Wye Mills Holiday Rentals

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Check prices for these dates

Tonight
11 Dec - 12 Dec
Tomorrow
12 Dec - 13 Dec
This weekend
12 Dec - 14 Dec
Next weekend
19 Dec - 21 Dec

Our top choices for Wye Mills holiday rentals

Interior
Floating 2 bed 2 bath condo stunning views of the bay

Floating 2 bed 2 bath condo stunning views of the bay

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
Fridge, microwave, oven, stovetop
Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.

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

Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.
Stevensville
10.0 out of 10, Exceptional, (15)
"The property is excellent for entertaining and family gatherings. Everything was clean and tastefully appointed."
United States
Kerrith D.
Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.
Smart TV
Cass-N-Reel Luxury Houseboat

Cass-N-Reel Luxury Houseboat

Cass-N-Reel Luxury Houseboat
Grasonville
10.0 out of 10, Exceptional, (47)
"Amazing views! Location is great, restaurants at walking distance, great bicicle trail, highly recommended!"
United States
Oliver C.
Cass-N-Reel Luxury Houseboat
Interior
200 steps to the beach!

200 steps to the beach!

200 steps to the beach!
Rock Hall
10.0 out of 10, Exceptional, (93)
"Beautiful, comfortable home in a great location. "
United States
Stephanie C.
200 steps to the beach!
Dining
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna

Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna

Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
Rock Hall
9.8 out of 10, Exceptional, (40)
"Ashleigh was amazing as a host, got right back to us on all questions and needs. "
United States
Tim B.
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
Marina
Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis

Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis

Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis
Annapolis
9.4 out of 10, Exceptional, (36)
"Very communicative host and the in apartment sauna and jacuzzi tub really helped us relax. A great stay overall!"
United States
George H.
Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis
Property grounds
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

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

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Downtown St. Michaels
9.6 out of 10, Exceptional, (124)
"Always a great stay at the John Bruff house! Location is perfect, great view of the harbor and even saw a free concert in the park!!"
United States
Meghan K.
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Property grounds
240' Private Beachfront @Kent Island Love Point - Great for Large Groups

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

240' Private Beachfront @Kent Island Love Point - Great for Large Groups
stevensville
10.0 out of 10, Exceptional, (197)
"This home was the perfect get-away for a group of friends!The accommodations were wonderful and the host went out of their way to ensure our stay was full of fun activities."
United States
David N.
240' Private Beachfront @Kent Island Love Point - Great for Large Groups
Private kitchen
Stunning Historic Downtown Home!! Within 2 Blocks of Fountain Park!!

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

Stunning Historic Downtown Home!! Within 2 Blocks of Fountain Park!!
Chestertown
10.0 out of 10, Exceptional, (3)
"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!!
Exterior detail
BAYSIDE BUNGALOW

BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (52)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
The price is HK$1,400
HK$2,103 total
includes taxes & fees
4 Jan - 5 Jan 2026
BAYSIDE BUNGALOW
Dining
Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!

Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!

Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!
Chester
10.0 out of 10, Exceptional, (126)
"This house was charming and comfortable. The view was spectacular. Neighbors and friendly. The whole place has a serene feel to it. In addition, the owners were very helpful and responsive. We will be back again!"
United States
Sue R.
Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!
Property grounds
First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (108)
"Amazing and neat and very private "
United States
Alexander M.
The price is HK$770
HK$1,236 total
includes taxes & fees
15 Dec - 16 Dec
First Floor Studio Apartment in Historic Chestertown
Exterior
Accessible, 3 Season Screened-in porch, Sauna, Fire Pit, Dog Friendly

Accessible, 3 Season Screened-in porch, Sauna, Fire Pit, Dog Friendly

Accessible, 3 Season Screened-in porch, Sauna, Fire Pit, Dog Friendly
Stevensville
10.0 out of 10, Exceptional, (57)
"It’s a fantastic property!! Perfect for a getaway weekend. Everything was as described. A great place to stay home and enjoy all the amenities."
United States
Kurt H.
Accessible, 3 Season Screened-in porch, Sauna, Fire Pit, Dog Friendly
TV
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

