Winfield Holiday Rentals

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Our top choices for Winfield holiday rentals

Cozy, dog-friendly, downtown

Cozy, dog-friendly, downtown
Frederick
10.0 out of 10, Exceptional, (26)
"Clean, great location, friendly owner"
United States
Christian M.
The price is NZ$328
includes taxes & fees
4 Jan - 5 Jan 2026
Cozy, dog-friendly, downtown

Pet-friendly, heart of downtown

Pet-friendly, heart of downtown
Frederick
10.0 out of 10, Exceptional, (8)
"Very convenient to everything. Quick walk to shops, breweries, and restaurants."
United States
JENNIFER
The price is NZ$322
includes taxes & fees
6 Jan - 7 Jan 2026
Pet-friendly, heart of downtown

Huge 1br apt, baby-friendly, dogs, walkable downtown

Huge 1br apt, baby-friendly, dogs, walkable downtown
Downtown Frederick
10.0 out of 10, Exceptional, (6)
"Very clean place, brand new kitchen counters and decor. Great location right on Market Street, with a nice walk to Carroll Creek Park in the heart of Frederick. A nearby highlight for us (1-1/2 block walk) was Gravel & Grind, a combo shop where we rented bikes and got lunch and coffee!"
United States
James L.
Huge 1br apt, baby-friendly, dogs, walkable downtown

Green Street Oasis Hot Tub, Fire Pit & Walk to Downtown

Green Street Oasis Hot Tub, Fire Pit & Walk to Downtown
Westminster
9.0 out of 10, Wonderful, (2)
"The stay was nice and as advertised. It was a little noisy at night with the split house and close neighbors, but it was a nice place. "
United States
Payson D.
The price is NZ$582
includes taxes & fees
6 Jan - 7 Jan 2026
Green Street Oasis Hot Tub, Fire Pit & Walk to Downtown

New townhouse

New townhouse
Frederick
9.4 out of 10, Exceptional, (9)
"This property was impeccably clean and so comfortable! The beds were incredibly cozy, and the kitchen was well-stocked. We felt right at home and enjoyed our stay immensely. Beds were comfortable, and kitchen well stocked. The location can't be beat, with so many attractions and wonderful restaurants within a short drive. Tons of nice touches for our arrival; great communication; easy access. We will definitely stay here again!"
United States
Traci U.
The price is NZ$595
includes taxes & fees
1 Jan - 2 Jan 2026
New townhouse

Secret' Desires-Adult Only

Secret' Desires-Adult Only
2.0 star property
Gaithersburg
The price is NZ$658
includes taxes & fees
5 Jan - 6 Jan 2026
Secret' Desires-Adult Only

Cozy Peaceful Basement Cabin Vibes

Cozy Peaceful Basement Cabin Vibes
Ijamsville
10.0 out of 10, Exceptional, (5)
"Good trip."
United States
Jewell F.
The price is NZ$621
includes taxes & fees
3 Jan - 4 Jan 2026
Cozy Peaceful Basement Cabin Vibes

Newly constructed 6 bedroom home

Newly constructed 6 bedroom home
Frederick
10.0 out of 10, Exceptional, (14)
"This is our second time staying here and we really love how easily we all fit in. It's clean, family friendly, and have lots of space."
United States
Bonnie S.
The price is NZ$802
includes taxes & fees
1 Jan - 2 Jan 2026
Newly constructed 6 bedroom home

Private, Peaceful Basement Apartment in a Serene Setting

Private, Peaceful Basement Apartment in a Serene Setting
2.0 star property
Sykesville
Private, Peaceful Basement Apartment in a Serene Setting

Updated 3BR Apartment in Westminster – Family Friendly

Updated 3BR Apartment in Westminster – Family Friendly
Westminster
8.0 out of 10, Very good, (5)
"Had a great stay here for a night. Was a good size for the four people we had stay. Beds were comfortable and the house was clean. "
United States
John M.
The price is NZ$537
includes taxes & fees
12 Jan - 13 Jan 2026
Updated 3BR Apartment in Westminster – Family Friendly

Experience Elevated Comfort: Luxe Breeze Townhouse.

