Housatonic holiday rentals

We found 534 holiday rentals — enter your dates for availability
Discover a selection of 11 homes and other holiday rentals in Housatonic that are perfect for your trip. Whether you're travelling with your children and pets, with friends or just your children, holiday homes have the amenities that you need and want for your stay, which might include parking and a fireplace. You're sure to find a property to rent for everyone's needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts – Housatonic

Showing deals for:11 Dec - 18 Dec

Open kitchen to great room, wonderful for cooking and entertaining
The great room with wonderful water views and working fireplace
Dining
Hot tub overlooking the lake
Exceptional
(86 reviews)

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

Lee

8% off
AU$6,369
for 7 nights, 1 home
AU$910 per night
includes taxes & fees
Spectacular setting on your own private lake close to it all!
Exterior
Private kitchen
Living area
Terrace/patio
Exceptional
(10 reviews)

Beautiful House in the Woods: Huge Yard, Hot Tub

Great Barrington

8% off
AU$5,117
for 7 nights, 1 home
AU$731 per night
includes taxes & fees
Beautiful House in the Woods: Huge Yard, Hot Tub
Property grounds
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

11% off
AU$5,210
for 7 nights, 1 home
AU$744 per night
includes taxes & fees
Sophisticated Lenox Retreat by Evergreen Home
Interior
Terrace/patio
Interior
Exterior
Exceptional
(102 reviews)

Waterfront Cottage 10 Min From Great Barrington

New Marlborough

8% off
AU$3,367
for 7 nights, 1 cottage
AU$481 per night
includes taxes & fees
Waterfront Cottage 10 Min From Great Barrington
Pool
Terrace/patio
Property grounds
Games room
Exceptional
(5 reviews)

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

Hillsdale

7% off
AU$7,697
for 7 nights, 1 home
AU$1,100 per night
includes taxes & fees
Hillsdale Retreat Farmhouse with Pool, Firepit, Hot Tub and Game Room
Exterior
Interior
Living area
Property grounds
Exceptional
(7 reviews)

Serene rustic cabin in the Berkshires!

West Stockbridge

8% off
AU$3,712
for 7 nights, 1 cabin
AU$530 per night
includes taxes & fees
Serene rustic cabin in the Berkshires!
A mudroom off the back leads to the large wooden deck
You will love dining and working in this rich and colorful room
Outdoor dining and grill on the 16' x 20' wooden deck.
The living room flows into the dining room.
Exceptional
(42 reviews)

An In-Town Beauty with Late Checkout

Great Barrington

8% off
AU$4,796
for 7 nights, 1 home
AU$685 per night
includes taxes & fees
An In-Town Beauty with Late Checkout
Pool
Interior
Living area
Interior
Exceptional
(40 reviews)

A Fun Farmhouse Near Ski Butternut

Great Barrington

8% off
AU$4,327
for 7 nights, 1 home
AU$618 per night
includes taxes & fees
A Fun Farmhouse Near Ski Butternut
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
(7 reviews)

Idyllic Retreat; Hot Tub/Sauna by Evergreen Home

Great Barrington

11% off
AU$7,590
for 7 nights, 1 home
AU$1,084 per night
includes taxes & fees
Idyllic Retreat; Hot Tub/Sauna by Evergreen Home
Private kitchen
Ultimate Relaxation! The hot tub will be warm and waiting for your arrival
Welcome Home!
Open floor plan, natural light in a stylish space
Exceptional
(9 reviews)

Best of the Berkshires + Hot Tub by Evergreen Home

Great Barrington

11% off
AU$3,950
for 7 nights, 1 home
AU$564 per night
includes taxes & fees
Best of the Berkshires + Hot Tub by Evergreen Home
Screened in porch
Terrace/patio
Property grounds
Dining room with butcher block table
Exceptional
(103 reviews)

Vacation in a Berkshire Farmhouse

West Stockbridge

8% off
AU$3,795
for 7 nights, 1 home
AU$542 per night
includes taxes & fees
Vacation in a Berkshire Farmhouse
Great room river view
River view from window
Blue House side entry from driveway
dining area
Exceptional
(44 reviews)

Renovated Colonial on the River! Fantastic Views

Stockbridge

8% off
AU$3,470
for 7 nights, 1 home
AU$496 per night
includes taxes & fees
Renovated Colonial on the River! Fantastic Views
Living Room
Great Barrington Castle house
Front view of home
Great Barrington Castle
Exceptional
(51 reviews)

NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE

Great Barrington

8% off
AU$4,856
for 7 nights, 1 home
AU$694 per night
includes taxes & fees
NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE
Never miss a thing with this expansive open concept kitchen and living room
After a hard day on the trails or a long day on the town, relax in this oasis
Truly nestled on 5+ acres and LESS than 0.8miles to downtown Great Barrington
Enjoy a beautiful crisp night under the lights
Exceptional
(28 reviews)

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

Great Barrington

6% off
AU$5,560
for 7 nights, 1 home
AU$794 per night
includes taxes & fees
Adventure Ready Ranch Sleeps 10 & 0.7 mi to GB Main St. Wi-Fi + HOT TUB.
Property grounds
Interior
Kitchen
Kitchen
Excellent
(14 reviews)

Canary Lodge - Berkshires Mountain Retreat - 6 Guests

West Stockbridge

8% off
AU$5,311
for 7 nights, 1 home
AU$759 per night
includes taxes & fees
Canary Lodge - Berkshires Mountain Retreat - 6 Guests
Living area
Living area
Living area
Terrace/patio
Exceptional
(8 reviews)

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

Chatham

7% off
AU$3,953
for 7 nights, 1 home
AU$565 per night
includes taxes & fees
Modern Log Chalet - 10 acres, views, and a pond!
Private kitchen
Room
Outdoor dining
Dining
Exceptional
(33 reviews)

The Hideaway: Berkshire Home - Village of Egremont

egremont

16% off
AU$3,269
for 7 nights, 1 home
AU$467 per night
includes taxes & fees
The Hideaway: Berkshire Home - Village of Egremont
Kitchen
Living Room
Front Gardens
Property grounds
Exceptional
(27 reviews)

Secluded Family Home in Serene Stockbridge Woods

Stockbridge

8% off
AU$4,557
for 7 nights, 1 home
AU$651 per night
includes taxes & fees
Secluded Family Home in Serene Stockbridge Woods
Living area
Interior
Room
Private kitchen
Exceptional
(60 reviews)

Amazing 2-bedroom apartment sunny and quiet in Great Barrington

Great Barrington

12% off
AU$1,626
for 7 nights, 1 apartment
AU$232 per night
includes taxes & fees
Amazing 2-bedroom apartment sunny and quiet in Great Barrington
Private kitchen
Outdoor dining
Dining
Exterior detail
Exceptional
(11 reviews)

Berkshires Getaway Walk to Distillery - No Pet Fee!

Sheffield

8% off
AU$3,842
for 7 nights, 1 home
AU$549 per night
includes taxes & fees
Berkshires Getaway Walk to Distillery - No Pet Fee!
Front view of house
Dining room
living room
Back yard morning.
Exceptional
(37 reviews)

Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT

Egremont

8% off
AU$4,077
for 7 nights, 1 home
AU$582 per night
includes taxes & fees
Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT
Exterior
Outdoor dining
Private kitchen
Private kitchen
Exceptional
(13 reviews)

Charming Berkshire Farmhouse: Your Cozy Retreat Awaits!

Monterey

8% off
AU$3,841
for 7 nights, 1 home
AU$549 per night
includes taxes & fees
Charming Berkshire Farmhouse: Your Cozy Retreat Awaits!
Our hanging egg chair is the most popular seat in the house #Instagram yourself!
Private entry is with the parking in the rear of the house.
Our combination living/dining room is a great size for four people.
Exterior
Exceptional
(24 reviews)

New Reno, New Everything! Crisp and Clean 2 Bedroom in Stockbridge Center.

Stockbridge

24% off
AU$2,594
for 7 nights, 1 apartment
AU$371 per night
includes taxes & fees
New Reno, New Everything! Crisp and Clean 2 Bedroom in Stockbridge Center.
Exterior
Property grounds
Interior
Interior
Wonderful
(6 reviews)

The Serendipity Spot

Great Barrington

7% off
AU$1,945
for 7 nights, 1 apartment
AU$278 per night
includes taxes & fees
The Serendipity Spot

  • 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

Find the perfect holiday rental for your Housatonic getaway

Learn about the unique charm of Housatonic with a stay in a holiday home rental. This city has something for everyone. If you need more space to accommodate a family holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.

