Pittsfield vacation rentals

The heart wants what the heart wants, and right now it's longing for a vacation. Now's the time to pack your suitcase and zip off to one of these top vacation rentals in or near Pittsfield:

• Make the most of conveniences like internet services and air conditioning at "Cozy Family - Friendly Log Cabin With 25ft Interior Fireplace + Modern Amenities". Situated around 25 miles from Pittsfield, this leading option has 3 bedrooms and good guest reviews.
• Another excellent choice is "Sunrise 3bedroom - 2 Story Remodeled Condo", which is around 14 miles from Pittsfield. Offering 3 bedrooms, a dining table and a microwave oven, it has everything you need to make your visit comfortable.

For even more great options, use the search bar at the top of the page to find the perfect Pittsfield vacation rental for you.

Pick a gorgeous log cabin from the many scattered in or near Pittsfield and you'll soon be inside your wooden hideaway, vino in hand, lounging by a blazing fire. But adventure is just outside your front door too. These cabins offer the perfect blend of comfort and fun:

• "Cozy Family - Friendly Log Cabin With 25ft Interior Fireplace + Modern Amenities": This fantastic escape is the perfect base if you love playing outdoors. Mountain biking and skiing are a number of activities you can do in the area when you're not unwinding in your cozy cabin.
• "Private And Artistic Log Cabin": After a busy day of trying out some popular local pastimes, such as skiing and water skiing, recharge your batteries at this charming property.

If you've been busier than an ant at a picnic lately, you deserve a break for a couple of glorious days. Clock off early on Friday and head to one of these weekend getaways in or near Pittsfield:

• "Trail Creek Hot Tub/sauna/pool Totally Renovated King Bed+2twins 1. 5 Bath" is around 12 miles south of Pittsfield and an ideal place to recharge your batteries. You'll like the amenities here, including a living room and nearby hunting activities.
• "Cabin - Cozy Hideaway Near Ludlow/okemo. Hot Tub" is another excellent option. It's located about 25 miles to the south of Pittsfield and features a TV, a smart TV and more.

You sure can. If you're tracking down a simple yet stylish stay, you can't go wrong with a studio apartment. These compact properties exude charm and are often conveniently placed in the heart of town. We recommend the following options in or near Pittsfield:

• Chill by yourself or take a few friends to "Trail Creek Hot Tub/sauna/pool Totally Renovated King Bed+2twins 1. 5 Bath". You'll have lots of amenities to take advantage of, including a pool and an iron and ironing board.
• "Amazing Mountain Condo - Right Across The Street To Killington Resort" is another terrific choice, offering all you need for a dream Pittsfield escape. Useful amenities here include nearby birdwatching activities and a balcony.

Whether you're looking for a comfy cottage or a house big enough to fit the family, you'll find the ideal place on Vrbo. Treat yourself to a mini break at one of these favorites in or near Pittsfield:

• Close to the center of Pittsfield, "Cabin - Cozy Hideaway Near Ludlow/okemo. Hot Tub" lays out the welcome mat for short-term guests. When you're not chilling out in your cozy digs, get out and discover all the cool stuff around you.
• Alternatively, spend a few relaxing nights at "Romantic Cozy Getaway - Booking Spring And Summer Now". This comfy, conveniently located property makes it easy to explore the area's sights.

Whether spent in a cabin, an apartment or a lodge, a romantic weekend getaway is a wonderful way to add some fire to your relationship. Whisk your sweetheart away for a couple of relaxing days at one of these escapes in or near Pittsfield:

• Located around 25 miles from Pittsfield, "Cozy Family - Friendly Log Cabin With 25ft Interior Fireplace + Modern Amenities" is the ideal place for starry-eyed couples. A fireplace and a restaurant dining guide are some of the amenities you'll find here.
• "Sunrise 3bedroom - 2 Story Remodeled Condo" is another retreat that's bound to impress. It's approximately 14 miles from Pittsfield and comes with skiing facilities and a sauna.

Big groups mean massive fun. They also mean finding someplace that'll comfortably fit your entire squad. Browse our large group vacation rentals in or around Pittsfield and get your favorite people together under the one roof:

• There's loads of space to enjoy yourselves at "Killington Area Home - 4 - Seasons And Hot Tub". Around 1 mile southeast of Pittsfield, this grand retreat has 3 bedrooms sleeping up to 15 guests. Amenities include mountain views and a garden.
• "Spectacular Mountain Views, 6 Bedroom" is another excellent option. It's around 1 mile to the east of Pittsfield, has 6 bedrooms and accommodates up to 12 guests. A kitchen and a firepit are among the things that'll help make your stay even more comfortable.

Of all the conveniences a vacation rental can have, a pool is one of the most coveted. Check out these houses for rent with a pool in or near Pittsfield and spend your days splashing about. Just don't forget to bring your inflatable pizza slice:

• Get into vacay mode at "Killington Big House: Largest Vacation Rental In Killington", where your biggest priority will be enjoying the pool. Amenities including coffee and tea making facilities and free toiletries help make this retreat a guest favorite.
• "Family And Dog - Friendly House In Killington" is the type of place you go to escape the everyday and make the most of your surroundings, starting with its pool. A separate dining area and a balcony are also on hand to make your stay as comfortable as possible.

Curious what the weather is like in Pittsfield? It has a humid continental climate, with average summertime temperatures ranging from 55 ºF to 75 ºF. If you'd like a little more inspiration on places to stay in this impressive destination, use the search bar at the top of the page and adjust the filters to scroll through our entire range of Pittsfield vacation rentals.

It's always more fun when you share those precious memories with the folks that are closest to your heart. Whether you're organizing a family reunion or catching up with friends, we'll have a large vacation rental that's right for you. Here are two of our best in and around Pittsfield:

• Invite your nearest and dearest to "Holiday Apartment Le Chalmieu For 1", which has 3 bedrooms that sleep up to 8 guests. This retreat is located 25 miles to the southwest of Pittsfield and comes with amenities such as childrens activities and a dishwasher.
• Another top option is "Sunrise 3bedroom - 2 Story Remodeled Condo". This vacation rental is 14 miles south of Pittsfield and features a video library, snowsport activities and more. With 3 bedrooms accommodating up to 8 people, you won't need to leave anyone off your invitation list.

If you're eager to sightsee, there are lots of family-friendly attractions nearby to put on your itinerary. Vermont State Fairgrounds, Hathaway Farm and Killington School for Tennis are excellent places to start.

Nothing is more important than family, which is why we'll help you find a place where you can truly connect. Stay in one of these family cabin rentals in or near Pittsfield and create wonderful new memories with the people you love the most:

• "Holiday Apartment Le Chalmieu For 1" - This sought-after escape offers a kitchen island and a kitchen and is around 25 miles to the southwest of the center of Pittsfield.
• "Cabin - Cozy Hideaway Near Ludlow/okemo. Hot Tub" - Another awesome option, this property comes with a video library, a living room and more. You'll find it around 25 miles to the south of Pittsfield.

For more options, use the search bar at the top of the page and adjust the filters to find the Pittsfield vacation rental that's perfect for your needs.