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Sheffield Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Sheffield vacation rentals

A living room with a wooden ceiling, a dining area with a piano, and a large window with a view of greenery.

1. Shallowbrook Farm: Where World-Record History Meets Private Luxury

Shallowbrook Farm: Where World-Record History Meets Private Luxury
Bradford
9.8 out of 10, Exceptional, (7 reviews)
"The games in the basement were great. The check in and check out was easy. Great communication. Would stay again! "
United States
Derek S.
The price is CA $1,439
CA $2,076 total
includes taxes & fees
Oct 20 - Oct 21
Shallowbrook Farm: Where World-Record History Meets Private Luxury
A modern, triangular wooden cabin with a glass front, surrounded by trees.

2. Cabin 4: Reconnect with each other and nature at The Wildflower.

Cabin 4: Reconnect with each other and nature at The Wildflower.
Princeton
The price is CA $351
CA $528 total
includes taxes & fees
Oct 14 - Oct 15
Cabin 4: Reconnect with each other and nature at The Wildflower.
A modern, triangular wooden cabin with a glass front, surrounded by trees.

3. Cabin 3: Escape to Enchantment, Aframe Glamping at The Wildflower.

Cabin 3: Escape to Enchantment, Aframe Glamping at The Wildflower.
Princeton
10.0 out of 10, Exceptional, (1 review)
"Amazing coozy cabin for a getaway! Definitely going back sometime!"
United States
Andres C.
The price is CA $372
CA $554 total
includes taxes & fees
Oct 14 - Oct 15
Cabin 3: Escape to Enchantment, Aframe Glamping at The Wildflower.
A modern, triangular wooden cabin with a glass front, surrounded by trees.

4. Cabin 2: Discover our good nature at The Wildflower

Cabin 2: Discover our good nature at The Wildflower
Princeton
10.0 out of 10, Exceptional, (1 review)
"Beautiful modern cabin in a secluded area yet with easy access to the town. Beautifully decorated inside and out. It’s amazing the amenities you can fit in a small space. We thoroughly enjoyed the fire table on our porch."
United States
Nicholas W.
The price is CA $372
CA $557 total
includes taxes & fees
Oct 13 - Oct 14
Cabin 2: Discover our good nature at The Wildflower
A modern, triangular wooden cabin with a glass front, surrounded by trees.

5. Cabin 1: Unplug, unwind, unearth your peace at The Wildflower.

Cabin 1: Unplug, unwind, unearth your peace at The Wildflower.
Princeton
The price is CA $372
CA $557 total
includes taxes & fees
Oct 18 - Oct 19
Cabin 1: Unplug, unwind, unearth your peace at The Wildflower.
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 Sheffield Hotel Reviews

AmericInn by Wyndham Princeton IL

AmericInn by Wyndham Princeton IL

10/10 Excellent
"Great place!"
Andrew 2-night trip
Posted 21 hours ago
AmericInn by Wyndham Princeton IL

Find out more about Sheffield

Everything you need to know about Sheffield 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 Sheffield 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 Sheffield vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Sheffield vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Sheffield. 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 Sheffield 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 Sheffield vacation rentals we have selected for you start as low as CA $528 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Sheffield rentals

At Expedia, we put the best Sheffield 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 Sheffield 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 Sheffield 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 Sheffield. 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 vacation rentals in Sheffield?

Yes, there are vacation rentals close to popular points of interest in Sheffield, or you can go with a more secluded option if you want a relaxing place to stay. Sheffield is known for its churches and festivals. Make sure you have time to check out the live music and parks during your trip.

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

Shallowbrook Farm: Where World-Record History Meets Private Luxury: This vacation home rental near Sheffield offers an outdoor pool, a fireplace, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 10 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a patio and a selection of games.

What’s there to see and do in Sheffield?

Enjoy the area's cultural attractions such as Wanee Theatre, or get outdoors into nature at a spot like Johnson Sauk Trail State Park. Mautino State Fish and Wildlife Area and Sheffield Village Hall are other places to visit while you're in town.

What are vacation rentals like in Sheffield?

Vacation rentals are private accommodations you can reserve for several days or longer in Sheffield. Vacation rentals feature amenities such as patios, hot tubs, and fire pits so you'll have everything you need. If you're concerned about a clean environment, vacation rentals can offer a sense of safety away from shared hotel elevators and busy reception areas while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental a great option for small groups.