Great Barrington holiday rentals

We found 689 holiday rentals — enter your dates for availability
Discover a selection of 97 homes, 13 apartments and other holiday rentals in Great Barrington that are perfect for your trip. Whether you’re staying in a holiday home with friends, family or just with your pet, you'll find the amenities that you need and want, including Wi-Fi and parking. Whatever you're looking for, you'll be sure to find a property to rent for everyone's needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts – Great Barrington

Showing deals for:1 Jan - 8 Jan

Living area
Exterior
Outdoor spa tub
Interior
Exceptional
(21 reviews)

Beautiful Home in AMAZING Berkshire Location

Lee

8% off
AU$6,808
for 7 nights, 1 home
AU$973 per night
includes taxes & fees
Beautiful Home in AMAZING Berkshire Location
Living room from back staircase
Interior
View of dining room from living room
Exterior
Exceptional
(53 reviews)

Beautiful Berkshire Farm House on 160+ Acres

Great Barrington

8% off
AU$10,522
for 7 nights, 1 home
AU$1,503 per night
includes taxes & fees
Beautiful Berkshire Farm House on 160+ Acres
Pool
Terrace/patio
Property grounds
Private kitchen
Exceptional
(5 reviews)

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

Hillsdale

8% off
AU$11,750
for 7 nights, 1 home
AU$1,679 per night
includes taxes & fees
Hillsdale Retreat Farmhouse with Pool, Firepit, Hot Tub and Game Room
Cottage Entrance
Kitchen
Patio off kitchen
Kitchen open to living room
Exceptional
(78 reviews)

Charming Cottage, New Marlborough Village Green in the Berkshires

New Marlborough

8% off
AU$2,442
for 7 nights, 1 cottage
AU$349 per night
includes taxes & fees
Charming Cottage, New Marlborough Village Green in the Berkshires
Terrace/patio
Private kitchen
Property grounds
Exterior
Exceptional
(10 reviews)

Beautiful House in the Woods: Huge Yard, Hot Tub

Great Barrington

8% off
AU$7,442
for 7 nights, 1 home
AU$1,063 per night
includes taxes & fees
Beautiful House in the Woods: Huge Yard, Hot Tub
Dining
Interior
Property grounds
Living area
Exceptional
(8 reviews)

Serene rustic cabin in the Berkshires!

West Stockbridge

8% off
AU$3,853
for 7 nights, 1 cabin
AU$550 per night
includes taxes & fees
Serene rustic cabin in the Berkshires!
Island with Kitchen drawer microwave, quartz countertops, refrigerator
Front showing deck on the side of the house in both levels
Interior
Kitchen island with 2 swivel chairs and pantry, and coat closet with barn doors
Exceptional
(134 reviews)

Gorgeous Mountain Views Retreat: Family & Nature

Hillsdale

8% off
AU$5,145
for 7 nights, 1 home
AU$735 per night
includes taxes & fees
Gorgeous Mountain Views Retreat: Family & Nature
Living area
Private kitchen
Living area
Exterior
Exceptional
(9 reviews)

Luxurious Mountain Retreat - Private 40-Acre Family Haven

Sheffield

8% off
AU$9,164
for 7 nights, 1 home
AU$1,309 per night
includes taxes & fees
Luxurious Mountain Retreat - Private 40-Acre Family Haven
Private kitchen
Interior
Exterior
Room
Exceptional
(62 reviews)

Amazing 2-bedroom apartment sunny and quiet in Great Barrington

Great Barrington

12% off
AU$1,687
for 7 nights, 1 apartment
AU$241 per night
includes taxes & fees
Amazing 2-bedroom apartment sunny and quiet in Great Barrington
Back patio with Hot Tub
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
Welcome Home!
Add a touch of warmth and charm to your dining experience!
Exceptional
(8 reviews)

Idyllic Retreat; Hot Tub/Sauna by Evergreen Home

Great Barrington

11% off
AU$8,378
for 7 nights, 1 home
AU$1,197 per night
includes taxes & fees
Idyllic Retreat; Hot Tub/Sauna by Evergreen Home
Dining room with butcher block table
Terrace/patio
Screened in porch
Queen bedroom
Exceptional
(103 reviews)

Vacation in a Berkshire Farmhouse

West Stockbridge

8% off
AU$4,053
for 7 nights, 1 home
AU$579 per night
includes taxes & fees
Vacation in a Berkshire Farmhouse
Enjoy a beautiful crisp night under the lights
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

6% off
AU$6,526
for 7 nights, 1 home
AU$932 per night
includes taxes & fees
Adventure Ready Ranch Sleeps 10 & 0.7 mi to GB Main St. Wi-Fi + HOT TUB.
Lobby
Living area
Living area
Interior
Excellent
(9 reviews)

