Sheffield Vacation Rentals

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Check prices for these dates

In two weeks
Apr 10 - Apr 12
In two months
May 22 - May 24
In three months
Jun 19 - Jun 21
In four months
Jul 17 - Jul 19

Our top choices for Sheffield vacation rentals

Interior

Guesthouse Cabin vacation rentals in Berkshire County

Guesthouse Cabin vacation rentals in Berkshire County
Sheffield
10.0 out of 10, Exceptional, (10 reviews)
"Great place. I highly recommend for a group or family. Amazing views! Beautiful property very private and quiet. Cabin was also very well stocked and had great outdoor space. "
United States
deborah d.
$629 nightly
The price is $703
Mar 25 - Mar 26
Total with taxes and fees
Guesthouse Cabin vacation rentals in Berkshire County
Property grounds

Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (42 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
$454 nightly
The price is $507
Mar 29 - Mar 30
Total with taxes and fees
Cheerful 3-bedroom cottage with woodstove
Property grounds

3-Bedroom Cabin Getaway With Rustic Charm

3-Bedroom Cabin Getaway With Rustic Charm
Cornwall
8.4 out of 10, Very Good, (6 reviews)
"Absolutely beautiful cottage exactly as pictured inside and out. "
United States
Michaela C.
$437 nightly
The price is $495
Mar 31 - Apr 1
Total with taxes and fees
3-Bedroom Cabin Getaway With Rustic Charm
Smart TV, books

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Sherwood Forest
9.8 out of 10, Exceptional, (14 reviews)
"Nicole was very attentive and very quick to respond to any question we had. Her cottage was perfect for a quiet getaway, just what everybody needs!"
United States
Matthew F.
$353 nightly
The price is $395
Mar 25 - Mar 26
Total with taxes and fees
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Exterior detail

CT Gate House Goshen CT, Gate House Goshen CT

CT Gate House Goshen CT, Gate House Goshen CT
Goshen
9.4 out of 10, Exceptional, (9 reviews)
"The property was great and the house was huge even for all 12 of us "
United States
Ryan L.
$630 nightly
The price is $646
Mar 25 - Mar 26
Total with taxes and fees
CT Gate House Goshen CT, Gate House Goshen CT
Exterior

Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Stockbridge
10.0 out of 10, Exceptional, (35 reviews)
"A college friends' retreat was fantastic, in part due to the location, cleanliness and amenities in this 3 bedroom house. Furniture was comfortable and kitchen was stocked with everything we needed. "
United States
cathy c.
$650 nightly
The price is $726
Mar 25 - Mar 26
Total with taxes and fees
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Fridge, microwave, oven, stovetop

Spacious 5-bedroom house in charming Lee with WiFi

Spacious 5-bedroom house in charming Lee with WiFi
Lee
8.8 out of 10, Excellent, (3 reviews)
"House was clean and made our Thanksgiving great with it's size and amenities. "
United States
Khalil S.
$655 nightly
The price is $732
Mar 31 - Apr 1
Total with taxes and fees
Spacious 5-bedroom house in charming Lee with WiFi
Dining

Whispering Estate Guest House - Countryside Getaway

Whispering Estate Guest House - Countryside Getaway
Goshen
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful property and great location. A true retreat. "
United States
Andrea B.
$780 nightly
The price is $884
Mar 25 - Mar 26
Total with taxes and fees
Whispering Estate Guest House - Countryside Getaway
TV

Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.0 out of 10, Wonderful, (10 reviews)
"This was the perfect location for our mom and daughters weekend! Spacious comfortable. Our only regret was that we didn’t stay longer!"
United States
Sarah B.
$530 nightly
The price is $560
Mar 25 - Mar 26
Total with taxes and fees
Treetop Hideaway in Tyringham
Exterior

Sequoia House Charming Goshen Getaway – Quiet Retreat in Litchfield Hills

Sequoia House Charming Goshen Getaway – Quiet Retreat in Litchfield Hills
Goshen
10.0 out of 10, Exceptional, (1 review)
"Without a doubt, we will be back! Your home was so beautiful, warm and comfortable. Our host was so helpful and friendly. We can't thank you enough for providing such a wonderful experience to our trip. "
United States
Linda D.
$525 nightly
The price is $595
Mar 25 - Mar 26
Total with taxes and fees
Sequoia House Charming Goshen Getaway – Quiet Retreat in Litchfield Hills
TV, fireplace, printers

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Great Barrington
10.0 out of 10, Exceptional, (4 reviews)
"Everything was well taken care of, the hosts were extremely nice, and the area is perfect! The city is also different and really cute! Will come back for sure!"
United States
Roberta
$1,189 nightly
The price is $1,328
Mar 25 - Mar 26
Total with taxes and fees
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Fridge, microwave, oven, stovetop

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (28 reviews)
"The house was pristine, bright, with everything we needed. We hope to come back again to enjoy the area. "
United States
maureen k.
$269 nightly
The price is $300
Mar 30 - Mar 31
Total with taxes and fees
Home in Great Barrington
Interior

Luxury Barn Retreat — All-Season Escape Awaits!

