Western Massachusetts vacation rentals

We found 1,849 vacation rentals — enter your dates for availability

Vacation rentals with weekly discounts - Western Massachusetts

Showing deals for:Jul 17 - Jul 24

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, yards and more
  • More for less

    More space, more privacy, more amenities — more value
  • A place for everyone

    We stand for diversity, inclusion and families everywhere.
    Learn more

Find out more about Western Massachusetts

Why visit Western Massachusetts

  • Outdoor Adventures: Western Massachusetts is perfect for hiking, biking, and exploring stunning lakes and mountains.
  • Cultural Experiences: Visit historic colleges and vibrant urban parks that showcase the region's rich history.
  • Charming Accommodations: Enjoy cozy cabins, private homes, and cottages that provide a home-like atmosphere amidst nature.
  • Family-Friendly Atmosphere: The area offers activities and attractions suitable for travelers of all ages.
  • Scenic Beauty: Experience breathtaking views and picturesque towns that define the charm of Western Massachusetts.

Popular types of accommodation around Western Massachusetts

Looking for the perfect getaway in Western Massachusetts? You’re in the right place. Our most popular vacation rental options include charming houses, cozy cottages, and comfortable apartments. Whether you’re interested in holiday cottages or spacious house rentals, we have a variety of Massachusetts cottages to suit your needs. Experience the beauty and tranquility of this region while enjoying the comforts of home.

  • Houses: These spacious homes offer a comfortable and private stay, perfect for families or groups looking to enjoy Western Massachusetts together.
  • Apartments: Ideal for solo travelers or couples, these self-contained units provide all the necessary amenities for a cozy stay.
  • Cottages: Quaint and charming, these rustic retreats are perfect for a peaceful getaway amidst nature.
  • Cabins: Embrace the outdoors in these cozy hideaways, often nestled in scenic locations.
  • Chalets: These stylish mountain lodges combine comfort and stunning views, perfect for a unique vacation experience.**

Top attractions near Western Massachusetts

Western Massachusetts offers a fantastic blend of outdoor adventure and cultural experiences, perfect for families and solo travelers alike. Explore historic colleges and universities, enjoy urban parks, and take in the stunning scenery. For a cozy stay, consider renting a cabin to fully immerse yourself in the natural beauty of the region. Whether you're seeking adventure or a relaxing getaway, Western Massachusetts has something for everyone.

  • Smith College: A historic college known for its stunning campus and rich cultural atmosphere, Smith College offers beautiful gardens and art exhibitions that reflect its commitment to the arts and education.
  • University of Massachusetts Amherst: This modern university combines vibrant city vibes with academic excellence. Visitors can explore its state-of-the-art facilities, lively campus life, and diverse cultural events.
  • Chesterfield Gorge: A breathtaking canyon perfect for outdoor enthusiasts, Chesterfield Gorge features scenic trails, stunning rock formations, and opportunities for hiking and nature photography.

Things to do recommended for couples

Ready for a romantic getaway in Western Massachusetts? Enjoy skiing together at Berkshire East Ski Resort or Blandford Ski Area, both offering thrilling outdoor vibes. For a cultural experience, catch a performance at Jacob's Pillow and immerse yourselves in the enchanting atmosphere of dance and entertainment.

Things to do recommended for families

Your family will have a blast at the Mullins Center, just 15 miles away, enjoying the energetic sports atmosphere. For relaxation, visit Land of Providence, 11 miles away, offering a serene vibe. Don't miss Spare Time Bowling, also 11 miles away, where adventure and family fun await.

Things to do recommended for groups

Experience a night of culture and entertainment at the Academy of Music Theater, only 10 miles away. For adventure seekers, hike the scenic Skyline Trail, 11 miles from your location, or browse unique finds at the Montague Bookmill, 13 miles away.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation around Western Massachusetts

If you’re traveling with a group, family, pets, or planning an extended stay, be sure to use the appropriate filters to match your needs. Here are some helpful booking tips for Vrbo.

  • Traveling to Western Massachusetts with a group: Think about how many bedrooms you will require, along with features like a full kitchen or outdoor areas for group gatherings. Thankfully, Vrbo allows you to easily filter for these options and many more.
  • Traveling to Western Massachusetts with young kids: Traveling with little ones can be quite challenging. It's important to prioritize their comfort and safety, along with finding age-appropriate amenities like a private pool. Additionally, think about how close you'll be to family-friendly attractions.
  • Taking your pets with you to Western Massachusetts: For many families, a trip just wouldn't feel complete without their furry companion by their side. If that resonates with you, be sure to explore Vrbo listings that welcome pets. Many of these pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Western Massachusetts: If you’re in search of vacation rentals that offer discounts for month-long stays, you’ve come to the perfect spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include amenities like parking, a well-equipped kitchen, or a private pool in your search.

