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39 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

$100

Responds fast!
avg. 1 hour 34 minutes

Price per night from

$100

(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

$130

Responds fast!
avg. 1 hour 34 minutes

Price per night from

$130

(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

$330

Responds fast!
avg. 1 hour 34 minutes

Price per night from

$330

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

$100

Responds fast!
avg. 1 hour 34 minutes

Price per night from

$100

Great rentals within 20 miles that match your search

Distance approx 5.87 km from Trappe

29

NEW! Colonial Home in Cambridge w/Wraparound Porch

Maryland / Cambridge

Cambridge house

3 7 min stay varies

  • 3 bedrooms
  • sleeps 7
  • min stay varies
  • Child Friendly
  • Air conditioning

Price per night from

$221

Responds fast!
avg. 55 minutes

Price per night from

$221

Distance approx 16.51 km from Trappe

(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

$625

Price per night from

$625

Distance approx 5.42 km from Trappe

16

Choptank River View House

Maryland / Cambridge

Cambridge house

6 14 3 nights min

  • 6 bedrooms
  • sleeps 14
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0 mi
  • Air conditioning

Price per night from

$1,000

Price per night from

$1,000

Distance approx 16.08 km from Trappe

(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

$700

Price per night from

$700

Distance approx 15.28 km from Trappe

(6) Excellent 

20

Tilghman Island Cottage for Six - Near Marina and Knapps Narrows Drawbridge

Talbot County / Tilghman

Tilghman cottage

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning
“We loved it!” We had a great (albeit too short!) family getaway at the Roost! The cottage is extremely clean, comfortable, well-maintained, and spacious. The kids (ages 6 and 20 months) loved it -- especially the bunk beds and the nice backyard, and t
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Price per night from

$200

Price per night from

$200

Distance approx 10.07 km from Trappe

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

$603

Price per night from

$603

Distance approx 13.04 km from Trappe

(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

$225

Price per night from

$225

Distance approx 12.51 km from Trappe

(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
“Crabtastic Great Escape” This cottage is the perfect great escape. Conveniently located in the middle of quaint St Michael's close to the harbor, restaurants, and shops. The property is clean and well-maintained with beautiful landscaping. The buildin
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Price per night from

$150

Responds fast!
avg. 3 hours 32 minutes

Price per night from

$150

Distance approx 12.46 km from Trappe

(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
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Price per night from

$290

Responds fast!
avg. 3 hours 32 minutes

Price per night from

$290

Distance approx 13.07 km from Trappe

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

$175

Responds fast!
avg. 55 minutes

Price per night from

$175

Distance approx 7.51 km from Trappe

8

6 Bdrm, 3.5 Bath, Cambridge Md Vacation Home

Maryland / Cambridge

Cambridge house

6 12 3 nights min

  • 6 bedrooms
  • sleeps 12
  • 3 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$869

Price per night from

$869

Distance approx 12.49 km from Trappe

(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

$150

Responds fast!
avg. 3 hours 32 minutes

Price per night from

$150

Distance approx 12.12 km from Trappe

(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

$229

Price per night from

$229

Distance approx 9.58 km from Trappe

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

$750

Responds fast!
avg. 3 hours 21 minutes

Price per night from

$750

Distance approx 13.36 km from Trappe

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

$245

Price per night from

$245

Distance approx 12.51 km from Trappe

(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

$160

Responds fast!
avg. 3 hours 32 minutes

Price per night from

$160

Distance approx 15.85 km from Trappe

(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

Distance approx 13.36 km from Trappe

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

$245

Price per night from

$245

Distance approx 13.58 km from Trappe

(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

$386

Price per night from

$386

Distance approx 12.47 km from Trappe

(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

$160

Responds fast!
avg. 3 hours 32 minutes

Price per night from

$160

Distance approx 13.73 km from Trappe

(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

$375

Price per night from

$375

Distance approx 19.58 km from Trappe

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

$139

Price per night from

$139

Distance approx 12.21 km from Trappe

(12) Very Good 

31

Stunning, Newer Chesapeake Waterfront Estate, Pool - 6/7 Bedrms 5 Baths

Maryland / Cambridge

Cambridge house

6 20 min stay varies

  • 6 bedrooms
  • sleeps 20
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.1 mi
  • Swimming pool
“Outstanding Vacation Rental” Our extended family (22 people - 13A/9K) had a great week at Saddle Beach. The house was beautiful and in very good condition. The option of being in the pool or the river during the day was wonderful. The house was cle
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Price per night from

$499

Responds fast!
avg. 3 hours 27 minutes

Price per night from

$499

Distance approx 13.86 km from Trappe

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

$202

Price per night from

$202

Distance approx 13.25 km from Trappe

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

$325

Price per night from

$325

Distance approx 13.58 km from Trappe

(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.
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Price per night from

$690

Price per night from

$690

Distance approx 12.2 km from Trappe

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

$285

Price per night from

$285

Distance approx 12.16 km from Trappe

17

Deerpond Carriage House

Maryland / Woolford

Woolford guest house

1 2 3 nights min

  • 1 bedroom
  • sleeps 2
  • 3 nights min
  • Swimming pool
  • Air conditioning
  • Private garden

Price per night from

$180

Price per night from

$180

Distance approx 13.16 km from Trappe

(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

$850

Responds fast!
avg. 1 hour 1 minutes

Price per night from

$850

Distance approx 8.85 km from Trappe

(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

$300

Price per night from

$300

Distance approx 8.99 km from Trappe

20

Maryland’s Eastern Shore Welcomes You

Maryland / Preston

Preston house

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Nearest beach 50 mi
  • Swimming pool
  • Child Friendly

Price per night from

$87

Price per night from

$87

Distance approx 11.07 km from Trappe

(15) Excellent 

35

Year Round Estate on Bay / Fam. Reunions / Slps 28

Maryland / Cambridge

Cambridge house

7 28 min stay varies

  • 7 bedrooms
  • sleeps 28
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Ask about children
“Unbelievable Home in an Unbelievable Setting!!!” Our family cant thank you enough for the memories made at captains quarters this summer. This was the first time getting away with the entire family (kids grandkids, grand parents, etc) and it was prop
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Price per night from

$1,000

Price per night from

$1,000

Distance approx 8.65 km from Trappe

(10) Excellent 

50

Cottage at Heron Cove, Chesapeake Bay, Cambridge

Maryland / Cambridge

Cambridge cottage

3 5 min stay varies

  • 3 bedrooms
  • sleeps 5
  • min stay varies
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$168

Price per night from

$168

Distance approx 9 km from Trappe

23

EASTERN SHORE MARYLAND WELCOMES YOU

Maryland / Preston

Preston house

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$75

Price per night from

$75