A lake surrounded by autumn-colored trees and a rocky shoreline.

Pittsfield Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sep - 20 Sep
In four months
16 Oct - 18 Oct

Our top choices for Pittsfield vacation rentals

TV

Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont

Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont
North Sherburne
10.0 out of 10, Exceptional, (1 review)
"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...
United States
Essa R.
The price is AED 727
AED 2,344 total
includes taxes & fees
23 Jun - 24 Jun
Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont
Outdoor dining

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

Glamping hut with WiFi in Ripton, biking, hiking, skiing
Ripton
9.6 out of 10, Exceptional, (7 reviews)
"Beautiful, magical location, and prompt communication."
United States
Alex
The price is AED 327
AED 613 total
includes taxes & fees
23 Jun - 24 Jun
Glamping hut with WiFi in Ripton, biking, hiking, skiing
Aerial view

Mountain Green

Mountain Green
2.0 star property
Killington
7.2 out of 10, Good, (25 reviews)
"I enjoy the location "
United States
troy
The price is AED 220
AED 756 total
includes taxes & fees
23 Jun - 24 Jun
Mountain Green
Private kitchen

new 2 bedroom close to killington and bike trails this is pet ok downstairs unit

new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
Mendon
9.8 out of 10, Exceptional, (6 reviews)
"Very pretty property, wish we could have spent more time there. Getting in and out was easy and there were plenty of options for food in town just a few minutes away. Great stay."
United States
Aurore H.
The price is AED 327
AED 844 total
includes taxes & fees
23 Jun - 24 Jun
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
Interior

Beautiful home located in the Mad River Valley

Beautiful home located in the Mad River Valley
Warren
9.6 out of 10, Exceptional, (44 reviews)
"Very convenient to Warren center. This house served us well as we were able to bring our dog over the Christmas holiday. Perfect house for a family. "
United States
Monica R.
Beautiful home located in the Mad River Valley
Smart TV, fireplace

Wobbly Cabin: 2BR/1.5 Bath Charming Killington Retreat Close to Everything

Wobbly Cabin: 2BR/1.5 Bath Charming Killington Retreat Close to Everything
Killington
10.0 out of 10, Exceptional, (15 reviews)
"Cannon was cozy, clean, and as described. "
United States
Addams S.
The price is AED 522
AED 1,762 total
includes taxes & fees
23 Jun - 24 Jun
Wobbly Cabin: 2BR/1.5 Bath Charming Killington Retreat Close to Everything
Fridge, microwave, oven, stovetop

Pristine Custom Cottage, Grand Piano, Massage Studio on Site

Pristine Custom Cottage, Grand Piano, Massage Studio on Site
Leicester
10.0 out of 10, Exceptional, (79 reviews)
"Great place to stay for a Vermont getaway! "
United States
Jeremy H.
The price is AED 471
AED 742 total
includes taxes & fees
28 Jun - 29 Jun
Pristine Custom Cottage, Grand Piano, Massage Studio on Site
Property grounds

Secluded retreat in the trees

Secluded retreat in the trees
Roxbury
10.0 out of 10, Exceptional, (43 reviews)
"Very cozy and easy check in!"
United States
Emily R.
The price is AED 628
AED 1,107 total
includes taxes & fees
18 Jul - 19 Jul
Secluded retreat in the trees
Fridge, oven, stovetop, coffee/tea maker

Brookside Cabin - Your Vermont Offgrid Escape

Brookside Cabin - Your Vermont Offgrid Escape
Brookfield
The price is AED 430
AED 1,345 total
includes taxes & fees
23 Jun - 24 Jun
Brookside Cabin - Your Vermont Offgrid Escape
Dining

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

Skiers Suite: 2RM/2BA Renovated Condo on the Bus Route w/ Pool. Discounted Ski Rentals. #332
Killington
9.4 out of 10, Exceptional, (11 reviews)
"Quick trip but would stay here again"
United States
John O.
Skiers Suite: 2RM/2BA Renovated Condo on the Bus Route w/ Pool. Discounted Ski Rentals. #332
Dining

Cozy Rutland Retreat

Cozy Rutland Retreat
Rutland
9.8 out of 10, Exceptional, (8 reviews)
"Very nice place to stay in Rutland."
United States
Dave M.
The price is AED 281
AED 694 total
includes taxes & fees
23 Jun - 24 Jun
Cozy Rutland Retreat
Outdoor dining

