Sheffield vacation rentals

We found 752 vacation rentals — enter your dates for availability

Nestled amidst the breathtaking landscapes of the Berkshires, Sheffield invites you to experience its outdoor adventures, historical charm, and stunning scenery. From thrilling winter skiing to serene summer hikes, this picturesque destination caters to families and groups seeking unforgettable escapades. Wander through quaint neighborhoods, explore captivating attractions like the Ashley House, and enjoy diverse accommodations, from cozy cottages to modern apartments. Embrace the comfort and convenience of a vacation rental, ensuring a home-like experience to enhance your getaway.

Holiday rentals with weekly discounts - Sheffield

Showing deals for:Dec 11 - Dec 18

Hot tub overlooking the lake
The great room with wonderful water views and working fireplace
Sunroom has Queen pull out sofa bed
Dining
Exceptional
(86 reviews)

Spectacular setting on your own private lake close to it all!

Lee

9% off
$607
$4,250 for 7 nights
All fees included
Spectacular setting on your own private lake close to it all!
View from entry into living room- perfect spot for relaxing!
Kitchen with counter seating for 4- door on the right to garage
Enclosed porch- view into back yard- dining/game table
Outdoor dining
Exceptional
(9 reviews)

Sophisticated Lenox Retreat by Evergreen Home

Lenox

12% off
$486
$3,405 for 7 nights
All fees included
Sophisticated Lenox Retreat by Evergreen Home
Private kitchen
Terrace/patio
Game room
Pool
Exceptional
(5 reviews)

Hillsdale Retreat Farmhouse with Pool, Firepit, Hot Tub and Game Room

Hillsdale

8% off
$747
$5,229 for 7 nights
All fees included
Hillsdale Retreat Farmhouse with Pool, Firepit, Hot Tub and Game Room
Terrace/patio
Private kitchen
Property grounds
Exterior
Exceptional
(10 reviews)

Beautiful House in the Woods: Huge Yard, Hot Tub

Great Barrington

8% off
$480
$3,361 for 7 nights
All fees included
Beautiful House in the Woods: Huge Yard, Hot Tub
Outdoor dining and grill on the 16' x 20' wooden deck.
You will love dining and working in this rich and colorful room
A mudroom off the back leads to the large wooden deck
The living room flows into the dining room.
Exceptional
(42 reviews)

An In-Town Beauty with Late Checkout

Great Barrington

8% off
$456
$3,195 for 7 nights
All fees included
An In-Town Beauty with Late Checkout
Reading nook with natural lighting
Fully screened porch!
Front Staircase
Kitchen with stainless steel appliances
Exceptional
(8 reviews)

Berkshires Colonial on 2 Acres by Evergreen Home

Richmond

13% off
$395
$2,762 for 7 nights
All fees included
Berkshires Colonial on 2 Acres by Evergreen Home
Welcome Home!
The open-concept living space seamlessly blends the comfort of the living room with the functionality of the kitchen, all adorned by a double sided
Back patio with Hot Tub
Add a touch of warmth and charm to your dining experience!
Exceptional
(7 reviews)

Idyllic Retreat; Hot Tub/Sauna by Evergreen Home

Great Barrington

12% off
$723
$5,061 for 7 nights
All fees included
Idyllic Retreat; Hot Tub/Sauna by Evergreen Home
Interior
Terrace/patio
Dining
Interior
Exceptional
(102 reviews)

Waterfront Cottage 10 Min From Great Barrington

Great Barrington

9% off
$315
$2,208 for 7 nights
All fees included
Waterfront Cottage 10 Min From Great Barrington
Private kitchen
Ultimate Relaxation!  The hot tub will be warm and waiting for your arrival
Welcome Home!
Dining Area, view into living room. Games, books, records all available for your enjoyment!
Exceptional
(9 reviews)

Best of the Berkshires + Hot Tub by Evergreen Home

Great Barrington

12% off
$362
$2,531 for 7 nights
All fees included
Best of the Berkshires + Hot Tub by Evergreen Home
Living Room

Great Barrington Castle house
Front view of home
Great Barrington Castle
Exceptional
(51 reviews)

NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE

Great Barrington

9% off
$453
$3,171 for 7 nights
All fees included
NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE
Seamless entertaining with the wide open concept, living room -kitchen- patio
After a hard day on the trails or a long day on the town, relax in this oasis
Never miss a thing with this expansive open concept kitchen and living room
Truly nestled on 5+ acres and LESS than 0.8miles to downtown Great Barrington
Exceptional
(29 reviews)

Adventure Ready Ranch Sleeps 10 & 0.7 mi to GB Main St. Wi-Fi + HOT TUB.

