Hancock holiday homes

We found 263 holiday rentals — enter your dates for availability
Discover a selection of 30 apartments, 45 flats and other holiday rentals in Hancock that are perfect for your trip. Whether you're going on holiday with family or friends, holiday rentals have the amenities that you expect for your stay, such as air conditioning and Wi-Fi. At the end of the day, you'll find a property to rent for everyone's needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts – Hancock

Showing deals for:11 Dec - 18 Dec

Workstation with a view!
view from the 2nd bedroom
Open plan dining area with water views and access to the sunroom
View from the lawn by the water
Exceptional
(65 reviews)

Lake Front Home in Heart of the Berkshires Near Jiminy Peak

Pittsfield

8% off
NZ$8,435
for 7 nights, 1 home
NZ$1,205 per night
includes taxes & fees
Lake Front Home in Heart of the Berkshires Near Jiminy Peak
Dining
Terrace/patio
Private kitchen
Living area
Exceptional
(20 reviews)

Family-friendly, private three bedroom cottage in the beautiful Berkshires

Williamstown

12% off
NZ$5,103
for 7 nights, 1 cottage
NZ$729 per night
includes taxes & fees
Family-friendly, private three bedroom cottage in the beautiful Berkshires
Interior
Living area
Interior
Exterior detail
Exceptional
(35 reviews)

Renovated Pittsfield Colonial by Evergreen Home

Pittsfield

11% off
NZ$7,280
for 7 nights, 1 home
NZ$1,040 per night
includes taxes & fees
Renovated Pittsfield Colonial by Evergreen Home
Front Staircase
Fully screened porch!
Dining Room w/ Doors to Screened Porch Dining Area
Reading nook with natural lighting
Exceptional
(8 reviews)

Berkshires Colonial on 2 Acres by Evergreen Home

Richmond

11% off
NZ$5,304
for 7 nights, 1 home
NZ$758 per night
includes taxes & fees
Berkshires Colonial on 2 Acres by Evergreen Home
Property grounds
Outdoor dining
Renovated kitchen
Interior
Exceptional
(39 reviews)

Large, family-friendly farmhouse located in the beautiful Berkshires

Williamstown

20% off
NZ$6,713
for 7 nights, 1 home
NZ$959 per night
includes taxes & fees
Large, family-friendly farmhouse located in the beautiful Berkshires
Entrance into house with wood burning stove to right and staircase
View from 2nd floor balcony (after leaves have fallen)
Smart TV in Downstairs room with view of entrance to house and doors to room
Large Smart HDTV with electric fireplace in living room, showing dining room
Exceptional
(73 reviews)

2400sf Secluded Family Mountain House 16 Acres- 2 min to Jiminy Peak- near Lenox

Williamstown

12% off
NZ$3,964
for 7 nights, 1 home
NZ$566 per night
includes taxes & fees
2400sf Secluded Family Mountain House 16 Acres- 2 min to Jiminy Peak- near Lenox
Country Inn heated pool & outdoor hot tub is open all year. Towels are provided
Spring at Jiminy Peak 2019
View from ski room to trail thru woods to Grouse Run - fantastic location!!
Night skiing view from living room
Exceptional
(46 reviews)

Perfect family getaway spot! Free standing private 4 BR home on Jiminy Peak.

Hancock

12% off
NZ$9,675
for 7 nights, 1 home
NZ$1,382 per night
includes taxes & fees
Perfect family getaway spot! Free standing private 4 BR home on Jiminy Peak.
Interior
BBQ dinner not included :)
50 inch TV for family movie night!
Interior
Exceptional
(10 reviews)

Family Fun in The Berkshires at Beautiful Hygge House

Richmond

8% off
NZ$6,278
for 7 nights, 1 home
NZ$897 per night
includes taxes & fees
Family Fun in The Berkshires at Beautiful Hygge House
Beaver Pond Pool/clubhouse
new backyard table
another view of same bedroom as well as makeup table
another view of kitchen
Exceptional
(17 reviews)

