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Wye Mills Vacation Rentals

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Check prices for these dates

In two weeks
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Wye Mills vacation rentals

Dining

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 ￥42,419
￥78,973 total
includes taxes & fees
Sep 17 - Sep 18
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Interior

2. 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 ￥13,883
￥46,161 total
includes taxes & fees
Sep 28 - Sep 29
Cass-Away Luxury Houseboat
Property grounds

3. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.8 out of 10, Exceptional, (125 reviews)
"A beautiful and comfortable accomodations."
United States
John R.
The price is ￥15,358
￥24,641 total
includes taxes & fees
Sep 29 - Sep 30
First Floor Studio Apartment in Historic Chestertown
Smart TV

4. Cass-N-Reel Luxury Houseboat

Cass-N-Reel Luxury Houseboat
Grasonville
10.0 out of 10, Exceptional, (50 reviews)
"Had a great time, great property and great location."
United States
Danny B.
The price is ￥15,425
￥43,266 total
includes taxes & fees
Oct 8 - Oct 9
Cass-N-Reel Luxury Houseboat
Smart TV, books

5. Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown
Chestertown
10.0 out of 10, Exceptional, (33 reviews)
"Wonderful spot in the center of historical Chestertown,"
United States
Anonymous traveler
The price is ￥34,706
￥54,481 total
includes taxes & fees
Sep 17 - Sep 18
Newly restored apartment in the heart of Chestertown
Exterior

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

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (47 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 ￥16,412
￥46,176 total
includes taxes & fees
Sep 21 - Sep 22
Charming Coastal/Country Home w/3 Acres & Sauna!
Exterior

7. 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 ￥15,463
￥45,775 total
includes taxes & fees
Sep 21 - Sep 22
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Dining

8. 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 ￥49,206
￥58,870 total
includes taxes & fees
Sep 23 - Sep 24
Family Retreat at Lansdowne Manor
Beach

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, (30 reviews)
"Great property! Great accommodations! Wonderful host"
United States
lisa p.
The price is ￥18,171
￥43,746 total
includes taxes & fees
Sep 17 - Sep 18
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Property grounds

10. Turnbridge Manor

Turnbridge Manor
Denton
9.8 out of 10, Exceptional, (18 reviews)
"Really nice place and you can walk to everything.Will stay again!"
United States
Glenn S.
The price is ￥55,530
￥94,015 total
includes taxes & fees
Sep 21 - Sep 22
Turnbridge Manor
Exterior detail

11. BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (65 reviews)
"Perfect little place for our weekend stay!"
United States
Diane V.
The price is ￥30,850
￥48,691 total
includes taxes & fees
Sep 17 - Sep 18
BAYSIDE BUNGALOW
Exterior

12. 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
7.6 out of 10, Good, (4 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 traveler
The price is ￥111,060
￥162,524 total
includes taxes & fees
Sep 21 - Sep 22
5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking
Exterior

13. 4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!

4 Bedroom Waterview - MD 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 ￥124,557
￥215,458 total
includes taxes & fees
Sep 29 - Sep 30
4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!
On the beach, sun loungers, beach towels

14. 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, (74 reviews)
"Just what was needed for our weekend stay."
United States
barbara s.
The price is ￥123,246
￥213,839 total
includes taxes & fees
Sep 20 - Sep 21
Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!
Smart TV

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 ￥29,153
￥44,146 total
includes taxes & fees
Oct 5 - Oct 6
Cozy 1-bedroom in-law suite in lovely Chestertown with AC
TV, fireplace

16. 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 ￥28,320
￥42,261 total
includes taxes & fees
Sep 21 - Sep 22
Secluded Cottage in Middle of Chestertown
Property grounds

17. 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 ￥46,978
￥70,802 total
includes taxes & fees
Sep 20 - Sep 21
Wren Retweet- Country Estate in Center of C’Town
Smart TV

18. Bayside Cottage steps from Rock Hall Harbor

Bayside Cottage steps from Rock Hall Harbor
Rock Hall
10.0 out of 10, Exceptional, (5 reviews)
"Great spot, close to everything in town - had a nice visit!"
United States
Adam S.
The price is ￥32,701
￥62,622 total
includes taxes & fees
Oct 1 - Oct 2
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

Best Western Plus Easton Inn & Suites

Best Western Plus Easton Inn & Suites

10/10 Excellent
"Comfortable beds. Clean room.. staff very courteous"
Raheem 1-night trip
Posted 4 hours ago
Best Western Plus Easton Inn & Suites

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?

Dollhouse in Central Historic St Michaels: This vacation home rental outside of Wye Mills offers a garden, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

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 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.