Wye Mills Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Vacation Rentals in Wye Mills

Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.

Stevensville
10.0 out of 10, Exceptional, (14)
"Very clean beautiful house! We stayed there for a wedding weekend and it was perfect. Great location. The hosts were wonderful and got back to us right away! Would love to go back one day."
United States
Tammy S.
Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.

Floating 2 bed 2 bath condo stunning views of the bay

2.0 star property
Stevensville
6.4 out of 10, (7)
"Beautiful view! Could hear the tiki bar music from the top. Easy to get to woth lots of things to do nearby. "
United States
Natalia F.
Floating 2 bed 2 bath condo stunning views of the bay

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Rock Hall
10.0 out of 10, Exceptional, (17)
"I loved the welcome basket! This place was extremely clean and had all the amenities that we needed. Much larger in person than even in the pictures. Walkable to town! "
United States
Tracy S.
The price is ¥18,148
¥43,691 total
includes taxes & fees
Nov 14 - Nov 15
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Cass-N-Reel Luxury Houseboat

Grasonville
10.0 out of 10, Exceptional, (45)
"If you’re looking for a great view sitting on the water, with a modern look, convenient to everything, you need to stay on the Cass-and-Reel Luxury Houseboat!!"
United States
Karen B.
Cass-N-Reel Luxury Houseboat

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

Saint Michaels
9.6 out of 10, Exceptional, (122)
"The house and location was perfect for a girls weekend with my mom and 2 daughters! The 1/2 bathrooms in each bedroom were nice to have upstairs!"
United States
Kimberly L.
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

Chesapeake Bay Harbor View in a central location to events/restaurants

2.5 star property
Rock Hall
10.0 out of 10, Exceptional, (1)
"House was clean, great location. Furniture needs a little updating but overall our stay was great! Would definitely stay here again."
United States
Todd W.
The price is ¥34,664
¥41,970 total
includes taxes & fees
Dec 13 - Dec 14
Chesapeake Bay Harbor View in a central location to events/restaurants

Stunning Historic Downtown Home!! Within 2 Blocks of Fountain Park!!

Chestertown
10.0 out of 10, Exceptional, (2)
"Overall a beautiful and well maintained place to stay! The location was perfect…within walking distance to everything! A very charming home! We were so happy we chose this property!"
United States
Dawn B.
Stunning Historic Downtown Home!! Within 2 Blocks of Fountain Park!!

Relax on Kent Island in 3 Bedroom Home w/Waterview

Stevensville
9.8 out of 10, Exceptional, (41)
"This is a great place for a small family and friends' weekend reunion."
United States
Paul G.
The price is ¥11,371
¥39,768 total
includes taxes & fees
Nov 16 - Nov 17
Relax on Kent Island in 3 Bedroom Home w/Waterview

Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

St Michaels
9.6 out of 10, Exceptional, (146)
"Perfect place to stay for a cousins reunion, Central location to all the shops and restaurants."
United States
Amh S.
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly

Stevensville
10.0 out of 10, Exceptional, (55)
"My wife and I have stayed at many different places over the years but this may be one of the most well maintained properties I've ever seen. It was a great place for us to unwind with our dog and we would certainly recommend this location for anyone looking to stay in the area"
United States
Nick B.
Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly

240' Private Beachfront @Kent Island Love Point - Great for Large Groups

stevensville
10.0 out of 10, Exceptional, (196)
"We had a great time with friends on our annual MD golf trip. Hal was great and the place was perfect for our group."
United States
Jason R.
240' Private Beachfront @Kent Island Love Point - Great for Large Groups

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

St. Michaels
9.8 out of 10, Exceptional, (44)
"This cottage is adorable. Great amenities and great location. We thoroughly enjoyed our time in St Michael’s."
United States
Audra B.
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

BAYSIDE BUNGALOW

Rock Hall
10.0 out of 10, Exceptional, (52)
"This stay was a wonderful, relaxing experience. The hosts were so friendly and welcoming and the cottage was charming. We lacked for nothing and especially enjoyed the bikes and the chance to bike around this lovely area. Highly recommend!"
United States
Jackie R.
BAYSIDE BUNGALOW

Modern Flat in the Heart of St. Michaels – Walk Everywhere

Saint Michaels
10.0 out of 10, Exceptional, (53)
"Beautiful, clean and well appointed in the perfect spot in downtown Saint Michael’s. Highly recommended!!"
United States
Jeffrey G.
Modern Flat in the Heart of St. Michaels – Walk Everywhere

Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

St Michaels
9.6 out of 10, Exceptional, (125)
"Beautiful little cottage! Location is perfect."
United States
John B.
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access

Sherwood
10.0 out of 10, Exceptional, (19)
"Gorgeous views and location. "
United States
Ryan D.
6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access

Kent Island Luxury Waterfront

Stevensville
10.0 out of 10, Exceptional, (8)
"Such a beautiful property. . Wonderful experience. Love to come back again. House is way better than we expected. Gorgeous views and had an amazing experience of moonrise abd sunrise"
United States
satarupa s.
Kent Island Luxury Waterfront

First Floor Studio Apartment in Historic Chestertown

Chestertown
9.6 out of 10, Exceptional, (106)
"Wonderful stay in a beautiful location convenient to everything. Host was outstanding."
United States
Randy B.
The price is ¥15,252
¥24,471 total
includes taxes & fees
Nov 25 - Nov 26
First Floor Studio Apartment in Historic Chestertown

RELAX- Eastern Shore Creek Home - 6 Guests

Grasonville
10.0 out of 10, Exceptional, (5)
"We had a real enjoyable and comfortable stay in this beautiful home. The hosts were very responsive and the amenities were much appreciated. The home made this special trip even more memorable."
United States
Sherry N.
RELAX- Eastern Shore Creek Home - 6 Guests

Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND

Sherwood
10.0 out of 10, Exceptional, (37)
"We went to Sherwood to celebrate a family event. The house was perfect - lots of room for everyone. Check-in was simple, house was in excellent condition and the owners made every effort to accommodate our needs (some extra equipment for little kids). We enjoyed the pool and the beautiful setting. Great stay!"
United States
James S.
Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in

Top Wye Mills Hotel Reviews

Find out more about Wye Mills

Search for holiday rentals in Wye Mills on Expedia! You can easily find your home rentals, villas, holiday apartments in Wye Mills using one of the methods below:

  • View our selection of featured holiday rentals in Wye Mills
  • Use the map to find apartments and other holiday homes in the Wye Mills neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Wye Mills while they last

Look no further and take a look at our great range of rental properties in Wye Mills!

Frequently asked questions

Can I find a vacation rental in Wye Mills?

Yes, we have vacation rentals near the most popular attractions in Wye Mills, or you can go with a secluded option if you want a relaxing place to stay. Wye Mills is known for its waterfront.

What are some of the best vacation home rentals that Wye Mills has to offer?

Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres. : This vacation home rental outside of Wye Mills is located next to a golf course and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a pool table.

What can I see and do in Wye Mills?

While exploring the area, visit family-friendly sights like Chesapeake Bay Maritime Museum, or get outside and enjoy nature at Chesapeake Bay Environmental Center. Wye Landing and Wye Oak State Park are other places to visit while you're in town.

What are vacation rentals like in Wye Mills?

Vacation rentals are private properties you can reserve for several days or more in Wye Mills. Vacation rentals feature amenities like WiFi and washers and dryers so your stay will be comfortable. If you're concerned about a clean environment, vacation rentals can provide a sense of safety away from public hotel elevators and busy lobbies while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great choice for a small group gathering.