Pittsfield Vacation Rentals

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Sep 25 - Sep 26
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Oct 3 - Oct 5

Vacation Rentals in Pittsfield

Killington Vermont Ski and Snowmobiling House
Interior

Killington Vermont Ski and Snowmobiling House

9.2 out of 10, Wonderful, (44)
"Was not listed that soaps and toilet paper is not included. Just would’ve preferred that be out in the listing "
Killington Vermont Ski and Snowmobiling House
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Front of property

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3.0 star property
9.0 out of 10, Wonderful, (49)
"very clean and easy to access close to mountain"
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Cozy Loft for two with Hot Tub & Mtn Views
Exterior

Cozy Loft for two with Hot Tub & Mtn Views

10.0 out of 10, Exceptional, (260)
"Great location, marvelous host, terrific property! I'll be returning for sure!"
Cozy Loft for two with Hot Tub & Mtn Views
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
TV, fireplace, DVD player, books

Romantic Retreat: Mt. Views, Hot Tub, Movie Theater

10.0 out of 10, Exceptional, (513)
"We just love the quiet and beauty of the area. We love to come here because our hosts very easy to communicate and enjoy being on vacation."
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
Mountain Green
Indoor pool

Mountain Green

2.0 star property
6.2 out of 10, (12)
"The condo was very cozy for a family of four and suited us perfectly. Beds were comfortable and condo was clean. "
The price is ￥25,850
￥34,677 total
includes taxes & fees
Sep 29 - Sep 30
Mountain Green
Pristine Custom Cottage, Grand Piano, Massage Studio on Site
Fridge, microwave, oven, stovetop

Pristine Custom Cottage, Grand Piano, Massage Studio on Site

10.0 out of 10, Exceptional, (60)
"My husband and I couldn't have been happier at Camp Tiger Ted. Our host was wonderful in every way, welcoming and responsive to us, clear about caring for his beautiful property, and helpful whenever we reached out. It was a bonus to have the lovely piano, which I took advantage of on several occasions. We visit this area of Vermont often and we certainly will consider staying again, and we've already recommended it to others!Thank you, David, for such a delightful visit."
The price is ￥17,270
￥27,609 total
includes taxes & fees
Oct 1 - Oct 2
Pristine Custom Cottage, Grand Piano, Massage Studio on Site
Great King Bed studio, close to lifts, spa, indoor pool and great restaurants!
Desk, free WiFi, bed sheets

Great King Bed studio, close to lifts, spa, indoor pool and great restaurants!

9.0 out of 10, Wonderful, (54)
"Cozy but all the amenities, great location"
The price is ￥12,724
￥25,311 total
includes taxes & fees
Sep 29 - Sep 30
Great King Bed studio, close to lifts, spa, indoor pool and great restaurants!
Cozy studio with balcony, full kitchen, and free WiFi - walk to lifts
Indoor pool

Cozy studio with balcony, full kitchen, and free WiFi - walk to lifts

8.0 out of 10, Very Good, (35)
"Convenient for skiing and visiting the greater VT area. Unit has what you need for your stay."
Cozy studio with balcony, full kitchen, and free WiFi - walk to lifts
Killington Retreat
Exterior

Killington Retreat

2.0 star property
9.6 out of 10, Exceptional, (11)
"Had a great time staying so close to Killington. Sauna, hot tub and pool were a great way to warm up after a day of skiing."
Killington Retreat
Vineyard Cabin
Property grounds

Vineyard Cabin

10.0 out of 10, Exceptional, (4)
"The cabin was lovely and I appreciated that my cat could stay with me and that I could park my 5x8 uhaul trailer on the property during my stay. Al was helpful in all matters, I was especially grateful that he helped me reattach the trailer to my car at the end of my stay."
Vineyard Cabin
Ski right to your newly remodled great condo, enjoy woodburning fireplace & SAVE
TV, fireplace, DVD player, books

Ski right to your newly remodled great condo, enjoy woodburning fireplace & SAVE

9.6 out of 10, Exceptional, (92)
"This condo provided everything we needed for a nice stay of skiing. We very much enjoyed our stay."
Ski right to your newly remodled great condo, enjoy woodburning fireplace & SAVE
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
Outdoor dining

Cozy Hideaway near Ludlow/Okemo. HOT TUB!!

