Wye Mills Vacation Rentals from CA $396: Short-Term Rentals for 2026

Q: 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.

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Wye Mills vacation rentals

A lighthouse with a white exterior, a balcony, and a metal roof.

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

Stevensville

Michael V.

CA $439 total

includes taxes & fees

Oct 26 - Oct 27

A house with a swimming pool, surrounded by a fence, and two red umbrellas.

2. First Floor Studio Apartment in Historic Chestertown

Chestertown

John R.

CA $224 total

includes taxes & fees

Oct 22 - Oct 23

A white building with a balcony on stilts, a metal roof, and a small tower with a light on top.

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

Stevensville

Anthony P.

CA $396 total

includes taxes & fees

Oct 21 - Oct 22

A gazebo on a sandy beach with a clear view of the ocean and rocky shoreline.

4. Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Rock Hall

lisa p.

CA $417 total

includes taxes & fees

Oct 25 - Oct 26

A building with a gabled roof and a circular vent on the roof.

5. BAYSIDE BUNGALOW

Rock Hall

Diane V.

CA $445 total

includes taxes & fees

Oct 23 - Oct 24

A living room with a fireplace, patterned furniture, a coffee table, and a bookshelf.

6. Secluded Cottage in Middle of Chestertown

Chestertown

Amy D.

CA $387 total

includes taxes & fees

Oct 28 - Oct 29

A backyard with a small waterfall, rocks, and a pond with lily pads. There are two blue chairs and a black pot near the waterfall.

7. Turnbridge Manor

Denton

Jessica H.

CA $874 total

includes taxes & fees

Oct 27 - Oct 28

A spacious living area with a dining table, sofa, and a kitchen in the background.

8. Newly restored apartment in the heart of Chestertown

Chestertown

Susan A.

CA $498 total

includes taxes & fees

Oct 21 - Oct 22

A bedroom with a bed, a ceiling fan, a door, and a view of the outdoors.

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

Chestertown

"Our first using VRBO. We were not sure what to expect but hoped it was as true as the listing. The home was cleaned and very nicely decorated. The bed was very comfortable and the home was spacious for two worked great. The water pressure was also great. Some small improvements will definitely give this place a 5 star. There was no closet to hang a men’s jacket or sun dresses; no mirror except in the bathroom and perhaps some coasters would help when spending some time reading in the living...

Miriam G.

CA $405 total

includes taxes & fees

Oct 26 - Oct 27

Three birds perched on a wooden structure by the water.

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

Stevensville

barbara s.

CA $1,951 total

includes taxes & fees

Oct 21 - Oct 22

A covered patio with a table and chairs, a grill, and a decorative railing.

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

Chestertown

Mandy D.

CA $679 total

includes taxes & fees

Oct 22 - Oct 23

A two-story house with a red roof, a brick chimney, and a small porch.

12. 5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking

Stevensville

"The house was clean. It is clear someone lives there full time and vacated the house for our stay. Their food and clothes remained in the property. It did not bother us, but not something we expected. The AC worked well. The owner communicated there were issues before we arrived that they were working to fix and left the number of the contractor in case we experienced issues. We were there the hottest weekend so far this year and did not have any issues. It does look like they are still...

Michele F.

CA $1,486 total

includes taxes & fees

Oct 23 - Oct 24

A two-story house with a backyard swimming pool, surrounded by trees and a well-maintained lawn.

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

Stevensville

David R.

CA $1,775 total

includes taxes & fees

Oct 21 - Oct 22

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Top Wye Mills Hotel Reviews

Wylder Tilghman Island

8/10 Good

"Beautiful setting. The hotel is a bit dated. Staff is very efficient and friendly."

Best Western Kent Narrows Inn

10/10 Excellent

"We were in town for a wedding. The hotel was close to the venue which is why we chose it. The staff was very friendly upon check in, the room was very clean, nice bathroom, comfortable bed and the view of the bay from our room was fabulous! The included breakfast was the standard breakfast items but very good!"

Sandaway Suites & Beach

10/10 Excellent

"This little B&B was a complete surprise. My high school friend and I were on the Eastern Shore for our 50th high school reunion and were looking for somewhere to stay. We ended up choosing Sandaway, quite honestly, b/c it was all that was available at the time. We had no expectations. What a stunning surprise to find one of the finest accommodations I've ever stayed in, regardless of price! There was not a single thing that a traveler may require that was not thought of - from hooks in the bath, plenty of towels, brochures in the room about local attractions, two luggage racks, extra blankets and pillows. There was a carafe of hot coffee and a basket of breakfast items left quietly on the room's attached porch in the morning. There was a sweet little "goodie" bag in the room when we arrived with waters, snacks and a warm welcome note. We were informed that room around the corner from ours that had various breakfast/snack items available in the morning that we were free to help ourselves to. The host Ben was extremely helpful and kind, and had a ready solution to any questions or issue. There was a Keurig machine in our room that we couldn't get to work. When we reached out to him, he not only brought us a new machine, he also brought us two carafes of freshly brewed coffee. The room was charming & immaculate (even the tv remote was protected with a bag), with a stunning view of the Bay. I cannot recommend Sandaway highly enough. I will def be returning with my husband!"

The Wildset

10/10 Excellent

"Loved my stay at Wildset. Place is very clean, cozy & comfortable. Staff very friendly. Convenience to everything in town. Only 2 issues I had was how long it took shower water to get hot. And it wasn’t super hot. Not sure if it was cause I was in main building. Other was a knocking noise which seemed to happen primarily while restaurant was open. Not sure if it was from the dishwasher or some other equipment. I’m a light sleeper too so some people may be able to sleep thru it. Would def stay here again!!"

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, cottages, 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 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 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Wye Mills vacation rentals we have selected for you start as low as CA $396 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 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.

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 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.

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Check prices for these dates

Our top choices for Wye Mills vacation rentals

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

2. First Floor Studio Apartment in Historic Chestertown

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

4. Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

5. BAYSIDE BUNGALOW

6. Secluded Cottage in Middle of Chestertown

7. Turnbridge Manor

8. Newly restored apartment in the heart of Chestertown

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

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

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

12. 5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking

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

Find vacation rentals that suit your style

Top Wye Mills Hotel Reviews

Wylder Tilghman Island

Holiday Inn Express Easton by IHG

St Michaels Inn

Best Western Kent Narrows Inn

The Inn at Chesapeake Bay Beach Club

The Tilghman Island Inn

Sandaway Suites & Beach

The Wildset

The Tidewater Inn

Find out more about Wye Mills

Frequently asked questions

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