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

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Downtown St. Michaels
9.8 out of 10, Exceptional, (45)
"Perfect location, everything as advertised. Highly recommend "
United States
Glen H.
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Smart TV
Cass-Away Luxury Houseboat

Cass-Away Luxury Houseboat

Cass-Away Luxury Houseboat
Grasonville
10.0 out of 10, Exceptional, (105)
"What a unique experience to stay on a houseboat. Such a fun locale & comfortable accommodations. "
United States
Robin L.
Cass-Away Luxury Houseboat
Exterior
Private Riverfront Home with Hot Tub, Kayaks, Paddleboards and Riverside Firepit

Private Riverfront Home with Hot Tub, Kayaks, Paddleboards and Riverside Firepit

Private Riverfront Home with Hot Tub, Kayaks, Paddleboards and Riverside Firepit
Grasonville
10.0 out of 10, Exceptional, (24)
"Place was fantastic!"
United States
larry
Private Riverfront Home with Hot Tub, Kayaks, Paddleboards and Riverside Firepit
Smart TV
Dollhouse in Central Historic St Michaels

Dollhouse in Central Historic St Michaels

Dollhouse in Central Historic St Michaels
Downtown St. Michaels
9.8 out of 10, Exceptional, (56)
"We highly enjoyed our stay. It was a great location and we got a lot of use out of the screened in porch. The coffee shop out back was a great visit in the morning. "
United States
Nitarah I.
Dollhouse in Central Historic St Michaels
Smart TV, fireplace, books
Stylish Home on the Choptank River (with Tidal Beach)

Stylish Home on the Choptank River (with Tidal Beach)

Stylish Home on the Choptank River (with Tidal Beach)
Preston
10.0 out of 10, Exceptional, (44)
"The house was great with a wonderful river view! Easily accommodated 5 adults."
United States
Karen
Stylish Home on the Choptank River (with Tidal Beach)
Exterior
Stay in the landmark Lighthouse!

Stay in the landmark Lighthouse!

Stay in the landmark Lighthouse!
Rock Hall
10.0 out of 10, Exceptional, (107)
"Beautiful home. Wish I could of stayed longer "
United States
Pat R.
Stay in the landmark Lighthouse!
Dining
Bayfront Retreat Near St. Michaels | Private Dock • Sunset Views

Bayfront Retreat Near St. Michaels | Private Dock • Sunset Views

Bayfront Retreat Near St. Michaels | Private Dock • Sunset Views
Tilghman Island
9.8 out of 10, Exceptional, (10)
"Great property!!! Absolutely would recommend!"
United States
John and Michele E.
Bayfront Retreat Near St. Michaels | Private Dock • Sunset Views
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.
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Top Wye Mills Hotel Reviews

Best Western Denton Inn

Best Western Denton Inn

10/10 Excellent
"Desk staff was friendly and courteous. Couldn’t stay for breakfast, but smelled great! Room was clean and comfortable."
Andrew 1-night trip
Posted 3 days ago
Best Western Denton Inn

Find out more about Wye Mills

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Frequently asked questions

Can I find a holiday rental in Wye Mills?

Yes, there are holiday rentals close to the most popular sights in Wye Mills, or you can select a more secluded option if you're looking for a relaxing stay. Wye Mills is known for its waterfront.

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

Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres. : This holiday home rental outside of Wye Mills is located on a river, and has a patio, a garden and a BBQ 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 that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as 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 holiday rentals like in Wye Mills?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Wye Mills. Holiday rentals feature extras such as WiFi and washers and dryers so you'll have everything you want. If you're concerned about a sanitised environment, a holiday rental can offer a sense of safety away from public hotel lifts and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular option for a small group gathering.