Windsor Vacation Rentals

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Our top choices for Windsor vacation rentals

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

2-bedroom 2nd Floor apartment in Mount Joy with off street parking
Mount Joy
9.8 out of 10, Exceptional, (32 reviews)
"Spacious, comfortable beds, convenient to restaurants, great price, 5 minutes to Spooky Nook. Clean, nice towels. Host left some drinks and snacks. I definitely recommend. We will be back."
United States
Kimberly
The price is CA $124
CA $213 total
includes taxes & fees
Jun 9 - Jun 10
2-bedroom 2nd Floor apartment in Mount Joy with off street parking

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

Work & Play! Home 1 Mi to Dtwn & Central Market
3.0 star property
York
The price is CA $168
CA $540 total
includes taxes & fees
Jun 8 - Jun 9
Work & Play! Home 1 Mi to Dtwn & Central Market

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

Work & Play! Home 1 Mi to Dtwn & Central Market
York
7.2 out of 10, Good, (5 reviews)
"House was in a good, central location. Cute home. Nice, comforting touches to the house. Beds were comfortable. "
United States
Melissa
The price is CA $150
CA $545 total
includes taxes & fees
Jun 10 - Jun 11
Work & Play! Home 1 Mi to Dtwn & Central Market

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

Cozy Dark & Moody Home, New Reno, 10 mins to Lanc!
Mountville
9.8 out of 10, Exceptional, (39 reviews)
"My family had a wonderful stay at this Pennsylvania home! The house was extremely clean, beautifully decorated, and very comfortable. It had everything we needed during our stay, and you can tell the owners put a lot of thought into making guests feel welcome. We truly enjoyed our time there and would definitely stay again. Highly recommend!"
United States
Jodi
The price is CA $168
CA $424 total
includes taxes & fees
Jun 7 - Jun 8
Cozy Dark & Moody Home, New Reno, 10 mins to Lanc!

Restful and Quaint Cottage

Restful and Quaint Cottage
Conestoga
9.8 out of 10, Exceptional, (132 reviews)
"My husband and I had such a wonderful stay here. Kevin was an excellent host who promptly responded to any questions we had. The cabin itself was beautiful and well maintained and was nestled in such a peaceful area. The hot tub was definitely an added bonus with such beautiful scenery! We would highly recommend a stay here and hope to stay here again ourselves!"
United States
Maureen H.
The price is CA $186
CA $385 total
includes taxes & fees
Jun 9 - Jun 10
Restful and Quaint Cottage

Modern Farmhouse Getaway I 2 BR, Sleeps up to 6

Modern Farmhouse Getaway I 2 BR, Sleeps up to 6
Elizabethtown
10.0 out of 10, Exceptional, (83 reviews)
"The house was wonderful, great spaces, very well equipped and decorated. The host was very kind and attentive to our needs throughout the stay. The area is rural and provides a quiet and beautiful backdrop for your adventure or getaway."
United States
Brian J.
Modern Farmhouse Getaway I 2 BR, Sleeps up to 6

The Pop Loft | Downtown Lancaster

The Pop Loft | Downtown Lancaster
West End
The price is CA $172
CA $357 total
includes taxes & fees
Jun 7 - Jun 8
The Pop Loft | Downtown Lancaster

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

Quaint -2-bedroom house in Lancaster with cool AC breeze
Prospect Heights
8.0 out of 10, Very good, (3 reviews)
"Very clean….convenient location "
United States
Paris
The price is CA $202
CA $255 total
includes taxes & fees
Jun 10 - Jun 11
Quaint -2-bedroom house in Lancaster with cool AC breeze

The Conservatory-20 min to Lanc!

The Conservatory-20 min to Lanc!
Mount Joy
9.4 out of 10, Exceptional, (41 reviews)
"We had a great time. Good location. Would stay again. "
United States
Deborah P.
The price is CA $168
CA $491 total
includes taxes & fees
Jun 7 - Jun 8
The Conservatory-20 min to Lanc!

Victorian Manor on Main w/ 6 beds-10 mins to Lanc!

Victorian Manor on Main w/ 6 beds-10 mins to Lanc!
Mountville
9.8 out of 10, Exceptional, (38 reviews)
"A group of coaches loved our stay here!! It was a beautiful home, clean, cozy, spacious, great location."
United States
Alexandra M.
The price is CA $201
CA $535 total
includes taxes & fees
Jun 8 - Jun 9
Victorian Manor on Main w/ 6 beds-10 mins to Lanc!

