Find Extended Stay Hotels in Pittsfield, VT

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Top Pittsfield Extended Stay Hotels | Reserve now, pay later

Our top choices for Pittsfield hotels with a kitchen

Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont

Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont
North Sherburne
10.0 out of 10, Exceptional, (1)
"Peak Hill, is a lovely and very clean home, with a fully stocked kitchen and comfy beds. This home is exactly as the pictures that are shown. We had a very small issue with the door lock (battery), called and it was fixed right away, wonderful service. The owner, Geri, we had the opportunity to meet and she is very kind and a pleasure to speak with. We travel alot and l bring pretty much my own kitchen, pillow...... with me where ever l go. However, l would of been fine using all at this...
United States
Essa R.
$550 nightly
The price is $616
Dec 15 - Dec 16
Total with taxes and fees
Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont

NEW! Smart 3BR Basecamp w/ Hot Tub, AC, EV Charger & Flat Parking

NEW! Smart 3BR Basecamp w/ Hot Tub, AC, EV Charger & Flat Parking
2.0 star property
North Sherburne
$662 nightly
The price is $742
Dec 15 - Dec 16
Total with taxes and fees
NEW! Smart 3BR Basecamp w/ Hot Tub, AC, EV Charger & Flat Parking

The Getaway 4 Bedroom Home

The Getaway 4 Bedroom Home
3.0 star property
Pittsfield
$881 nightly
The price is $974
Dec 16 - Dec 17
Total with taxes and fees
The Getaway 4 Bedroom Home

The Getaway: Relax with hot tub, fire pit, and mountain views—just 15 mins from Killington slopes!

The Getaway: Relax with hot tub, fire pit, and mountain views—just 15 mins from Killington slopes!
Pittsfield
$727 nightly
The price is $814
Dec 16 - Dec 17
Total with taxes and fees
The Getaway: Relax with hot tub, fire pit, and mountain views—just 15 mins from Killington slopes!

Sleep Woodstock Motel

Sleep Woodstock Motel
2.0 star property
Woodstock
9.6 out of 10, Exceptional, (549)
"The staff at this motel are 5 star! Lisa went above and beyond to make my stay easy since I was there for a medical procedure. "
United States
Crystal
$158 nightly
The price is $174
Dec 14 - Dec 15
Total with taxes and fees
Sleep Woodstock Motel

Hampton Inn Rutland

Hampton Inn Rutland
2.5 star property
Rutland
9.0 out of 10, Wonderful, (969)
"Very clean, good location, and super helpful staff!"
United States
Sheryl
$147 nightly
The price is $162
Dec 21 - Dec 22
Total with taxes and fees
Hampton Inn Rutland

On The River Inn

On The River Inn
4.0 star property
West Woodstock
9.4 out of 10, Exceptional, (1001)
"Lovely setting with great rooms and a terrific staff. Unfortunately the bar was closed but the lounge area is a perfect place to enjoy each other’s company and your own libations "
United States
Jean
$177 nightly
The price is $195
Dec 15 - Dec 16
Total with taxes and fees
On The River Inn

My Place Hotel-Randolph VT

My Place Hotel-Randolph VT
2.0 star property
Randolph Center
9.4 out of 10, Exceptional, (342)
"Awesome staff and great room with Kitchenette"
United States
Mary
$113 nightly
The price is $124
Jan 4 - Jan 5, 2026
Total with taxes and fees
My Place Hotel-Randolph VT

North Star Lodge and Resort

North Star Lodge and Resort
2.0 star property
Killington
8.6 out of 10, Excellent, (1001)
"Spotless room also very accommodating and friendly! Loved our short stay!"
United States
Candace
$160 nightly
The price is $176
Jan 4 - Jan 5, 2026
Total with taxes and fees
North Star Lodge and Resort