Great Barrington

7% off
$506
$3,542 for 7 nights
All fees included
Adventure Ready Ranch Sleeps 10 & 0.7 mi to GB Main St. Wi-Fi + HOT TUB.
Great room river view
River view from window
Alfresco dining
Blue House side entry from driveway
Exceptional
(44 reviews)

Renovated Colonial on the River! Fantastic Views

Housatonic

8% off
$332
$2,325 for 7 nights
All fees included
Renovated Colonial on the River! Fantastic Views
Property grounds
Interior
Living area
Exterior
Exceptional
(7 reviews)

Serene rustic cabin in the Berkshires!

West Stockbridge

9% off
$354
$2,478 for 7 nights
All fees included
Serene rustic cabin in the Berkshires!
Living area
Interior
Interior
Private kitchen
Exceptional
(40 reviews)

A Fun Farmhouse Near Ski Butternut

Great Barrington

8% off
$402
$2,813 for 7 nights
All fees included
A Fun Farmhouse Near Ski Butternut
Living area
Private kitchen
Living area
Exterior
Exceptional
(9 reviews)

Luxurious Mountain Retreat - Private 40-Acre Family Haven

Southfield

9% off
$849
$5,943 for 7 nights
All fees included
Luxurious Mountain Retreat - Private 40-Acre Family Haven
Property grounds
Interior
Kitchen
Interior
Excellent
(14 reviews)

Canary Lodge - Berkshires Mountain Retreat - 6 Guests

West Stockbridge

9% off
$505
$3,535 for 7 nights
All fees included
Canary Lodge - Berkshires Mountain Retreat - 6 Guests
Front Gardens
Living Room
Back Porch
Property grounds
Exceptional
(27 reviews)

Secluded Family Home in Serene Stockbridge Woods

South Lee

9% off
$414
$2,898 for 7 nights
All fees included
Secluded Family Home in Serene Stockbridge Woods
Terrace/patio
Living area
Living area
Living area
Exceptional
(8 reviews)

Modern Log Chalet - 10 acres, views, and a pond!

Chatham

8% off
$364
$2,549 for 7 nights
All fees included
Modern Log Chalet - 10 acres, views, and a pond!
Kitchen open to living room
Kitchen
Cottage Entrance
Patio off kitchen
Exceptional
(78 reviews)

Charming Cottage, New Marlborough Village Green in the Berkshires

Great Barrington

9% off
$215
$1,503 for 7 nights
All fees included
Charming Cottage, New Marlborough Village Green in the Berkshires
After a day in the snow
Property grounds
Property grounds
Interior
Exceptional
(14 reviews)

Secluded Mountainside House with Outdoor Sauna, Surrounded by Trees.

Sheffield

13% off
$322
$2,256 for 7 nights
All fees included
Secluded Mountainside House with Outdoor Sauna, Surrounded by Trees.
Exterior
Two Tier Decking with Grill on Lower Deck
Room
Open Living Area
Exceptional
(14 reviews)

Copake Lake Rustic All-Season 3 Bdrm, 2 Bath Home with Lake Rights

Hillsdale

9% off
$306
$2,142 for 7 nights
All fees included
Copake Lake Rustic All-Season 3 Bdrm, 2 Bath Home with Lake Rights
Screened in porch
Terrace/patio
Property grounds
Dining room with butcher block table
Exceptional
(103 reviews)

Vacation in a Berkshire Farmhouse

West Stockbridge

9% off
$359
$2,513 for 7 nights
All fees included
Vacation in a Berkshire Farmhouse
Game, puzzle and play table - plenty of chairs.
Porch opens up from dining room. Ceiling fan and lights above.
Come and unwind.
Entrance view.
Exceptional
(43 reviews)