Getaway on Grant, heart of Downtown with parking

Getaway on Grant, heart of Downtown with parking
Chestnut Hill
9.8 out of 10, Exceptional, (49 reviews)
"Terrific accommodations within walking distance to some shops and restaurants! Will definitely stay at this location again! "
United States
Jennifer M.
The price is CA $302
CA $590 total
includes taxes & fees
Jun 17 - Jun 18
Getaway on Grant, heart of Downtown with parking

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

Close to lot of shopping areas, eateries, bars and more. Ideal for monthly stays
West Lancaster
9.4 out of 10, Exceptional, (40 reviews)
"Parking was no problem, in driveway or near in the street. "
United States
Maria
The price is CA $225
CA $486 total
includes taxes & fees
Jun 9 - Jun 10
Close to lot of shopping areas, eateries, bars and more. Ideal for monthly stays

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

Located right at the center of Elizabethtown , Lancaster, York and Hershey park.
Elizabethtown
10.0 out of 10, Exceptional, (41 reviews)
"As advertised, was perfect for our stay. "
United States
Jason M.
The price is CA $189
CA $485 total
includes taxes & fees
Jun 7 - Jun 8
Located right at the center of Elizabethtown , Lancaster, York and Hershey park.

Enola Trail Getaway *bikes*rural

Enola Trail Getaway *bikes*rural
Pequea
10.0 out of 10, Exceptional, (6 reviews)
"I had a great time and the place was very beautiful and peaceful "
United States
Brittany R.
The price is CA $217
CA $625 total
includes taxes & fees
Jun 8 - Jun 9
Enola Trail Getaway *bikes*rural

Lovely Downtown Townhome

Lovely Downtown Townhome
Ross
8.8 out of 10, Excellent, (118 reviews)
"Amazing host and stay! My family and I had a wonderful time here visiting Lancaster. My daughter forgot her stuffed animal and the host helped and returned it to her. Thank you!"
United States
Patrick S.
The price is CA $125
CA $290 total
includes taxes & fees
Jun 8 - Jun 9
Lovely Downtown Townhome

Row-home 3min drive to Central Market,Office,Patio w/ Fire Pit, Artistic Accents

Row-home 3min drive to Central Market,Office,Patio w/ Fire Pit, Artistic Accents
East Side
10.0 out of 10, Exceptional, (29 reviews)
"Great bachelorette stay with a small group of ladies!"
United States
Tiffany N.
The price is CA $219
CA $540 total
includes taxes & fees
Jun 8 - Jun 9
Row-home 3min drive to Central Market,Office,Patio w/ Fire Pit, Artistic Accents

Beautiful Boho Villa on Vine in the heart of Lancaster

Beautiful Boho Villa on Vine in the heart of Lancaster
Historic Downtown Lancaster
9.4 out of 10, Exceptional, (53 reviews)
"Had a very comfortable stay. The house is beautifully renovated! "
United States
susan t.
The price is CA $222
CA $500 total
includes taxes & fees
Jun 10 - Jun 11
Beautiful Boho Villa on Vine in the heart of Lancaster

Historic Stone House on Beaver Creek

Historic Stone House on Beaver Creek
New Providence
10.0 out of 10, Exceptional, (55 reviews)
"House was beautiful...we had everything we needed for our over night stay. "
United States
Jamie F.
The price is CA $276
CA $569 total
includes taxes & fees
Jun 10 - Jun 11
Historic Stone House on Beaver Creek

The Garden House

The Garden House
Chestnut Hill
10.0 out of 10, Exceptional, (13 reviews)
"Cute and cozy home, all the right amenities stocked, easy in easy out, communicative host, excellent location! All the things we needed."
United States
Eleanor L.
The price is CA $189
CA $459 total
includes taxes & fees
Jun 8 - Jun 9
The Garden House

Four Bed Family Stay. Near Sight and Sound. Hot Tub. Full Kitchen.

Four Bed Family Stay. Near Sight and Sound. Hot Tub. Full Kitchen.
East Side
9.8 out of 10, Exceptional, (57 reviews)
"The amenities, the clear communication, and the accommodations are always superb! We love spending time here!"
United States
Laura H.
Four Bed Family Stay. Near Sight and Sound. Hot Tub. Full Kitchen.
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 Windsor Hotel Reviews

Find out more about Windsor

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Windsor. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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?

Lovely Downtown Townhome: This vacation home rental near Windsor offers a garden, a selection of books, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family.

What’s there to see and do in Windsor?

Explore the area and family-friendly sights such as Field of Screams, or get out into nature at a spot like Dallastown Lions Club Community Park. Heritage Hill Golf Course and AvalancheXpress 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.