Pittsfield Vacation Rentals from $226: 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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In two weeks

In two months

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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.

$570 nightly

Sep 22 - Sep 23

Total with taxes and fees

North Sherburne

Matthew R.

$402 nightly

Sep 22 - Sep 23

Total with taxes and fees

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Top Pittsfield Hotel Reviews

My Place Hotel-Randolph VT

8/10 Good

"The hotel is clean it is rural with nothing within view a gas station and McDonald’s down the hill by the interstate. They had coffee for you in the morning but no breakfast. For the price it should include it. They had a few items and sodas , no prices and rarely anyone at the counter to ask. We did have an issue with the toilet. It moved and made a loud noise as you got up. I told the staff one morning and she stated it would be repaired when we got back that evening. It was not."

The Jackson

8/10 Good

"The Hostess at the wine and cheese hour was very kind and helpful. That was the only time we saw anyone! The house is divided into separate areas and we were in the oldest part. The bed was comfortable, bathroom nice, amenities nice but wouldn’t book again because of the very narrow and steep stairs. My husband is 80, hauling luggage up those kind of stairs is dangerous. That would be the only reason not to return."

Sleep Woodstock Motel

10/10 Excellent

"Clean, cozy, and comfortable. I stayed here for a quick work trip and loved the cozy room. The hand drawn paintings on the wall were super cute. The room was clean and I could easily control the temperature. Although it’s on a busy road, the road noise was minimal at night and they provided ear plugs just in case. I would happily stay here again."

Woodstock Inn & Resort

8/10 Good

"Woodstock itself is absolutely beautiful and has a wonderful atmosphere. However, we had a few issues in both common areas, and our room that significantly impacted our experience. First, the cleanliness of the lobby was disappointing. I noticed that it was noticeably dusty and had visible spiderwebs in several areas, which did not create a welcoming first impression. Second, the bathroom and bed did not live up to the luxurious standard expected. Both the bathroom sink and bathtub drained incredibly slowly. This resulted in an unpleasant backflow of water whenever I tried to use them, which felt very unhygienic. Lastly, the bed was lopsided and very uncomfortable. The boxspring on both sides of the bed was covered in stains, which took away from the charm and comfort of the room. Everything else was great, and with a little more attention to room cleanliness, this place would be flawless."

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 $226 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

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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

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

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

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

5. Gnome Home Mountain Ski Chalet w/Sauna Killington

6. 4BR Killington Home Perfect for Families, Pet-Friendly

7. CubsCorner - Pool, Sauna, Gym, Close to Mountain!

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

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

10. Robin`s Nest- Pool, Gym, Fireplace, Near the AT

11. Snowarts- Game room, Fireplace, Close to golf!

12. Lakewood Lodge: 4BR/2.5BA Killington Home | Private Hot Tub, Wood Fire, Kent Pond & EV Charging

13. Killington condo 5 min to killington resort

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

15. Mountain Green

16. Pico's Doorstep: Ski On/Off. Steps to Lifts! Close to Killington.

17. Renovated 4BR House w/ Hot Tub & Fire Pit: Near Killington Lifts & Dining

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

19. Tanglewood Vista at Killington: Great Group Ski Home Close to Mountain. Hot Tub.

20. The Suites at Killington Center

Find vacation rentals that suit your style

Top Pittsfield Hotel Reviews

My Place Hotel-Randolph VT

The Jackson

Emrose Luxury Cabins

Brandon Inn

Comfort Inn Rutland - Killington

Killington Mountain Lodge, Tapestry Collection by Hilton

Sleep Woodstock Motel

On The River Inn

Woodstock Inn & Resort

Find out more about Pittsfield

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