Experience Elevated Comfort: Luxe Breeze Townhouse.
Owings Mills
9.6 out of 10, Exceptional, (4)
"Awesome stay and great location. Very quiet neighborhood, made the stay comfortable and relaxing. Very spacious and modern. "
United States
Jesse H.
The price is NZ$977
includes taxes & fees
7 Jan - 8 Jan 2026
Experience Elevated Comfort: Luxe Breeze Townhouse.

Charming studio with 1 queen sofa bed and 1 full bath . With AC, WiFi and TV

Charming studio with 1 queen sofa bed and 1 full bath . With AC, WiFi and TV
Woodbine
The price is NZ$256
includes taxes & fees
12 Jan - 13 Jan 2026
Charming studio with 1 queen sofa bed and 1 full bath . With AC, WiFi and TV

Cozy Studio with Private Entrance.

Cozy Studio with Private Entrance.
Lochearn
The price is NZ$299
includes taxes & fees
1 Jan - 2 Jan 2026
Cozy Studio with Private Entrance.

New Lakefront Escape | Kayak, Patio & MiniGolf

New Lakefront Escape | Kayak, Patio & MiniGolf
Columbia
The price is NZ$567
includes taxes & fees
5 Jan - 6 Jan 2026
New Lakefront Escape | Kayak, Patio & MiniGolf

The blissful house in Howard County with 3 bedrooms 3 bathrooms.

The blissful house in Howard County with 3 bedrooms 3 bathrooms.
Marriottsville
The price is NZ$1,506
includes taxes & fees
4 Jan - 5 Jan 2026
The blissful house in Howard County with 3 bedrooms 3 bathrooms.

Private Guest House - Please note does NOT sleeps 30

Private Guest House - Please note does NOT sleeps 30
Reisterstown
6.8 out of 10, (3)
"Providing a better equipped kitchen will improve this listing for future guests."
United States
Jennifer M.
Private Guest House - Please note does NOT sleeps 30

Cozy Guesthouse in Woodstock, MD

Cozy Guesthouse in Woodstock, MD
Woodstock
2.0 out of 10, (1)
"We didn’t stay. We when arrived, instead of a room in the guest house, we were expected to stay in a tentlike structure. In addition, the bathroom facilities were outdoor showers and commodes that required a climb up a set of stairs. Luckily we were able to secure a room at another facility. The owner supposedly requested a refund for me but I haven’t heard whether this has been approved."
United States
Marie E M.
The price is NZ$394
includes taxes & fees
1 Jan - 2 Jan 2026
Cozy Guesthouse in Woodstock, MD
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 Winfield Hotel Reviews

Find out more about Winfield

Everything you need to know about Winfield 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 Winfield holiday rental for you. At Expedia, you can take your pick from private holiday 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 Winfield holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Winfield holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winfield. 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 Winfield 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 Winfield holiday rentals we have selected for you start as low as NZ$299 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Winfield rentals

At Expedia, we put the best Winfield 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 Winfield 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 Winfield 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 Winfield. 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 Winfield?

Yes, there are holiday rentals close to the most popular sights in Winfield, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Winfield has to offer?

The blissful house in Howard County with 3 bedrooms 3 bathrooms.: This holiday home rental outside of Winfield offers a fireplace, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop and a microwave.

What’s there to see and do in Winfield?

Explore the area and family-friendly sights such as Adventure Park USA, or get out into nature at a spot like Northwest Regional Park. Elk Run Vineyards and Old Westminster Winery are a couple of places you'll find in the wider area.

What’s a holiday rental in Winfield like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Winfield. Holiday rentals provide amenities such as kitchens and laundry facilities so you'll have everything you want. If you're concerned about cleanliness, a holiday rental can provide a sense of seclusion away from public hotel lifts and busy reception areas while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive option for family trips.