9.8 out of 10, Exceptional, (219)
"We had a wonderful stay! The house was extremely clean, and well organized. It has everything we need. "
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
Killington Sapphire
Living area

Killington Sapphire

9.2 out of 10, Wonderful, (7)
"Everything we needed to enjoy your family trip!"
Killington Sapphire
Secluded retreat in the trees
Exterior

Secluded retreat in the trees

10.0 out of 10, Exceptional, (27)
"The place was great ,it fit into our budget and the owners were more than helpful."
The price is ￥18,751
￥35,002 total
includes taxes & fees
Oct 1 - Oct 2
Secluded retreat in the trees
Stetson Hollow Cabin by Stetson Brook
Fireplace, books

Stetson Hollow Cabin by Stetson Brook

9.8 out of 10, Exceptional, (153)
"My best friend and I came to the cute cabin. We got to see lots of Vermont items that are nearby. "
The price is ￥35,717
￥67,838 total
includes taxes & fees
Oct 19 - Oct 20
Stetson Hollow Cabin by Stetson Brook
MountainView - Luxurious 5800SF Retreat with Breathtaking 4-Season Views!
Interior

MountainView - Luxurious 5800SF Retreat with Breathtaking 4-Season Views!

10.0 out of 10, Exceptional, (72)
"We absolutely LOVED our stay. The house and all its amenities were perfect for our ski trip, and we would be thrilled to come back again some time. "
MountainView - Luxurious 5800SF Retreat with Breathtaking 4-Season Views!
Trail Creek 41 | Condo in Killington near lifts/hiking with pool & rec room
Interior

Trail Creek 41 | Condo in Killington near lifts/hiking with pool & rec room

9.2 out of 10, Wonderful, (15)
"Well appointed and excellent location!"
Trail Creek 41 | Condo in Killington near lifts/hiking with pool & rec room
Classic Vermont Farmhouse near Sugarbush Resort
Exterior

Classic Vermont Farmhouse near Sugarbush Resort

9.6 out of 10, Exceptional, (42)
"House is centrally located, old but in decent condition. Rooms are clean and updated. We enjoyed our stay"
Classic Vermont Farmhouse near Sugarbush Resort
Charming waterfront 2BR house, private beach, waterfall, firepit, wifi, kayak
Terrace/patio

Charming waterfront 2BR house, private beach, waterfall, firepit, wifi, kayak

2.0 star property
9.8 out of 10, Exceptional, (77)
"The feel was so relaxing, felt like home.Im at a loss for words was just wonderful."
Charming waterfront 2BR house, private beach, waterfall, firepit, wifi, kayak
Ski In/Out Sunrise West Glade 3 BR 3 BA Trailside, Sauna, Pool, Hot Tub
3 bedrooms, iron/ironing board, free WiFi, bed sheets

Ski In/Out Sunrise West Glade 3 BR 3 BA Trailside, Sauna, Pool, Hot Tub

3.0 star property
9.4 out of 10, Exceptional, (15)
"Very nice townhouse."
Ski In/Out Sunrise West Glade 3 BR 3 BA Trailside, Sauna, Pool, Hot Tub
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Pittsfield Hotel Reviews

The Mountain Inn at Killington

The Mountain Inn at Killington

10/10 Excellent
"Very easy check-in. Lovely staff, very friendly, and helpful. The only thing missing is a tea coffee maker in the room. Otherwise, everything else is excellent."
Patricia 1-night trip
Posted 18 hours ago
The Mountain Inn at Killington

Find out more about Pittsfield

Find out more about Pittsfield

Search for holiday rentals in Pittsfield on Expedia! You can easily find your home rentals, villas, holiday apartments in Pittsfield using one of the methods below:

  • View our selection of featured holiday rentals in Pittsfield
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Look no further and take a look at our great range of rental properties in Pittsfield!

Explore a world of travel with Expedia

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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?

Quiet Modern Luxury Home w/ Memory Foam Beds, A/C, FAST WiFi and Full Kitchen: This vacation home rental outside of Pittsfield is located on a river and has a fireplace, a patio, 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. You can relax into your vacation with a garden and a selection of books.

How many vacation rentals are there in Pittsfield?

Expedia has 30 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.