Pittsfield Vacation Homes

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Our top choices for Pittsfield holiday homes

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

North Sherburne

HK$4,881 total

includes taxes & fees

9 Jun - 10 Jun

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.

HK$5,122 total

includes taxes & fees

9 Jun - 10 Jun

Killington

HK$6,204 total

includes taxes & fees

9 Jun - 10 Jun

Spacious Central 4BR, Ski, Bike,Hike, Explore Downtown

Rutland

Dominic C.

HK$3,420 total

includes taxes & fees

9 Jun - 10 Jun

Tanglewood Vista at Killington: Great Group Ski Home Close to Mountain. Hot Tub.

Killington

Mark B.

HK$5,712 total

includes taxes & fees

10 Jun - 11 Jun

The Navillus House: Hot Tub, Ski On/Ski Off, A/C. Discounted Ski Rentals.

Killington

John D.

HK$8,310 total

includes taxes & fees

9 Jun - 10 Jun

Beautiful home located in the Mad River Valley

Warren

Monica R.

Alpine Chalet Grill, Fire pit, Pool, Gym, CornHole

Killington

Kathleen G.

HK$6,974 total

includes taxes & fees

9 Jun - 10 Jun

Top of the Hill Modern Retreat

East Warren

Michael Q.

HK$5,017 total

includes taxes & fees

11 Jun - 12 Jun

RoundTop Chalet | Hot Tub, Fire Pit & Mountain Views near Killington & Okemo

Plymouth

"Everything about the property was beautiful and relaxing. We loved our stay .... We did however run into one issue, while we were enjoying the property, someone claiming to be there to service the hot tub decided to let themselves in with the lock code unannounced while we were undressed and stood there listening to us and only when the dog ran down there did he announce himself. Not sure if simple sent them or if they showed up on their own accord but boy did we get quite the scare and hope...

Adam S.

HK$4,501 total

includes taxes & fees

9 Jun - 10 Jun

Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock

Stockbridge

Sophie L.

HK$4,306 total

includes taxes & fees

9 Jun - 10 Jun

Smart TV, fireplace, video games, stereo

The Big Lebearski- AC, Grill, Fire Pit, Hot tub!

Killington

Tom W.

HK$5,152 total

includes taxes & fees

9 Jun - 10 Jun

Feel the real VT! Lakes, hikes, a foodies delight!

Proctor

Rebecca

HK$4,490 total

includes taxes & fees

15 Jun - 16 Jun

Mad Mountain Meadows - Stunning Mountain Views!

East Warren

Elizabeth D.

HK$5,060 total

includes taxes & fees

14 Jun - 15 Jun

Ski Home/Arcade Mountain Views Near Killington/Woodstock

Stockbridge

Kevin M.

HK$4,306 total

includes taxes & fees

9 Jun - 10 Jun

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Top Pittsfield Hotel Reviews

Days Inn by Wyndham Rutland/Killington Area

10/10 Excellent

"Pretty decent"

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."

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