Sheffield vacation rentals

We found 688 vacation rentals — enter your dates for availability

Discover a selection of 23 homes and other vacation rentals in Sheffield that are perfect for your trip. Whether you’re staying in a vacation home with a group or just with your pet, you'll have the amenities you expect and more, such as WiFi and cable TV. Whatever you're looking for, you're sure to find a rental to meet everyone's needs, including a place that is accessible or non-smoking.

Vacation rentals with weekly discounts - Sheffield

Showing deals for:Aug 1 - Aug 8
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The historic area of Sheffield awaits your stay

Enjoy the history and other features of Sheffield. This city is well-known for its casino gaming and local tours. If you need more space to accommodate a family vacation or friends trip, rental homes often come with separate dining areas and spacious living rooms.

Pack your camera for that postcard-worthy shot

From historic buildings to panoramic vistas, your Instagram feed will thank you for choosing a Sheffield vacation rental. Home to the picturesque Old Covered Bridge, you'll also find the 18th-century Colonel John Ashley House, now a museum featuring period architecture and furnishings. The babbling brooks and flowing rivers of the surrounding Housatonic River valley are peppered with scenic waterfalls. Mount Everett State Reservation offers jaw-dropping panoramic views of Massachusetts, New York, and Connecticut from its peak. Get your adrenaline rush by careening down the slopes of Catamount Ski Area or Butternut Basin.

Antiquing on the Appalachian Trail

If the thought of digging through glittering antique shops for rare finds is your idea of paradise, you've come to the right place. The impressive number of shops, combined with the regular farmers' markets, cements Sheffield's historic small town vibe. For those not into antiquing, there are outdoor activities galore, including swimming, boating, fishing, and biking, just to name a few (and don't forget the skis in the winter). A Sheffield vacation rental also puts you on the path of the Appalachian Trail, so pack your sturdiest boots to get a taste of one of the country's most epic hikes.

Bundle up, baby, it's cold out there

With snowfalls that more than double the national annual average, you'll want a cozy sweater for curling up by the fire at your Sheffield vacation rental. The beautiful blankets of white covering the town make braving the below-freezing temperatures from November to April worth it. Summers are pleasant, with highs typically in the 70s and 80s from June to September. The fall is a leaf peeper's dream, with fiery foliage that people drive from miles around to see. While the exact time varies from year to year, the colors typically peak in October.

Among feathers, falls, and forests

When it's not covered in white, the stunning landscape of the Berkshires is green as far as the eye can see. A number of cascades, including Ashley Falls, can be found sprinkled throughout the creeks and rivers of the Housatonic River valley. You'll pass through a large number of working farms on your way to Mount Everett, the high point in the area's verdant landscape of old growth and dwarf forests. For wildlife encounters, head to Bartholomew's Cobble, the town's 329-acre nature sanctuary that's home to more than 700 plant species and 250 species of birds.

Transportation to and around Sheffield

The nearest airport is in Albany Intl. Airport (ALB), located 49.6 mi (79.9 km) from the city center. If you can't find a flight that works for your travel itinerary, you could also fly into Hudson, NY (HCC-Columbia County), which is 22.3 mi (35.9 km) away.

Frequently asked questions

What is the most popular type of vacation rental accommodation in Sheffield?
Based on our data, cottages are the most sought-after property type in Sheffield. But of course, everyone’s idea of an awesome stay isn’t going to be the same. Vrbo has vacation homes of all sizes and shapes, and we’ll help you to find the perfect fit for you.
How much does it cost to rent a vacation rental in Sheffield?
The average price for a vacation rental in Sheffield can vary based on factors like time of year, length of stay and property type. Whether you’re in search of a sprawling villa with space for the whole family or a cozy cabin that’s perfect for two, just add your dates of travel to view stays with exceptional value.
How much does it cost to rent a beach house in Sheffield?
The average price for a vacation home near the beach in Sheffield will depend on when you’ll be there and the size and style of property you’re looking for. You can easily and quickly find prices on Vrbo by entering your destination and preferred travel dates. Then use our handy filter tool to choose the number of bedrooms and amenities that you need, like WiFi, a pool and air conditioning.
Are there pet-friendly vacation rentals in Sheffield?
With 28 properties that allow pets, your furry buddy can join in the fun on your Sheffield getaway. Use our filter tool to browse our pet-friendly vacation rentals and find a stay that’ll set tails wagging on Vrbo.
Can I rent a house with a pool in Sheffield?
Grab your swimsuit and inflatable swan, because there are six houses with a private pool in Sheffield. Stay at one of these superb vacation homes and every day will be a pool day. Simply enter your travel dates into Vrbo, then check the “pool” filter to find the ideal place for a splashing good time!
What are popular rental amenities in Sheffield?
A sauna, a nearby waterfront and a lake view are rated the most popular rental amenities in Sheffield. Whether you’re heading away as a party of one, with your better half or a group of friends, Vrbo will help you find a vacation rental that suits your style with all the features you need.
Are there large group vacation rentals in Sheffield?
With six properties that can host 10 people or more in Sheffield, you won’t have to limit the invite list. From extended family vacations to events like Thanksgiving or Christmas parties, Vrbo will help you find a large group rental that fits the occasion.
Are there vacation rentals in Sheffield that welcome kids?
Sheffield has 28 family-friendly vacation homes. And discovering a stay that welcomes youngsters is a cinch with our “Properties good for families” filter. As well as having the whole place to yourselves, you’ll also get amenities and perks such as multiple bedrooms, kitchens and pools.
What are the top attractions for families in Sheffield?
Spend a fun day out with the whole family at Ashley House. This popular attraction is close to the heart of Sheffield.
Are there one-bedroom vacation rentals in Sheffield?
Sheffield has two one-bedroom rentals on offer. Often located in popular areas because of their smaller size, a one-bedroom vacation property is great if you’re traveling with a buddy or your partner. And with home comforts like wireless internet and more privacy than a standard hotel, you’ll be able to chill out while sightseeing around this amazing destination.
Can I find two-bedroom vacation rentals in Sheffield?
Sheffield has four two-bedroom vacation rentals for you to pick from. Enjoy a vacation home with all the privacy and comfort you want at an attractive price on Vrbo.
Are there vacation rentals with WiFi in Sheffield?
Sheffield has 13 vacation rentals with WiFi, so you can stay connected while you’re traveling. Simply check the “WiFi” box in our handy search filter to find the perfect property. From streaming TV shows with the family to updating your social media, these Vrbo homes make it a breeze to go online.
How can I find vacation rentals with air conditioning in Sheffield?
Select your travel dates and then use the filter tool to locate vacation rentals with ac in Sheffield on Vrbo. With 23 air-conditioned properties available, you can look forward to a cool and comfortable stay.
How old do you have to be to rent a vacation rental in Sheffield?
The minimum age is usually 16, 18 or 21. It can vary across properties on Vrbo, so check the rules of your chosen Sheffield vacation home before booking your stay.
How long can I rent a vacation rental in Sheffield for?
It’s down to the Sheffield property. To browse available options offering extended stays, simply type your travel dates and guest number into Vrbo. You can enjoy having the whole place to yourself, along with the comforts of home like a full kitchen, air conditioning and a yard where the kids can burn off energy. Keep your eyes open for any long-term stays that offer discounted weekly or monthly prices.
Does Vrbo offer discounts for vacation homes in Sheffield?
On Vrbo, we’ve got plenty of amazing bargains and discounts for Sheffield. Browse our newly listed homes, as well as our weekly and monthly discounts on vacation rentals. Whether you’re after a weekend getaway or an extended stay, Vrbo has options for every style and budget.

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