Cheshire holiday rentals

We found 315 holiday rentals — enter your dates for availability
Discover a selection of 5 homes and other holiday rentals in Cheshire that are perfect for your trip. Holiday homes provide the best amenities for your stay with friends, family or just your pet, such as parking and a TV. Whatever you're looking for, you'll find a property to rent to meet everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts – Cheshire

Showing deals for:25 Dec - 1 Jan

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

Lake Front Home in Heart of the Berkshires Near Jiminy Peak

Pittsfield

8% off
AU$7,977
for 7 nights, 1 home
AU$1,140 per night
includes taxes & fees
Lake Front Home in Heart of the Berkshires Near Jiminy Peak
Dining
Terrace/patio
Room
Living area
Exceptional
(20 reviews)

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

Williamstown

16% off
AU$4,310
for 7 nights, 1 cottage
AU$616 per night
includes taxes & fees
Family-friendly, private three bedroom cottage in the beautiful Berkshires
Interior
Living area
Interior
Outdoor dining
Exceptional
(35 reviews)

Renovated Pittsfield Colonial by Evergreen Home

Pittsfield

11% off
AU$6,409
for 7 nights, 1 home
AU$916 per night
includes taxes & fees
Renovated Pittsfield Colonial by Evergreen Home
Renovated kitchen
Outdoor dining
Dining
Interior
Exceptional
(39 reviews)

Large, family-friendly farmhouse located in the beautiful Berkshires

Williamstown

20% off
AU$5,791
for 7 nights, 1 home
AU$827 per night
includes taxes & fees
Large, family-friendly farmhouse located in the beautiful Berkshires
Smart TV in Downstairs room with view of entrance to house and doors to room
View from 2nd floor balcony (after leaves have fallen)
Large Smart HDTV with electric fireplace in living room, showing dining room
Entrance into house with wood burning stove to right and staircase
Exceptional
(73 reviews)

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

Williamstown

12% off
AU$4,116
for 7 nights, 1 home
AU$588 per night
includes taxes & fees
2400sf Secluded Family Mountain House 16 Acres- 2 min to Jiminy Peak- near Lenox
Private kitchen
Private kitchen
Living area
Room
Exceptional
(19 reviews)

Cozy Condo Near MASS MoCA

North Adams

12% off
AU$3,887
for 7 nights, 1 home
AU$555 per night
includes taxes & fees
Cozy Condo Near MASS MoCA
another view of same bedroom as well as makeup table
new backyard table
kitchen and laundry room area
another view of kitchen
Exceptional
(17 reviews)

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

Lanesborough

23% off
AU$5,025
for 7 nights, 1 apartment
AU$718 per night
includes taxes & fees
3 BR+ 4level WINTER SKI RENTAL LOOKING 4 SEASONAL RENTER 1 MILE OFF OF JIMINEY
Bathroom
Interior
Interior
Room
Exceptional
(6 reviews)

Historic Stone Church in The Berkshires

Lanesborough

8% off
AU$3,819
for 7 nights, 1 home
AU$546 per night
includes taxes & fees
Historic Stone Church in The Berkshires
King size bed in 2nd story primary bedroom
Living area
Interior
Interior
Very good
(5 reviews)

Walk to campus; open concept kitchen/living;nature trail at end of this quiet st

Williamstown

14% off
AU$2,909
for 7 nights, 1 home
AU$416 per night
includes taxes & fees
Walk to campus; open concept kitchen/living;nature trail at end of this quiet st

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Why people love visiting charming Cheshire

The lake and wildlife create a pretty picture of Cheshire. Well known for its skiing, hiking and restaurants, this romantic city won't disappoint. Whether you're planning a family holiday, romantic stay or trip with friends, holiday rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Activities and attractions in and around Cheshire

Are you hoping to discover attractions to visit during your stay? Venture out of your holiday home and experience everything that makes Cheshire a one-of-a-kind holiday spot. These are some of the top attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Jiminy Peak Mountain Resort (6.6 mi / 10.6 km)
  • Waubeeka Golf Links (7.6 mi / 12.3 km)
  • Bousquet Ski Area (11.8 mi / 18.9 km)
  • Berkshire East Ski Resort (15.2 mi / 24.5 km)
  • Wyndhurst Golf & Club (16 mi / 25.8 km)
  • Williams College Taconic Golf Course (10 mi / 16.1 km)

