Holiday Rentals in Wye Mills

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Holiday Rentals in Wye Mills

Chesapeake Houseboat Getaway on Kent Island, Maryland

9.8 out of 10, Exceptional, (23)
"Our weekend stay at Julia’s Arc was truly the perfect weekend!!! The location is perfect and the boat is so clean, cozy, beautifully decorated, and generously stocked. We felt so calm and happy during our whole stay. The top deck is a perfect spot to have a cup of coffee or watch the sunset. Plus, the host, Julia was so accommodating and sweet. We really hope to go back soon! "
Chesapeake Houseboat Getaway on Kent Island, Maryland

240' Private Beachfront @Kent Island Love Point - Great for Large Groups

10.0 out of 10, Exceptional, (182)
"We all had wonderful stay at Love point! "
240' Private Beachfront @Kent Island Love Point - Great for Large Groups

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (81)
"Clean, well appointed, plenty of space, all small amenities were thought of. We would definitely come back. Very responsive owner too!"
The price is €143
includes taxes & fees
13 May - 14 May
First Floor Studio Apartment in Historic Chestertown

❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

9.6 out of 10, Exceptional, (27)
"Nice and peaceful stay for a quick local getaway. "
The price is €249
includes taxes & fees
22 Apr - 23 Apr
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

Circa 1700 Chesapeake Colonial home on the National Register.

9.8 out of 10, Exceptional, (50)
"Very cool house with great host. Very spacious. Excellent kitchen and very cozy. It would have been helpful to know about the staircases. We had an 8 month pregnant woman and 2 year old that were not able to come but it would have been an issue as getting to the single bed rooms is challenging."
Circa 1700 Chesapeake Colonial home on the National Register.

Stay in the landmark Lighthouse!

10.0 out of 10, Exceptional, (98)
"This is our second time staying at The Lighthouse and we had a wonderful time! It is perfect for three couples. The kitchen is large and fully equipped . The living room/dining room is spacious. The house was clean and ready for us. The property manager, Diane was responsive and very helpful. "
Stay in the landmark Lighthouse!

Relax on Kent Island in 3 Bedroom Home w/Waterview

9.8 out of 10, Exceptional, (34)
"Clean, Spacious, and exactly as advertised! "
The price is €245
includes taxes & fees
20 Apr - 21 Apr
Relax on Kent Island in 3 Bedroom Home w/Waterview

Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna

10.0 out of 10, Exceptional, (34)
"Wonderful stay for 75th and 50th birthday celebrations.Everyone from age 4 to 75 had a terrific time. So much to do we did not leave the property. View of the Chesapeake Bay is amazing - from sunrise to gorgeous sunsets. Plenty of room for everyone. Great communication from host with instructions and area suggestions. 5 Star"
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna

Eastern Shore Waterside Cottage Near St. Michaels

10.0 out of 10, Exceptional, (19)
"Had a great visit. House was perfect and the area is absolutely gorgeous"
Eastern Shore Waterside Cottage Near St. Michaels

Minutes from Downtown Easton and St. Michaels | Pool | Kayaks | Private Dock

10.0 out of 10, Exceptional, (16)
"Our 5th year traveling to the eastern shore of Maryland. The house was great. Loved everything about Pool"
Minutes from Downtown Easton and St. Michaels | Pool | Kayaks | Private Dock

Accessible, Screened-in porch, Water Access, Sauna, Fire Pit, Dog Friendly

10.0 out of 10, Exceptional, (39)
"This place is great. From the layout, to the sauna, screened in porch and backyard, the owners have thought hard about what features make for a luxurious, comfortable and fun experience. They were also very helpful with all aspects of the process - booking, arrival times, access to the home, help with what to do while there. "
Accessible, Screened-in porch, Water Access, Sauna, Fire Pit, Dog Friendly

Waterfront Sunset Bayview: sleeps 6

10.0 out of 10, Exceptional, (12)
"Great house, great owner, family had a blast! Thank you!"
Waterfront Sunset Bayview: sleeps 6

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

9.6 out of 10, Exceptional, (114)
"The house is quaint and very clean. It could use a refresh. Can't beat the location. You can walk to everything. "
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