Where to stay near Western Massachusetts

Western Massachusetts is a hidden gem for outdoor enthusiasts and adventure seekers. With breathtaking views, charming towns, and family-friendly atmospheres, it's the ideal getaway for a relaxing vacation. Explore nearby lakes and discover vacation rentals in great locations that offer the perfect blend of tranquility and excitement. Whether you're hiking in the mountains or enjoying local attractions, Western Massachusetts promises an unforgettable experience for every traveler.

  • Northampton: Nestled approximately 10 miles away from Western Massachusetts, Northampton is a vibrant city known for its rich cultural scene and outdoor activities. This charming destination is home to historic and modern colleges, making it a hub for education and creativity. Visitors can enjoy music concerts, art galleries, and a variety of local shops and restaurants. The nearby lake offers opportunities for relaxation and recreation, while the scenic landscapes provide an ideal backdrop for outdoor adventures. Northampton perfectly blends a lively city atmosphere with a touch of nature, making it a must-visit.
  • Chesterfield: Located a mere 2 miles from Western Massachusetts, Chesterfield is a hidden gem for those seeking outdoor adventures and scenic beauty. This small city is surrounded by stunning natural landscapes, including a canyon gorge and nature reserve, ideal for hiking and exploration. With its serene parks, Chesterfield invites travelers to immerse themselves in the tranquil atmosphere and enjoy activities like skiing in the winter months. It's a perfect spot for nature lovers looking to escape the hustle and bustle of city life while experiencing the best of the great outdoors.
  • Holyoke: Situated about 14 miles from Western Massachusetts, Holyoke is a family-friendly city that offers a mix of urban and outdoor experiences. Known for its historic and modern colleges, Holyoke boasts attractions such as an amusement park and shopping centers, making it a great destination for families and tourists alike. Visitors can engage in educational opportunities, enjoy thrilling rides, or explore the city's rich history. With its welcoming atmosphere and diverse range of activities, Holyoke is an excellent choice for anyone looking to enjoy a fun and enriching vacation.

Best time to go to Western Massachusetts

If you're planning a trip to Western Massachusetts, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from June to August, while off-peak times, like January and March to April tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January23.2°F (-4.9°C)Light RainMostly CloudyLowAverage
February24.8°F (-4.0°C)Light RainMostly CloudyAverageAverage
March32.5°F (0.3°C)Light RainMostly CloudyLowSlightly Low
April44.2°F (6.800000000000001°C)Light RainMostly CloudyLowSlightly Low
May58.6°F (14.8°C)Light RainMostly SunnyAverageAverage
June66.6°F (19.200000000000003°C)Light RainMostly SunnyHighAverage
July72.7°F (22.6°C)Light RainMostly SunnyHighSlightly High
August70.9°F (21.6°C)Light RainMostly SunnyHighSlightly High
September62.8°F (17.1°C)Light RainMostly SunnyAverageSlightly Low
October49.8°F (9.9°C)Light RainMostly SunnyAverageAverage
November38.8°F (3.8°C)Light RainMostly SunnyAverageAverage
December29.7°F (-1.3°C)Light RainMostly CloudyAverageSlightly High

Booking with Vrbo is a breeze

Are you hoping to save on your next adventure? Staying flexible with your travel dates can really pay off, as prices can vary significantly. Additionally, opting for a longer stay often leads to substantial savings. To discover the perfect Vrbo property that fits your budget, utilize our filters to sort by price, location, and type of vacation rental. We're here to help you make the most of your travel experience.

Vrbo Trips: Effortless planning

Vrbo's unique Trip Board offers you a dedicated space to plan new adventures, pick up right where you left off, or easily view and organize your travel arrangements. You can find properties you've saved and booked categorized under Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Travel to lively Western Massachusetts

The area's live music and museums are just a few of the reasons to vacation in Western Massachusetts. Renowned for its university setting, sporting events and hiking, this city welcomes all visitors. If you're looking for accommodations with space to entertain friends and family, Vrbo has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.