3 BR+ 4level WINTER SKI RENTAL LOOKING 4 SEASONAL RENTER 1 MILE OFF OF JIMINEY

Lanesborough

22% off
NZ$6,253
for 7 nights, 1 apartment
NZ$893 per night
includes taxes & fees
3 BR+ 4level WINTER SKI RENTAL LOOKING 4 SEASONAL RENTER 1 MILE OFF OF JIMINEY
Backside of barn
Interior
Heidi visiting Jane's 18th Century Studio
Interior
Exceptional
(99 reviews)

19th c. Barn in the Berkshires

Cheshire

8% off
NZ$4,977
for 7 nights, 1 home
NZ$711 per night
includes taxes & fees
19th c. Barn in the Berkshires
view into large bathroom
Dining
Living Room, wow!
Interior
Exceptional
(17 reviews)

New listing! Dublinshire Farm #3: Stunning grand apt in lovely country barn.

Richmond

17% off
NZ$4,267
for 7 nights, 1 apartment
NZ$610 per night
includes taxes & fees
New listing! Dublinshire Farm #3: Stunning grand apt in lovely country barn.
Bathroom
Interior
Interior
Property grounds
Exceptional
(6 reviews)

Historic Stone Church in The Berkshires

Lanesborough

8% off
NZ$4,786
for 7 nights, 1 home
NZ$684 per night
includes taxes & fees
Historic Stone Church in The Berkshires

  • 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

Why people love visiting cosy Hancock

The area's museums and entertainment are just some of the reasons to come on holiday to Hancock. This city's skiing, mountain views and hiking draw many visitors. A holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Activities and attractions in and around Hancock

Are you hoping to find attractions to see during your stay? You'll be sure to enjoy Hancock for its skiing and hiking. Venture out of your cosy holiday rental and experience everything that makes Hancock a fun place to get away to. Here are some of the top attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Jiminy Peak Mountain Resort (0.7 mi / 1.2 km)
  • Waubeeka Golf Links (7.9 mi / 12.6 km)
  • Bousquet Ski Area (9.2 mi / 14.7 km)
  • Wyndhurst Golf & Club (14.2 mi / 22.8 km)
  • Zema's Nursery (5.4 mi / 8.6 km)
  • Balderdash Cellars (9.5 mi / 15.3 km)

Exploring the natural landscape of Hancock

Whether you're an active traveller or just want to appreciate the scenery, Hancock is a great place to get outside. These are some of the area's most stunning sights, all within 30 miles (48.2 km) of the city centre:

  • Mount Greylock State Reservation Visitor Center (3.5 mi / 5.7 km)
  • Pontoosuc Lake (3.9 mi / 6.3 km)
  • Brodie Mountain (6.4 mi / 10.2 km)
  • Mount Greylock State Reservation (8.3 mi / 13.3 km)
  • Mount Greylock (8.5 mi / 13.8 km)
  • Wahconah Falls State Park (9.5 mi / 15.3 km)

Seasonal weather averages in Hancock

Travellers enjoy Hancock for its skiing. If you've planned your trip around snowy activities, consider visiting in January, March, February or November, when snowfall averages 18 cm and temperatures average -3°C.

How to get to and around Hancock

The nearest airport is in Pittsfield, MA (PSF-Pittsfield Municipal), located 8.5 mi (13.6 km) from the city centre. 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 28.1 mi (45.2 km) away.