Exploring the natural landscape of Cheshire

Whether you're looking for fun outdoor activities or just want to appreciate the scenery, Cheshire is a great place to get outside. Here are a few of the area's most eye-catching features, all within 30 miles (48.2 km) of the city centre:

  • Mount Greylock State Reservation Visitor Center (2.6 mi / 4.2 km)
  • Mount Greylock (5.2 mi / 8.4 km)
  • Mount Greylock State Reservation (5.6 mi / 9 km)
  • Wahconah Falls State Park (5.7 mi / 9.2 km)
  • Pontoosuc Lake (6.3 mi / 10.2 km)
  • Brodie Mountain (6.5 mi / 10.5 km)

Transport to and around Cheshire

The nearest airport is in Pittsfield, MA (PSF-Pittsfield Municipal), located 11.5 mi (18.5 km) from the city centre. If you can't find a flight that's convenient for your trip, you could also fly into Hudson, NY (HCC-Columbia County), which is 33.6 mi (54 km) away.

Frequently asked questions

What is the best area to stay in Cheshire when booking a holiday rental?
When considering a holiday rental in Cheshire, Massachusetts, one of the most appealing areas to stay is near the serene surroundings of the Berkshire Mountains. This picturesque location offers a tranquil escape, great for those looking to unwind in nature. The neighbourhood is characterised by its charming rural atmosphere and proximity to outdoor activities.In this area, you will find a selection of properties that cater to various preferences, from cosy cabins to more spacious homes that can accommodate families or groups. There is a welcoming sense of community and a peaceful environment, making it an ideal choice for a relaxing getaway.Just a short distance away, visitors can explore the stunning landscapes of Mount Greylock State Reservation, which is famous for its scenic hiking trails and breathtaking views, particularly in the autumn when the foliage is at its finest. Additionally, the nearby town of Adams boasts the renowned Natural Bridge State Park, where you can marvel at the unique natural rock formation and enjoy a leisurely stroll through the park's serene surroundings.
Where are the best Cheshire ski resort rentals?
For skiing near Cheshire, Massachusetts, the closest ski resorts are located in the nearby towns of Hancock and Pittsfield. In Hancock, you can find a range of rental options that provide convenient access to Jiminy Peak, a popular ski area. Here, visitors can choose from cosy lodges and mountain cabins, many of which come equipped with amenities like full kitchens, fireplaces, and access to ski storage, making it easy to unwind after a day on the slopes.In Pittsfield, there are additional rental opportunities, including charming homes and apartments that cater to families and groups. These properties often feature modern conveniences such as Wi-Fi, outdoor spaces for relaxation, and proximity to local dining and shopping options. The vibrant downtown area offers a variety of eateries and shops, enhancing the overall experience for travellers.Moreover, the surrounding Berkshire Mountains provide beautiful scenery and opportunities for winter activities beyond skiing, such as snowshoeing and sledding. Rentals in this region frequently boast stunning views, and many homes include features like hot tubs or game rooms, making them ideal for a comfortable and entertaining stay.
What is the most popular type of holiday rental accomodation in Cheshire?
In Cheshire, holiday houses are the most popular type of holiday rental, with about 15 available throughout the area. These properties typically offer spacious layouts, making them ideal for families or groups. Guests can expect amenities such as fully equipped kitchens, comfortable living areas, and outdoor spaces for relaxing and enjoying the natural surroundings.
Are there any family house rentals in Cheshire?
In Cheshire, Massachusetts, there are several family-friendly house rentals available, making it an excellent choice for those travelling with children. Visitors can find properties located in quiet neighbourhoods, providing ample space for families to unwind. Many of these homes typically feature well-equipped kitchens, comfortable living rooms, and outdoor areas for kids to play.The locale is also close to various outdoor activities, including hiking trails and scenic parks, which offer opportunities for family outings and exploration. Nearby attractions, such as the beautiful Berkshire Mountains and local lakes, provide options for both leisure and adventure.
Can I rent a holiday home with a pool or hot tub in Cheshire?
In Cheshire, Massachusetts, several holiday homes are available for rent that feature pools or hot tubs. This quaint town, located in the Berkshires, offers a serene escape with beautiful natural surroundings. Many of these properties come equipped with private pools or hot tubs, providing a superb spot for relaxation after a day of exploring the area. Additionally, travellers can expect amenities such as spacious living areas, fully equipped kitchens, and outdoor spaces ideal for gatherings or family activities.
