Sheffield Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
May 15 - May 17
In two months
Jun 26 - Jun 28
In three months
Jul 24 - Jul 26
In four months
Aug 21 - Aug 23

Our top choices for Sheffield vacation rentals

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.
$452 nightly
The price is $505
May 6 - May 7
Total with taxes and fees
Cheerful 3-bedroom cottage with woodstove
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.
$772 nightly
The price is $876
May 3 - May 4
Total with taxes and fees
Whispering Estate Guest House - Countryside Getaway
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, (36 reviews)
"Charming house in a wonderful setting in the Berkshires. "
United States
Mark Cristen J.
$650 nightly
The price is $726
May 4 - May 5
Total with taxes and fees
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Fridge, microwave, oven, stovetop

A Country Lodge Straight Out of the Pages of a Great Novel

A Country Lodge Straight Out of the Pages of a Great Novel
Pine Plains
10.0 out of 10, Exceptional, (13 reviews)
"Our group of parents and riders had a great stay during the Millbrook Horse Trials in July. Clean facility, ample room, responsive host. Would stay again."
United States
Hessie S.
$1,302 nightly
The price is $1,473
May 3 - May 4
Total with taxes and fees
A Country Lodge Straight Out of the Pages of a Great Novel
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)
"Very nice cabin, responsive host."
United States
Nick R.
$353 nightly
The price is $395
May 3 - May 4
Total with taxes and fees
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Interior

Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.2 out of 10, Wonderful, (14 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
May 3 - May 4
Total with taxes and fees
Cozy Riverside Berkshires Retreat
TV

Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.2 out of 10, Wonderful, (11 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.
$533 nightly
The price is $563
May 4 - May 5
Total with taxes and fees
Treetop Hideaway in Tyringham
Desk, iron/ironing board, WiFi, bed sheets

The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite
Hillsdale
9.2 out of 10, Wonderful, (5 reviews)
"Clean, industrial, very comfy bed, easy to book and to check in and out. Would stay again."
United States
Deidre H.
$178 nightly
The price is $199
May 3 - May 4
Total with taxes and fees
The Brooks Motel: Exceptional Suite
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
$1,190 nightly
The price is $1,329
May 13 - May 14
Total with taxes and fees
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
3 bedrooms, iron/ironing board, WiFi, bed sheets

Cozy. Clean. Free bagel shop. 3 Fireplaces.

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (1 review)
"The host was very responsive and friendly. The house was well equipped and very comfortable. We did get breakfast at the Great Barrington Bagel Company and had a great breakfast. Highly recommend!"
United States
Mary R.
$478 nightly
The price is $534
May 3 - May 4
Total with taxes and fees
Cozy. Clean. Free bagel shop. 3 Fireplaces.
Fridge, microwave, oven, stovetop

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (31 reviews)
"The house was pristine, bright, with everything we needed. We hope to come back again to enjoy the area. "
United States
maureen k.
$288 nightly
The price is $321
May 4 - May 5
Total with taxes and fees
Home in Great Barrington
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.
$337 nightly
The price is $376
May 3 - May 4
Total with taxes and fees
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
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.
$728 nightly
The price is $813
May 9 - May 10
Total with taxes and fees
Spacious 5-bedroom house in charming Lee with WiFi
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.
$343 nightly
The price is $384
May 5 - May 6
Total with taxes and fees
rural, serene + sophisticated space
Interior

Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (6 reviews)
"Emma's property is adorable! Clean, well appointed with fresh flowers on the table to great us. Smooth and easy communication from start to finish. Really close to Tanglewood and all the activities Western Massachusetts has to offer."
United States
Cheryl F.
$240 nightly
The price is $268
May 6 - May 7
Total with taxes and fees
Sweet Cozy Victorian in Housatonic. Close to everything.
Exterior

Secluded escape w/ hot tub + pizza oven+ fireplace

Secluded escape w/ hot tub + pizza oven+ fireplace
Taghkanic
$948 nightly
The price is $1,062
May 20 - May 21
Total with taxes and fees
Secluded escape w/ hot tub + pizza oven+ fireplace
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.
$282 nightly
The price is $318
May 4 - May 5
Total with taxes and fees
BLUSH: Boutique TINY home*private spa*walk to town
Dining

Sugar Shack - 300 square feet of pure sweetness.

Sugar Shack - 300 square feet of pure sweetness.
Chatham
10.0 out of 10, Exceptional, (3 reviews)
"By far one of my favorite rentals. Everything was perfect and the details were amazing. Not only do I highly recommend, I amSURE I will be returning soon. "
United States
Sue G.
$316 nightly
The price is $356
May 4 - May 5
Total with taxes and fees
Sugar Shack - 300 square feet of pure sweetness.
Exterior

Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
$264 nightly
The price is $295
May 27 - May 28
Total with taxes and fees
Real Estate: Therapy - Lake, Laundry, Love it
Property grounds

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Chatham
9.4 out of 10, Exceptional, (3 reviews)
"Mark was very accommodating and always available immediately if I had a question. The place was very clean and comfortable. Perfect location. We would love to come back in the summer when we can use the fire pit and the creek in the back. "
United States
Jessica V.
$277 nightly
The price is $310
May 4 - May 5
Total with taxes and fees
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Sheffield Hotel Reviews

Berkshires Untold

Berkshires Untold

10/10 Excellent
"It’s an amazing property! Beautiful inside and out! We ate supper there, we were the only ones, but it was excellent!"
Ken 1-night trip
Posted 1 hour ago
Berkshires Untold

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 $302 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?

Cozy Riverside Berkshires Retreat: This vacation home rental near Sheffield is located on a river and has a fireplace, a garden, and air-conditioning to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and kitchenware, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

How many vacation rentals are there in Sheffield?

With 25 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, Magnolia Bluffs Casino and Three Mile Pond Wildlife Management Area 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.