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77 Houses

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

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

$375

Responds fast!
avg. 1 hour 2 minutes

Price per night from

$375

(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

$400

Responds fast!
avg. 1 hour 2 minutes

Price per night from

$400

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

$150

Price per night from

$150

(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

Price per night from

$285

Price per night from

$285

(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

$750

Price per night from

$750

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

$329

Price per night from

$329

(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

Price per night from

$250

Price per night from

$250

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

$300

Price per night from

$300

(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

$1,500

Price per night from

$1,500

(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

(5) Excellent 

17

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

Maryland / Kent Island

Kent Island house

4 10 2 nights min

  • 4 bedrooms
  • sleeps 10
  • 2 nights min
  • Nearest beach 1 mi
  • Child Friendly
  • Air conditioning

Price per night from

$599

Price per night from

$599

9

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

Kent Island / Stevensville

Stevensville house

4 12 3 nights min

  • 4 bedrooms
  • sleeps 12
  • 3 nights min
  • Nearest beach 0 mi
  • Child Friendly
  • Air conditioning

Price per night from

$650

Price per night from

$650

Great rentals within 20 miles that match your search

Distance approx 14.67 km from Kent Island Show on Map

(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

Distance approx 13.99 km from Kent Island Show on Map

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

$598

Price per night from

$598

Distance approx 11.66 km from Kent Island Show on Map

24

Shady Side House on Chesapeake Bay Near Marina!

Maryland / Shady Side

Shady Side house

2 5 min stay varies

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

Price per night from

$185

Responds fast!
avg. 1 hour 2 minutes

Price per night from

$185

Distance approx 14.55 km from Kent Island Show on Map

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

$250

Responds fast!
avg. 3 hours 15 minutes

Price per night from

$250

Distance approx 18.47 km from Kent Island

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

$500

Price per night from

$500

Distance approx 7.23 km from Kent Island Show on Map

55

Charming Annapolis home with stunning water views

Maryland / Annapolis

Annapolis house

4 11 min stay varies

  • 4 bedrooms
  • sleeps 11
  • min stay varies
  • Child Friendly
  • Pet Friendly

Price per night from

$500

Price per night from

$500

Distance approx 14.41 km from Kent Island

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 19.1 km from Kent Island

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

$300

Price per night from

$300

Distance approx 14.56 km from Kent Island Show on Map

(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

Distance approx 9.13 km from Kent Island Show on Map

(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 14.23 km from Kent Island

(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 14.04 km from Kent Island

(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 9.04 km from Kent Island Show on Map

(2) Excellent 

52

Walk to Shops/Eateries Charming Cottage. Dogs Wel.

Maryland / Annapolis

Annapolis house

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Nearest beach 6 mi
  • Child Friendly
  • Car not necessary

Price per night from

$250

Responds fast!
avg. 1 hour 49 minutes

Price per night from

$250

Distance approx 11.73 km from Kent Island 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

$200

Price per night from

$200

Distance approx 9.87 km from Kent Island Show on Map

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

$495

Price per night from

$495

Distance approx 14.97 km from Kent Island

29

Custom Annapolis Home w/ Private Pool & Hot Tub!

Maryland / Riva

Riva house

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$289

Responds fast!
avg. 53 minutes

Price per night from

$289

Distance approx 14.23 km from Kent Island

(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

Price per night from

$690

Price per night from

$690

Distance approx 12.11 km from Kent Island 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

$285

Price per night from

$285

Distance approx 7.01 km from Kent Island Show on Map

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

$448

Responds fast!
avg. 28 minutes

Price per night from

$448

Distance approx 7.5 km from Kent Island Show on Map

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

$994

Responds fast!
avg. 1 hour 30 minutes

Price per night from

$994

Distance approx 9.57 km from Kent Island Show on Map

(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

Price per night from

$425

Price per night from

$425

Distance approx 12.77 km from Kent Island Show on Map

4

Lochhaven house for rent

Maryland / Edgewater

Edgewater house

3 2 7 nights min

  • 3 bedrooms
  • sleeps 2
  • 7 nights min
  • Air conditioning
  • Private garden

Price per night from

$100

Price per night from

$100

Distance approx 11.02 km from Kent Island 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

$849

Responds fast!
avg. 1 hour 1 minutes

Price per night from

$849

Distance approx 9.03 km from Kent Island 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

$449

Price per night from

$449

Distance approx 10.29 km from Kent Island Show on Map

(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

$350

Responds fast!
avg. 2 hours 3 minutes

Price per night from

$350