Bennington Vacation Homes

Historic Henry Covered bridge over the Walloomsac River e in Bennington, Vermont

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Our top choices for Bennington holiday homes

Peaceful getaway at birds of a feather

Shaftsbury

Margaret D.

HK$1,921 total

includes taxes & fees

14 Apr - 15 Apr

Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts

Stratton

Lin M.

HK$1,908 total

includes taxes & fees

14 Apr - 15 Apr

Stratton Mountain Home - Hot Tub, Fire Pit & Game Loft

Jamaica

Lee Anna C.

HK$6,946 total

includes taxes & fees

14 Apr - 15 Apr

Cozy Home in Pownal VT

Pownal

Jess M.

HK$1,475 total

includes taxes & fees

16 Apr - 17 Apr

Stratton Mountain Home - Hot Tub, Sauna, Fire Pit, & MORE!

Jamaica

s w.

HK$7,043 total

includes taxes & fees

14 Apr - 15 Apr

Cozy 3 Bedroom Condo in the Heart of Manchester VT

Manchester

Rafael

HK$4,370 total

includes taxes & fees

15 Apr - 16 Apr

Your Vermont Mountain Haven Pet Friendly home with Hot tub!

Winhall

Meghan C.

HK$5,157 total

includes taxes & fees

14 Apr - 15 Apr

1812 House, 2 Stays, 1 home

Manchester

HK$5,172 total

includes taxes & fees

14 Apr - 15 Apr

Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym

Winhall

Colleen H.

HK$6,017 total

includes taxes & fees

27 Apr - 28 Apr

Two Brooks Lodge

Bennington

"Stayed at this property everything was as stated but then property manager made me pay cleaning fee and deposit through cash app , Then later Said I didn’t pay for property when I clearly did had receipts then after confronted by Expedia , He lies say I left the house a mess and that displaced half the water out of the hot tub that I didn’t use at all and didn’t do the dishes which I did , not to mentions I paid a cleaning fee either way . So this unprofessional listing gets keep the deposit...

Hunter

HK$1,836 total

includes taxes & fees

14 Apr - 15 Apr

3BR Family Home in Manchester, VT -Near Downtown, Outlets & Ski Resorts

Richville

HK$3,325 total

includes taxes & fees

27 Apr - 28 Apr

Idyllic Village Estate: Luxury Villa Historic Barn

Manchester

"It was a fantastic stay! The house is beautiful with stunning views in every direction. It is well-appointed and very comfortable. It has special amenities like a hot tub and party barn. Communication with the host was easy; he responded almost immediately and was quite pleasant. He gave us lots of useful information and even honored a couple of unique requests. This is a super special property. "

Elizabeth C.

HK$14,256 total

includes taxes & fees

14 Apr - 15 Apr

Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!

Hoosick Falls

Jon

HK$2,400 total

includes taxes & fees

15 Apr - 16 Apr

Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route

Ludlow

Lisa W.

HK$2,375 total

includes taxes & fees

14 Apr - 15 Apr

Stratton Woods · Secluded Vermont Cabin Retreat

Wardsboro

kim k.

HK$3,064 total

includes taxes & fees

14 Apr - 15 Apr

Florida Mountain Log Cabin

Florida

Tristan e.

HK$2,638 total

includes taxes & fees

14 Apr - 15 Apr

14mi to Mt. Snow! Arcade, Private Suite, King Bed!

Whitingham

Jacklyn D.

HK$3,991 total

includes taxes & fees

14 Apr - 15 Apr

Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle

Ludlow

Hannah M.

HK$2,348 total

includes taxes & fees

27 Apr - 28 Apr

Charming Chester Farmhouse near Near VT Slopes

Chester Depot

Stephanie F.

HK$3,219 total

includes taxes & fees

14 Apr - 15 Apr

4 bedrooms, travel cot, Internet, bed sheets

Outdoor Adventure Hub! Family Home in West Dover

West Dover

Louis

HK$4,240 total

includes taxes & fees

14 Apr - 15 Apr

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Top Bennington Hotel Reviews

Hotel Vervana, Trademark Collection by Wyndham

8/10 Good

"Great friendly staff and decent room - could’ve used a couch or more seating surfaces but otherwise ok. "

Vermont Downtown Oasis - Two Bedroom in Picturesque Downtown

10/10 Excellent

"Wonderful location with awesome hosts, clean rooms and everything we needed for a first time visit to Vermont. With very easily walkable shopping (don’t miss the shop below the room!) and excellent options this was an unforgettable experience for us. We are very thankful to have stayed here! We definitely recommend!"

Perfect for a peaceful get away in clean fresh Vermont air!

10/10 Excellent

"We had the most wonderful stay! The house and the property were beautiful, the amentities were excellent, and Linda Jane was an incredibly generous and accommodating host. We visit Bennington every year for Thanksgiving with family and we hope to rent with Linda Jane again in the future."

Green Mountain Getaway

8/10 Good

"The place was super easy to access and clean. We were just staying for one week night and didn't use the kitchen, so I can't speak to that. I recommend packing noise-canceling headphones for anyone who will be staying in the front bedroom (with the green carpet). Someone else in the building woke us up around 1:30am and was listening to something loud above us, so we ended up moving to the back bedroom. If you need all three bedrooms, though, you may need something to block out noise. "

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