Wye Mills Vacation Rentals

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Nov 14 - Nov 15
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Nov 15 - Nov 16
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Nov 21 - Nov 23

Vacation Rentals in Wye Mills

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
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.

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.
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!

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 ￥18,215
￥43,853 total
includes taxes & fees
Nov 15 - Nov 16
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Marina
Cass-N-Reel Luxury Houseboat

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
Fridge, microwave, oven, stovetop
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

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
Property grounds
First Floor Studio Apartment in Historic Chestertown

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 ￥15,308
￥24,561 total
includes taxes & fees
Nov 17 - Nov 18
First Floor Studio Apartment in Historic Chestertown
Private kitchen
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, (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!!
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

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

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
Outdoor dining
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, (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
Outdoor dining
BAYSIDE BUNGALOW

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

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

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
Interior
Kent Island Luxury Waterfront

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
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!

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!
Outdoor dining
Downtown St. Michaels | Porch + Pet-Friendly

Downtown St. Michaels | Porch + Pet-Friendly

Saint Michaels
Downtown St. Michaels | Porch + Pet-Friendly
Marina
Relax on Kent Island in 3 Bedroom Home w/Waterview

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 ￥11,365
￥39,747 total
includes taxes & fees
Nov 18 - Nov 19
Relax on Kent Island in 3 Bedroom Home w/Waterview
Smart TV, fireplace
RELAX- Eastern Shore Creek Home - 6 Guests

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

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 ￥34,792
￥42,125 total
includes taxes & fees
Nov 15 - Nov 16
Chesapeake Bay Harbor View in a central location to events/restaurants
Smart TV, fireplace, books, printers
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi

Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi

2.0 star property
Stevensville
10.0 out of 10, Exceptional, (6)
"This VRBO was very clean. Since it is a fairly new addition to VRBO, we thought it could use a little more info, like a portfolio with the combination to the bike locks, where to go to eat and visit, etc. Also, the only coffeemaker was a Keurig and we didn’t bring any K-cups. The 4 of us had a nice 50th Anniversary long weekend."
United States
Sharon M.
The price is ￥61,697
￥135,219 total
includes taxes & fees
Dec 1 - Dec 2
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi
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

Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG

10/10 Excellent
"Room was very clean and in good repair, not beat up and in need of an overhaul."
Clifford 1-night trip
Posted 4 days ago
Holiday Inn Express Annapolis East-Kent Island by IHG

Find out more about Wye Mills

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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?

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.