Pittsfield Vacation Rentals from ￥30,283: Search Short-Term Rentals

Q: 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.

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Our top choices for Pittsfield vacation rentals

NEW! Smart 3BR Basecamp w/ Hot Tub, AC, EV Charger & Flat Parking

North Sherburne

￥100,503 total

includes taxes & fees

Jun 10 - Jun 11

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

North Sherburne

"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...

Essa R.

￥105,601 total

includes taxes & fees

Jun 10 - Jun 11

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

Ripton

Alex

￥26,727 total

includes taxes & fees

Jun 11 - Jun 12

Unique Vacation Rental in an Old Farmhouse in Windsor County, Vermont

South Royalton

￥24,345 total

includes taxes & fees

Jun 13 - Jun 14

Escape to this private and peaceful tiny home with hot tub in Sharon, VT!

Sharon

Serge

￥47,535 total

includes taxes & fees

Jun 10 - Jun 11

Secluded retreat in the trees

Roxbury

Jules

￥39,768 total

includes taxes & fees

Jun 15 - Jun 16

Historic Converted Concrib Glamping Cabin in the Heart of Vermont, Perfect for a Weekend Retreat in Nature

South Royalton

￥44,153 total

includes taxes & fees

Jun 12 - Jun 13

Mountain Green

Killington

troy

￥31,768 total

includes taxes & fees

Jun 25 - Jun 26

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Top Pittsfield Hotel Reviews

Killington Mountain Lodge, Tapestry Collection by Hilton

8/10 Good

"Very nice bed with comfortable mattress"

Lincoln Inn & Gallery

6/10 Okay

"My primary complaint was the morning we checked out. Actually we just dropped the key in the basket. You would think with checkout at 10:00 the proprietor would be around to see us off at 9:30. Instead, he was nowhere to be found. The desk had a phone number to call which I did, and the cordless phone rang at the desk but he did not have it with him so we left with the answering machine going off. I just wanted some ice to keep our stuff cold till our next stop. Instead I stopped at a gas station to get ice. Sometimes the devil is in the details."

Mountain Sports Inn

8/10 Good

"This is the 4th or 5th time I have stayed here but in the past it was only for a night or two. This time we were there for 5 nights. There were good things and bad, I’ll start with the bad. My biggest complaints were space for clothing, temperature, and the bed. There are two little drawers in each nightstand, but otherwise all storage areas are open. I prefer to have my underclothes in drawers. That’s a preference thing, but nice to know in advance. The temperature was fine during the day but once you close the blackout drapes, you lose any ability to cool using the window units. The first two nights it was cool enough outside to open a window and that kept it cooler. The last night I was there I slept in top of the cover and blanket (took off comforter first night and never put back on) most of the night to stay cool. If you like to sleep cool (I prefer 67 or 68 degrees), bring a fan. Or maybe ask if they had one, I literally thought of that the last night I was there so didn’t. The bed was harder than I remember it being any other time we stayed and the pillows were flat and hard. It’s also on a spring frame, so every time you move it creaked. We could have asked for more pillows but made do. I would definitely stay again but if it was a longer stay in warmer weather, I would plan ahead and bring a fan. The breakfast was great and had been added to since we last stayed. Ample parking, good WiFi (went down once, but was quickly restored), nice location and friendly people."

Find out more about Pittsfield

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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?

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 26 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.

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Check prices for these dates

Our top choices for Pittsfield vacation rentals

NEW! Smart 3BR Basecamp w/ Hot Tub, AC, EV Charger & Flat Parking

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

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

Unique Vacation Rental in an Old Farmhouse in Windsor County, Vermont

Escape to this private and peaceful tiny home with hot tub in Sharon, VT!

Secluded retreat in the trees

Historic Converted Concrib Glamping Cabin in the Heart of Vermont, Perfect for a Weekend Retreat in Nature

Mountain Green

Stetson Hollow Cabin by Stetson Brook

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

Cedarbrook Deluxe 1 bedroom Queen Suite with outdoor heated pool 102

Dreamy Artist Chalet in Secluded Historic Village

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

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

Newly Renovated Studio! Amazing Views/Location 3F9. Pool. Hot Tub, Shuttle.

Killington Cabin - Left Unit: Great for families, Cozy, Close to Mountain. Hot Tub. Wood Stove.

Killington condo 5 min to killington resort

Cozy Rutland Retreat

Killington Center Renovated Studio with Kitchenette on Bus Route and Discounted Ski Rentals.

Pristine Custom Cottage, Grand Piano, Massage Studio on Site

Find vacation rentals that suit your style

Top Pittsfield Hotel Reviews

Killington Mountain Lodge, Tapestry Collection by Hilton

Days Inn by Wyndham Rutland/Killington Area

The Mountain Inn at Killington

Mountain Meadows Lodge

Hampton Inn Rutland

Lincoln Inn & Gallery

Mountain Sports Inn

On The River Inn

My Place Hotel-Randolph VT

Find out more about Pittsfield

Frequently asked questions

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