The Race Mountain House

Sheffield

21% off
AU$6,833
for 7 nights, 1 home
AU$976 per night
includes taxes & fees
The Race Mountain House
Private kitchen
Room
Dining
Outdoor dining
Exceptional
(33 reviews)

The Hideaway: Berkshire Home - Village of Egremont

egremont

16% off
AU$3,638
for 7 nights, 1 home
AU$520 per night
includes taxes & fees
The Hideaway: Berkshire Home - Village of Egremont
Alfresco dining
River view from window
Blue House side entry from driveway
Great room river view
Exceptional
(44 reviews)

Renovated Colonial on the River! Fantastic Views

Stockbridge

8% off
AU$3,839
for 7 nights, 1 home
AU$548 per night
includes taxes & fees
Renovated Colonial on the River! Fantastic Views
View of the river.
Porch opens up from dining room. Ceiling fan and lights above.
Entrance view.
Game, puzzle and play table - plenty of chairs.
Exceptional
(43 reviews)

Converted Berkshire schoolhouse on a quiet river

New Marlborough

8% off
AU$2,870
for 7 nights, 1 home
AU$410 per night
includes taxes & fees
Converted Berkshire schoolhouse on a quiet river
Dining
Living area
Exterior
Terrace/patio
Exceptional
(10 reviews)

Cozy Log Cabin Retreat with Pool on 4 Acres

North Canaan

7% off
AU$3,118
for 7 nights, 1 home
AU$445 per night
includes taxes & fees
Cozy Log Cabin Retreat with Pool on 4 Acres
Living area
Interior
Property grounds
Exterior
Exceptional
(13 reviews)

Guesthouse Cabin vacation rentals in Berkshire County

Sheffield

21% off
AU$4,663
for 7 nights, 1 cabin
AU$666 per night
includes taxes & fees
Guesthouse Cabin vacation rentals in Berkshire County
Property grounds
Interior
Kitchen
Kitchen
Excellent
(14 reviews)

Canary Lodge - Berkshires Mountain Retreat - 6 Guests

West Stockbridge

8% off
AU$5,459
for 7 nights, 1 home
AU$780 per night
includes taxes & fees
Canary Lodge - Berkshires Mountain Retreat - 6 Guests
Property grounds
Property grounds
After a day in the snow
We highly recommend the Sauna
Exceptional
(14 reviews)

Secluded Mountainside House with Outdoor Sauna, Surrounded by Trees.

Sheffield

12% off
AU$3,568
for 7 nights, 1 home
AU$510 per night
includes taxes & fees
Secluded Mountainside House with Outdoor Sauna, Surrounded by Trees.
Private kitchen
Outdoor dining
Private kitchen
Exterior
Exceptional
(13 reviews)

Charming Berkshire Farmhouse: Your Cozy Retreat Awaits!

Monterey

8% off
AU$3,986
for 7 nights, 1 home
AU$569 per night
includes taxes & fees
Charming Berkshire Farmhouse: Your Cozy Retreat Awaits!
Room
Property grounds
Exterior
Interior
Wonderful
(6 reviews)

The Serendipity Spot

Great Barrington

7% off
AU$2,018
for 7 nights, 1 apartment
AU$288 per night
includes taxes & fees
The Serendipity Spot
Welcome Home!
Ultimate Relaxation! The hot tub will be warm and waiting for your arrival
Open floor plan, natural light in a stylish space
Private kitchen
Exceptional
(9 reviews)

Best of the Berkshires + Hot Tub by Evergreen Home

Great Barrington

11% off
AU$4,169
for 7 nights, 1 home
AU$596 per night
includes taxes & fees
Best of the Berkshires + Hot Tub by Evergreen Home
Interior
Front Entrance
dining room
kitchen
Exceptional
(15 reviews)

Beautiful Berkshire Home - Enjoy summer, fall & winter attractions

Sheffield

8% off
AU$6,149
for 7 nights, 1 home
AU$878 per night
includes taxes & fees
Beautiful Berkshire Home - Enjoy summer, fall & winter attractions

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

The lively city of Great Barrington awaits you

The area's live music and theatre scene are just some of the reasons to come on holiday to Great Barrington. Well known for its rock climbing, hiking and cafes, this scenic city won't disappoint. With a holiday rental, you get a home away from home – many rentals offer full kitchens and outdoor grills for some home cooking.