Frequently asked questions

What is the best area to stay in Hancock when booking a holiday rental?
When considering a holiday rental in Hancock, Massachusetts, the area surrounding the picturesque Berkshires is highly recommended. This charming region is renowned for its stunning natural beauty, making it an ideal backdrop for a relaxing getaway.One of the top attractions in the vicinity is the Jiminy Peak Mountain Resort, which offers a variety of year-round activities, including skiing in the winter and mountain biking in the summer. Just a short drive away, you can also explore the scenic landscapes of the Appalachian Trail, great for hiking enthusiasts and nature lovers alike.In terms of holiday rentals, the Hancock area boasts a selection of properties, ranging from cosy cabins to spacious lodges, suiting different tastes and group sizes. Staying here not only provides easy access to outdoor activities but also allows you to enjoy the tranquil atmosphere and stunning views that define this beautiful part of Massachusetts.
Where are the best Hancock ski resort rentals?
For the best ski resort rentals near Hancock, Massachusetts, consider looking in the nearby areas of Jiminy Peak and the charming town of Hancock itself. Jiminy Peak is a popular ski destination just a short drive away, offering a range of accommodation options from ski-in/ski-out condos to cosy lodges. Many of these properties come with amenities such as heated pools, fitness centres, and communal areas with fireplaces, great for relaxing after a day on the slopes.In the town of Hancock, you can find quaint cabins and rustic homes that provide a peaceful retreat with easy access to skiing. These rentals often feature amenities like full kitchens, outdoor decks, and some even have hot tubs, allowing guests to unwind in comfort. Additionally, the scenic surroundings offer opportunities for hiking and snowshoeing during the winter months.The area is also close to local dining options and shops, adding convenience for those looking to explore beyond the slopes.
What is the most popular type of holiday rental accomodation in Hancock?
In Hancock, condos are the most popular type of holiday rental, with around 124 available in the area. These condos are often situated in picturesque settings, providing easy access to the beautiful natural surroundings and local attractions. Most units feature modern amenities, including fully equipped kitchens, comfortable living spaces, and some even have balconies or patios for enjoying the serene views.Apartments are also a significant option, with about 96 available, offering a similar blend of comfort and convenience. These typically include amenities such as open-plan living areas, kitchen facilities, and access to communal spaces. For those seeking more space, around 52 holiday houses offer larger accommodations, often featuring multiple bedrooms, private outdoor areas, and amenities like barbecues, making them ideal for families or groups.
Are there any family house rentals in Hancock?
In Hancock, Massachusetts, there are numerous family-friendly holiday rentals available, with around 48 options to choose from. Visitors will find a range of properties located in this picturesque region, which is known for its stunning natural surroundings and outdoor activities. Many homes in the area come equipped with spacious living areas, full kitchens for preparing family meals, and outdoor spaces superb for children to play. Amenities such as Wi-Fi and heating ensure a comfortable stay, regardless of the season.This locale is ideally situated near the scenic Berkshires, providing easy access to hiking trails, lakes, and cultural attractions. Families can enjoy exploring local attractions like the Jiminy Peak Mountain Resort, which offers summer and winter activities, or the nearby town of Williamstown, renowned for its museums and galleries.
Can I rent a holiday home with a pool or hot tub in Hancock?
In Hancock, Massachusetts, there are plenty of holiday homes available for rent that feature pools and hot tubs, with approximately 59 options to choose from. This picturesque area is located in the Berkshires, offering a tranquil retreat surrounded by nature. Many of the properties come equipped with private pools, hot tubs, and spacious outdoor areas, ideal for relaxation after a day of exploring the stunning landscapes.Travellers can expect amenities such as fully equipped kitchens, comfortable living spaces, and sometimes even game rooms or home theatres, superb for family gatherings or group getaways. The nearby attractions, including hiking trails, lakes, and cultural sites, provide plenty of opportunities for adventure and leisure.
Are there pet-friendly house rentals in Hancock?
In Hancock, Massachusetts, there are several pet-friendly house rentals available, making it a great choice for travellers wanting to bring their furry companions along. Many of these holiday homes offer amenities such as spacious backyards, fully equipped kitchens, and comfortable living areas, ideal for families or groups.The area itself is surrounded by beautiful natural landscapes, including the nearby Pittsfield State Forest, which provides ample opportunities for hiking and exploring with pets. Additionally, the scenic views of the Berkshires enhance the overall experience, allowing guests to enjoy both relaxation and outdoor recreation during their stay.
Are there any remote work holiday rentals in Hancock?
