Book Holiday Homes in Wye Mills

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Wye Mills

Pet-Friendly Home on Chester River w/ Dock!

Pet-Friendly Home on Chester River w/ Dock!

2 out of 5
Chestertown
When you stay at this vacation home in Chestertown, you'll be within a 5-minute drive of Washington College.
Pet-Friendly Home on Chester River w/ Dock!
Dollhouse in Central Historic St Michaels

Dollhouse in Central Historic St Michaels

St Michaels
With a stay at this vacation home in St. Michaels, you'll be within a 10-minute walk of Chesapeake Bay Maritime Museum and St. Michaels Museum.
Dollhouse in Central Historic St Michaels
Waterfront family resort Lodge with private pier, game room and bar

Waterfront family resort Lodge with private pier, game room and bar

Centreville
Located in Centreville, this vacation home is on a river, within a 10-minute drive of Hazel Miner Monument and Earle Landing.
Waterfront family resort Lodge with private pier, game room and bar
Save an average of 15% on thousands of hotels when you're signed in
A waterfront gem with dock, kayaks great water views.  Sleeps up to 12.

A waterfront gem with dock, kayaks great water views. Sleeps up to 12.

Rock Hall
Located in Rock Hall, this vacation home is on the waterfront, within a 10-minute drive of The Mainstay and Waterman’s Museum.
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
Relax on Kent Island in 3 Bedroom Home w/Waterview

Relax on Kent Island in 3 Bedroom Home w/Waterview

Stevensville
The price is AU$413 per night from 5 Jan to 6 Jan
AU$413
includes taxes & fees
5 Jan - 6 Jan 2025
Located in Stevensville, this vacation home is within a 15-minute drive of Matapeake State Park and Paul Reed Smith Guitars.
Relax on Kent Island in 3 Bedroom Home w/Waterview
Waterfront w/upper sundeck and private pier located near Rock Hall,  sleeps 18.

Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.

Rock Hall
Located in Rock Hall, this vacation home is on the waterfront, within a 10-minute drive of The Mainstay and Waterman’s Museum.
Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.
Walk to Everything House

Walk to Everything House

Saint Michaels
With a stay at this vacation home in St. Michaels, you'll be within a 10-minute walk of Chesapeake Bay Maritime Museum and St. Michaels Museum.
Walk to Everything House
RANCH AT ROYAL OAK- Exclusive waterfront pool pier

RANCH AT ROYAL OAK- Exclusive waterfront pool pier

Royal Oak
With a stay at this vacation home in Royal Oak, you'll be on the waterfront, and 8.3 mi (13.3 km) from St. Michaels Winery and 8.4 mi (13.6 km) from St. Michaels ...
RANCH AT ROYAL OAK- Exclusive waterfront pool pier
Waterfront Paradise on the Eastern Shore of Chesapeake Bay

Waterfront Paradise on the Eastern Shore of Chesapeake Bay

Rock Hall
Located in Rock Hall, this vacation home is on the waterfront, within a 10-minute drive of Eastern Neck National Wildlife Refuge and The Mainstay.
Waterfront Paradise on the Eastern Shore of Chesapeake Bay
Don't see what you're looking for?
See all available properties in Wye Mills
View all properties
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.

Wye Mills Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Wye Mills vacation homes are the perfect way for you to wing it.

Holiday houses in Wye Mills let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Wye Mills in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Wye Mills adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Wye Mills with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Wye Mills vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Wye Mills Holiday Homes essential information

Accommodation
196 Holiday Homes
Lowest Price
AU$150
Highest Price
AU$706
Popular accommodation
Pet-Friendly Home on Chester River w/ Dock!, Dollhouse in Central Historic St Michaels, Waterfront family resort Lodge with private pier, game room and bar, A waterfront gem with dock, kayaks great water views. Sleeps up to 12., Relax on Kent Island in 3 Bedroom Home w/Waterview, Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18., Walk to Everything House, RANCH AT ROYAL OAK- Exclusive waterfront pool pier, Waterfront Paradise on the Eastern Shore of Chesapeake Bay

Top trending hotels in Wye Mills

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

3 out of 5
3028 KENT NARROW WAY S, Grasonville, MD
Fully refundableReserve now, pay when you stay
The price is AU$210 per night from 25 Dec to 26 Dec
AU$210
includes taxes & fees
25 Dec - 26 Dec
Located in Grasonville, Hyatt Place Kent Narrows & Marina is in the historical district, a 2-minute drive from Chesapeake Exploration Center and 7 minutes from ...
Hyatt Place Kent Narrows & Marina
Inn at Perry Cabin

Inn at Perry Cabin

5 out of 5
308 Watkins Ln, St. Michaels, MD
The price is AU$706 per night from 9 Jan to 10 Jan
AU$706
includes taxes & fees
9 Jan - 10 Jan 2025
A stay at Inn at Perry Cabin places you in the heart of St. Michaels, within a 15-minute walk of Chesapeake Bay Maritime Museum and St. Michaels Museum.
Inn at Perry Cabin
Best Western Kent Narrows Inn

Best Western Kent Narrows Inn

2.5 out of 5
3101 Main Street, Grasonville, MD
Fully refundableReserve now, pay when you stay
The price is AU$160 per night from 29 Dec to 30 Dec
AU$160
includes taxes & fees
29 Dec - 30 Dec
A stay at Best Western Kent Narrows Inn places you in the heart of Grasonville, a 2-minute drive from Chesapeake Exploration Center and 7 minutes from Island ...
Best Western Kent Narrows Inn
Save an average of 15% on thousands of hotels when you're signed in
St Michaels Inn

St Michaels Inn

2.5 out of 5
1228 S Talbot Street, St. Michaels, MD
Fully refundableReserve now, pay when you stay
The price is AU$150 per night from 5 Jan to 6 Jan
AU$150
includes taxes & fees
5 Jan - 6 Jan 2025
When you stay at St Michaels Inn in St. Michaels, you'll be in the historical district, within a 5-minute drive of St. Michaels Winery and Chesapeake Bay Maritime ...
St Michaels Inn
Don't see what you're looking for?
See all available properties in Wye Mills
View all properties
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.