Pittsfield Holiday Homes from £228: Search Holiday Homes in Pittsfield

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

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Our top choices for Pittsfield holiday homes

A spacious living area with a red sectional sofa, a wooden dining table, and a kitchen in the background.

1. 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.

includes taxes & fees

5 Oct - 6 Oct

A modern living room with a red sectional sofa, a round coffee table, wooden ceiling beams, a kitchen area, and a balcony with a view of trees.

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

North Sherburne

A living room with a wooden console table, a potted plant, and two clocks. A staircase and a fireplace with a TV are in the background.

3. Ski Home/Arcade Mountain Views Near Killington/Woodstock

Stockbridge

Kevin M.

includes taxes & fees

5 Oct - 6 Oct

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

Stockbridge

Sophie L.

includes taxes & fees

5 Oct - 6 Oct

A wooden cabin with a snow-covered ground, a wooden fence, and a door with a window above it.

5. Luxury Condo Tucked in the Heart of Killington

Killington

includes taxes & fees

2 Nov - 3 Nov

A spacious living room with a fireplace, a television, and a large window.

6. 4BR Killington Home Perfect for Families, Pet-Friendly

North Sherburne

Christina V.

includes taxes & fees

5 Oct - 6 Oct

A cozy living room with a stone fireplace, a large sectional sofa, and a wooden ceiling.

7. The Tower House | Hot Tub | Firepit | Dog-Friendly

Killington

Patrick B.

includes taxes & fees

5 Oct - 6 Oct

A cozy room with a wooden ceiling, a large window with a snowy view, a sofa, and a dining table with chairs.

8. Family and friend friendly upper ski cabin with bunks, sleeps 8

Killington

includes taxes & fees

5 Oct - 6 Oct

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Top Pittsfield Hotel Reviews

Greenbrier Inn

10/10 Excellent

"Great breakfast and late snack there whenever you want."

The Shire Woodstock

10/10 Excellent

"We had Deluxe King River view - deluxe has a fireplace and shares a balcony with rocking chairs. The room was great except a couple little maintenance issues (I told the front desk and hope they fix). And it’s a great location walkable to downtown, great views of river and hills, and the inn has fire pits ready to go. Too bad coffee makers are in the hallway, not in the room, and there’s no breakfast (they said they might start next year). We went nearby for breakfast, and a good market is just across the street."

Brandon Inn

8/10 Good

"This lovely inn is a unique experience. I loved the building and furnishings, and my dog and I enjoyed exploring the garden area. The people were helpful and friendly, and breakfast was nice. I did have a little trouble with the electronic lock on the door to my room, but was eventually able to get in each time. Also, I couldn’t find a remote for the TV in the room, and when I called the phone number for assistance, the voice mailbox was full so I couldn’t leave a message. I didn’t care that much about watching TV so I didn’t bother to follow up."

On The River Inn

8/10 Good

"We had a river view suite. Trouble was you couldn’t see the river. There was to much undergrowth and trees, so you couldn’t tell there was a river there. The view from our balcony was beautiful, out onto the large lawn and a small pond. The TVs are old, so you couldn’t stream. Make sure you tell the front desk or put out your door hanger or you won’t get your room refreshed. The bar seemed open only during dinner hours. During our stay, one night the chief was “out” and they only served burgers. Breakfast was around $18, we never went down. Our room was large and bathroom adequate. It’s a 10 minute drive to town. It’a satisfactory hotel, but not worth the price."

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Pittsfield Holiday Homes information

Number of reviews	187
Accommodation	604 Holiday Homes
Lowest Price	£228
Highest Price	£911

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Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Pittsfield holiday homes

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

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

3. Ski Home/Arcade Mountain Views Near Killington/Woodstock

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

5. Luxury Condo Tucked in the Heart of Killington

6. 4BR Killington Home Perfect for Families, Pet-Friendly

7. The Tower House | Hot Tub | Firepit | Dog-Friendly

8. Family and friend friendly upper ski cabin with bunks, sleeps 8

9. Liquid Lodge Lower: 2BR Duplex near Killington with 4 PM Checkout

10. Lakewood Lodge: 4BR/2.5BA Killington Home | Private Hot Tub, Wood Fire, Kent Pond & EV Charging

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

12. 25 Rocky Ridge Rd - Killington Retreat: Group Ski House! Close to Mountain! Hot Tub.

13. Private Killington Home w/ Indoor Hot Tub and 2 Living Rooms

14. CozyDen- Location, Fireplace, Ski Off/ Shuttle On

15. SnowArts, Wood Burning fireplace, Close to slopes

16. Alpine Chalet- Fireplace, Pool, Gym, At Pico

17. Cozy 3BR, 2-Story Retreat with Hot Tub, Pet Friendly, Deck, Grill, Fire Table, 5 min to Killington

18. Renovated 4BR House w/ Hot Tub & Fire Pit: Near Killington Lifts & Dining

19. Estelle Cottage- Private Sauna, Hot tub, Pool, AC

20. Summit House on George | Renovated | 5 Mins to K-1 | Lift & Rental Deals

Find holiday rentals that suit your style

Top Pittsfield Hotel Reviews

Greenbrier Inn

Comfort Inn Rutland - Killington

Mountain Sports Inn

The Jackson

The Shire Woodstock

Brandon Inn

Turn of River Lodge

Days Inn by Wyndham Rutland/Killington Area

On The River Inn

Find out more about Pittsfield

Pittsfield Holiday Homes information

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