Luxury Barn Retreat — All-Season Escape Awaits!
East Chatham
10.0 out of 10, Exceptional, (2 reviews)
"Accommodations were even better than we expected. The rooms were very clean, and there are unique (and sometimes whimsical, other times thought-provoking) decorations/pictures throughout the barn. The kitchen was basically a chef’s kitchen- all appliances were top notch. The backyard was spacious, and even contained a (non-working) pay phone booth! My wife loved the swinging two-seat chair on the porch! "
United States
Timothy S.
$560 nightly
The price is $627
Mar 25 - Mar 26
Total with taxes and fees
Luxury Barn Retreat — All-Season Escape Awaits!
Exterior

Dugway Hideaway Walking Distance to Lime Rock Park

Dugway Hideaway Walking Distance to Lime Rock Park
Salisbury
9.2 out of 10, Wonderful, (15 reviews)
"Super clean, great communication and Super location if you are going to the track. Love my stay there, will definitely do it again and definitely recommend."
United States
Brig
$277 nightly
The price is $307
Mar 30 - Mar 31
Total with taxes and fees
Dugway Hideaway Walking Distance to Lime Rock Park
Interior

rural, serene + sophisticated space

rural, serene + sophisticated space
Red Hook
10.0 out of 10, Exceptional, (8 reviews)
"Beautiful property with unique accommodations in the Hudson Valley"
United States
BRIAN PATRICK M.
$346 nightly
The price is $388
Mar 25 - Mar 26
Total with taxes and fees
rural, serene + sophisticated space
Exterior

Secluded escape w/ hot tub + pizza oven+ fireplace

Secluded escape w/ hot tub + pizza oven+ fireplace
Taghkanic
$980 nightly
The price is $1,098
Apr 1 - Apr 2
Total with taxes and fees
Secluded escape w/ hot tub + pizza oven+ fireplace
Interior

Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.0 out of 10, Wonderful, (12 reviews)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
$270 nightly
The price is $302
Mar 25 - Mar 26
Total with taxes and fees
Cozy Riverside Berkshires Retreat
Smart TV, books

Sun Filled Lenox Retreat - Minutes to Tanglewood!

Sun Filled Lenox Retreat - Minutes to Tanglewood!
Lee
9.6 out of 10, Exceptional, (5 reviews)
"Very charming, comfortable, and clean. It was in a great location and only minutes away from a lot of sightseeing locations. House management was very accommodating and friendly. I would stay here again."
United States
Paulo I.
$412 nightly
The price is $460
Mar 25 - Mar 26
Total with taxes and fees
Sun Filled Lenox Retreat - Minutes to Tanglewood!
Terrace/patio

BLUSH: Boutique TINY home*private spa*walk to town

BLUSH: Boutique TINY home*private spa*walk to town
Chatham
10.0 out of 10, Exceptional, (7 reviews)
"We loved this property. All the bells and whistles as far as amenities go for a Vrbo! Great location and place to unwind, unplug ,and reconnect!"
United States
scott B.
$286 nightly
The price is $323
Mar 30 - Mar 31
Total with taxes and fees
BLUSH: Boutique TINY home*private spa*walk to town
Interior

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Sherwood Forest
10.0 out of 10, Exceptional, (5 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
$331 nightly
The price is $370
Apr 1 - Apr 2
Total with taxes and fees
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
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

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent
"Great, neat, convoy my son. "
Donna Marie 3-night trip
Posted 1 hour ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel

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, 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 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 low season months. For more hustle and bustle, you may prefer to visit Sheffield 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 $300 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 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.

Explore a world of travel with Expedia

Frequently asked questions

Can I find a vacation rental in Sheffield?

Yes, you can find vacation rentals near popular attractions in Sheffield, or you can select a more secluded option if you'd like a relaxing place to stay. Sheffield is known for its casinos and local tours.

What are some of the best vacation rentals that Sheffield has to offer?

Luxury Private Estate in the Berkshires | Whitney by AvantStay: This highly rated vacation home rental in Sheffield offers a fireplace, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the foosball table in this rental home to help you unwind.

How many vacation rentals are there in Sheffield?

With 24 Expedia vacation rentals, you're sure to find just the right place for your Sheffield stay.

What’s there to see and do in Sheffield?

Housatonic River and Thom Reed UFO Monument Park are a couple of scenic spots to enjoy the outdoors, whereas Ashley House is one of the cultural attractions. While here, Lime Kiln Farm Wildlife Sanctuary and Magnolia Bluffs Casino are other places worth a visit.

What are vacation rentals like in Sheffield?

Vacation rentals are private accommodations you can stay in for a couple days or more in Sheffield. Vacation rentals feature extras like WiFi and washers and dryers so you'll have a home away from home. If you're concerned about a clean environment, a vacation rental can provide a sense of seclusion away from shared hotel elevators and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive choice for a family trip.