Secluded retreat in the trees

Secluded retreat in the trees
Roxbury
10.0 out of 10, Exceptional, (36)
"Absolutely beautiful! So pleased with everything about our stay!"
United States
Gwen B.
$210 nightly
The price is $235
Dec 14 - Dec 15
Total with taxes and fees
Secluded retreat in the trees
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Find out more about Pittsfield

Discover top Pittsfield attractions

Nestled in the scenic Green Mountains, Pittsfield, Vermont, offers a plethora of activities and points of interest that cater to travelers. Begin your adventure with a hike on the nearby Appalachian Trail, where breathtaking vistas and serene landscapes await. For families, the nearby Killington Resort provides year-round fun, from skiing and snowboarding in winter to mountain biking and hiking in summer, ensuring that everyone can find their thrill. Art enthusiasts can explore the local galleries showcasing works by talented Vermont artists, while the charming local shops offer unique crafts and handmade goods perfect for souvenirs. Foodies will relish the farm-to-table dining experiences in the area, featuring seasonal ingredients sourced from local farms. When it comes to accommodations, consider staying in a cozy lodge or elegant inn in the heart of Pittsfield, where attentive service and comfortable amenities create a welcoming retreat after a day of exploration. Enjoy the tranquility of the countryside while indulging in quality hospitality, making your visit both memorable and fulfilling.

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Most booked related extended stays in Pittsfield in 2026

Frequently asked questions

What are the best long-term hotels in Pittsfield?
In addition to kitchens, the most popular long-term hotels come with useful amenities that'll have you feeling right at home. Pittsfield Chalet has conveniences designed to make a vacation of a couple of weeks or longer comfortable, like a fireplace and a stovetop. Newly Built Killington Vermont Ski House is another popular option. A patio and a dryer help make this place a terrific choice for an extended stay in Pittsfield.
What are the best extended stay hotels with kitchens in Pittsfield?
When you're traveling for a long while with your family, eating out can get tiring — not to mention heavy on the travel budget. That's why it makes sense to choose long-term stays equipped with a kitchen, like Large Killington/pico Ski House. It offers handy features that make vacationing with your crew a breeze, including a fireplace and a barbecue grill. Sweet Life - Vermont Chalet - 6 Person Indoor Hot Tub will also help you save a tidy sum on restaurant bills. Cook your favorite meals and make the most of this stay's amenities, such as pet-friendly facilities and a barbecue grill.
Can I find extended stay hotels with pools in Pittsfield?
Nothing screams good times like a pool does. Pack your bikini or board shorts and kick back poolside at Spectacular Mountain Views, 6 Bedroom. A kitchen, a dining table and a barbecue grill are among the amenities here. Another option for your extended stay in Pittsfield is Sweet Life - Vermont Chalet - 6 Person Indoor Hot Tub. The family won't want to get out of the pool at this getaway, which also comes with shopping, an oven and a kitchen so you can make your own meals.Pittsfield has a humid continental climate and temperatures range between 55 ºF and 75 ºF during summer. If you'd like to spend a large portion of your break swimming, this would be a great time to visit.
Why book an extended stay hotel in Pittsfield through Expedia?
Lock in your extended stay hotel in Pittsfield through Expedia and you're guaranteed to save. In addition to our exclusive member offers and reward programs, we make finding the perfect long-term stay a piece of cake. Use our filter tool to search for properties based on location, ratings, affordability and more. Some long-term rentals may offer weekly rates to help you keep extra money in your pocket. Usually equipped with useful amenities like a dining area and kitchen, your next extended stay in Pittsfield is just a few clicks away!
What can I expect from an extended stay hotel?
Save your hard-earned money while enjoying some extra perks with an extended stay hotel in Pittsfield. Whether you want a small studio for yourself or a spacious apartment that'll fit your whole crew, these types of properties provide amenities that'll make you feel at home. As well as standard offerings like a pool and a restaurant, many extended stay hotels have kitchens and a washer and dryer. This means you can cook up a storm and wash your own clothes, letting you keep some extra cash in your wallet. Competitive weekly rates will help you stretch your savings even further.

Top Pittsfield Hotel Reviews

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