A covered wooden structure with a sloped roof, surrounded by greenery and trees.

Sheffield Vacation Rentals

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Check prices for these dates

In two weeks
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Our top choices for Sheffield vacation rentals

Property grounds

1. Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (43 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
$365 nightly
The price is $408
Sep 28 - Sep 29
Total with taxes and fees
Cheerful 3-bedroom cottage with woodstove
Coffee/tea maker, fridge, microwave, oven

2. Cozy 1-bedroom studio in serene Great Barrington with AC

Cozy 1-bedroom studio in serene Great Barrington with AC
Great Barrington
9.4 out of 10, Exceptional, (3 reviews)
"Great location, great property, great host"
United States
Shelly B.
$148 nightly
The price is $165
Sep 27 - Sep 28
Total with taxes and fees
Cozy 1-bedroom studio in serene Great Barrington with AC
Coffee/tea maker, fridge, microwave, oven

3. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (38 reviews)
"Perfect location to walk into town - clean, light, airy and neat space. Enjoyable visit!"
United States
HEATHER G.
$276 nightly
The price is $308
Sep 15 - Sep 16
Total with taxes and fees
Home in Great Barrington
Beach nearby, sun loungers, beach towels

4. Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake

Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
Great Barrington
10.0 out of 10, Exceptional, (4 reviews)
"We had a wonderful visit. They were so accommodating and great location to downtown. We’ll stay again!"
United States
Kristin O.
$286 nightly
The price is $320
Sep 14 - Sep 15
Total with taxes and fees
Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
Interior

5. Riverside Retreat in the Berkshires

Riverside Retreat in the Berkshires
Great Barrington
9.6 out of 10, Exceptional, (25 reviews)
"If you like cuddly cats, book it! A quick night stay while in town for a wedding and Studly was a perfect host… and Marissa :)Easy location, was nice to watch the fish jump and bald eagle hunt for his breakfast as we enjoyed our coffee on the step."
United States
Kelly B.
$269 nightly
The price is $301
Sep 21 - Sep 22
Total with taxes and fees
Riverside Retreat in the Berkshires
Interior

6. Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (10 reviews)
"The host did a great job of prepping the place and being welcoming to us. It was clean and thoughtfully designed. So happy we found this spot!"
United States
Peter S.
$267 nightly
The price is $298
Sep 25 - Sep 26
Total with taxes and fees
Sweet Cozy Victorian in Housatonic. Close to everything.
Terrace/patio

7. Ideal location for summer and winter activities with plenty of outdoor space.

Ideal location for summer and winter activities with plenty of outdoor space.
Hillsdale
9.8 out of 10, Exceptional, (79 reviews)
"Excellent host!"
United States
Kenny
$339 nightly
The price is $380
Sep 13 - Sep 14
Total with taxes and fees
Ideal location for summer and winter activities with plenty of outdoor space.
3 bedrooms, iron/ironing board, WiFi, bed sheets

8. Cozy. Clean. Free bagel shop. 3 Fireplaces.

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (2 reviews)
"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.
$495 nightly
The price is $552
Sep 14 - Sep 15
Total with taxes and fees
Cozy. Clean. Free bagel shop. 3 Fireplaces.
Lobby

9. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,139 reviews)
"Clean & comfortable stay"
United States
Robert
$109 nightly
The price is $121
Oct 1 - Oct 2
Total with taxes and fees
Berkshire Mountain Lodge
Smart TV, books

10. Fantastic 2-bedroom house with AC in quaint Hillsdale.

Fantastic 2-bedroom house with AC in quaint Hillsdale.
Hillsdale
$600 nightly
The price is $672
Sep 13 - Sep 14
Total with taxes and fees
Fantastic 2-bedroom house with AC in quaint Hillsdale.
TV

11. Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.2 out of 10, Wonderful, (11 reviews)
"We had coordinated an early check-in, but when we arrived, the house hadn’t been cleaned yet which was a miscommunication. I reached out to Catherine and she promptly responded and got the cleaners RIGHT over. The house was spotless and in wonderful condition for the rest of our stay, and it was dealt with very quickly and wonderfully. Would definitely stay again. The house was great for our girls trip. Also the beds are very comfortable!! "
United States
Samantha G.
$546 nightly
The price is $577
Sep 21 - Sep 22
Total with taxes and fees
Treetop Hideaway in Tyringham
TV, fireplace, printers

12. 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, (7 reviews)
"Beautiful house with great amenities in a convenient location. We loved the open concept that provided a great space for cooking, hanging out and playing games together while enjoying a beautiful view. The gameroom was so much fun, and we’d love to visit again when the sauna is finished. Our family of 6 and family dog loved it!"
United States
Rebecca K.
$1,189 nightly
The price is $1,328
Sep 13 - Sep 14
Total with taxes and fees
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Outdoor dining

13. Cozy Camper tucked into the woods

Cozy Camper tucked into the woods
Sandisfield
$220 nightly
The price is $245
Sep 14 - Sep 15
Total with taxes and fees
Cozy Camper tucked into the woods
Outdoor spa tub

14. 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, (16 reviews)
"Great place and welcoming stay!"
United States
Frank M.
$371 nightly
The price is $415
Sep 15 - Sep 16
Total with taxes and fees
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Interior

15. 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, (9 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
$335 nightly
The price is $374
Sep 14 - Sep 15
Total with taxes and fees
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
2 bedrooms, WiFi, bed sheets

16. Quintessential Berkshire Escape - Artist Home, Tucked Away in Nature

Quintessential Berkshire Escape - Artist Home, Tucked Away in Nature
Otis
$306 nightly
The price is $341
Sep 14 - Sep 15
Total with taxes and fees
Quintessential Berkshire Escape - Artist Home, Tucked Away in Nature
Interior

17. Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
8.0 out of 10, Very Good, (1 review)
"Very good trip overall. Great location. Just a few things needed to make it over the top!"
United States
William C B.
$260 nightly
The price is $290
Sep 16 - Sep 17
Total with taxes and fees
Real Estate: Therapy - Lake, Laundry, Love it
Interior

18. Peaceful and cozy 1 bed 1 bath in quaint Winchester

Peaceful and cozy 1 bed 1 bath in quaint Winchester
Winchester
$197 nightly
The price is $223
Sep 13 - Sep 14
Total with taxes and fees
Peaceful and cozy 1 bed 1 bath in quaint Winchester
Exterior

19. 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, (40 reviews)
"The house was lovely - my sisters and I had a wonderful time. Everything was warm and welcoming - it felt like home! We hope to make it an annual visit :)"
United States
Anonymous traveler
$766 nightly
The price is $856
Sep 28 - Sep 29
Total with taxes and fees
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Pool

20. Hudson NY’S Country Serenity Guest Suite.

Hudson NY’S Country Serenity Guest Suite.
Hudson
9.2 out of 10, Wonderful, (5 reviews)
"Close proximity to Hudson & Chatham."
United States
David P.
$337 nightly
The price is $377
Sep 13 - Sep 14
Total with taxes and fees
Hudson NY’S Country Serenity Guest Suite.
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

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South

10/10 Excellent
"Very helpful staff, very convenient to dining, shopping and activities"
peter 1-night trip
Posted 1 hour ago
Quality Inn Lee - Lenox South

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 $121 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?

Antique Farmhouse Totally Restored : This highly rated vacation home rental in Sheffield is located in a rural location and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals are there in Sheffield?

With 23 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, Three Mile Pond Wildlife Management Area and Mount Everett State Reservation 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.