Activities and attractions in Housatonic

Do you want to discover attractions to see in the area? Venture out of your holiday home and experience everything that Housatonic has to offer. Here are some of the major attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Ski Butternut (6.2 mi / 10 km)
  • Wyndhurst Golf & Club (7.7 mi / 12.4 km)
  • Catamount Ski Area (8.6 mi / 13.9 km)
  • Bousquet Ski Area (11.5 mi / 18.5 km)
  • Otis Ridge (14.7 mi / 23.7 km)
  • Furnace Brook Winery at Hilltop Orchards (9.1 mi / 14.6 km)

Exploring the natural landscape of Housatonic

Whether you're looking for fun outdoor activities or just want to take in the scenery, Housatonic is a great place to spend some time outside. These are a few of the area's most stunning sights, all within 30 miles (48.2 km) of the city centre:

  • Berkshire Botanical Garden (3.2 mi / 5.1 km)
  • Naumkeag Museum (3.4 mi / 5.5 km)
  • Lake Mansfield Park (4.1 mi / 6.6 km)
  • Housatonic River (4.6 mi / 7.5 km)
  • Housatonic River Walk (4.6 mi / 7.5 km)
  • Stockbridge Bowl (5.7 mi / 9.1 km)

Travelling to and around Housatonic

Fly into Pittsfield, MA (PSF-Pittsfield Municipal), the closest airport, located 11.9 mi (19.1 km) from the city centre. If you can't find a flight that works for your travel itinerary, you might consider flying into Hudson, NY (HCC-Columbia County), which is 17.5 mi (28.1 km) away.

