Pittsfield Holiday Rentals

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Check prices for these dates

Tonight
5 Oct - 6 Oct
Tomorrow
6 Oct - 7 Oct
Next weekend
10 Oct - 12 Oct
In two weeks
17 Oct - 19 Oct

Holiday Rentals in Pittsfield

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)
"Private and great location. Communication was amazing. For the price it felt like an absolute steal. Will definitely be going back in the winter for a ski trip. "
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, (261)
"Great location, marvelous host, terrific property! I'll be returning for sure!"
Cozy Loft for two with Hot Tub & Mtn Views
Mountain Green
Indoor pool

Mountain Green

2.0 star property
6.6 out of 10, (13)
"Great communication from Jeff."
The price is HK$1,520
HK$2,040 total
includes taxes & fees
13 Oct - 14 Oct
Mountain Green
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, (515)
"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
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, (63)
"Very clean, cozy environment. Property owner was very nice and helped with any questions we had. 100% would book again!!"
The price is HK$945
HK$1,512 total
includes taxes & fees
15 Oct - 16 Oct
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 HK$665
HK$1,324 total
includes taxes & fees
6 Oct - 7 Oct
Great King Bed studio, close to lifts, spa, indoor pool and great restaurants!
Killington Retreat
Exterior

Killington Retreat

2.0 star property
9.6 out of 10, Exceptional, (13)
"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
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)
"Me and my friends stayed here for a week. It was clean when we got there. The pool and hot tub were really nice. Over all it was a nice stay and we enjoyed the area!!"
Trail Creek 41 | Condo in Killington near lifts/hiking with pool & rec room
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
Vineyard Cabin
Property grounds

Vineyard Cabin

10.0 out of 10, Exceptional, (4)
"Cozy cabin, pet friendly, lovely views! "
Vineyard Cabin
Stetson Hollow Cabin by Stetson Brook
Fireplace, books

Stetson Hollow Cabin by Stetson Brook

9.8 out of 10, Exceptional, (154)
"My best friend and I came to the cute cabin. We got to see lots of Vermont items that are nearby. "
The price is HK$1,681
HK$3,451 total
includes taxes & fees
19 Oct - 20 Oct
Stetson Hollow Cabin by Stetson Brook
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
Outdoor dining

Cozy Hideaway near Ludlow/Okemo. HOT TUB!!

9.8 out of 10, Exceptional, (220)
"Was a nice place to unwind and unplug from the city over the holiday weekend. Very clean and was homey. "
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
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
Glamping hut with WiFi in Ripton, biking, hiking, skiing
Property grounds

Glamping hut with WiFi in Ripton, biking, hiking, skiing

The price is HK$693
HK$1,299 total
includes taxes & fees
7 Oct - 8 Oct
Glamping hut with WiFi in Ripton, biking, hiking, skiing
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
🌺Luxury Estate🌳 25 Gorgeous Acres of Privacy 🌳Family Getaway🌳Swimming Pond🌺
Exterior

🌺Luxury Estate🌳 25 Gorgeous Acres of Privacy 🌳Family Getaway🌳Swimming Pond🌺

9.8 out of 10, Exceptional, (15)
"The Property and surrounding country were spectacular and me and my family and our pets had a lovely time. If you love the outdoors and staying in a wonderful home this is the place!"
🌺Luxury Estate🌳 25 Gorgeous Acres of Privacy 🌳Family Getaway🌳Swimming Pond🌺
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)
"Great spot, top end house! ATV tour excellent "
MountainView - Luxurious 5800SF Retreat with Breathtaking 4-Season Views!
Nana's House
Exterior detail

Nana's House

10.0 out of 10, Exceptional, (45)
"I'm not much for reviews, but everything about this place was perfect! We can't wait to go back!"
Nana's House
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-On/Off - private sauna - right next to lift - 1GB WiFi - Renovated
Fridge, microwave, oven, stovetop

Ski-On/Off - private sauna - right next to lift - 1GB WiFi - Renovated

9.8 out of 10, Exceptional, (60)
"Ski in/ Ski out Great locationJoel was very helpful and friendly. Really enjoyed our stay. "
Ski-On/Off - private sauna - right next to lift - 1GB WiFi - Renovated
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

Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington

10/10 Excellent
"Room had an odd smell to it…."
Justine 1-night trip
Posted 2 days ago
Comfort Inn Rutland - 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
  • Use the map to find apartments and other holiday homes in the Pittsfield neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Pittsfield while they last

Look no further and take a look at our great range of rental properties in Pittsfield!

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?

Charming waterfront 2BR house, private beach, waterfall, firepit, wifi, kayak: This holiday home rental outside Pittsfield is located on the waterfront, and has a fireplace, a balcony and cable TV to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. Kick off your shoes and enjoy yourself with a garden and a selection of books.

How many holiday rentals are there in Pittsfield?

Expedia has 31 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. Roger Clark Memorial Central Library and Pittsfield Town Hall 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.