Pittsfield Vacation Rentals from $209: Search Short-Term Rentals

Q: What are some of the best vacation rentals that Pittsfield has to offer?

Killington area home - 4-seasons, hot tub and A/C : This highly rated vacation home rental in Pittsfield is located in the mountains and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

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Our top choices for Pittsfield vacation rentals

1. Ski Home/Arcade Mountain Views Near Killington/Woodstock

Stockbridge

Kevin M.

$494 nightly

Aug 31 - Sep 1

Total with taxes and fees

2. Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock

Stockbridge

Sophie L.

$494 nightly

Aug 31 - Sep 1

Total with taxes and fees

3. Gnome Home Mountain Ski Chalet w/Sauna Killington

Stockbridge

Gerald S.

$484 nightly

Sep 2 - Sep 3

Total with taxes and fees

4. Killington condo 5 min to killington resort

Killington

Nicholas C.

$301 nightly

Aug 31 - Sep 1

Total with taxes and fees

5. Mountain Green

Killington

Keith

$208 nightly

Sep 30 - Oct 1

Total with taxes and fees

6. Luxury Condo Tucked in the Heart of Killington

Killington

$262 nightly

Aug 31 - Sep 1

Total with taxes and fees

7. Jack S`Bearo- AC, Pool, Mountain Views, Hiking, Gym

Killington

Joseph S.

$241 nightly

Aug 31 - Sep 1

Total with taxes and fees

8. Resort condo with mountain views, full kitchen, and free WiFi

Killington

Jason B.

$336 nightly

Aug 31 - Sep 1

Total with taxes and fees

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Top Pittsfield Hotel Reviews

The Mountain Inn at Killington

10/10 Excellent

"We loved this hotel. We were here in the summer, so we enjoyed the outdoor seating and the outdoor heated pool, plus very close distance to Killington Adventure Center (could have walked but we chose to drive). The game room was great for our teenagers, with a full pool table and board games. The staff was extremely friendly and knowledgable of the area, and gave suggestions for nearby restauarants and hikes. The upstairs has a large indoor lounge area to relax outside your hotel room with friends, which I can see being awesome after a day of skiing."

On The River Inn

10/10 Excellent

"This was one of the nicest hotels I have ever stayed in! We had a river view room with rocking chairs on the balcony, s’mores kits were offered every night (pick up by the front desk) and 2 fire pits to choose from. Game room was cute (although the air hockey table’s fan wasn’t strong on one side), library was absolutely gorgeous. Loved having water refilling stations on 2 of the 3 floors and 24/7 coffee/tea stations, too. Queen beds were very comfy, and the room was so spacious. I’d love another piece of furniture with drawers to keep our stuff though - we lived out of our suitcases because there was only an armoire with 3 half drawers. And maybe another towel bar or hooks in the bathroom to hang the towels to dry, especially if you have 4 people in a room. Breakfast buffet (included with our Expedia stay but extra for others) was always hot & fresh. We had 4 breakfasts: French toast, pancakes, waffles, french toast again. There was always fresh homemade pastries and muffins, yogurt, and oatmeal. I would have loved some fresh fruit like berries to go with the yogurt instead of apples and oranges. Staff was always so nice and helpful, especially at breakfast. Housekeeping forgot twice to give us the 4 fresh towels (gave 3 instead) but we got replacements when we asked at the desk."

The Shire Woodstock

8/10 Good

"We enjoyed our stay very much. We found our stay to very quiet. The back of the property was so peaceful and relaxing sitting by the river, listening to the birds and the gurgling of the river as it moves along. The room was comfortable with a fridge and freezer for snacks/fruit etc. I'd like to see another chair in the room so that 2 people can sit by the window and experience the view although this wasn't a game changer."

Emrose Luxury Cabins

10/10 Excellent

"The Cabins are very nice clean and cozy , love how well they were thought out to fit everything so perfectly in a small space . Full bathroom , full kitchen and nice size refrigerator and microwave . Perfect for a romantic getaway . Plus the outdoor accommodations were great . And can’t wait for the soon to come restaurant and lounge for the guests . A++ stay . Staff were very nice and helpful"

Find out more about Pittsfield

Everything you need to know about Pittsfield vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Pittsfield vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Pittsfield vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Pittsfield vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Pittsfield. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Pittsfield in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $209 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Pittsfield rentals

At Expedia, we put the best Pittsfield vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Pittsfield rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Pittsfield vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Pittsfield. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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Frequently asked questions

Can I find a vacation rental in Pittsfield?

Yes, there are vacation rentals close to popular sights in Pittsfield, or you can choose a more remote option if you're looking for relaxation. Pittsfield is known for its bars and restaurants.

What are some of the best vacation rentals that Pittsfield has to offer?

Killington area home - 4-seasons, hot tub and A/C: This highly rated vacation home rental in Pittsfield is located in the mountains and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals are there in Pittsfield?

Expedia has 28 vacation rentals for your stay in Pittsfield.

What can I see and do in Pittsfield?

While exploring the area, visit family-friendly sights like Killington Adventure Center, or get outside and enjoy nature at Green Mountain National Forest. Roger Clark Memorial Central Library and Pittsfield Town Hall are other places to visit while you're in town.

What are vacation rentals like in Pittsfield?

Vacation rentals are private properties you can reserve for a few days or a quick weekend in Pittsfield. Vacation rentals provide amenities such as hot tubs, fire pits, and patios so you'll feel just like you're staying in your own home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of privacy away from public hotel elevators and lobbies bustling with people while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great choice for a small group gathering.

Pittsfield Vacation Rentals

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Our top choices for Pittsfield vacation rentals

1. Ski Home/Arcade Mountain Views Near Killington/Woodstock

2. Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock

3. Gnome Home Mountain Ski Chalet w/Sauna Killington

4. Killington condo 5 min to killington resort

5. Mountain Green

6. Luxury Condo Tucked in the Heart of Killington

7. Jack S`Bearo- AC, Pool, Mountain Views, Hiking, Gym

8. Resort condo with mountain views, full kitchen, and free WiFi

9. Fabulous 4-bedroom chalet in tranquil Killington getaway with gorgeous Hot tub

10. Killington resort: Walk to Mountain, Biking & Pool

11. FirBear- AC, Pool, Hot Tub, Sauna, Tennis, Gym

12. Mountain Basecamp Near Killington | Fireplace + Pool Access

13. new 2 bedroom close to killington and bike trails this is pet ok downstairs unit

14. The Tower House | Hot Tub | Firepit | Dog-Friendly

15. BearNecessities- Pool, Hot Tub, Gym

16. Welcoming condo near the slopes with free WiFi and full kitchen

17. CozyDen - AC, Grill, Bike to Mountain, Porch!

18. The Woods Resort and Spa Killington: 2 BR / 2 BA Renovated Condos w/ Great Amenities V7

19. Cozy Rutland Retreat

20. High-floor resort condo with free WiFi and full kitchen - walk to lifts

Find vacation rentals that suit your style

Top Pittsfield Hotel Reviews

The Mountain Inn at Killington

Find out more about Pittsfield

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