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Holiday Rentals in Wye Mills

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Our top choices for Wye Mills holiday rentals

1. Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Grasonville
9.6 out of 10, Exceptional, (16 reviews)
"This was a lovely find and had more amenities than the pictures provided with seating for 8, an air fryer, and a Keurig. There was a full kitchen, so cooking was easy. The king bed was very comfortable. It is near the outlet malls and is in a great location. The owner is very nice and accommodating. "
United States
Robin
The price is €359
includes taxes & fees
1 Sept - 2 Sept
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

2. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.8 out of 10, Exceptional, (124 reviews)
"Exactly as advertised. Great room, clean and highly recommended. "
United States
S G.
The price is €140
includes taxes & fees
8 Sept - 9 Sept
First Floor Studio Apartment in Historic Chestertown

3. Cass-Away Luxury Houseboat

Cass-Away Luxury Houseboat
Grasonville
10.0 out of 10, Exceptional, (107 reviews)
"Wonderful stay. House boat was amazing and hosts helpful and responsive! "
United States
Jamie L.
The price is €274
includes taxes & fees
25 Sept - 26 Sept
Cass-Away Luxury Houseboat

4. Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown
Chestertown
10.0 out of 10, Exceptional, (32 reviews)
"Wonderful spot in the center of historical Chestertown,"
United States
Anonymous traveller
The price is €307
includes taxes & fees
30 Aug - 31 Aug
Newly restored apartment in the heart of Chestertown

5. Charming Coastal/Country Home w/3 Acres & Sauna!

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (46 reviews)
"Great location, house was very clean, ample space and Adam was super communicative. Will definitely stay again!"
United States
Michelle P.
The price is €247
includes taxes & fees
31 Aug - 1 Sept
Charming Coastal/Country Home w/3 Acres & Sauna!

6. Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Stevensville
9.8 out of 10, Exceptional, (55 reviews)
"We had a wonderful stay. The house was perfect and Adam stayed in contact constantly in case we needed anything. But our stay went smoothly and we had everything we needed."
United States
Dawn G.
The price is €235
includes taxes & fees
31 Aug - 1 Sept
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

7. Waterfront Escape with Pool Nature Lover Paradise

Waterfront Escape with Pool Nature Lover Paradise
Stevensville
10.0 out of 10, Exceptional, (3 reviews)
"N"
United States
Maria S.
The price is €1,028
includes taxes & fees
30 Aug - 31 Aug
Waterfront Escape with Pool Nature Lover Paradise

8. 5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking

5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking
Stevensville
6.8 out of 10, (3 reviews)
"The place was very clean and Host was ok the shopping was six miles away, not in walking distance, we had no pets on this trip."
United States
Anonymous traveller
The price is €898
includes taxes & fees
30 Aug - 31 Aug
5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking

9. 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, (28 reviews)
"Great property! Great accommodations! Wonderful host"
United States
lisa p.
The price is €248
includes taxes & fees
30 Aug - 31 Aug
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

10. BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (63 reviews)
"Perfect little place for our weekend stay!"
United States
Diane V.
The price is €275
includes taxes & fees
30 Aug - 31 Aug
BAYSIDE BUNGALOW

11. Family Retreat at Lansdowne Manor

Family Retreat at Lansdowne Manor
Centreville
10.0 out of 10, Exceptional, (12 reviews)
"We had an amazing stay for a wedding weekend! Beautiful grounds, beautiful house, lots of room for kids and dogs. Would definitely stay again! "
United States
Emily C.
The price is €312
includes taxes & fees
23 Sept - 24 Sept
Family Retreat at Lansdowne Manor

12. Wren Retweet- Country Estate in Center of C’Town

Wren Retweet- Country Estate in Center of C’Town
Chestertown
10.0 out of 10, Exceptional, (75 reviews)
"Perfect location for exploring the cutest town. "
United States
Mandy D.
The price is €433
includes taxes & fees
31 Aug - 1 Sept
Wren Retweet- Country Estate in Center of C’Town

13. Turnbridge Manor

Turnbridge Manor
Denton
9.8 out of 10, Exceptional, (16 reviews)
"Really nice place and you can walk to everything.Will stay again!"
United States
Glenn S.
The price is €539
includes taxes & fees
1 Sept - 2 Sept
Turnbridge Manor

14. Secluded Cottage in Middle of Chestertown

Secluded Cottage in Middle of Chestertown
Chestertown
10.0 out of 10, Exceptional, (2 reviews)
"Robert and Elizabeth were great hosts. They are very communicative and flexible. The house itself is lovely, with nicely decorated rooms and so spacious! The location can’t be beat. Will definitely stay here again."
United States
Amy D.
The price is €247
includes taxes & fees
1 Sept - 2 Sept
Secluded Cottage in Middle of Chestertown

15. Cozy 1-bedroom in-law suite in lovely Chestertown with AC

Cozy 1-bedroom in-law suite in lovely Chestertown with AC
Chestertown
The price is €254
includes taxes & fees
10 Sept - 11 Sept
Cozy 1-bedroom in-law suite in lovely Chestertown with AC

16. Stay by MD's Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!

Stay by MD's Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!
Stevensville
10.0 out of 10, Exceptional, (43 reviews)
"Fantastic, property, location and positive interaction with owner."
United States
David R.
The price is €1,224
includes taxes & fees
31 Aug - 1 Sept
Stay by MD's Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!

17. Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!

Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!
Stevensville
10.0 out of 10, Exceptional, (76 reviews)
"Just what was needed for our weekend stay."
United States
barbara s.
The price is €1,230
includes taxes & fees
7 Sept - 8 Sept
Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!

18. Bayside Cottage steps from Rock Hall Harbor

Bayside Cottage steps from Rock Hall Harbor
Rock Hall
10.0 out of 10, Exceptional, (4 reviews)
"Great spot, close to everything in town - had a nice visit!"
United States
Adam S.
The price is €309
includes taxes & fees
29 Sept - 30 Sept
Bayside Cottage steps from Rock Hall Harbor
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

Find out more about Wye Mills

Everything you need to know about Wye Mills holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Wye Mills holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Wye Mills holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Wye Mills holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Wye Mills holiday rentals we have selected for you start as low as €140 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Wye Mills rentals

At Expedia, we put the best Wye Mills holiday 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 holiday.

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. 

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?

Relax on Kent Island in a 4 Bedroom Home w/Waterview!: This holiday home rental outside of Wye Mills offers a patio, a garden and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

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 Eastern Neck National Wildlife Refuge. 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.