Greenfield holiday rentals

We found 68 holiday rentals — enter your dates for availability
Discover a selection of holiday rentals in Greenfield that are perfect for your trip. Holiday homes provide the amenities that you need and want for your stay with friends, family or just your pet, such as Wi-Fi and cable TV. At the end of the day, you'll be able to choose a property to rent to meet everyone's needs, including a place that is accessible or non-smoking.

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Lively Greenfield will entice you

Enjoy the area's live music, festivals and culture with a rental holiday home in Greenfield. This romantic city is known for its shopping, cafes and riverfront. 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 Greenfield

Are you hoping to find attractions to see during your stay? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Greenfield a one-of-a-kind holiday spot. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Northfield Mountain Recreation Center (6.7 mi / 10.8 km)
  • Berkshire East Ski Resort (14.1 mi / 22.7 km)
  • Elements Hot Tub Spa (15.3 mi / 24.6 km)
  • Thomas Memorial Golf Course (2 mi / 3.2 km)
  • Bald Mountain Pottery (7.3 mi / 11.7 km)
  • Honora Winery (18.1 mi / 29.2 km)

Exploring the natural landscape of Greenfield

Whether you're looking for exciting outdoor activities or just want to appreciate the scenery, you'll be sure to find the perfect setting for your holiday in Greenfield. Here are a few of the area's most enchanting features, all within 30 miles (48.2 km) of the city centre:

  • High Ledges Wildlife Sanctuary (6.7 mi / 10.7 km)
  • Deerfield River (7.3 mi / 11.7 km)
  • Lake Wyola State Park (10.2 mi / 16.3 km)
  • Swift River (15.6 mi / 25.1 km)
  • Look Memorial Park (17.4 mi / 28 km)
  • Jacksonville Pond (18.4 mi / 29.6 km)

How to get to and around Greenfield

The nearest airport is in Westfield, MA (BAF-Barnes Municipal), located 29.6 mi (47.7 km) from the city centre. If you're unable to find a flight that fits your schedule, you could also fly into Hartford, CT (BDL-Bradley Intl.), which is 45.7 mi (73.5 km) away.

If you'd prefer to travel by train, the main station is Greenfield Station.

