Windsor Vacation Rentals from $154: Search Short-Term Rentals

Q: What's the top vacation rental that Windsor has to offer?

The Loft at Riverside : This vacation home rental near Windsor is equipped with a patio, air-conditioning, and WiFi to help you feel comfortable during your stay. Kitchen amenities include a fridge, a stovetop, and a microwave.

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Our top choices for Windsor vacation rentals

Restful and Quaint Cottage

Conestoga

Emily S.

$252 nightly

May 20 - May 21

Total with taxes and fees

Close to lot of shopping areas, eateries, bars and more. Ideal for monthly stays

West Lancaster

Maria

$290 nightly

May 20 - May 21

Total with taxes and fees

Modern Farmhouse Getaway I 2 BR, Sleeps up to 6

Elizabethtown

Brian J.

$279 nightly

May 26 - May 27

Total with taxes and fees

Beautiful Boho Villa on Vine in the heart of Lancaster

Historic Downtown Lancaster

Cheryl H.

$280 nightly

May 20 - May 21

Total with taxes and fees

Located right at the center of Elizabethtown , Lancaster, York and Hershey park.

Elizabethtown

Lorelei F.

$310 nightly

May 24 - May 25

Total with taxes and fees

The Carew House Sleeps 10 Fenced 4BR Full Kitchen Steps2 YCP

York

$427 nightly

May 21 - May 22

Total with taxes and fees

2-bedroom 2nd Floor apartment in Mount Joy with off street parking

Mount Joy

Christina C.

$139 nightly

May 20 - May 21

Total with taxes and fees

Enola Trail Getaway bikesrural

Pequea

Brittany R.

$393 nightly

May 20 - May 21

Total with taxes and fees

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Top Windsor Hotel Reviews

Inn at York

6/10 Okay

"Stains on sheets and towels, no breakfast but I’ didn’t expect it at that price. Sketchy motel and dirty outside and inside the carpets are horrible. Ppl yelling and up at all hours through the night. But again cheap so can’t expect much."

SureStay Plus by Best Western Elizabethtown Lancaster

10/10 Excellent

"I was a bit hesitant to book as I saw a few comments speak on the hotel being noisy or the interior was very old. However, it was a good stay. The staff was nice, the place was well maintained, the breakfast was pretty good and there weren't any issues with noise. The atmosphere was calm and quiet, and the interior was good. I would go back"

Ramada by Wyndham York Harrisburg Hershey

6/10 Okay

"The floor was dirty and sticky. The room had a pee oder. Everything else in the room was fine. Beds were cleans and comfy. Bathroom was fine and the sink area was good. The staff was prompt with the towels, toilet paper and trash. The breakfast was good. First 2 nights we slept great. The second 2 nights we did not. People were running up and down the hallways yelling, Banging on the rooms they were in. Screaming and cussing, smoking pot and cigarettes. Hallway was filled with cigarette smoke. This is a nonsmoking hotel... If you want quiteness then this hotel may not be for you but if you are looking at the cost then go for it. This hotel may have ♿ but it isn't up to code for the ADA. You have to go past the front door and turn around to get in with a wheelchair. The door doesn't automatically open either. The other front entrance you have to lift the front wheels up in order to get on the little ramp to go inside. That door also doesn't self open. I was able to do so with my daughter who is in a wheelchair but others may not be able to access the handicap entrance. Also I haven't received my 100.00 deposit back. It hasn't been submitted and I was told after house keeping checked the room then it would be issued."

Days Inn & Suites by Wyndham Lancaster Amish Country

4/10 Poor

"Bathroom in our room was a disaster uneven tiles on the floor the shower stall looked like it was being held together by plaster the shower knob just spun in circles so it took a very long time to figure out the temperature control for each shower someone took!"

Cork Factory Hotel Lancaster

6/10 Okay

"The hotel is unique and fun. I wish I could have gotten cold water to drink at the coffee/tea setup. Staff were fine; we didn’t have a lot of interaction. I think parking could be a little more well-defined. There’s a big lot but lots of signs about no parking; however, they didn’t apply on the weekend, we later were told. The room was clean and had what we needed for our 1 night stay."

Find out more about Windsor

Everything you need to know about Windsor 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 Windsor vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 Windsor vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Windsor vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Windsor. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Windsor in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $154 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Windsor rentals

At Expedia, we put the best Windsor 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 Windsor 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 Windsor 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 Windsor. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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Frequently asked questions

Can I find vacation rentals in Windsor?

Yes, we offer vacation rentals near popular points of interest in Windsor, or you can go with a more secluded option if you're looking for relaxation.

What's the top vacation rental that Windsor has to offer?

The Loft at Riverside: This vacation home rental near Windsor is equipped with a patio, air-conditioning, and WiFi to help you feel comfortable during your stay. Kitchen amenities include a fridge, a stovetop, and a microwave.

What’s there to see and do in Windsor?

Explore the area and family-friendly sights such as Corn Cob Acres Field of Fun, or get out into nature at a spot like Dallastown Lions Club Community Park. Heritage Hill Golf Course and Haines Shoe House are a couple of places you'll find in the larger area.

What’s a vacation rental in Windsor like?

Vacation rentals are private properties you can stay in for a long or short time in Windsor. Vacation rentals provide amenities such as patios, hot tubs, and fire pits to help you enjoy your stay. If you're concerned about a sanitized environment, a vacation rental can offer a sense of safety away from shared hotel elevators and busy reception areas while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular choice for a family trip.

Windsor Vacation Rentals

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Check prices for these dates

Our top choices for Windsor vacation rentals

Restful and Quaint Cottage

Close to lot of shopping areas, eateries, bars and more. Ideal for monthly stays

Modern Farmhouse Getaway I 2 BR, Sleeps up to 6

Beautiful Boho Villa on Vine in the heart of Lancaster

Located right at the center of Elizabethtown , Lancaster, York and Hershey park.

The Carew House Sleeps 10 Fenced 4BR Full Kitchen Steps2 YCP

2-bedroom 2nd Floor apartment in Mount Joy with off street parking

Enola Trail Getaway *bikes*rural

Cozy Dark & Moody Home, New Reno, 10 mins to Lanc!

The Roundtop Chalet romantic couple’s getaway

Beautiful Farmhouse close to Lanc, Hershey, Etown!

Unique tiny home experience in a one of a kind tiny home community!

Getaway on Grant, heart of Downtown with parking

Luxury Stay in Elizabethtown

Quaint -2-bedroom house in Lancaster with cool AC breeze

The Quiet House on Main Street minutes from Everywhere

An adorable tiny home perfect for your tiny getaway!

Work & Play! Home 1 Mi to Dtwn & Central Market

1st Floor Condo: Min to Nook, Amish Ctry, Hershey, Lancaster City: PetFriendly

Authentic working horse farm stay! Quiet, rural, and close to nature!

Find vacation rentals that suit your style

Top Windsor Hotel Reviews

Inn at York

Find out more about Windsor

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Enola Trail Getaway bikesrural