Sheffield Vacation Rentals

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Oct 25 - Oct 26
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Vacation Rentals in Sheffield

Dining
Guesthouse Cabin vacation rentals in Berkshire County
Guesthouse Cabin vacation rentals in Berkshire County
10.0 out of 10, Exceptional, (9)
"Really enjoyed the cabin. The pictures don’t do the view justice as it’s an amazing vista overlooking the Berkshires. "
United States
Tom S.
The price is ￥59,510
￥105,163 total
includes taxes & fees
Oct 30 - Oct 31
Guesthouse Cabin vacation rentals in Berkshire County
Exterior
Antique Farmhouse Totally Restored
Antique Farmhouse Totally Restored
9.8 out of 10, Exceptional, (93)
"Enjoyed the property, location and charming house that was well stocked with everything we needed."
United States
Sharon S.
Antique Farmhouse Totally Restored
Indoor pool, outdoor pool, pool umbrellas, sun loungers
The Ponds at Foxhollow
The Ponds at Foxhollow
3.0 star property
8.6 out of 10, Excellent, (132)
"We were 4 adult friends sharing a 2-bedroom and enjoyed the size of the space and the location of the condo was under a 10 min drive to all the sights"
United States
michelle
The Ponds at Foxhollow
Game room
Pet Friendly Riverfront Home in Great Barrington
Pet Friendly Riverfront Home in Great Barrington
9.0 out of 10, Wonderful, (2)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is ￥30,899
￥39,287 total
includes taxes & fees
Oct 26 - Oct 27
Pet Friendly Riverfront Home in Great Barrington
Terrace/patio
Spacious 5-bedroom house in charming Lee with WiFi
Spacious 5-bedroom house in charming Lee with WiFi
8.0 out of 10, Very Good, (1)
"House was large, clean, and comfortable. "
United States
John Z.
The price is ￥68,787
￥126,863 total
includes taxes & fees
Nov 2 - Nov 3
Spacious 5-bedroom house in charming Lee with WiFi
Fridge, microwave, oven, stovetop
Amore Estate - beautiful room with many places to explore and relax in.
Amore Estate - beautiful room with many places to explore and relax in.
9.2 out of 10, Wonderful, (31)
"Beautiful property. The house and grounds, including a beautiful pool were amazing. Loved sitting on the porch and watching the birds.So much to do in the Berkshires, would definitely like to come back."
United States
Jacquie S.
Amore Estate - beautiful room with many places to explore and relax in.
Interior
Peace and quiet on the lake
Peace and quiet on the lake
9.6 out of 10, Exceptional, (226)
"Property was very clean and had all amenities that we needed. It was perfect for a cozy winter getaway weekend. Would definitely stay there again! "
United States
Anika J.
Peace and quiet on the lake
Exterior detail
The Kemble- Built by a US Secretary of State in Lenox
The Kemble- Built by a US Secretary of State in Lenox
10.0 out of 10, Exceptional, (17)
"Loved the property. Perfect for our gathering."
United States
Stephanie R.
The Kemble- Built by a US Secretary of State in Lenox
Exterior
Summer Lake Cottage, private beach, Berkshire Hills, small village
Summer Lake Cottage, private beach, Berkshire Hills, small village
9.4 out of 10, Exceptional, (84)
"The house is very comfortable and perfect for visiting with family and friends.We enjoyed the roomy kitchen space. The porch is great for relaxing and gazing at the tranquil lake. We appreciated the use of the canoe and the dock."
United States
Jenny P.
Summer Lake Cottage, private beach, Berkshire Hills, small village
Exterior
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
9.6 out of 10, Exceptional, (228)
"Great place to get away from it all. Very quiet. Short drive to trailheads and restaurants and all the other hustle and bustle of the Berkshires."
United States
Donald G.
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Dining
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
9.6 out of 10, Exceptional, (15)
"We came for a concert at Tanglewood. Property was just as photos described, walking distance to downtown Lee restaurants, easy access to highway and other towns. Great spot for multiple family or friends to get together."
United States
Karyn P.
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
Property grounds
Tranquil Lakeside Escape in the Berkshires
Tranquil Lakeside Escape in the Berkshires
10.0 out of 10, Exceptional, (1)
"perfect location to go everywhere in the Berkshires"
United States
Edward G.
Tranquil Lakeside Escape in the Berkshires
Outdoor dining
The Goshen Glass Chalet
The Goshen Glass Chalet
9.6 out of 10, Exceptional, (41)
"The chalet was great. Plenty of room, very cozy and in a very quiet neighborhood community. "
United States
Tracy F.
The Goshen Glass Chalet
Smart TV, fireplace
Charming cottage with lake access, wood burning fire place, and WiFi
Charming cottage with lake access, wood burning fire place, and WiFi
2.0 star property
9.0 out of 10, Wonderful, (8)
"Had a wonder fun stay! The place had everything you would need and the hosts were very helpful. We would definitely stay again!"
United States
sarah d.
Charming cottage with lake access, wood burning fire place, and WiFi
Exterior
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
10.0 out of 10, Exceptional, (1)
"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
The price is ￥95,994
￥214,605 total
includes taxes & fees
Oct 26 - Oct 27
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Terrace/patio
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental
9.4 out of 10, Exceptional, (69)
"Wonderful time !! Location was perfect and we really enjoyed our time here "
United States
Sue P.
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental
Interior
Private Island - Largest Fresh Water Reservoir in Mass
Private Island - Largest Fresh Water Reservoir in Mass
8.6 out of 10, Excellent, (9)
"We had a great time. The owner Bill was a great host."
United States
Drew D.
Private Island - Largest Fresh Water Reservoir in Mass
Fridge, microwave, oven, stovetop
Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!
Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!
10.0 out of 10, Exceptional, (55)
"We loved Manor Lane! It had every amenity you could ask for. The house is fun and charming and there are thoughtful touches everywhere you look! We had fun watching movies in the living room, playing games in the lounge, cooking family meals in the spectacular kitchen and playing tennis in the sunshine. A perfect 10!"
United States
Emily R.
Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!
Exterior
The Blue Elm - A Historic Berkshire Cottage
The Blue Elm - A Historic Berkshire Cottage
10.0 out of 10, Exceptional, (11)
"Everything was great...and beautiful!"
United States
Nicole L.
The price is ￥30,518
￥61,019 total
includes taxes & fees
Oct 26 - Oct 27
The Blue Elm - A Historic Berkshire Cottage
Exterior
Quiet 2BR/1BA Forest-View Barn Apartment – Newly Renovated, Peaceful Escape
Quiet 2BR/1BA Forest-View Barn Apartment – Newly Renovated, Peaceful Escape
7.4 out of 10, Good, (3)
"The barn was a great spot for some quality time with friends. We picked some herbs and rotator from the garden and made an amazing toast. Would definitely stay here again."
United States
Adam L.
Quiet 2BR/1BA Forest-View Barn Apartment – Newly Renovated, Peaceful Escape
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

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

10/10 Excellent
"Clean room"
Joseph 1-night trip
Posted 21 hours ago
Hampton Inn & Suites Berkshires-Lenox

Find out more about Sheffield

Search for holiday rentals in Sheffield on Expedia! You can easily find your home rentals, villas, holiday apartments in Sheffield using one of the methods below:

  • View our selection of featured holiday rentals in Sheffield
  • Use the map to find apartments and other holiday homes in the Sheffield neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Sheffield while they last

Look no further and take a look at our great range of rental properties in Sheffield!

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 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 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.