Wye Mills Rentals

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53 Houses

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

Great rentals within 20 miles that match your search

Distance approx 16.16 km from Wye Mills

(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

$284

Price per night from

$284

Distance approx 15.72 km from Wye Mills

(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

$623

Price per night from

$623

Distance approx 12.9 km from Wye Mills

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

$1,394

Price per night from

$1,394

Distance approx 19.71 km from Wye Mills

24

NEW! Annapolis Home w/ Deck & Whitehall Bay Access

Maryland / Cape Saint Claire

Cape Saint Claire house

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Child Friendly
  • Air conditioning

Price per night from

$219

Responds fast!
avg. 55 minutes

Price per night from

$219

Distance approx 14.94 km from Wye Mills

(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

$698

Price per night from

$698

Distance approx 15.65 km from Wye Mills

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

$374

Responds fast!
avg. 55 minutes

Price per night from

$374

Distance approx 16.46 km from Wye Mills

(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

$399

Responds fast!
avg. 55 minutes

Price per night from

$399

Distance approx 13.15 km from Wye Mills

(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
…see more

Price per night from

$150

Responds fast!
avg. 3 hours 32 minutes

Price per night from

$150

Distance approx 11.98 km from Wye Mills

(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

$294

Price per night from

$294

Distance approx 13.15 km from Wye Mills

(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

$289

Responds fast!
avg. 3 hours 32 minutes

Price per night from

$289

Distance approx 17.44 km from Wye Mills

(4) Very Good 

11

Chester River House with Views

Maryland / Chestertown

Chestertown house

3 7 2 nights min

  • 3 bedrooms
  • sleeps 7
  • 2 nights min
  • Child Friendly

Price per night from

$155

Responds fast!
avg. 1 hour 40 minutes

Price per night from

$155

Distance approx 13.16 km from Wye Mills

(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 13.87 km from Wye Mills

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

$747

Responds fast!
avg. 3 hours 21 minutes

Price per night from

$747

Distance approx 13.93 km from Wye Mills

(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

$249

Price per night from

$249

Distance approx 15.75 km from Wye Mills

(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

$339

Responds fast!
avg. 3 hours 15 minutes

Price per night from

$339

Distance approx 13.02 km from Wye Mills

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

$328

Price per night from

$328

Distance approx 18.36 km from Wye Mills

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

$244

Price per night from

$244

Distance approx 13.16 km from Wye Mills

(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 12.42 km from Wye Mills

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

$598

Price per night from

$598

Distance approx 12.04 km from Wye Mills

(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

$284

Price per night from

$284

Distance approx 18.36 km from Wye Mills

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

$244

Price per night from

$244

Distance approx 18.34 km from Wye Mills

(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

$385

Price per night from

$385

Distance approx 13.17 km from Wye Mills

(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 18.25 km from Wye Mills

(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

$374

Price per night from

$374

Distance approx 13.72 km from Wye Mills

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

$324

Price per night from

$324

Distance approx 13.21 km from Wye Mills

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

$284

Price per night from

$284

Distance approx 18.7 km from Wye Mills

(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

$88

Responds fast!
avg. 2 hours 19 minutes

Price per night from

$88

Distance approx 11.86 km from Wye Mills

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

$299

Price per night from

$299

Distance approx 18.7 km from Wye Mills

(7) Excellent 

10

Charming Apartment in Historic Chestertown, MD

Maryland / Chestertown

Chestertown apartment

1 2 3 nights min

  • 1 bedroom
  • sleeps 2
  • 3 nights min
  • Nearest beach 24 mi
  • Child Friendly
  • Air conditioning

Price per night from

$99

Responds fast!
avg. 2 hours 19 minutes

Price per night from

$99

Distance approx 12.43 km from Wye Mills

(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

$847

Responds fast!
avg. 1 hour 1 minutes

Price per night from

$847

Distance approx 9.45 km from Wye Mills

(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

$439

Price per night from

$439

Distance approx 14.8 km from Wye Mills

(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

$598

Price per night from

$598

Distance approx 14.34 km from Wye Mills

(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

$299

Price per night from

$299

Distance approx 16.23 km from Wye Mills

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 15.28 km from Wye Mills

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

$648

Price per night from

$648

Distance approx 8.67 km from Wye Mills

(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

$399

Price per night from

$399

Distance approx 16.31 km from Wye Mills

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