Are there pet-friendly house rentals in Cheshire?
In Cheshire, Massachusetts, there are several pet-friendly house rentals available, making it a suitable destination for travellers with pets. Many of these holiday homes offer convenient amenities such as fully equipped kitchens, spacious living areas, and outdoor spaces, allowing you to enjoy a comfortable stay. Some properties may even feature fenced yards, providing a safe area for your pets to roam.The charming surroundings of Cheshire also offer opportunities for outdoor activities with your furry companions. Nearby parks and natural areas invite exploration, with trails superb for walking or hiking. Additionally, the picturesque scenery of the Berkshires enhances the experience, providing a tranquil backdrop for your holiday.
Are there any remote work holiday rentals in Cheshire?
In Cheshire, Massachusetts, there are around 12 holiday rentals that cater to remote work needs. Many of these properties provide essential amenities such as high-speed Wi-Fi and dedicated workspaces, making it easy for travellers to maintain productivity while enjoying their stay. The area offers a peaceful environment surrounded by natural beauty, great for unwinding after a day of work.Cheshire's proximity to outdoor recreational activities, including hiking trails and scenic parks, adds to its appeal, allowing guests to explore the stunning landscapes of the Berkshires during their downtime. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Cheshire?
In Cheshire, popular rental amenities include kitchens, allowing guests to prepare their meals comfortably. Many properties also offer onsite parking for convenience, as well as decks or patios where visitors can relax outdoors. A fireplace is a common feature, providing a warm and cosy atmosphere during cooler evenings. Additionally, gardens are often found, offering a pleasant space for outdoor activities or quiet reflection.
When is the best time to visit Cheshire for a holiday rental?
The best time to book a holiday rental in Cheshire is during the peak season from June to August, with July standing out as the most popular month. This vibrant period invites visitors to enjoy the great outdoors, with plenty of opportunities for hiking, fishing, and exploring the beautiful landscapes that Massachusetts has to offer. The warm summer weather, typically ranging from 15 to 30 degrees Celsius, creates great conditions for enjoying the region's natural beauty.During these months, Cheshire comes alive with numerous events and activities, making it a fantastic time for travellers. Whether you're hiking the scenic trails or relaxing by one of the nearby lakes, the charm of the area shines through.For those looking to save a bit on their holiday, consider planning a visit in December. While this month may be quiet, it offers its own unique appeal with the serene beauty of winter landscapes, as well as opportunities for cozy indoor activities and holiday festivities.Ultimately, your choice will depend on whether you prefer the bustling atmosphere of summer or the peacefulness of winter.
What are the top attractions in Cheshire?
In Cheshire, Massachusetts, visitors can enjoy a variety of attractions that highlight the area's natural beauty and rich history. One of the primary draws is the scenic Mount Greylock, the highest peak in Massachusetts, which offers hiking trails with stunning views and opportunities for outdoor activities year-round. The nearby Greylock State Reservation features numerous trails and picnic areas, making it a superb spot for nature enthusiasts.The town itself has a charming small-town atmosphere, with historical sites such as the Cheshire Historical Society, where visitors can learn about the local heritage. Additionally, the surrounding Berkshires region is renowned for its cultural attractions, including art galleries, music festivals, and theatre performances.For those interested in more recreational activities, the nearby Cheshire Lake provides opportunities for fishing, boating, and swimming during the warmer months, while the winter months offer access to nearby ski resorts.
Are all fees included in the Cheshire 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 Cheshire holiday homes with parking?
Stayz offers a wide selection of holiday homes in Cheshire 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 Cheshire holiday homes?
You can find great discounts on holiday homes in Cheshire 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 Cheshire holiday home booking on Stayz?
To find Cheshire 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 Cheshire?
A long-stay holiday home in Cheshire 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 Cheshire holiday home?
Book your Cheshire 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 Cheshire?
Prices for holiday homes in Cheshire 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 Cheshire 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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