Frequently asked questions

What is the best area to stay in Housatonic when booking a holiday rental?
When considering a holiday rental in Housatonic, Massachusetts, the area around the town centre is a great choice. This charming neighbourhood offers a delightful mix of local culture and scenic beauty, making it an inviting spot for visitors. You'll find a variety of properties available, ranging from quaint cottages to more spacious homes, allowing for flexibility depending on your group size and preferences.One of the top attractions nearby is the picturesque Housatonic River, where you can enjoy leisurely walks along the banks or partake in activities such as kayaking and fishing. Additionally, the town is conveniently located close to the stunning Berkshire Mountains, providing ample opportunities for hiking and outdoor adventures.Another point of interest is the nearby Norman Rockwell Museum, which celebrates the life and art of the renowned American painter, making it a must-visit for art enthusiasts.
Where are the best Housatonic ski resort rentals?
For the best ski resort rentals near Housatonic, Massachusetts, travellers should consider the nearby town of Great Barrington, which is a short drive from the slopes of Butternut Basin Ski Area. In Great Barrington, visitors can find a variety of charming properties, including well-appointed cabins and modern apartments. Many of these rentals come with amenities such as fully equipped kitchens, comfortable living areas, and some even feature hot tubs or fireplaces, superb for warming up after a day on the mountain.Also, the region boasts beautiful views of the Berkshire hills, making it an appealing choice for those looking to enjoy both skiing and the scenic landscape. Properties in the downtown area of Great Barrington offer easy access to local shops, cafes, and restaurants, providing a vibrant après-ski scene. Further afield, the quaint village of Stockbridge offers additional rental options, often in historic homes that exude character, with amenities that may include outdoor spaces and proximity to cultural attractions such as the Norman Rockwell Museum.
What is the most popular type of holiday rental accomodation in Housatonic?
In Housatonic, holiday houses are the most popular type of holiday rental, with about 33 available in the area. These properties typically offer spacious living arrangements, often featuring multiple bedrooms, fully equipped kitchens, and outdoor areas for relaxation, making them ideal for families or groups. Additionally, there are several charming cottages scattered throughout Housatonic, providing a quaint and cosy atmosphere for travellers looking for a more intimate stay.
Are there any family house rentals in Housatonic?
In Housatonic, Massachusetts, there are numerous family-friendly house rentals available, with around 11 options to choose from. This charming area is surrounded by scenic landscapes and offers a variety of activities for families. Properties often include spacious living rooms, fully equipped kitchens for preparing family meals, and outdoor areas where children can enjoy themselves. Many homes also feature essential amenities such as Wi-Fi and laundry facilities, ensuring a convenient stay.Visitors will appreciate the proximity to local attractions, including the picturesque Berkshire Mountains, which provide opportunities for hiking and outdoor adventures. Nearby, the town of Great Barrington offers vibrant shops, restaurants, and cultural experiences, making it easy for families to explore the local scene.
Can I rent a holiday home with a pool or hot tub in Housatonic?
In Housatonic, there are several holiday homes available for rent that feature pools or hot tubs, making it a delightful choice for those seeking relaxation. This charming town, located in the picturesque Berkshires, offers a range of properties, from modern villas to rustic cottages, many of which provide outdoor pools and hot tubs, ideal for unwinding after a day of exploring the scenic surroundings.Travellers can expect amenities such as fully equipped kitchens, spacious living areas, and outdoor entertainment spaces, great for family gatherings or group retreats. The serene natural landscape surrounding Housatonic enhances the experience, with opportunities for hiking, visiting local attractions, and enjoying the vibrant arts scene in nearby towns.
Are there pet-friendly house rentals in Housatonic?
In Housatonic, Massachusetts, there are several pet-friendly house rentals available, making it a suitable destination for travellers bringing their furry companions. Many of these holiday homes come equipped with amenities such as spacious outdoor areas, fully furnished kitchens, and comfortable living spaces, allowing guests to enjoy a homely atmosphere during their stay.The town's charming surroundings offer opportunities for outdoor activities with pets, including nearby walking trails and parks that welcome animals. The scenic beauty of the Berkshires adds to the appeal, with options for hiking and exploring nature, superb for those looking to enjoy the great outdoors alongside their pets.
Are there any remote work holiday rentals in Housatonic?
In Housatonic, Massachusetts, there are a variety of remote work-friendly holiday rentals available, with around 33 options to choose from. This charming town, situated in the scenic Berkshires, provides a peaceful environment ideal for those looking to blend work and leisure. Many of the properties come equipped with essential amenities for remote work, including desks and reliable Wi-Fi, ensuring that guests can stay productive during their stay.The area is known for its beautiful outdoor spaces, with nearby attractions such as the Housatonic River and numerous hiking trails, offering opportunities to unwind after a day of work. Additionally, the town features local shops and eateries, adding convenience for those looking to explore the community while enjoying their remote working experience. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Housatonic?
In Housatonic, popular holiday rental amenities include well-equipped kitchens, which allow travellers to prepare their own meals and enjoy a homely dining experience. Many properties also feature onsite parking, making it convenient for guests who arrive by car. Outdoor spaces such as patios or porches provide a lovely setting for relaxation and enjoying the fresh air, while some rentals may include additional amenities like a blender for those looking to whip up smoothies or other drinks.
When is the best time to visit Housatonic for a holiday rental?
The most popular time to visit Housatonic is in January, when winter enthusiasts flock to this charming town for a variety of snow-based activities. During this month, you can indulge in skiing, snowboarding, and snowshoeing, all within a scenic landscape that transforms into a winter wonderland. The cold temperatures, typically ranging from -5 to 5 degrees Celsius, create a great backdrop for cosy evenings by the fire in your holiday rental.As you move into the peak season from March to May, Housatonic comes alive with the beauty of spring. This period is ideal for those who enjoy hiking and exploring the great outdoors, as the trails begin to thaw and wildflowers bloom. The pleasant weather makes it a fantastic time for sightseeing and enjoying local events, such as art fairs and farmers' markets.If you're looking for a more budget-friendly option, consider visiting in February. Although it's the low season, this month offers a unique charm with fewer crowds, allowing for a more intimate experience in this picturesque town. You can still enjoy winter activities, perhaps at a more leisurely pace, while taking in the serene surroundings.
What are the top attractions in Housatonic?
In Housatonic, Massachusetts, visitors can enjoy a variety of attractions that highlight the area's natural beauty and cultural charm. The nearby Housatonic River offers opportunities for fishing, kayaking, and scenic walks along its banks. The charming downtown area features quaint shops and eateries, great for a leisurely afternoon.A short drive away, the picturesque town of Great Barrington is known for its vibrant arts scene and hosts several events throughout the year, including the popular Great Barrington Farmers Market. Nature enthusiasts can explore the stunning landscapes of Monument Mountain, which provides hiking trails with breathtaking views of the surrounding Berkshires.For those interested in history, the nearby Bidwell House Museum presents a glimpse into the region's past with its beautifully preserved 18th-century home and engaging tours.
Are all fees included in the Housatonic 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 Housatonic holiday homes with parking?
Stayz offers a wide selection of holiday homes in Housatonic 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 Housatonic holiday homes?
You can find great discounts on holiday homes in Housatonic 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 Housatonic holiday home booking on Stayz?
To find Housatonic 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 Housatonic?
A long-stay holiday home in Housatonic 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 Housatonic holiday home?
Book your Housatonic 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 Housatonic?
Prices for holiday homes in Housatonic 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 Housatonic 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.