Activities and attractions in and around Great Barrington

Are you looking for attractions to see during your stay? You'll be sure to enjoy Great Barrington for its hiking and skiing. Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Great Barrington a one-of-a-kind holiday spot. Here are some of the top attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Ski Butternut (2.3 mi / 3.7 km)
  • Catamount Ski Area (6.3 mi / 10.1 km)
  • Wyndhurst Golf & Club (11.3 mi / 18.1 km)
  • Otis Ridge (13.4 mi / 21.5 km)
  • Bousquet Ski Area (15.7 mi / 25.3 km)
  • Hudson Chatham Winery (16.3 mi / 26.3 km)

Exploring the natural landscape of Great Barrington

Whether you're looking for exciting outdoor activities or just want to appreciate the scenery, Great Barrington is a great place to get out in nature. These are a few of the area's noteworthy features, all within 30 miles (48.2 km) of the city centre:

  • Housatonic River Walk (0.1 mi / 0.2 km)
  • Housatonic River (0.1 mi / 0.2 km)
  • Lake Mansfield Park (0.7 mi / 1.1 km)
  • Lake Buel (4.8 mi / 7.7 km)
  • Naumkeag Museum (6.9 mi / 11.1 km)
  • Berkshire Botanical Garden (7.4 mi / 11.8 km)

Seasonal weather averages in Great Barrington

Travellers enjoy Great Barrington for its skiing. To make the most of the cold weather activities, you might consider visiting in January, March, February or November, when snowfall averages 18 cm and temperatures average -2°C.

Transport options to and around Great Barrington

The nearest airport is in Pittsfield, MA (PSF-Pittsfield Municipal), located 16.2 mi (26.1 km) from the city centre. If you can't find a flight that's convenient for your trip, you might consider flying into Hudson, NY (HCC-Columbia County), which is 19.2 mi (30.9 km) away.

