

Escape To This Oxford, Md Waterfront Home - Kayaking, Canoeing & Relaxing

4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Relax in Tilghman Island, vacation rental in St. Michaels

Relax in Tilghman Island

4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Holidays at the Cove  - plenty of space to gather while making memories, vacation rental in St. Michaels

Holidays at the Cove - plenty of space to gather while making memories

5 bedrooms
7 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
New Modern Waterfront Farmhouse Built 2018, vacation rental in St. Michaels

New Modern Waterfront Farmhouse Built 2018

4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Travelers Rest! Dock, Pool Eastern Shore Private Retreat St. Micheals / Easton, vacation rental in St. Michaels

Travelers Rest! Dock, Pool Eastern Shore Private Retreat St. Micheals / Easton

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Eastern Shore Getaway Near St. Michaels, vacation rental in St. Michaels

Eastern Shore Getaway Near St. Michaels

1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Waterfront Getaway on the Choptank River, vacation rental in St. Michaels

Waterfront Getaway on the Choptank River

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
3BR 1BA Private Beach / Pool / Boat Launch / Pier / Golf Cart and much more!, vacation rental in St. Michaels

3BR 1BA Private Beach / Pool / Boat Launch / Pier / Golf Cart and much more!

3 bedrooms
1 bathroom
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Main House at Grandview at Pleasure Point, vacation rental in St. Michaels

Main House at Grandview at Pleasure Point

5 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
More info
Check in
Check out
Payment Protection
Not to early to think about joining us this Spring and Summer., vacation rental in St. Michaels

Not to early to think about joining us this Spring and Summer.

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
BEST Exposure on the Bay for SUNSETS with Pool, Dock & Spa, vacation rental in St. Michaels

BEST Exposure on the Bay for SUNSETS with Pool, Dock & Spa

3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Private waterfront estate with pool, convenient to Easton and St. Michaels, vacation rental in St. Michaels

Private waterfront estate with pool, convenient to Easton and St. Michaels

5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
KI Golf House-A PAR for the Course & Mile to Beach, vacation rental in St. Michaels

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
Chesapeake Bay Waterfront ARTectural Home, vacation rental in St. Michaels

Chesapeake Bay Waterfront ARTectural Home

3 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Peaceful, Waterfront Home on 3 Acres (pier + western view w/gorgeous sunsets), vacation rental in St. Michaels

Peaceful, Waterfront Home on 3 Acres (pier + western view w/gorgeous sunsets)

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
Payment Protection
Cottage 2 at Grandview Pleasure Point, vacation rental in St. Michaels

Cottage 2 at Grandview Pleasure Point

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Payment Protection
Abay Palace of Kent Narrows in a King Bed, vacation rental in St. Michaels

Abay Palace of Kent Narrows in a King Bed

1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
More info
Check in
Check out
Payment Protection
Comfortable, Spacious & Fun! 6+ Acres Pool & Shore. 4 Master Suites Waterview, vacation rental in St. Michaels

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 1a at Grandview Pleasure Point, vacation rental in St. Michaels

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, vacation rental in St. Michaels

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, vacation rental in St. Michaels

Tranquil Easton Waterfront Property

3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Payment Protection
Enhanced cleaning/sanitizing-Sittin' on the Dock by the Bay Next to Marina/Beach, vacation rental in St. Michaels

Enhanced cleaning/sanitizing-Sittin' on the Dock by the Bay Next to Marina/Beach

4 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Kent Island Beach House II:Chesapeake Bay Fisherman's Village at Kentmorr Marina, vacation rental in St. Michaels

Kent Island Beach House II:Chesapeake Bay Fisherman's Village at Kentmorr Marina

4 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
More info
Check in
Check out
Payment Protection
St. Michaels Area Cottage - Walk to Water & Marina, vacation rental in St. Michaels

St. Michaels Area Cottage - Walk to Water & Marina

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check in
Check out
Payment Protection
Kent Island House with Pool and Bay Views!, vacation rental in St. Michaels

Kent Island House with Pool and Bay Views!

3 bedrooms
3 bathrooms
Sleeps 13
Match: Sleeps
More info
Check in
Check out
Payment Protection
Tentrr Signature Site - Wye Island View, vacation rental in St. Michaels

Tentrr Signature Site - Wye Island View

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Payment Protection
Newly-managed Waterfront Kent Island home, vacation rental in St. Michaels

Newly-managed Waterfront Kent Island home

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
Payment Protection
New! Stunning Waterfront with pool for Naval Academy families!, vacation rental in St. Michaels

New! Stunning Waterfront with pool for Naval Academy families!

4 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
More info
Check in
Check out
Payment Protection
PreviousNext
1
Frequently Asked Questions about St. Michaels