Pittsfield Holiday Rentals from NZ$466: 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

12 Nov - 13 Nov

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

12 Nov - 13 Nov

A rustic cabin with a wooden deck, surrounded by dense greenery and a rocky landscape.

3. Gnome Home Mountain Ski Chalet w/Sauna Killington

Stockbridge

Gerald S.

includes taxes & fees

12 Nov - 13 Nov

A two-story building with a dark brown exterior, a covered porch, and a number '303' sign.

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

North Sherburne

Matthew R.

includes taxes & fees

20 Nov - 21 Nov

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

5. 4BR Killington Home Perfect for Families, Pet-Friendly

North Sherburne

Christina V.

A spacious living area with a wooden ceiling, a sofa, a chair, a television, and a staircase.

6. Delightful 2-bedroom, solar-powered cabin in charming Vermont awaits you

Chittenden

includes taxes & fees

12 Nov - 13 Nov

A modern house with a stone facade, a large deck, and outdoor seating.

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

Killington

SHEEPDOG 1.

includes taxes & fees

15 Nov - 16 Nov

A modern living room with a fireplace, a large sectional sofa, and a television mounted above the fireplace.

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

Killington

Olaf G.

includes taxes & fees

12 Nov - 13 Nov

9. The Suites at Killington Center

Killington

includes taxes & fees

22 Nov - 23 Nov

A living room with a sofa, a dining table with chairs, a kitchen area with wooden cabinets, and a bar.

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

Killington

Susanne B.

includes taxes & fees

12 Nov - 13 Nov

A modern kitchen with a microwave, stove, and red stools. A living area with a fireplace and a TV is visible in the background.

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

Killington

John O.

includes taxes & fees

12 Nov - 13 Nov

A modern kitchen with stainless steel appliances, a dining area with a glass table, and a living room with a fireplace.

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

Killington

Riley T.

Pass snacks across the counter without leaving the conversation in the main room.

13. Trailside Loft at Pico | Ski-In/Out Condo w/ Loft + 2BR | Steps to Lift

Killington

Casey C.

includes taxes & fees

12 Nov - 13 Nov

A bedroom with a large bed, a TV mounted on the wall, and a sliding door leading to a bathroom.

14. Jack S`Bearo - Slopes, Fireplace, Pool

Killington

Joseph S.

includes taxes & fees

12 Nov - 13 Nov

A modern kitchen with white cabinets, a built-in microwave, and a stainless steel refrigerator.

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

Killington

Lisa

includes taxes & fees

12 Nov - 13 Nov

A living room with a sofa, coffee table, and fireplace. There is a large window and a balcony with outdoor furniture.

16. FirBear- Pool, Gym, Fireplace, Hot tub!

The Woods

Kristin G.

includes taxes & fees

12 Nov - 13 Nov

A modern living room with a glass coffee table, a sofa, a TV mounted on the wall, a fireplace, and a blue accent wall.

17. Tranquil Peaks Studio at Killington Center - Perfect for a Getaway in the Heart of Killington

Killington

Carla M.

includes taxes & fees

12 Nov - 13 Nov

An aerial view of a residential area with houses, a swimming pool, and a parking lot.

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

Killington

Asad B.

includes taxes & fees

12 Nov - 13 Nov

A residential area with houses, a swimming pool, and a mountain backdrop.

19. The Suites: Next Door - Studio at Killington Resort on the Bus Route. Discounted Ski Rentals. 531

Killington

Nathan H.

includes taxes & fees

15 Nov - 16 Nov

A modern kitchen with a central island, stainless steel appliances, and wooden cabinets.

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

Killington

Spencer P.

includes taxes & fees

12 Nov - 13 Nov

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Find holiday rentals that suit your style

Top Pittsfield Hotel Reviews

A spacious living room with a stone fireplace, wooden furniture, and a large potted plant.

The Trailside Inn

North Sherburne

8/10 Good

Tony

Snowed Inn

Killington

10/10 Excellent

Just like a hallmark card. The most friendliest and helpful staff you can find. We loved relaxing here and taking in the atmosphere. Lots of amazing restaurants within walking distance and the free shuttle was really helpful in getting around. So many small touches that made this place one of our favourite places to stay. AMAZING! We came in summer and hope to comeback one day in the winter and experience the snow and ski fields.

Melissa

A modern kitchen with a central island, stainless steel appliances, and a dining area with chairs.

Sleep Woodstock Motel

Woodstock

10/10 Excellent

Colin

A spacious room with a stone fireplace, leather furniture, and large windows offering a view of greenery.

The Jackson

West Woodstock

10/10 Excellent

Julie

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 favorite 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 depends 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 NZ$466 per night. Entering your travel dates in the search wizard you might find 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.

Pittsfield Holiday Rentals

Change your mind

Treat yourself

Be picky

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. Gnome Home Mountain Ski Chalet w/Sauna Killington

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

5. 4BR Killington Home Perfect for Families, Pet-Friendly

6. Delightful 2-bedroom, solar-powered cabin in charming Vermont awaits you

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

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

9. The Suites at Killington Center

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

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

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

13. Trailside Loft at Pico | Ski-In/Out Condo w/ Loft + 2BR | Steps to Lift

14. Jack S`Bearo - Slopes, Fireplace, Pool

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

16. FirBear- Pool, Gym, Fireplace, Hot tub!

17. Tranquil Peaks Studio at Killington Center - Perfect for a Getaway in the Heart of Killington

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

19. The Suites: Next Door - Studio at Killington Resort on the Bus Route. Discounted Ski Rentals. 531

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

Find holiday rentals that suit your style

Top Pittsfield Hotel Reviews

The Trailside Inn

8/10 Good

Find out more about Pittsfield

Pittsfield holiday rentals: An excellent choice for every season

How to find incredible deals on Pittsfield rentals

Frequently Asked Questions

Can I find a holiday rental in Pittsfield?

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

How many holiday rentals are there in Pittsfield?

What can I see and do in Pittsfield?

What are holiday rentals like in Pittsfield?