In Hancock, Massachusetts, there are numerous remote work holiday rentals available, with around 236 options for those looking to combine work and leisure. Many of these properties are well-equipped for remote work, featuring amenities such as free Wi-Fi, dedicated desks, and comfortable desk chairs to ensure productivity during your stay.Travellers can expect a variety of accommodations, from cosy cabins to spacious homes, often set in serene surroundings conducive to focus and relaxation. The area is also great for outdoor enthusiasts, with nearby attractions like Jiminy Peak Mountain Resort, offering opportunities for hiking and skiing, depending on the season. To help narrow your search, insert your dates and apply the "WiFi" filter on Bookabach.
What are popular rental amenities in Hancock?
In Hancock, popular rental amenities include kitchens, which allow guests to prepare their own meals, and fitness facilities for those looking to maintain their workout routines while on holiday. Additionally, onsite parking is available, making it convenient for travellers with vehicles. Many rentals also feature sofa beds, providing extra sleeping space for larger groups or families. Coffee and tea makers are common as well, ensuring guests can enjoy a warm beverage at their leisure.
When is the best time to visit Hancock for a holiday rental?
The peak season for visiting Hancock runs from July to September, making it the most popular time for holiday rentals in this picturesque Massachusetts town. During these summer months, outdoor enthusiasts flock to the area to enjoy a myriad of activities, including hiking in the nearby Berkshires, swimming in serene lakes, and exploring charming local attractions.July, in particular, stands out as the prime month, offering warm temperatures that typically range from 15 to 30 degrees Celsius. This is great for those seeking comfortable weather to fully immerse themselves in outdoor adventures and sightseeing. You'll find a vibrant and lively option, with numerous events and festivals that celebrate the local culture, ensuring there's always something exciting to experience.For travellers looking for a more budget-friendly option, November presents a wonderful opportunity to visit Hancock. While this month falls outside the peak season, it offers a peaceful ambiance with stunning autumn colours. The crisp air and beautiful foliage create a great backdrop for leisurely walks and scenic drives, allowing you to appreciate the natural beauty without the summer crowds.Ultimately, the best time to visit Hancock for a holiday rental hinges on your preferences. If you thrive on the energy of the bustling summer season, July and August are ideal.
What are the top attractions in Hancock?
In Hancock, Massachusetts, visitors can enjoy a range of attractions that highlight the area's natural beauty and outdoor recreation. The Jiminy Peak Mountain Resort is a key attraction, offering skiing and snowboarding in the winter, along with hiking and mountain biking trails during the warmer months. The resort is located in the nearby area and provides various family-friendly activities.For those interested in cultural experiences, the Hancock Shaker Village is a popular site where guests can learn about the Shaker community's history and view preserved buildings set amidst picturesque landscapes. The village also features beautiful gardens and exhibits that provide insight into Shaker craftsmanship and lifestyle.Nature enthusiasts can explore the serene surroundings of the Berkshire Mountains, with opportunities for hiking, fishing, and enjoying the picturesque scenery. Nearby, the Appalachian Trail runs through the region, offering extensive trails for both novice and experienced hikers.
Are all fees included in the Hancock holiday homes prices shown on Bookabach?
Bookabach 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 Hancock holiday homes with parking?
Bookabach offers a wide selection of holiday homes in Hancock 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 Hancock holiday homes?
You can find great discounts on holiday homes in Hancock on Bookabach, 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 Hancock holiday home booking on Bookabach?
To find Hancock holiday rentals with free cancellation, just use Bookabach'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, Bookabach makes it easy to book with confidence.
Can I find long-stay holiday homes in Hancock?
A long-stay holiday home in Hancock 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 Bookabach?
Bookabach'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 Hancock holiday home?
Book your Hancock 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 Bookabach booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Hancock?
Prices for holiday homes in Hancock 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. Bookabach offers something for every taste and budget, from affordable homes in Hancock to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach 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 Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, 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 Bookabach as a host?
Joining Bookabach 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, Bookabach 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 Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

More holiday ideas