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55 Houses

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

$687

Price per night from

$687

(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

$301

Price per night from

$301

Great rentals within 20 miles that match your search

Distance approx 12.31 km from Royal Oak

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 12.31 km from Royal Oak

(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

$379

Responds fast!
avg. 1 hour 34 minutes

Price per night from

$379

Distance approx 12.31 km from Royal Oak

(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

$131

Responds fast!
avg. 1 hour 34 minutes

Price per night from

$131

Distance approx 19.48 km from Royal Oak

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

$797

Price per night from

$797

Distance approx 7.43 km from Royal Oak 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

$803

Price per night from

$803

Distance approx 12.6 km from Royal Oak

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

$231

Responds fast!
avg. 10 minutes

Price per night from

$231

Distance approx 12.14 km from Royal Oak

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

$1,147

Price per night from

$1,147

Distance approx 12.31 km from Royal Oak

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

Distance approx 14.24 km from Royal Oak

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. 14 minutes

Price per night from

$430

Distance approx 12.59 km from Royal Oak

(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 14.21 km from Royal Oak

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

$871

Price per night from

$871

Distance approx 18.23 km from Royal Oak

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 6.02 km from Royal Oak 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

$246

Price per night from

$246

Distance approx 19.56 km from Royal Oak

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

$501

Price per night from

$501

Distance approx 16 km from Royal Oak

(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

$327

Price per night from

$327

Distance approx 7.75 km from Royal Oak 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

$601

Price per night from

$601

Distance approx 6.17 km from Royal Oak 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

$387

Price per night from

$387

Distance approx 1 km from Royal Oak 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

$860

Responds fast!
avg. 3 hours 21 minutes

Price per night from

$860

Distance approx 19.17 km from Royal Oak

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

$301

Price per night from

$301

Distance approx 14.63 km from Royal Oak

(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
…see more

Price per night from

$572

Price per night from

$572

Distance approx 6.24 km from Royal Oak Show on Map

(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

$376

Price per night from

$376

Distance approx 6.02 km from Royal Oak 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

$246

Price per night from

$246

Distance approx 5.35 km from Royal Oak Show on Map

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

$201

Price per night from

$201

Distance approx 6.17 km from Royal Oak Show on Map

(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

$691

Price per night from

$691

Distance approx 3.53 km from Royal Oak Show on Map

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

$286

Price per night from

$286

Distance approx 14.55 km from Royal Oak

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

$181

Price per night from

$181

Distance approx 16.88 km from Royal Oak

12

Beautiful Kent Island 4BR, Perfect Location, Close to Chesapeake Bay Beach Club!

Kent Island / Chester

Chester house

4 12 2 nights min

  • 4 bedrooms
  • sleeps 12
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$301

Price per night from

$301

Distance approx 4.58 km from Royal Oak Show on Map

(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

$1,147

Responds fast!
avg. 1 hour 1 minutes

Price per night from

$1,147

Distance approx 14.77 km from Royal Oak

(1) Excellent 

32

KENT ISLAND-OCEAN VIEW Home for rent -4 bedrooms EASTERN SHORE sleeps 10-12

Maryland / Kent Island

Kent Island house

4 10 2 nights min

  • 4 bedrooms
  • sleeps 10
  • 2 nights min
  • Nearest beach 5 mi
  • Swimming pool
  • Air conditioning

Price per night from

$1,720

Price per night from

$1,720

Distance approx 16.52 km from Royal Oak

(15) Excellent 

35

Luxury vacation condominum with private beach

Kent Island / Chester

Chester house

4 10 2 nights min

  • 4 bedrooms
  • sleeps 10
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.2 mi
  • Child Friendly

Price per night from

$441

Price per night from

$441

Distance approx 15.19 km from Royal Oak

(5) Excellent 

17

KI Golf House-A PAR for the Course & Mile to Beach

Maryland / Kent Island

Kent Island house

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Nearest beach 1 mi
  • Child Friendly
  • Air conditioning

Price per night from

$401

Responds fast!
avg. 1 hour 7 minutes

Price per night from

$401

Distance approx 13.66 km from Royal Oak

(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
…see more

Price per night from

$1,001

Price per night from

$1,001

Distance approx 13.55 km from Royal Oak

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

$100

Price per night from

$100

Distance approx 15.57 km from Royal Oak

9

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

Kent Island / Stevensville

Stevensville house

4 12 min stay varies

  • 4 bedrooms
  • sleeps 12
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$476

Responds fast!
avg. 1 hour 7 minutes

Price per night from

$476

Distance approx 11.2 km from Royal Oak

(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 13.6 km from Royal Oak

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

$86

Price per night from

$86