Converted Berkshire schoolhouse on a quiet river

Great Barrington

8% off
$281
$1,969 for 7 nights
All fees included
Converted Berkshire schoolhouse on a quiet river
Interior
Living area
Living area
Living area
Excellent
(9 reviews)

The Race Mountain House

Sheffield

38% off
$496
$3,472 for 7 nights
All fees included
The Race Mountain House
  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, yards and more
  • More for less

    More space, more privacy, more amenities — more value
  • A place for everyone

    We stand for diversity, inclusion and families everywhere.
    Learn more

Find out more about Sheffield

Why visit Sheffield

  • Outdoor Adventures: Sheffield offers stunning national parks and serene lakes, perfect for hiking, skiing, and eco-friendly experiences.
  • Charming Neighborhoods: Explore friendly neighborhoods with a romantic atmosphere and picturesque rustic farmland.
  • Family-Friendly Activities: Enjoy a variety of attractions suitable for both families and solo travelers, ensuring fun for everyone.
  • Vibrant Downtown: Nearby downtown Stockton provides a lively experience with shops, dining, and entertainment options.
  • Diverse Accommodations: Find cozy vacation rentals, from private homes to modern apartments, tailored to every traveler's needs.

Popular types of accommodation in Sheffield

Experience the charm of Sheffield with our diverse vacation rentals. Whether you’re seeking a cozy private vacation home, a picturesque cottage, or a modern apartment, we have options to fit every traveler’s needs. From Sheffield apartments for rent to spacious house rentals, you’ll find the perfect base for your adventures. Discover the best Sheffield rentals and enjoy your stay with transparency, savings, and reassurance.

  • Houses: The top choice for visitors in Sheffield, these homes offer a spacious and comfortable environment ideal for families or groups.
  • Cottages: A close second, cottages provide a quaint and charming atmosphere, perfect for a relaxing getaway.
  • Apartments: A popular option for solo travelers or couples, apartments offer convenience and easy access to local attractions.
  • Cabins: Perfect for those seeking a rustic experience, cabins immerse you in nature with cozy accommodations.
  • Condos: Offering modern amenities, condos are a great choice for those who want a blend of comfort and style.**

Top attractions near Sheffield

Sheffield, Massachusetts, is an ideal destination for ski enthusiasts and adventure seekers alike. Visitors can explore stunning national parks, nature reserves, and serene lakes, making it perfect for those who crave outdoor and eco-friendly experiences. Whether you're planning a family trip or a solo adventure, Sheffield offers a variety of attractions to satisfy your thirst for adventure and relaxation in the great outdoors.

  • Bash Bish Falls State Park: Located 7 miles from Sheffield, this state park is renowned for its stunning waterfall and lush trails, offering adventure and breathtaking scenery amidst nature's beauty.
  • Housatonic River: Only 6 miles away, this picturesque river provides fantastic views and outdoor activities, perfect for kayaking, fishing, or simply enjoying a peaceful day by the water.
  • Umpachene Falls Park: Just 4 miles from Sheffield, this charming waterfall park is ideal for outdoor enthusiasts and couples seeking romance, featuring serene surroundings and adventurous trails.

Things to do recommended for couples

For a romantic getaway in Sheffield, explore the slopes at Ski Butternut, savor wines at Les Trois Emme Winery, and enjoy live music at Music Mountain. Each activity offers a perfect blend of adventure and intimacy, making your couple's vacation unforgettable.

Things to do recommended for families

Your family will love exploring Lake Mansfield Park, a serene recreational area just 7 miles from Sheffield, perfect for relaxation. Additionally, Tyringham Cobble, located 12 miles away, offers beautiful landscapes and a tranquil atmosphere for an enjoyable day outdoors.

Things to do recommended for groups

Groups visiting Sheffield can hike the scenic Housatonic River Walk, enjoy a cultural evening at the Mahaiwe Performing Arts Center, and experience adventure at the Catamount Aerial Adventure Park, all within a short drive, offering a perfect blend of outdoor fun and entertainment.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Sheffield

If you’re traveling with a group, family, or pets, or if you’re planning an extended stay, be sure to apply the appropriate filters to meet your needs. Here are some helpful Vrbo booking tips for you.

