Pittsfield Vacation Rentals

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Vacation Rentals in Pittsfield

Our top choices for Pittsfield vacation rentals

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

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

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 CA $269
CA $362 total
includes taxes & fees
Aug 24 - Aug 25
Mountain Green

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 CA $118
CA $235 total
includes taxes & fees
Aug 28 - Aug 29
Great King Bed studio, close to lifts, spa, indoor pool and great restaurants!

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

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

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 CA $333
CA $637 total
includes taxes & fees
Sep 10 - Sep 11
Stetson Hollow Cabin by Stetson Brook

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."
The price is CA $193
CA $353 total
includes taxes & fees
Sep 3 - Sep 4
Secluded retreat in the trees

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

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

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

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

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!!

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!!

Quiet Modern Luxury Home w/ Memory Foam Beds, A/C, FAST WiFi and Full Kitchen

10.0 out of 10, Exceptional, (109)
"Nice rental for our family and the owner was very rsponsive."
Quiet Modern Luxury Home w/ Memory Foam Beds, A/C, FAST WiFi and Full Kitchen

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

9.8 out of 10, Exceptional, (220)
"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.

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

Off Grid Glamping Shed with River Access

2.0 star property
The price is CA $81
CA $129 total
includes taxes & fees
Aug 21 - Aug 22
Off Grid Glamping Shed with River Access

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

The price is CA $123
CA $230 total
includes taxes & fees
Aug 28 - Aug 29
Glamping hut with WiFi in Ripton, biking, hiking, skiing

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.
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Top Pittsfield Hotel Reviews

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?

Brand new 2021 Reno of Federal Style House, steps from Downtown Brandon: This vacation home rental outside of Pittsfield is located in the city center and has a fireplace, a patio, and a barbecue grill 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 you can cook with friends or family. You can relax into your vacation with a garden and an arcade game room.

How many vacation rentals are there in Pittsfield?

Expedia has 39 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.