Frequently asked questions

What is the best area to stay in Great Barrington when booking a holiday rental?
When considering a holiday rental in Great Barrington, Massachusetts, the downtown area is often regarded as one of the best places to stay. This charming neighbourhood offers a delightful mix of boutique shops, art galleries, and a variety of dining options, making it an ideal base for exploring the local culture. A popular attraction in the area is the Mahaiwe Performing Arts Centre, which hosts a range of live performances and events, adding to the vibrant setting of downtown.Another appealing neighbourhood is the surrounding countryside, which provides a more tranquil experience. Here, visitors can enjoy the natural beauty of the Berkshires, with opportunities for hiking and outdoor activities just a short drive away. Additionally, the Norman Rockwell Museum is nearby, celebrating the works of the famed illustrator and providing insight into American art and culture.In terms of properties, the downtown area features a range of options, from quaint inns to modern holiday rentals, suiting various preferences and budgets. The countryside offers charming cottages and homes, great for those seeking a peaceful retreat while still being close to the attractions of Great Barrington.
Where are the best Great Barrington ski resort rentals?
For the best ski resort rentals in Great Barrington, visitors should focus on the areas around Butternut Ski Area, which is just a short drive from the town centre. The nearby neighbourhoods of Great Barrington itself and the quaint village of Housatonic offer a range of holiday rentals, including cosy cabins and spacious chalets, ideal for families or groups looking to enjoy a winter getaway.Many properties in these locations come equipped with amenities such as full kitchens, fireplaces, and comfortable living spaces to unwind after a day on the slopes. Some rentals may also feature outdoor decks or hot tubs, great for soaking in after an exhilarating day of skiing.In addition to skiing, Great Barrington boasts a vibrant arts scene, with local galleries and theatres contributing to its charm. The town is home to a variety of restaurants and shops, making it convenient for travellers to explore the local culture and cuisine. Properties in the heart of Great Barrington often allow easy access to these attractions, enhancing the overall experience.
What is the most popular type of holiday rental accomodation in Great Barrington?
In Great Barrington, holiday houses are the most prevalent type of holiday rental, with around 336 available throughout the area. These properties typically feature spacious layouts with multiple bedrooms, fully equipped kitchens, and outdoor spaces for relaxing. Many of them are situated near the scenic attractions of the Berkshires, providing easy access to hiking trails and local parks. Additionally, there are about 48 cottages that offer a charming, rustic experience, complete with cosy interiors and often a fireplace. For those seeking a more compact option, around 20 apartments are available, ideal for couples or solo travellers, featuring essential amenities and convenient locations close to shops and restaurants. There are also several condos that provide a blend of comfort and modern living, often within well-maintained complexes.
Are there any family house rentals in Great Barrington?
In Great Barrington, there are a variety of family-friendly house rentals available, with around 82 options throughout the area. This charming town in the Berkshires offers a beautiful backdrop for family holidays, with properties situated in neighbourhoods that provide both comfort and convenience. Many homes feature spacious living rooms, fully equipped kitchens, and outdoor spaces where families can gather and enjoy the fresh air.Visitors will find amenities such as Wi-Fi, laundry facilities, and sometimes even game rooms or private gardens. Proximity to attractions like the picturesque Lake Mansfield, which is great for swimming and picnicking, as well as the vibrant downtown area filled with shops and restaurants, ensures that there are plenty of activities for everyone.
Can I rent a holiday home with a pool or hot tub in Great Barrington?
In Great Barrington, there are plenty of holiday homes available for rent that feature pools and hot tubs, with around 21 options to choose from. This charming town in the Berkshires is known for its stunning natural scenery and vibrant cultural scene. Many of the properties come equipped with private pools and hot tubs, providing a ideal setting for relaxation after a day of exploring.Travellers can expect amenities such as spacious outdoor areas, fully equipped kitchens, and comfortable living spaces, ideal for families or groups. Some rentals may also include features like fire pits, barbecue grills, and easy access to hiking trails, allowing guests to fully immerse themselves in the outdoors.
Are there pet-friendly house rentals in Great Barrington?
In Great Barrington, there are numerous pet-friendly house rentals available, making it an excellent choice for travellers with furry companions. The area offers a charming mix of holiday homes that typically feature modern amenities such as fully equipped kitchens, spacious living areas, and outdoor spaces for pets to enjoy. Many rentals also provide additional comforts like fireplaces, Wi-Fi, and laundry facilities, ensuring a pleasant stay.The neighbourhood is surrounded by natural beauty, with easy access to various parks and outdoor activities. Nearby, visitors can explore the scenic paths of the Housatonic River Walk or venture into the vast landscapes of the Berkshire Mountains, where hiking trails are abundant and pet-friendly. Additionally, the town is home to pet-friendly cafes and shops, ideal for those travelling with pets.
Are there any remote work holiday rentals in Great Barrington?
In Great Barrington, Massachusetts, there are numerous remote work holiday rentals available, with around 424 options to choose from. This charming town in the Berkshires offers a blend of natural beauty and a vibrant cultural scene, making it an ideal setting for those looking to work remotely. Many of the properties feature essential amenities such as free Wi-Fi, dedicated workspaces, and comfortable living areas, allowing for a productive work environment.Travellers can expect a variety of accommodations, including spacious homes and cosy cabins, often equipped with conveniences like full kitchens and outdoor spaces, superb for taking breaks amidst the stunning surroundings. The town's proximity to outdoor activities, including hiking and skiing in the nearby mountains, adds to its appeal for remote workers seeking a balance between work and leisure. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Great Barrington?
In Great Barrington, popular rental amenities include kitchens, which allow guests to prepare their own meals, and outdoor spaces such as decks or patios, great for enjoying the scenic views of the Berkshires. Many properties also feature fireplaces, adding a cosy touch, especially during the colder months. Onsite parking is commonly available, making it convenient for those travelling by car. Additionally, travellers can expect coffee and tea makers in their rentals, ensuring a warm beverage is always at hand to start the day.
When is the best time to visit Great Barrington for a holiday rental?
The best time to visit Great Barrington for a holiday rental is during the peak season from June to August, with July being particularly popular among tourists. This vibrant period offers an array of outdoor activities, including hiking in the beautiful Berkshire Mountains and exploring local art galleries and shops. The warm summer weather, with temperatures typically ranging from 15 to 30 degrees Celsius, allows for comfortable sightseeing and enjoying the stunning natural surroundings.During these summer months, you'll find a lively option filled with festivals and events, making it an ideal time for travellers. The picturesque town comes alive with outdoor concerts, farmers' markets, and opportunities to enjoy the local cuisine.For those looking for a more budget-friendly experience, consider visiting in November. This quieter month showcases the charm of Great Barrington as the autumn colours linger, providing a beautiful backdrop for leisurely walks and exploration of the area's quaint streets and local attractions without the crowds.Ultimately, your choice of when to visit Great Barrington will depend on whether you prefer the energetic vibe of the summer months or a more tranquil experience in the fall.
What are the top attractions in Great Barrington?
In Great Barrington, visitors can enjoy a charming mix of outdoor activities and cultural experiences. The downtown area is vibrant, featuring unique shops, galleries, and eateries that reflect the local community's artistic flair. A highlight is the Mahaiwe Performing Arts Centre, which hosts a variety of live performances and film screenings.For nature enthusiasts, the nearby Monument Mountain offers hiking trails with stunning views of the Berkshires, making it a popular spot for both locals and visitors. The Appalachian Trail also runs through the region, providing ample opportunities for hiking and exploring the natural beauty of the area.Additionally, the picturesque Lake Mansfield is superb for swimming, picnicking, and enjoying the serene surroundings.
Are all fees included in the Great Barrington holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Great Barrington holiday homes with parking?
Stayz offers a wide selection of holiday homes in Great Barrington with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Great Barrington holiday homes?
You can find great discounts on holiday homes in Great Barrington on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Great Barrington holiday home booking on Stayz?
To find Great Barrington holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Great Barrington?
A long-stay holiday home in Great Barrington is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Great Barrington holiday home?
Book your Great Barrington holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Great Barrington?
Prices for holiday homes in Great Barrington vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Great Barrington to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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