Fabulous 4-bedroom chalet in tranquil Killington getaway with gorgeous Hot tub

Fabulous 4-bedroom chalet in tranquil Killington getaway with gorgeous Hot tub
North Sherburne
8.2 out of 10, Very Good, (13 reviews)
"We had a great time!"
United States
Matthew R.
The price is AED 450
AED 1,529 total
includes taxes & fees
23 Jun - 24 Jun
Fabulous 4-bedroom chalet in tranquil Killington getaway with gorgeous Hot tub
Fireplace, books

Stetson Hollow Cabin by Stetson Brook

Stetson Hollow Cabin by Stetson Brook
Warren
9.8 out of 10, Exceptional, (168 reviews)
"The cabin was very cozy. The host was very receptive and flexible."
United States
william p.
The price is AED 793
AED 1,625 total
includes taxes & fees
23 Jun - 24 Jun
Stetson Hollow Cabin by Stetson Brook
Interior

Modern Killington Farmhouse Condo: Close to it all! 412

Modern Killington Farmhouse Condo: Close to it all! 412
Killington
10.0 out of 10, Exceptional, (57 reviews)
"Fantastic spot for hitting mountains as a family. Incredibly clean, convenience, and comfortable. Couldn’t be better! EV charging on site was the icing on the cake "
United States
Tyler L.
The price is AED 418
AED 1,340 total
includes taxes & fees
23 Jun - 24 Jun
Modern Killington Farmhouse Condo: Close to it all! 412
Fridge, microwave, oven, stovetop

Jack S`Bearo- AC, Pool, Mountain Views, Hiking, Gym

Jack S`Bearo- AC, Pool, Mountain Views, Hiking, Gym
Killington
10.0 out of 10, Exceptional, (15 reviews)
"Host was very responsive and the home was great! "
United States
Rebecca B.
The price is AED 463
AED 1,000 total
includes taxes & fees
23 Jun - 24 Jun
Jack S`Bearo- AC, Pool, Mountain Views, Hiking, Gym
TV, fireplace, Netflix, streaming services

Killington Cabin: Right Unit - Sleeps 10 in 4 BR, 2 BA Cozy Escape

Killington Cabin: Right Unit - Sleeps 10 in 4 BR, 2 BA Cozy Escape
Killington
9.8 out of 10, Exceptional, (65 reviews)
"Amazing location, cozy cabin with plenty of beds for sleeping , owners were super responsive will def love to stay again!"
United States
Robert D.
The price is AED 487
AED 1,954 total
includes taxes & fees
24 Jun - 25 Jun
Killington Cabin: Right Unit - Sleeps 10 in 4 BR, 2 BA Cozy Escape
Exterior

Beautiful home located in the Mad River Valley

Beautiful home located in the Mad River Valley
Warren
10.0 out of 10, Exceptional, (25 reviews)
"We had a great time! "
United States
Allie T.
Beautiful home located in the Mad River Valley
Dining

Killington resort: Walk to Mountain, Biking & Pool

Killington resort: Walk to Mountain, Biking & Pool
Killington
9.8 out of 10, Exceptional, (32 reviews)
"Excellent VRBO. Perfect location to the mountain. Condo was modern and clean and very comfortable. Would go back again!! "
United States
Sheri L.
The price is AED 420
AED 1,261 total
includes taxes & fees
25 Jun - 26 Jun
Killington resort: Walk to Mountain, Biking & Pool
Interior

103 Deluxe One bedroom Queen Suite w/ outdoor heated pool

103 Deluxe One bedroom Queen Suite w/ outdoor heated pool
Killington
9.6 out of 10, Exceptional, (18 reviews)
"Would stay again!"
United States
Hannah M.
The price is AED 382
AED 578 total
includes taxes & fees
23 Jun - 24 Jun
103 Deluxe One bedroom Queen Suite w/ outdoor heated pool
Property grounds

Cozy cabin >> Hottub, WiFi, AC. Easy access to outdoors activities year around

Cozy cabin >> Hottub, WiFi, AC. Easy access to outdoors activities year around
Hancock
10.0 out of 10, Exceptional, (4 reviews)
"The host was easy to communicate with, gracious and helpful. Amenities were generous and everything was in excellent condition. Really enjoyed the quiet treed setting and the hot tub."
United States
Elizabeth N.
The price is AED 625
AED 1,506 total
includes taxes & fees
28 Jun - 29 Jun
Cozy cabin >> Hottub, WiFi, AC. Easy access to outdoors activities year around
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.
View all properties
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

Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

10/10 Excellent
"Nice place!"
Matt 1-night trip
Posted 3 hours ago
Killington Mountain Lodge, Tapestry Collection by Hilton

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?

Killington area home - 4-seasons, hot tub and A/C: This highly rated vacation home rental in Pittsfield is located in the mountains and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals are there in Pittsfield?

Expedia has 29 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.