Rock Hall Rentals

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55 Houses

(1) Excellent 

10

Summer House

Maryland / Rock Hall

Rock Hall bungalow

3 8 2 nights min

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

Price per night from

$285

Price per night from

$285

8

Bay Cottage

Maryland / Rock Hall

Rock Hall house

2 5 2 nights min

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

Price per night from

$287

Responds fast!
avg. 3 hours 15 minutes

Price per night from

$287

(3) Excellent 

12

Sailors Crossing

Maryland / Rock Hall

Rock Hall house

3 10 2 nights min

  • 3 bedrooms
  • sleeps 10
  • 2 nights min
  • Child Friendly
  • Pet Friendly

Price per night from

$340

Responds fast!
avg. 3 hours 15 minutes

Price per night from

$340

8

Bayside Retreat

Maryland / Rock Hall

Rock Hall house

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$264

Responds fast!
avg. 3 hours 15 minutes

Price per night from

$264

88

Great vacation rental located in the waterfront town of Rock Hall

Maryland / Rock Hall

Rock Hall house

4 7 1 night min

  • 4 bedrooms
  • sleeps 7
  • 1 night min
  • Child Friendly

Price per night from

$100

Responds fast!
avg. 2 hours 9 minutes

Price per night from

$100

Great rentals within 20 miles that match your search

Distance approx 19.45 km from Rock Hall

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 8.67 km from Rock Hall

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

$1,399

Price per night from

$1,399

Distance approx 13.27 km from Rock Hall

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

$172

Price per night from

$172

Distance approx 10.64 km from Rock Hall

(3) Excellent 

7

Cottage On Kent

Maryland / Chestertown

Chestertown cottage

1 3 1 night min

  • 1 bedroom
  • sleeps 3
  • 1 night min
  • Air conditioning
  • Private garden

Price per night from

$195

Price per night from

$195

Distance approx 10.61 km from Rock Hall

(5) Excellent 

Certificate of Excellence

28

Cozy & Spacious Chestertown Home

Maryland / Chestertown

Chestertown house

4 8 2 nights min

  • 4 bedrooms
  • sleeps 8
  • 2 nights min
  • Nearest beach 5 mi
  • Swimming pool
  • Child Friendly

Certificate of Excellence

Price per night from

$250

Responds fast!
avg. 2 hours 43 minutes

Price per night from

$250

Distance approx 14.44 km from Rock Hall

(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

$859

Price per night from

$859

Distance approx 4.9 km from Rock Hall

(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

$338

Responds fast!
avg. 3 hours 30 minutes

Price per night from

$338

Distance approx 13.17 km from Rock Hall

(2) Excellent 

10

C/ean & Cozy

Maryland / Annapolis

Annapolis room

1 2 1 night min

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

Price per night from

$59

Price per night from

$59

Distance approx 8.81 km from Rock Hall

11

Love Point Bay Vacation Home

Kent Island / Stevensville

Stevensville apartment

2 6 2 nights min

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

Price per night from

$377

Price per night from

$377

Distance approx 19.08 km from Rock Hall

21

Annapolis Area Waterfront Home

Maryland / Annapolis

Annapolis house

5 11 min stay varies

  • 5 bedrooms
  • sleeps 11
  • min stay varies
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$630

Price per night from

$630

Distance approx 12.99 km from Rock Hall

(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 7.78 km from Rock Hall

(14) Excellent 

19

Love Point Waterfront

Maryland / Kent Island

Kent Island house

3 12 3 nights min

  • 3 bedrooms
  • sleeps 12
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 5 mi
  • Child Friendly
“Love Point Retreat” I stayed at Paula's property 3 times so far. We stayed once in October 2014 and twice in April 2015. Here is how I would break it up: Owner: Paula is very nice, accommodating and extremely responsive. She was easy to deal with, ans
…see more

Price per night from

$250

Price per night from

$250

Distance approx 17.66 km from Rock Hall

(1) Excellent 

17

Excellent Location in Downtown Annapolis- walk to everything !

