Pet-friendly Hotels in Pittsfield

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Sep 11 - Sep 13

Top 5 Pet-friendly Hotels in Pittsfield at a glance

The Mountain Inn at Killington — 2.5-star hotel in Killington. Guest rating: 9.2/10 — Wonderful.
Après Inn Killington — 2-star hotel in Killington. Guest rating: 9.4/10 — Exceptional.
Sleep Woodstock Motel — 2-star hotel in Woodstock. Guest rating: 9.6/10 — Exceptional.
Brandon Inn — 3-star hotel in Brandon. Guest rating: 8.8/10 — Excellent.
Hampton Inn Rutland — 2.5-star hotel in Rutland. Guest rating: 9.0/10 — Wonderful.

Pet-friendly Hotels in Pittsfield

Properties are selected based on real traveler reviews and popularity among guests who’ve booked a night in Pittsfield on Hotels.com. These Pittsfield Pet-friendly Hotels consistently deliver on quality, location and traveler experience. Last updated on September 2, 2026.

Breakfast and dinner served

Outdoor pool, a heated pool

Breakfast and dinner served

Superior Double Queen with Balcony | In-room safe, blackout drapes, WiFi (free), individually decorated

The Mountain Inn at Killington

Killington

CNY751

CNY868 total

includes taxes & fees

Sep 6 - Sep 7

Exterior

Exterior

Basic Studio Suite | Memory foam beds, desk, WiFi (free), bed sheets

Premium Room, 1 Queen Bed | Memory foam beds, desk, WiFi (free), bed sheets

Après Inn Killington

Killington

CNY696

CNY765 total

includes taxes & fees

Sep 7 - Sep 8

Deluxe Suite | Private kitchen | Coffee/tea maker, mini-fridge, microwave, freezer

Exterior

Deluxe Suite | Desk, blackout drapes, iron/ironing board, WiFi (free)

Desk, blackout drapes, iron/ironing board, WiFi (free)

Sleep Woodstock Motel

Woodstock

CNY593

CNY652 total

includes taxes & fees

Sep 7 - Sep 8

Front of property

Front of property

Exterior

Exterior

Brandon Inn

Brandon

CNY760

CNY836 total

includes taxes & fees

Oct 4 - Oct 5

Free daily buffet breakfast

Exterior

Exterior

Suite, 1 King Bed, Jetted Tub | Living area | 32-inch LCD TV with cable channels, TV, pay movies

Hampton Inn Rutland

Rutland

CNY932

CNY1,025 total

includes taxes & fees

Sep 9 - Sep 10

Lobby

Exterior

Coffee/tea maker, mini-fridge, microwave

Lobby

Best Western Inn & Suites Rutland-Killington

Rutland

CNY1,204

CNY1,324 total

includes taxes & fees

Sep 8 - Sep 9

The Jewel | Living area | TV

The Jewel | Laptop workspace, iron/ironing board, individually decorated

The Jewel | Living room | TV

Campion | Living area | TV

The Mountain Top Inn & Resort

Chittenden

CNY1,857

CNY2,024 total

includes taxes & fees

Sep 7 - Sep 8

Elite Cabin, 1 King Bed, Sauna | Laptop workspace, blackout drapes, WiFi (free), individually decorated

Fitness facility

Exterior

Family Cabin, 2 Queen Beds | Room amenity

Emrose Luxury Cabins

Brandon

CNY1,089

CNY1,231 total

includes taxes & fees

Sep 13 - Sep 14

Lobby

Indoor pool

Reception

Free daily on-the-go breakfast

Days Inn by Wyndham Rutland/Killington Area

Rutland

CNY823

CNY905 total

includes taxes & fees

Sep 7 - Sep 8

Exterior

Terrace/patio

Lobby sitting area

Lobby

Killington Mountain Lodge, Tapestry Collection by Hilton

Killington

CNY1,068

CNY1,175 total

includes taxes & fees

Sep 7 - Sep 8

BBQ/picnic area

Premium bedding, pillowtop beds, desk, blackout drapes

Coffee/tea maker, full-size fridge, microwave, stovetop

Front of property

My Place Hotel-Randolph VT

Randolph Center

CNY1,231

CNY1,341 total

includes taxes & fees

Sep 28 - Sep 29

Lobby

Classic Room, 2 Queen Beds | Desk, iron/ironing board (on request), WiFi (free), bed sheets

Shower, free toiletries, hair dryer, towels

Front of property

Middlebury Sweets Motel

Middlebury

CNY1,035

CNY1,139 total

includes taxes & fees

Sep 9 - Sep 10

Exterior

Property grounds

Front of property

Interior detail

The Lilac Inn

Brandon

CNY1,606

CNY1,767 total

includes taxes & fees

Sep 8 - Sep 9

Property grounds

Iron/ironing board, WiFi (free), bed sheets

Premium Corner River View | Iron/ironing board, WiFi (free), bed sheets

BBQ/picnic area

The Shire Woodstock

Woodstock

CNY1,553

CNY1,845 total

includes taxes & fees

Sep 6 - Sep 7

Front of property

Signature Suite, Garden View | Laptop workspace, iron/ironing board (on request), WiFi (free)

Front of property

Signature Double Room, Courtyard View | Laptop workspace, iron/ironing board (on request), WiFi (free)

Stay At Jimmy's

Woodstock

CNY2,346

CNY2,581 total

includes taxes & fees

Sep 10 - Sep 11

Exterior

Room 22 | WiFi (free), bed sheets

Front of property

Dinner served

Kedron Valley Inn

South Woodstock

CNY2,481

CNY2,729 total

includes taxes & fees

Sep 9 - Sep 10

Exterior

Outdoor spa tub

Cabin 5 (Pet Friendly) - Owl's Branch | Living area | Flat-screen TV, fireplace, DVD player, foosball

Cabin 5 (Pet Friendly) - Owl's Branch | Exterior

Robert Frost Mountain Cabins

Ripton

CNY2,548

CNY2,777 total

includes taxes & fees

Sep 8 - Sep 9

Lobby

4 restaurants; breakfast, lunch, and dinner served

Sauna, hot tub, steam room, body treatments, aromatherapy

Interior

Woodstock Inn & Resort

Woodstock

CNY2,337

CNY2,867 total

includes taxes & fees

Sep 7 - Sep 8

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