Activities and attractions in Western Massachusetts

Are you looking for attractions to see in the city? Although it can be tempting to stay in your comfortable vacation rental, you'll want to experience everything that makes Western Massachusetts a fun place to get away. These are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Berkshire East Ski Resort (16.8 mi / 27.1 km)
  • Elements Hot Tub Spa (17.5 mi / 28.2 km)
  • Otis Ridge (17.6 mi / 28.3 km)
  • Olympia Ice Center (20.3 mi / 32.6 km)
  • The Ranch Golf Club (20.4 mi / 32.8 km)
  • Greenock Country Club (21.1 mi / 33.9 km)

Exploring the natural landscape of Western Massachusetts

Whether you're an adventurous traveler or just want to spend some time taking in the scenery, Western Massachusetts is a great place to get out in nature. These are some of the area's noteworthy natural features, all within 30 miles (48.2 km) of the city center:

  • Chesterfield Gorge (2 mi / 3.2 km)
  • Swift River (5.6 mi / 9.1 km)
  • Look Memorial Park (8.8 mi / 14.1 km)
  • Ashfield Lake (11.3 mi / 18.1 km)
  • Paradise Pond (11.6 mi / 18.6 km)
  • Smith College Botanic Garden (11.6 mi / 18.7 km)

Transportation options to and around Western Massachusetts

Fly into Westfield, MA (BAF-Barnes Municipal), the closest airport, located 15.8 mi (25.5 km) from the city center. If you're unable to find a flight that fits your schedule, you can also fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is 22.5 mi (36.3 km) away.

If you're traveling by train, Northampton Station, Holyoke Station and Amherst Station are the main stations that serve the city.

Frequently asked questions

What is the most popular type of vacation rental accommodation in Western Massachusetts?
Apartments are the most popular type of vacation rental in Western Massachusetts, according to our data. Even if you've got something else in mind, Vrbo has vacation homes in all sizes and shapes. Explore our options to find your perfect Western Massachusetts pad.
How much does it cost to rent a vacation rental in Western Massachusetts?
Length of stay, property type and time of year are among the factors that can affect the price of a vacation home. Simply add your dates of travel to find your perfect escape. From comfy cabins to plush villas, all Vrbo vacation rentals offer incredible value.
How much does it cost to rent a beach house in Western Massachusetts?
Prices for beach houses in Western Massachusetts differ depending on the type and size of the property and when you plan to travel. Simply enter your dates of travel into Vrbo and the number of guests to view available options and prices. From there you can use our filters to tailor your search by nearby activities, ratings, amenities and more.
Are there pet-friendly vacation rentals in Western Massachusetts?
Yes. There are. You'll have your pick of 175 vacation rentals that allow pets in Western Massachusetts. Lots of our pet-friendly vacation rentals even come with an outdoor space for your fur child to run around in, doggie beds, complimentary treats and proximity to parks and green space. Apply the "Pets allowed" filter to find your pawfect pad on Vrbo.
Are there large group vacation rentals in Western Massachusetts?
Western Massachusetts has 158 vacation homes that can host 10 or more guests. These properties come with enough space to share good times with loved ones.
Are there one-bedroom vacation rentals in Western Massachusetts?
Yes, Western Massachusetts has 98 one-bedroom rentals available. Often located in prime areas thanks to their compact size, a one-bedroom vacation rental is perfect if you're traveling with a pal or your partner. And with comforts such as WiFi and more privacy, you'll be able to chill out while exploring this fabulous destination.
Can I find two-bedroom vacation rentals in Western Massachusetts?
You can select from 206 two-bedroom rentals in Western Massachusetts. Settle the kids into the second room or maybe fill it with a couple of your nearest and dearest friends. There's a comfy spot for whoever's lucky enough to be joining in on the fun.
Are there vacation rentals with WiFi in Western Massachusetts?
Western Massachusetts has 349 vacation rentals with WiFi, so you'll be able to stay connected while traveling. Simply check the "WiFi" box in our handy search filter to find the perfect property. From streaming Hollywood blockbusters to updating your social media, these Vrbo homes will keep you online.
How can I find vacation rentals with air conditioning in Western Massachusetts?
You'll have your pick of 662 vacation rentals with air conditioning in Western Massachusetts giving you that cool, cool breeze and extra bit of comfort. Simply enter your dates of travel and then use our handy filter tool to find properties with air conditioning.
How old do you have to be to rent a vacation rental in Western Massachusetts?
It's advisable to check with the Western Massachusetts vacation property you're looking at on Vrbo as age restrictions differ. However, normally it's 16, 18 or 21.
How long can I rent a vacation rental in Western Massachusetts for?
How long you can rent a vacation rental in Western Massachusetts is up to the property. Just enter your chosen dates to look at a list of options offering extended stays. With many amenities like full kitchens and air conditioning, as well as some offering weekly or monthly discounts, you're sure to get a terrific place to call your home away from home in Western Massachusetts.
Does Vrbo offer discounts for vacation homes in Western Massachusetts?
Weekend break or a much-needed extended vacation, Vrbo has some fantastic deals and discounts in Western Massachusetts that'll suit your style and your budget. Browse our weekly and monthly discounts on vacation rentals, or see what's just been added with one of our newly listed homes. Whatever kind of getaway you're after, you'll find the ideal place to stay — without blowing your budget.

More Vacation Ideas