Tilghman Rentals

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38 Houses

Great rentals within 20 miles that match your search

Distance approx 10.76 km from Tilghman

(5) Very Good 

17

Seahorse Guest Cottage near the Bay, dog friendly

Calvert County / North Beach

North Beach cottage

1 5 2 nights min

  • 1 bedroom
  • sleeps 5
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.2 mi
  • Child Friendly

Price per night from

$184

Responds fast!
avg. 1 hour 22 minutes

Price per night from

$184

Distance approx 16.67 km from Tilghman

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

$264

Responds fast!
avg. 10 minutes

Price per night from

$264

Distance approx 17.42 km from Tilghman

(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

$380

Responds fast!
avg. 1 hour 34 minutes

Price per night from

$380

Distance approx 16.34 km from Tilghman

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

$1,149

Price per night from

$1,149

Distance approx 17.42 km from Tilghman

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

Distance approx 6.39 km from Tilghman Show on Map

(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

Distance approx 19 km from Tilghman

(1) Excellent 

24

New! Beachfront 4BR St. Leonard Cottage w/ Deck!

Calvert County / St. Leonard

Saint Leonard cottage

4 8 2 nights min

  • 4 bedrooms
  • sleeps 8
  • 2 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$184

Responds fast!
avg. 39 minutes

Price per night from

$184

Distance approx 17.42 km from Tilghman

(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

Distance approx 5.86 km from Tilghman Show on Map

(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

$718

Price per night from

$718

Distance approx 17.42 km from Tilghman

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

Distance approx 11.88 km from Tilghman

24

Chesapeake Beach Apt. Walk to Bay, Beach & Marina!

Calvert County / Chesapeake Beach

Chesapeake Beach apartment

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Air conditioning

Price per night from

$81

Responds fast!
avg. 10 minutes

Price per night from

$81

Distance approx 15.68 km from Tilghman

55

Charming Annapolis home with stunning water views

Maryland / Annapolis

Annapolis house

4 11 5 nights min

  • 4 bedrooms
  • sleeps 11
  • 5 nights min
  • Child Friendly
  • Pet Friendly

Price per night from

$575

Price per night from

$575

Distance approx 15.47 km from Tilghman

26

Annapolis Crows Nest Cottage: Chesapeake Bay View

Maryland / Annapolis

Annapolis villa

5 20 min stay varies

  • 5 bedrooms
  • sleeps 20
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.2 mi
  • Child Friendly

Price per night from

$796

Price per night from

$796

Distance approx 12.11 km from Tilghman

25

Waterfront Stevensville House w/ Pier & 2 Decks!

Kent Island / Stevensville

Stevensville house

5 12 min stay varies

  • 5 bedrooms
  • sleeps 12
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$430

Responds fast!
avg. 10 minutes

Price per night from

$430

Distance approx 17.12 km from Tilghman

17

Serene Waterfront Apartment on Kent Island

Kent Island / Stevensville

Stevensville apartment

1 2 min stay varies

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

Price per night from

$173

Price per night from

$173

Distance approx 10.06 km from Tilghman

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

Distance approx 9.58 km from Tilghman

(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

$458

Responds fast!
avg. 10 minutes

Price per night from

$458

Distance approx 11.79 km from Tilghman

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

$212

Responds fast!
avg. 10 minutes

Price per night from

$212

Distance approx 17.79 km from Tilghman

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

$996

Price per night from

$996

Distance approx 2.91 km from Tilghman Show on Map

(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

Distance approx 2.75 km from Tilghman Show on Map

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

$282

Price per night from

$282

Distance approx 8.68 km from Tilghman Show on Map

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

Distance approx 2.82 km from Tilghman Show on Map

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. 12 minutes

Price per night from

$201

Distance approx 7.8 km from Tilghman Show on Map

(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

Distance approx 7.78 km from Tilghman Show on Map

(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

Distance approx 11.05 km from Tilghman

11

Panoramic Views of Herrington Harbour on the Bay.

Calvert County / North Beach

North Beach house

3 8 1 night min

  • 3 bedrooms
  • sleeps 8
  • 1 night min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$575

Price per night from

$575

Distance approx 10.53 km from Tilghman

9

Renovated Luxury Waterview House

Calvert County / North Beach

North Beach house

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Child Friendly

Price per night from

$345

Price per night from

$345

Distance approx 18.87 km from Tilghman

10

Harbor Cottage at the Chesapeake Bay

Calvert County / St. Leonard

Saint Leonard cottage

2 6 3 nights min

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

Price per night from

$298

Price per night from

$298

Distance approx 8.07 km from Tilghman Show on Map

(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

Distance approx 16.48 km from Tilghman

(3) Excellent 

21

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

Kent Island / Chester

Chester house

4 8 3 nights min

  • 4 bedrooms
  • sleeps 8
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 14 mi
  • Child Friendly
“Unbelievable value” We were a family group of 3 couples plus an infant traveling to a wedding at the Usna chapel. The home was just wonderful, had a great view, was very clean, and was well equipped for the cooking being planned. Stores, restaurants,
…see more

Price per night from

$328

Price per night from

$328

Distance approx 7.79 km from Tilghman Show on Map

(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

Distance approx 15 km from Tilghman

(1) Excellent 

32

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

Kent Island / Chester

Chester house

4 10 2 nights min

  • 4 bedrooms
  • sleeps 10
  • 2 nights min
  • Nearest beach 127 mi
  • Swimming pool
  • Child Friendly

Price per night from

$862

Price per night from

$862

Distance approx 7.77 km from Tilghman Show on Map

(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

Distance approx 11.89 km from Tilghman

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

$690

Price per night from

$690

Distance approx 3.49 km from Tilghman Show on Map

(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 2.65 km from Tilghman Show on Map

(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

$444

Price per night from

$444

Distance approx 2.75 km from Tilghman Show on Map

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

$282

Price per night from

$282

Distance approx 7.78 km from Tilghman Show on Map

(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