Pittsfield Vacation Rentals from $197: 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. Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont

North Sherburne

"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...

Essa R.

$566 nightly

Aug 24 - Aug 25

Total with taxes and fees

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

North Sherburne

$539 nightly

Aug 24 - Aug 25

Total with taxes and fees

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

Stockbridge

Sophie L.

$534 nightly

Aug 23 - Aug 24

Total with taxes and fees

4. Mountain Green

Killington

Keith

$210 nightly

Aug 26 - Aug 27

Total with taxes and fees

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

Stockbridge

Kevin M.

$534 nightly

Aug 23 - Aug 24

Total with taxes and fees

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

North Sherburne

Matthew R.

$399 nightly

Aug 24 - Aug 25

Total with taxes and fees

7. Killington Center Renovated Studio with Kitchenette on Bus Route and Discounted Ski Rentals.

Killington

Asad B.

8. Killington condo 5 min to killington resort

Killington

Nicholas C.

$301 nightly

Aug 23 - Aug 24

Total with taxes and fees

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Top Pittsfield Hotel Reviews

On The River Inn

8/10 Good

"Staff was friendly and the room was clean. Nice social atmosphere, game rooms."

Sleep Woodstock Motel

10/10 Excellent

"This is one of the cleanest places I have ever stayed, including five star hotels. Even though it was an older building, the bathroom and shower was spotless. The bed was comfortable and having a full fridge in freezer as well as a working Keurig and pods was everything I needed. Would highly recommend this place!! and I appreciate them being dog friendly"

The Jackson

8/10 Good

"If you are looking for a quiet B & B type experience, a little bit off the beaten path, then this could be a great option for you. Our room was on the second floor with a narrow wooden staircase which made it challenging to bring our multiple bags up to the room. We opted to pull a few necessities out of our main bag and just bring in a carry on, which worked fine. The rooms are lovely and comfortably furnished. The bed was comfortable. One of the "charms" of staying in a B&B type lodging is getting to meet your hosts. We went into town for dinner, so missed the complimentary wine and cheese offering. Other than that, all communication (check-in, questions and checkout) was entirely electronic and we did not see anyone throughout our one-night stay. That felt strange and impersonal to us, but perhaps our expectations were too high. I think we would have been happier in a more traditional hotel setting."

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 $197 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.

Room 1

Check prices for these dates

Our top choices for Pittsfield vacation rentals

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

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

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

4. Mountain Green

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

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

7. Killington Center Renovated Studio with Kitchenette on Bus Route and Discounted Ski Rentals.

8. Killington condo 5 min to killington resort

9. Gnome Home Mountain Ski Chalet w/Sauna Killington

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

11. Sweet Suite! Modern, Pool, 2RM, 2BA, Ski Resort 532

12. The Swirl Suite at Killington: Renovated 2RM/2BA Suite. Sleeps 6. Discounted Ski Rentals.

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

14. Wobbly Cabin: 2BR/1.5 Bath Charming Killington Retreat Close to Everything

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

16. The Suites at Killington Center

17. Pristine Custom Cottage, Grand Piano, Massage Studio on Site

18. Relaxing Mountain Condo Steps from Killington Resort; Views, Pool & Shuttle!

19. BearNecessities- Pool, Hot Tub, Gym

20. Killington Cabin: Right Unit - Sleeps 10 in 4 BR, 2 BA Cozy Escape

Find vacation rentals that suit your style

Top Pittsfield Hotel Reviews

On The River Inn

Sleep Woodstock Motel

My Place Hotel-Randolph VT

Emrose Luxury Cabins

Killington Mountain Lodge, Tapestry Collection by Hilton

The Jackson

The Mountain Inn at Killington

Days Inn by Wyndham Rutland/Killington Area

Hampton Inn Rutland

Find out more about Pittsfield

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