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68 Houses

42

Waterfront Room Rentals 2 with Private Beach

Talbot County / Trappe

Trappe room

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

(1) Very Good 

34

Waterfront Room Rentals 1 with Private Beach

Talbot County / Trappe

Trappe room

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$149

Responds fast!
avg. 1 hour 34 minutes

Price per night from

$149

(3) Very Good 

15

Halos'Haven Vacation Rental

St. Michaels / McDaniel

McDaniel house

5 10 2 nights min

  • 5 bedrooms
  • sleeps 10
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$802

Price per night from

$802

(3) Very Good 

36

Comfortable, Spacious & Fun! 6+ Acres Pool & Shore. 4 Master Suites Waterview

Talbot County / Wittman

Wittman log cabin

5 10 min stay varies

  • 5 bedrooms
  • sleeps 10
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 6 mi
  • Swimming pool

Price per night from

$716

Price per night from

$716

(5) Average 

55

Waterfront Vacation Home with Private Beach

Talbot County / Trappe

Trappe house

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 97 mi
  • Child Friendly

Price per night from

$378

Responds fast!
avg. 1 hour 34 minutes

Price per night from

$378

4

St. Michaels Area Waterfront Retreat with pier, pool, kayaks and bikes

Talbot County / Royal Oak

Royal Oak house

5 11 min stay varies

  • 5 bedrooms
  • sleeps 11
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$686

Price per night from

$686

44

Waterfront Room Rentals 3 with Private Beach

Talbot County / Trappe

Trappe room

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

(1) Excellent 

18

St. Michaels Waterfront Home W/Dock for 2 boats

Talbot County / Neavitt

Neavitt house

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$258

Price per night from

$258

(11) Very Good 

30

Large Historic Thomas Harrison House on Harbor in St. Michaels Town

Talbot County / St. Michaels

St. Michaels house

7 9 min stay varies

  • 7 bedrooms
  • sleeps 9
  • min stay varies
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning
“Perfect in every way!” I stayed at the Thomas Harrison house a few weeks ago and all I can say is..."if you are planning on coming to St. Michael's you need to stay at this house." This house is perfect in every way. It has all the accommodations that
…see more

Price per night from

$332

Responds fast!
avg. 3 hours 11 minutes

Price per night from

$332

(2) Excellent 

18

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

Talbot County / St. Michaels

St. Michaels house

1 6 2 nights min

  • 1 bedroom
  • sleeps 6
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$263

Price per night from

$263

(7) Very Good 

23

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

Talbot County / St. Michaels

St. Michaels cottage

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$184

Responds fast!
avg. 3 hours 11 minutes

Price per night from

$184

8

Cottage 1a at Grandview Pleasure Point

Talbot County / Bozman

Bozman house

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets

Price per night from

$246

Price per night from

$246

(24) Excellent 

27

Location Location! St Michaels-- In Town Cottage!

Talbot County / St. Michaels

St. Michaels house

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Beach / lakeside relaxation
  • Child Friendly
  • Car not necessary

Price per night from

$172

Responds fast!
avg. 3 hours 11 minutes

Price per night from

$172

(13) Excellent 

24

Premier Cottage in St. Michaels- In Town Location!

Talbot County / St. Michaels

St. Michaels house

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$172

Responds fast!
avg. 3 hours 11 minutes

Price per night from

$172

28

St. Michaels Area Cottage - Walk to Water & Marina

Talbot County / Neavitt

Neavitt house

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$201

Responds fast!
avg. 8 minutes

Price per night from

$201

(2) Excellent 

12

Pot Pie House

Talbot County / St. Michaels

St. Michaels house

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Air conditioning

Price per night from

$258

Price per night from

$258

15

Tranquil Easton Waterfront Property

Talbot County / Easton

Easton house

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$687

Price per night from

$687

18

Historic Waterfront Property with Wi-Fi and Dock

Talbot County / St. Michaels

St. Michaels house

3 8 2 nights min

  • 3 bedrooms
  • sleeps 8
  • 2 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$859

Responds fast!
avg. 3 hours 21 minutes

Price per night from

$859

(3) Excellent 

24

Best sunrise in St. Michaels....Broadview Bay House

Talbot County / St. Michaels

St. Michaels house

6 12 min stay varies

  • 6 bedrooms
  • sleeps 12
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$600

Price per night from

$600

6

Cottage 1b at Grandview Pleasure Point

Talbot County / Bozman

Bozman cottage

1 2 7 nights min

  • 1 bedroom
  • sleeps 2
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$281

Price per night from

$281

(5) Excellent 

22

Sandy Pines: Enjoy Harris Creek w/Pool and Boats

Talbot County / St. Michaels

St. Michaels house

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$430

Price per night from

$430

(3) Very Good 

25

Waterview Cottage In St. Michaels!

