Wye Mills Vacation Rentals

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Oct 31 - Nov 2

Vacation Rentals in Wye Mills

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.
10.0 out of 10, Exceptional, (14)
"Everything was exactly as described on the listing. It’s the perfect spot for a peaceful and relaxing getaway, all while being close to a charming town. The hosts were very pleasant and easy to communicate with. I highly recommend this place! "
United States
Michael T.
Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.
Marina
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
7.0 out of 10, Good, (6)
"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
Marina
Cass-N-Reel Luxury Houseboat
Cass-N-Reel Luxury Houseboat
10.0 out of 10, Exceptional, (42)
"Great location - very convenient to 50 and restaurants - very clean - greatly appreciated the water and potato chips"
United States
dewey b.
Cass-N-Reel Luxury Houseboat
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!
9.6 out of 10, Exceptional, (121)
"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!
Beach
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
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.
$258 nightly
The price is $285
Oct 24 - Oct 25
Total with taxes and fees
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Marina
Relax on Kent Island in 3 Bedroom Home w/Waterview
Relax on Kent Island in 3 Bedroom Home w/Waterview
9.8 out of 10, Exceptional, (41)
"We had a great stay! The property has everything we needed and host was easy to communicate with "
United States
Stephanie S.
$296 nightly
The price is $314
Nov 16 - Nov 17
Total with taxes and fees
Relax on Kent Island in 3 Bedroom Home w/Waterview
Private beach
6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access
6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access
10.0 out of 10, Exceptional, (18)
"House was great and the golf cart excellent"
United States
Bradley E.
6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access
Outdoor dining
240' Private Beachfront @Kent Island Love Point - Great for Large Groups
240' Private Beachfront @Kent Island Love Point - Great for Large Groups
10.0 out of 10, Exceptional, (194)
"We had an amazing stay. The owner has literally thought of everything to make your stay the best experience! We had a range of ages in our family and everyone loved it. The beach was amazing."
United States
Jennifer C.
240' Private Beachfront @Kent Island Love Point - Great for Large Groups
Outdoor dining
BAYSIDE BUNGALOW
BAYSIDE BUNGALOW
10.0 out of 10, Exceptional, (51)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
$260 nightly
The price is $276
Oct 25 - Oct 26
Total with taxes and fees
BAYSIDE BUNGALOW
Exterior
Dollhouse in Central Historic St Michaels
Dollhouse in Central Historic St Michaels
9.6 out of 10, Exceptional, (55)
"Great location. House is old and therefore a little quirky, but overall comfortable. "
United States
Karen L.
Dollhouse in Central Historic St Michaels
Fridge, microwave, oven, stovetop
Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy
Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy
9.8 out of 10, Exceptional, (43)
"House was beautiful! Right on the bay and easily accommodated our group. "
United States
James T.
Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy
Fridge, microwave, oven, stovetop
Walk to Everything House
Walk to Everything House
10.0 out of 10, Exceptional, (83)
"Great location to all shopping and restaurants! Walk to Blue Crab coffee behind back yard! "
United States
Kim D.
Walk to Everything House
Marina
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
9.6 out of 10, Exceptional, (124)
"We had a wonderful stay. This was our second time staying here and we loved it. Very quay, cozy and clean. Everything as advertised. Location is perfect as it is a very walkable town. This place is right in the middle. The owner was very friendly, open and communicative. And I had a big surprise when we returned. My neck pillow I had forgotten and left it 2 years ago was still there sitting in a closet. We hope to return next year. "
United States
David W.
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Property grounds
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
9.6 out of 10, Exceptional, (144)
"This is such a great house - perfect location. Very roomy and comfortable. The owner is super responsive as well. Highly recommend!"
United States
maggie k.
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Marina
Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac
Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac
10.0 out of 10, Exceptional, (95)
"Beautiful home in a quiet community. "
United States
Rebecca K.
Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac
Outdoor dining
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
9.8 out of 10, Exceptional, (191)
"Very clean perfect location for St. Michael’s everything is walking distance from the house looking forward to coming back. "
United States
Frank G.
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Fridge, microwave, oven, stovetop
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
9.8 out of 10, Exceptional, (44)
"Wonderful home in excellent location!!"
United States
Sydney S.
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Property grounds
First Floor Studio Apartment in Historic Chestertown
First Floor Studio Apartment in Historic Chestertown
9.6 out of 10, Exceptional, (105)
"A charming studio in a quiet neighborhood. great directions from host on how to use the property - "
United States
Mary
$144 nightly
The price is $159
Oct 27 - Oct 28
Total with taxes and fees
First Floor Studio Apartment in Historic Chestertown
Smart TV, fireplace
RELAX- Eastern Shore Creek Home - 6 Guests
RELAX- Eastern Shore Creek Home - 6 Guests
10.0 out of 10, Exceptional, (5)
"Great property that is well kept. It is a short drive to several wonderful restaurants and an outlet shopping center."
United States
J E.
RELAX- Eastern Shore Creek Home - 6 Guests
Smart TV
One-level waterfront home with beach and stunning views all the way to the Bay Bridge
One-level waterfront home with beach and stunning views all the way to the Bay Bridge
2.0 star property
9.8 out of 10, Exceptional, (16)
"Amazing location and home. "
United States
Kim M.
One-level waterfront home with beach and stunning views all the way to the Bay Bridge
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
"Had a king room which was very spacious."
Joseph 1-night trip
Posted 4 days ago
Best Western Denton Inn

Find out more about Wye Mills

Everything you need to know about Wye Mills vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Wye Mills vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Wye Mills vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Wye Mills vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Wye Mills. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Wye Mills in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $159 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Wye Mills rentals

At Expedia, we put the best Wye Mills vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Wye Mills rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Wye Mills vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Wye Mills. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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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?

240' Private Beachfront @Kent Island Love Point - Great for Large Groups: This vacation home rental outside of Wye Mills is located on the beach and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

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.