  • Traveling to Sheffield with a group: Think about how many bedrooms you'll require, along with any additional features like a full kitchen or outdoor area for group gatherings. Luckily, you can easily filter for these options and many more on Vrbo.
  • Traveling to Sheffield with young kids: Traveling with young kids can be tough. It's important to prioritize their comfort and safety, along with suitable amenities like a private pool. Additionally, keeping in mind your closeness to family-friendly attractions can enhance your experience.
  • Taking your pets with you to Sheffield: For many families, a vacation isn't truly perfect without their furry companion by their side. If this resonates with you, explore Vrbo properties that welcome pets. Many of these pet-friendly accommodations come equipped with feeding dishes and cozy beds, ensuring that everyone feels at home.
  • Planning for a long term stay visiting Sheffield: If you're in search of vacation rentals offering discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Sheffield

Sheffield, Massachusetts, is a charming destination perfect for adventure seekers and history buffs alike. Explore the picturesque rustic farmland and relax in friendly neighborhoods that offer a romantic atmosphere. Nearby, downtown Stockton provides a vibrant experience, while the surrounding areas showcase the serene beauty of Western Florida. Whether you're looking for family-friendly activities or thrilling sports, Sheffield has something for everyone to enjoy during their vacation.

  • Great Barrington: Located 6 miles from Sheffield, Great Barrington is a vibrant city known for its outdoor adventure and sports experiences. This charming town is a popular destination for skiing enthusiasts, with easy access to ski fields and resorts. In addition to winter sports, visitors can enjoy the stunning landscapes of nearby lakes and mountains, perfect for hiking and exploring during the warmer months. Great Barrington also boasts a lively downtown area filled with unique shops, restaurants, and cultural attractions, making it an ideal spot for a day trip or a weekend getaway.
  • The Berkshires: Just 11 miles from Sheffield, The Berkshires is a picturesque region renowned for its breathtaking outdoor scenery and adventure opportunities. This area is a haven for outdoor enthusiasts, offering numerous ski resorts and trails for skiing and snowboarding in the winter, as well as hiking and biking in the summer. The Berkshires is dotted with beautiful lakes and mountains, providing a serene backdrop for relaxation and exploration. Additionally, the region hosts various events and conferences, making it a hub for both leisure and business travelers alike.
  • Ashley Falls: Only 4 miles from Sheffield, Ashley Falls is a quaint city that attracts visitors seeking ski adventures and sports activities. The area provides access to excellent ski fields and resorts, making it a popular choice for winter sports fans. Beyond skiing, Ashley Falls offers charming local attractions, including parks and the town hall, where you can learn more about the area's history. With its friendly atmosphere and close-knit community, Ashley Falls is an inviting destination for those looking to experience the beauty and excitement of the Berkshires.

Best time to go to Sheffield

If you're planning a trip to Sheffield, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in June to July and September, while off-peak times, like February and November to December tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January23.2°F (-4.9°C)Light RainMostly CloudyAverageSlightly Low
February24.8°F (-4.0°C)Light RainMostly CloudySlightly LowAverage
March32.5°F (0.3°C)Light RainMostly CloudyAverageSlightly Low
April44.2°F (6.8°C)Light RainMostly CloudyAverageSlightly Low
May55.9°F (13.3°C)Light RainMostly SunnyAverageAverage
June63.7°F (17.6°C)Light RainMostly SunnySlightly HighAverage
July69.8°F (21.0°C)Light RainMostly SunnySlightly HighAverage
August67.8°F (19.9°C)Light RainMostly SunnyAverageSlightly High
September60.8°F (16.0°C)Light RainMostly SunnySlightly HighAverage
October49.8°F (9.9°C)Light RainMostly SunnyAverageAverage
November37.8°F (3.2°C)Light RainMostly SunnySlightly LowSlightly High
December29.7°F (-1.3°C)Light RainMostly CloudySlightly LowSlightly High

Booking with Vrbo is a breeze

Are you hoping to save on your upcoming travels? Being flexible with your travel dates can really help, as prices tend to vary. Additionally, opting for a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, take advantage of our filters to narrow down your options by price, location, and type of vacation rental.

Vrbo Trips: Planning made easy

Vrbo's cutting-edge Trip Board offers you a dedicated space to plan new adventures, pick up from where you last were, and manage your travel itineraries. You can easily find the properties you've saved and booked under Potential, Upcoming, or Current Trips. To explore the Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

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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