Pittsfield Holiday Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
18 Aug - 19 Aug
Tomorrow
19 Aug - 20 Aug
This weekend
22 Aug - 24 Aug
Next weekend
29 Aug - 31 Aug

Holiday 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
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, (253)
"We had the most amazing week from check in to check out! We cant wait to come back."
Cozy Loft for two with Hot Tub & Mtn Views
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, (47)
"very clean and easy to access close to mountain"
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Mountain Green
Indoor pool

Mountain Green

2.0 star property
6.6 out of 10, (10)
"The condo was very cozy for a family of four and suited us perfectly. Beds were comfortable and condo was clean. "
The price is HK$1,519
HK$2,037 total
includes taxes & fees
19 Aug - 20 Aug
Mountain Green
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)
"There were dead bugs in the bathroom sink and bath, but it's fairly easy to clean them. Everything else in the room is great!"
The price is HK$669
HK$1,331 total
includes taxes & fees
19 Aug - 20 Aug
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
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, (505)
"Our stay at the Vermont Cabin "Romantic Retreat" was amazing. Owner was very communicative and made our stay stress free. Even though it's listed as a romantic retreat, it was great for the family too. The cabin was well stocked with everything we needed during our stay and the hottub was definitely a hit. We cant wait for our next stay."
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
Classic Vermont Cabin on 2.5 acres Lake Frontage
Property grounds

Classic Vermont Cabin on 2.5 acres Lake Frontage

9.8 out of 10, Exceptional, (110)
"Very quiet, well appointed cottage! So peaceful, beautiful scenery and VERY accommodating host!"
Classic Vermont Cabin on 2.5 acres Lake Frontage
Secluded retreat in the trees
Exterior

Secluded retreat in the trees

10.0 out of 10, Exceptional, (24)
"The place was great ,it fit into our budget and the owners were more than helpful."
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, (148)
"Perfect retreat inside a charming cabin for a ski getaway. Enjoy memorable family moments. "
The price is HK$1,878
HK$3,540 total
includes taxes & fees
10 Sept - 11 Sept
Stetson Hollow Cabin by Stetson Brook
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, (75)
"Beautiful area and gorgeous leaves. Liked having a weber grill."
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
9.6 out of 10, Exceptional, (12)
"Very nice townhouse."
Ski In/Out Sunrise West Glade 3 BR 3 BA Trailside, Sauna, Pool, Hot Tub
Trail Creek 75 | Condo in Killington
Interior

Trail Creek 75 | Condo in Killington

10.0 out of 10, Exceptional, (15)
"Having six in this place was tight, but we enjoyed our time. "
Trail Creek 75 | Condo in Killington
Woodstock Carriage House-280 acres-Views-Gardens-Skiing-Farm-2.5 miles from town
Fridge, microwave, oven, stovetop

Woodstock Carriage House-280 acres-Views-Gardens-Skiing-Farm-2.5 miles from town

10.0 out of 10, Exceptional, (54)
"Margarete and Alice welcomed us upon arrival. The house was the quintessential New England home! It was super clean, our bed was very comfortable with soft welcoming linens. The views are incredible, and the property provided much needed peace and tranquility. The weather was not the best but we managed to find plenty to do in the area. Alice, Margarete's black lab, took us for a hike on the property. She was an excellent playful guide! We look forward to returning to this peaceful retreat in...
Woodstock Carriage House-280 acres-Views-Gardens-Skiing-Farm-2.5 miles from town
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
Outdoor dining

Cozy Hideaway near Ludlow/Okemo. HOT TUB!!

9.8 out of 10, Exceptional, (214)
"Cozy and scenic property here with more than enough space, great spot with a dog, to go hiking, or just relax."
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
5/2 Old Farmhome-Beautiful Valley Views-Near Skiing-Sugarbush
Property grounds

5/2 Old Farmhome-Beautiful Valley Views-Near Skiing-Sugarbush

9.4 out of 10, Exceptional, (77)
"Great place to stay and great host!"
The price is HK$782
HK$2,497 total
includes taxes & fees
24 Aug - 25 Aug
5/2 Old Farmhome-Beautiful Valley Views-Near Skiing-Sugarbush
Glamping hut with WiFi in Ripton, biking, hiking, skiing
Property grounds

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

The price is HK$696
HK$1,306 total
includes taxes & fees
20 Aug - 21 Aug
Glamping hut with WiFi in Ripton, biking, hiking, skiing
Alpine Village Chalet
Interior

Alpine Village Chalet

2.0 star property
10.0 out of 10, Exceptional, (7)
"Our stay at this cozy cabin was just what we needed. Ample room, comfortable beds, clean linens and a superb property in a quiet neighbourhood, our kids enjoyed the yard full of snow and their bunking “nook” upstairs. We loved the time together and enjoyed the amenities offered. The owners were always quick to respond. We recommend for a quiet weekend away. "
Alpine Village Chalet
PRIVATE & AFFORDABLE charming custom ranch in S. Woodstock. WIFI and AC.
Exterior

PRIVATE & AFFORDABLE charming custom ranch in S. Woodstock. WIFI and AC.

9.8 out of 10, Exceptional, (219)
"Our stay was amazing! The house offered everything we needed, was spacious and clean. Working with the owners was also easy. Would definitely recommend and stay again!"
PRIVATE & AFFORDABLE charming custom ranch in S. Woodstock. WIFI and AC.
SPRING IN THE GREEN MOUNTAINS/PET FRIENDLY-WOOF
Fridge, microwave, oven, stovetop

SPRING IN THE GREEN MOUNTAINS/PET FRIENDLY-WOOF

10.0 out of 10, Exceptional, (89)
"terrific time at this wonderful cabin. they had everything we needed to have fun on the lake."
SPRING IN THE GREEN MOUNTAINS/PET FRIENDLY-WOOF
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Pittsfield Hotel Reviews

Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area

10/10 Excellent
"Clean and comfortable. Good value for what you get. Would stay again. "
David 1-night trip
Posted 21 hours ago
Days Inn by Wyndham Rutland/Killington Area

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?

Brand new 2021 Reno of Federal Style House, steps from Downtown Brandon: This holiday home rental outside of Pittsfield is located in the city centre, 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. You can relax into your holiday with a garden and an arcade/games room.

How many holiday rentals are there in Pittsfield?

Expedia has 39 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.