Talbot County / St. Michaels

St. Michaels cottage

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$184

Responds fast!
avg. 3 hours 11 minutes

Price per night from

$184

(1) Excellent 

9

Cottage 2 at Grandview Pleasure Point

Talbot County / Bozman

Bozman house

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$387

Price per night from

$387

12

Harris Cove Cottages LLC

Talbot County / St. Michaels

St. Michaels cottage

1 4 1 night min

  • 1 bedroom
  • sleeps 4
  • 1 night min
  • Child Friendly
  • Air conditioning

Price per night from

$229

Price per night from

$229

14

Halo's Haven Guest Quarters

Talbot County / St. Michaels

St. Michaels house

3 6 1 night min

  • 3 bedrooms
  • sleeps 6
  • 1 night min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$373

Price per night from

$373

15

Lakeside Private Apartment

Talbot County / Wye Mills

Wye Mills apartment

1 5 1 night min

  • 1 bedroom
  • sleeps 5
  • 1 night min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$160

Price per night from

$160

(13) Excellent 

34

Main House at Grandview at Pleasure Point

Talbot County / Bozman

Bozman house

5 13 7 nights min

  • 5 bedrooms
  • sleeps 13
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 15 mi
  • Swimming pool
“5 out of 5” I spent a long weekend at the main house, and it was easily the best weekend of the summer! The location is phenomenal. The house sits on large stretch of beautiful waterfront property. The views from the piers and the pool are exquisite.
…see more

Price per night from

$790

Price per night from

$790

7

St. Michael's Premier in Town Summer Cottage!

Talbot County / St. Michaels

St. Michaels house

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$327

Price per night from

$327

(1) Average 

38

St. Michaels award-winning waterfront BayCottage, pool, docks, sundeck, grounds

Talbot County / St. Michaels

St. Michaels villa

6 12 2 nights min

  • 6 bedrooms
  • sleeps 12
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 7 mi
  • Swimming pool

Price per night from

$1,145

Responds fast!
avg. 1 hour 1 minutes

Price per night from

$1,145

(10) Excellent 

24

RESTORED WATERFRONT COTTAGE

Talbot County / Royal Oak

Royal Oak cottage

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$344

Price per night from

$344

Great rentals within 20 miles that match your search

Distance approx 13.02 km from Talbot County Show on Map

26

Love Point Luxury Waterfront in Stevensville

Kent Island / Stevensville

Stevensville house

3 10 3 nights min

  • 3 bedrooms
  • sleeps 10
  • 3 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$1,401

Price per night from

$1,401

Distance approx 11.81 km from Talbot County Show on Map

(1) Excellent 

26

Huge Stevensville House Overlooking Eastern Shore!

Kent Island / Stevensville

Stevensville house

3 10 min stay varies

  • 3 bedrooms
  • sleeps 10
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$459

Responds fast!
avg. 14 minutes

Price per night from

$459

Distance approx 19.07 km from Talbot County Show on Map

24

Shady Side House on Chesapeake Bay Near Marina!

Maryland / Shady Side

Shady Side house

2 5 2 nights min

  • 2 bedrooms
  • sleeps 5
  • 2 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$185

Responds fast!
avg. 10 minutes

Price per night from

$185

Distance approx 16.23 km from Talbot County Show on Map

(3) Very Good 

14

Retreat at a quiet, water front cottage

Maryland / Chestertown

Chestertown house

3 8 2 nights min

  • 3 bedrooms
  • sleeps 8
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Private garden
“A best kept secret!” I have had the pleasure of staying at Cliff Point many times. The view cannot be matched, water views more than 180 degrees, sunsets are stunning. But on top of that the house is so comfortable and charming, spacious and cozy. Ch
…see more

Price per night from

$339

Responds fast!
avg. 3 hours 30 minutes

Price per night from

$339

Distance approx 19.44 km from Talbot County Show on Map

12

Clean & Spacious

Maryland / Cape Saint Claire

Cape Saint Claire house

4 9 1 night min

  • 4 bedrooms
  • sleeps 9
  • 1 night min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$351

Price per night from

$351

Distance approx 19.12 km from Talbot County Show on Map

24

Charming Artists Home in Eastport/Annapolis

Maryland / Annapolis

Annapolis house

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Ask about children
  • Air conditioning

Price per night from

$376

Price per night from

$376

Distance approx 17.62 km from Talbot County Show on Map

(2)  

26

3BR Annapolis Home on Oyster Creek w/Amazing Views

Maryland / Annapolis

Annapolis house

3 9 2 nights min

  • 3 bedrooms
  • sleeps 9
  • 2 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$351

Responds fast!
avg. 14 minutes

Price per night from

$351

Distance approx 19.72 km from Talbot County Show on Map

(1)  

7

Charming Townhouse - Steps to City Dock and USNA

Maryland / Annapolis

Annapolis house

3 8 3 nights min

  • 3 bedrooms
  • sleeps 8
  • 3 nights min
  • Child Friendly
  • Car not necessary
  • Ask about pets

Price per night from

$516

Price per night from

$516