Maryland / Annapolis

Annapolis house

3 7 2 nights min

  • 3 bedrooms
  • sleeps 7
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$343

Responds fast!
avg. 2 hours 21 minutes

Price per night from

$343

Distance approx 18.25 km from Rock Hall

(6) Excellent 

19

Charming and Spacious Annapolis Victorian

Maryland / Annapolis

Annapolis house

6 12 min stay varies

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

Price per night from

$859

Responds fast!
avg. 1 hour 34 minutes

Price per night from

$859

Distance approx 13.17 km from Rock Hall

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

$350

Price per night from

$350

Distance approx 15.58 km from Rock Hall

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

Distance approx 17.76 km from Rock Hall

4

Perfect Annapolis with Lots of Parking & Hot Tub

Maryland / Annapolis

Annapolis townhouse

4 10 2 nights min

  • 4 bedrooms
  • sleeps 10
  • 2 nights min
  • Child Friendly

Price per night from

$567

Price per night from

$567

Distance approx 17.36 km from Rock Hall

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 17.89 km from Rock Hall

23

Charming Eastport Home

Maryland / Annapolis

Annapolis house

3 8 5 nights min

  • 3 bedrooms
  • sleeps 8
  • 5 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$250

Price per night from

$250

Distance approx 18.19 km from Rock Hall

31

NEW! Annapolis House in Bay Ridge Maryland!

Maryland / Annapolis

Annapolis house

3 6 min stay varies

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

Price per night from

$449

Responds fast!
avg. 10 minutes

Price per night from

$449

Distance approx 10.54 km from Rock Hall

(1) Excellent 

7

Cozy Apartment in Chestertown

Maryland / Chestertown

Chestertown apartment

1 2 1 night min

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

Price per night from

$101

Responds fast!
avg. 2 hours 19 minutes

Price per night from

$101

Distance approx 18.12 km from Rock Hall

(3) Very Good 

30

Beautiful Murray Hill Home (Annapolis)

Maryland / Annapolis

Annapolis house

4 9 min stay varies

  • 4 bedrooms
  • sleeps 9
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Ask about pets
“Comfortable and secure in a great home - almost as good as at ho” The house is set is a terrific neighborhood of annapolis within easy walking distance to two small parks on the water and to town. We all found the house a delight - the design, decor
…see more

Price per night from

$425

Price per night from

$425

Distance approx 11.85 km from Rock Hall

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 18.61 km from Rock Hall

43

The Yellow House- Gorgeous Southern Colonial

Maryland / Annapolis

Annapolis house

6 14 4 nights min

  • 6 bedrooms
  • sleeps 14
  • 4 nights min
  • Beach / lakeside relaxation
  • Nearest beach 1 mi
  • Child Friendly

Price per night from

$1,140

Responds fast!
avg. 1 hour 32 minutes

Price per night from

$1,140

Distance approx 13.97 km from Rock Hall

4

Brookstone RV

Maryland / Edgemere

Edgemere caravan/mobile home

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min
  • Child Friendly

Price per night from

$75

Price per night from

$75

Distance approx 18.51 km from Rock Hall

24

NEW! Charming Annapolis Home w/ Yard-5 Mins to DT!

Maryland / Annapolis

Annapolis house

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Child Friendly
  • Air conditioning

Price per night from

$319

Price per night from

$319

Distance approx 19.01 km from Rock Hall

(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

$350

Responds fast!
avg. 14 minutes

Price per night from

$350

Distance approx 17.31 km from Rock Hall

(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

Distance approx 14.44 km from Rock Hall

(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

$1,718

Price per night from

$1,718

Distance approx 10.88 km from Rock Hall

(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

$440

Price per night from

$440

Distance approx 16.39 km from Rock Hall

(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

$400

Responds fast!
avg. 1 hour 7 minutes

Price per night from

$400

Distance approx 7.04 km from Rock Hall

(22) Excellent 

34

Waterfront House, Eastern Shore Chesapeake Bay

Maryland / Centreville

Centreville house

4 8 3 nights min

  • 4 bedrooms
  • sleeps 8
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$458

Price per night from

$458

Distance approx 18.2 km from Rock Hall

(19) Excellent 

25

*BOOK NOW* Beautiful Cottage in historic Annapolis

Maryland / Annapolis

Annapolis cottage

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 1 mi
  • Child Friendly

Price per night from

$401

Responds fast!
avg. 2 hours 13 minutes

Price per night from

$401