Cass-N-Reel Luxury Houseboat

10.0 out of 10, Exceptional, (24)
"We had an amazing trip to Kent Narrows. The boat house was perfect - clean, cozy, with great views! Loved the balcony. Despite the cold weather, we thoroughly enjoyed our trip! Got to eat delicious seafood at the nearby restaurants, try the amazing cream of crab soup, Maryland crabcakes, & rockfish. Got to see oysters being unloaded from a boat at the nearby coffee shop. We love that the town is on the water. Everywhere you go has a great view. Our visit was only made better by the place we...
The price is €265
includes taxes & fees
15 May - 16 May
Cass-N-Reel Luxury Houseboat

25-50% Off~Private Beach~Hot Tub~Fire Table~

10.0 out of 10, Exceptional, (22)
"Our girls' weekend at this VRBO was absolutely perfect! From the moment we walked in, we were blown away by the gorgeous interior and stunning views. The house was fully equipped with everything we needed, making our stay incredibly comfortable and convenient. The hot tub was a huge hit and added an extra touch of luxury to our getaway.The beds were incredibly comfortable, and the entire house was spotlessly clean upon our arrival. We truly appreciated the attention to detail.The host was...
25-50% Off~Private Beach~Hot Tub~Fire Table~

BAYSIDE BUNGALOW

10.0 out of 10, Exceptional, (34)
"We had a wonderful weekend at Bayside Bungalow. Chris and Paul have really set up a great spot to enjoy some peace and quiet on the Chesapeake Bay. Thank you for your hospitality and attention to detail!Sincerely,J, J and L"
The price is €237
includes taxes & fees
28 Apr - 29 Apr
BAYSIDE BUNGALOW

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

9.8 out of 10, Exceptional, (34)
"Great location with two parking spots and a small yard. Great for family vacation. "
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND

10.0 out of 10, Exceptional, (33)
"The Chesapeake Mansion was even better than it looks on the VRBO listing. Huge house but still managed to feel warm and inviting, never cold or stand-offish. We cooked big dinners for our group of 12 and the kitchen was perfect for that. Billiards room was fun, amazing bar room, also an exercise room. Walking out on the dock was always a treat. With 12 people, folks could always find a place to chill out when they wanted, but we also had big rooms where we could all get together for chatting and...
Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND

Waterfront Annapolis Home: Fire Pit & Fishing Pier

9.2 out of 10, Wonderful, (34)
"My boyfriend and I spent a long weekend at the house, and we had a great time. The water view was beautiful even though it was a bit chilly for fishing unfortunately. We did a lot of eating, shopping and sightseeing around Annapolis and the location was great. Thanks again!"
Waterfront Annapolis Home: Fire Pit & Fishing Pier

Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

9.8 out of 10, Exceptional, (177)
"Such a beautiful home-perfect location, filled with antiques plus everything needed for a fun getaway. The house is located right off of Talbott Street- enjoyed walking to local bakery/coffee shop- Sprout, eating breakfast at Carpenter Street Saloon and shopping. Great communication with our host who was so knowledgeable about the area. Church bells rang throughout the day. Beautiful views all around. Easy walk to the Lighthouse and Maritime Museum."
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
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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Other types of properties in Wye Mills you may be interested in

Hyatt Place Kent Narrows & Marina

3.0 star property
9.4 out of 10, Exceptional, (519)
"Wonderful place to stay. Clean, friendly and helpful staff, beautiful waterfront views, breakfast is free. My only complaint is there was no microwave in our room and the mattress was way too soft. "
The price is €101
includes taxes & fees
21 Apr - 22 Apr
Hyatt Place Kent Narrows & Marina

Inn at Perry Cabin

5.0 star property
9.6 out of 10, Exceptional, (340)
"Our stay here was excellent. The highlight was arguably the check-in, where we were surprised with a birthday welcome, as well as a little onesie for our soon to arrive baby girl. This was a birthday/baby moon trip and we shared this info prior to arrival, and the staff was incredible in providing us with the warmest welcome we've ever had. We will definitely be back. "
The price is €513
includes taxes & fees
15 May - 16 May
Inn at Perry Cabin

Best Western Kent Narrows Inn

2.5 star property
8.2 out of 10, Very good, (1000)
"Good location easy to find. Close to a main highway "
The price is €88
includes taxes & fees
22 Apr - 23 Apr
Best Western Kent Narrows Inn
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.

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?

240' Private Beachfront @Kent Island Love Point - Great for Large Groups: This holiday home rental outside of Wye Mills is located on the beach, and has a fireplace, a patio and a BBQ 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 that 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 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.