Pittsfield Holiday Rentals from AU$304: Search Short-Term Rentals

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Our top choices for Pittsfield holiday rentals

A modern living room with a red sectional sofa, a round coffee table, wooden ceiling beams, a kitchen area, and a balcony with a view of trees.

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

North Sherburne

"On our 30th Anniversary trip to Vermont, New Hampshire and Maine we fell in love with Killington, Vermont. So much so we left the coast of Maine and last minute booked our remaining two nights back in Killington at the Poweder Run Lodge. The lodge was a wonderful experience! The location was beautiful, spacious, clean, had a fully stocked kitchen and spectacular views. The hosts were kind and easy to communicate with. We are older and need a continuous running fan and a little softer bed when we...

Heidi P.

includes taxes & fees

21 Oct - 22 Oct

A spacious living area with a red sectional sofa, a wooden dining table, and a kitchen in the background.

2. 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.

includes taxes & fees

18 Oct - 19 Oct

A spacious living room with a fireplace, a television, and a large window.

3. 4BR Killington Home Perfect for Families, Pet-Friendly

North Sherburne

Christina V.

A cozy cabin interior with a wooden ceiling, a dining area with a table and chairs, a sofa, a television, and a fireplace.

4. Cabin at Killington Left: 4BR with Wood Stove, Deck and Hot Tub

Killington

Leslie P.

includes taxes & fees

18 Oct - 19 Oct

A sign for Whifletree with a view of a golf course and mountains in the background.

5. Whiffletree Cozy Condo: 2-Bedroom Condo in Killington, VT with Garden View and Ski Rental Deals

Killington

Brandy

includes taxes & fees

18 Oct - 19 Oct

An indoor swimming pool with tiled flooring, a seating area with chairs, and large windows allowing natural light.

6. Rabbit Hole Trail Creek, Pool, Hot Tub, Fireplace

Killington

Amy G.

A house with a large porch, a covered entryway, and a deck.

7. Royalbear - Hot Tub, Fireplace, Close to Slopes

Killington

Max P.

8. 7 Bedrooms in the Heart of Killington - Game Room, Hot Tub, Easily Sleeps 16

Killington

Sorel F.

includes taxes & fees

19 Oct - 20 Oct

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Top Pittsfield Hotel Reviews

My Place Hotel-Randolph VT

10/10 Excellent

"Excellent"

Brandon Inn

10/10 Excellent

"The Brandon Inn was lovely- clean, comfortable and the staff were all amazingly helpful, cheerful and fun. To note, I have severe fragrance allergies but there were no scents or perfumes added to the linens or the rooms- I was so grateful! The only "issue" was the severe lack of water pressure and tepid temperature "hot' water in my 3rd floor suite. It was disappointing. They referred me to 22Park Eatery (next door) for dinner since their dining room was closed due to a private wedding (I didn't know that in advance) - and it was an excellent referral! So grateful. I'd stay here again without hesitation."

Find out more about Pittsfield

Everything you need to know about Pittsfield holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Pittsfield holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search.

Pittsfield holiday 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Pittsfield holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Pittsfield holiday rentals we have selected for you start as low as AU$304 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Pittsfield rentals

At Expedia, we put the best Pittsfield holiday 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 holiday.

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.

Frequently asked questions

Can I find a holiday rental in Pittsfield?

Yes, there are holiday rentals close to the most popular sights in Pittsfield, or you can select a more secluded option if you're looking for a relaxing stay. Pittsfield is known for its bars and restaurants.

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

PRIVATE & AFFORDABLE charming custom ranch in S. Woodstock. WIFI and AC.: This holiday home rental outside Pittsfield is located in a rural location, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many holiday rentals are there in Pittsfield?

Expedia has 28 holiday 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. Pittsfield Town Hall and Roger Clark Memorial Central Library are other places to visit while you're in town.

What are holiday rentals like in Pittsfield?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Pittsfield. Holiday rentals offer extras like laundry facilities and kitchens so you'll have all the conveniences of home. If you're concerned about a clean environment, holiday rentals can offer a sense of seclusion away from public hotel lifts and lobbies packed with people while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive option for family gatherings.

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Check prices for these dates

Our top choices for Pittsfield holiday rentals

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

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

3. 4BR Killington Home Perfect for Families, Pet-Friendly

4. Cabin at Killington Left: 4BR with Wood Stove, Deck and Hot Tub

5. Whiffletree Cozy Condo: 2-Bedroom Condo in Killington, VT with Garden View and Ski Rental Deals

6. Rabbit Hole Trail Creek, Pool, Hot Tub, Fireplace

7. Royalbear - Hot Tub, Fireplace, Close to Slopes

8. 7 Bedrooms in the Heart of Killington - Game Room, Hot Tub, Easily Sleeps 16

9. Charming TREEHOUSE in remote location

10. large ski ranch hot tub close to killington pets ok

11. Charming and meticulously cleaned cabin with panoramic view of the Green Mtns

12. Top of the Hill Modern Retreat

13. Private pet-friendly cabin in the woods w/ private campfire pit & screened porch

14. Gnome Home Mountain Ski Chalet w/Sauna Killington

15. Fabulous 4-bedroom chalet in tranquil Killington getaway with Hot tub two Kings

16. Killington Center 632: a spacious 2RM/2BA condo in the heart of Killington. Discounted ski rentals.

17. Skiers Suite: 2RM/2BA Renovated Condo on the Bus Route w/ Pool. Discounted Ski Rentals. #332

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

19. The Suites at Killington Center

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

Find holiday rentals that suit your style

Top Pittsfield Hotel Reviews

My Place Hotel-Randolph VT

Turn of River Lodge

Courtyard Middlebury

Mountain Meadows Lodge

Comfort Inn Rutland - Killington

Brandon Inn

The Shire Woodstock

Emrose Luxury Cabins

Après Inn Killington

Find out more about Pittsfield

Frequently asked questions

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