Frequently asked questions

What is the best area to stay in Greenfield when booking a holiday rental?
When considering a holiday rental in Greenfield, Massachusetts, a popular area to stay is the downtown district. This vibrant neighbourhood offers a charming mix of local shops, cafes, and restaurants, making it a delightful base for visitors. One of the top attractions in the area is the Greenfield Energy Park, a lovely space that features walking trails, gardens, and seasonal events, providing an excellent spot for relaxation and enjoying nature.Another appealing aspect of downtown Greenfield is its proximity to the historic Park Theatre, which hosts a variety of performances and events throughout the year. The area boasts a selection of properties, ranging from quaint apartments to larger homes, suiting different preferences and group sizes.
Where are the best Greenfield ski resort rentals?
For ski resort rentals near Greenfield, Massachusetts, the nearest ski options are found in the Berkshire Mountains, particularly at resorts like Jiminy Peak, which is about an hour's drive away. In the town of Hancock, close to Jiminy Peak, visitors can find various rental accommodations ranging from cosy cabins to larger lodges suitable for families or groups. Many of these properties feature amenities such as fully equipped kitchens, fireplaces for warmth, and communal spaces that encourage relaxation after a day on the slopes.Additionally, the nearby town of Williamstown offers charming rentals that provide easy access to both the ski areas and local attractions, such as the Williams College Museum of Art and beautiful hiking trails in the surrounding hills. Accommodations in this area often come with modern conveniences, including Wi-Fi, outdoor decks, and sometimes hot tubs, providing an inclusive setting for après-ski gatherings.For those looking to explore more, the scenic landscapes of the Berkshires offer ample opportunities for outdoor activities, including snowshoeing and cross-country skiing, making the area an excellent choice for winter sports enthusiasts.
What is the most popular type of holiday rental accomodation in Greenfield?
In Greenfield, apartments are the most common type of holiday rental, with about 15 available in various neighbourhoods throughout the town. These apartments typically feature fully equipped kitchens, comfortable living spaces, and essential amenities to make guests feel at home. For those seeking more space, several holiday houses are also offered, providing additional bedrooms, private outdoor areas, and often amenities like BBQ facilities.
Are there any family house rentals in Greenfield?
In Greenfield, Massachusetts, there are several family-friendly house rentals available, making it an excellent choice for those travelling with children. Many of these homes are situated in peaceful neighbourhoods, offering spacious living areas great for family gatherings. Visitors can expect amenities such as fully equipped kitchens, which allow for easy meal preparation, and outdoor spaces where kids can play safely.The town boasts a variety of attractions, including the nearby Greenfield Energy Park, which features a playground and picnic areas, providing fun and relaxation for all ages. Additionally, the local library and community centre often host family-friendly events.
Are there pet-friendly house rentals in Greenfield?
In Greenfield, there are several pet-friendly house rentals available, offering a variety of amenities for travellers. Many of these properties feature spacious living areas, fully equipped kitchens, and outdoor spaces where pets can play. The surrounding area is known for its picturesque landscapes, making it an ideal spot for nature lovers and those seeking a peaceful retreat.Greenfield also provides easy access to nearby parks, such as the Greenfield Community Park, which is great for walking pets and enjoying the outdoors. Additionally, the charming downtown area has pet-friendly cafes and shops, allowing visitors to explore the local scene without leaving their furry companions behind.
Are there any remote work holiday rentals in Greenfield?
In Greenfield, Massachusetts, there are a number of remote work-friendly holiday rentals available, with around 18 options to choose from. The town is known for its picturesque landscapes and vibrant community, making it an appealing destination for those looking to combine work and leisure. Many of the properties come equipped with essential amenities for remote work, including free Wi-Fi, dedicated office spaces, and comfortable living areas conducive to productivity.Additionally, you can enjoy the charm of the local area with access to nearby parks, walking trails, and quaint shops, providing a great balance between work and relaxation. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Greenfield?
In Greenfield, popular rental amenities include well-equipped kitchens, which allow guests to prepare their own meals and enjoy home-cooked dining. Onsite parking is another sought-after feature, providing convenience for those travelling by car. Many rentals also offer coffee and tea makers for a comforting start to the day. For those needing to work during their stay, office spaces are available in some properties, ensuring a productive environment. Additionally, blenders are often included, great for making smoothies or other refreshments.
When is the best time to visit Greenfield for a holiday rental?
The best time to visit Greenfield for a holiday rental is during the summer months, particularly in July. This period marks the peak season, where the warm weather invites visitors to explore the lush landscapes and engage in a variety of outdoor activities. With temperatures typically ranging from 15 to 30 degrees Celsius, it's a comfortable time for hiking, biking, and enjoying the scenic beauty of the Connecticut River.July is especially vibrant, as the town hosts various events and festivals that showcase local culture and create a lively option. You'll find plenty of opportunities to immerse yourself in the community, whether you're attending farmers' markets or enjoying live music in the parks.For those looking for more budget-friendly options, November presents an excellent opportunity to visit Greenfield. This month, while quieter, offers a chance to enjoy the beautiful autumn scenery as the leaves change colour. It's an ideal time for peaceful walks and enjoying the crisp air, making for a lovely retreat without the summer crowds.Ultimately, your choice of when to visit Greenfield can depend on whether you seek the excitement of summer activities or the tranquil charm of late autumn.
What are the top attractions in Greenfield?
In Greenfield, Massachusetts, visitors can enjoy a variety of attractions that showcase the town's charm and natural beauty. One of the highlights is the Greenfield Energy Park, a lovely green space featuring walking paths, a pond, and a playground, making it a superb spot for families. The park often hosts community events, providing a glimpse into local culture.Another significant attraction is the Historic Federal Courthouse, which reflects the town's rich history and architectural heritage. Nearby, the Greenfield Community College campus offers art exhibits and performances throughout the year, contributing to the vibrant local arts scene.For those interested in nature, the nearby Montague Plains Wildlife Management Area offers trails for hiking and opportunities for birdwatching, making it a fantastic destination for outdoor enthusiasts.
Are all fees included in the Greenfield 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 Greenfield holiday homes with parking?
Stayz offers a wide selection of holiday homes in Greenfield 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 Greenfield holiday homes?
You can find great discounts on holiday homes in Greenfield 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 Greenfield holiday home booking on Stayz?
To find Greenfield 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 Greenfield?
A long-stay holiday home in Greenfield 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 Greenfield holiday home?
Book your Greenfield 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 Greenfield?
Prices for holiday homes in Greenfield 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 Greenfield 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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