Williamstown Holiday House Rentals from AU$292: Search Holiday Homes

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The Purple Pub with outdoor seating and autumn foliage.

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Our top choices for Williamstown holiday homes

A wicker basket with a plant on a table, a green bottle, and a cushion on a chair.

A bedroom with a large bed, a window, and a chandelier.

A modern living room with a sofa, a round mirror, two floor lamps, a vase with green plants, and a small round table with a book.

A house with a front porch, a large window, and a potted plant with purple flowers.

1. Walk to Williams * Steam Sauna * Ritz-Carlton Bed

Walk to Williams * Steam Sauna * Ritz-Carlton Bed

Williamstown

10.0 out of 10, Exceptional, (2 reviews)

10/10

Exceptional

(2 reviews)

"Easy breezy, short walk to walk into town/Williams Campus. Down to Earth, yet sophisticated vibe, great art scene. "

Michelle B.

The price is AU$880

AU$880

includes taxes & fees

22 Nov - 23 Nov

Walk to Williams * Steam Sauna * Ritz-Carlton Bed

A wooden kitchen with a central island, bar stools, and a dining table with chairs.

A living room with a floral sofa, a black leather chair, a small table, and a patterned rug.

A kitchen with wooden cabinets, a stainless steel refrigerator, a gas stove, and a built-in oven.

A cozy living room with wooden walls, a floral sofa, a white table, and a patterned rug.

2. Cozy Home in Pownal VT

Cozy Home in Pownal VT

Pownal

10.0 out of 10, Exceptional, (13 reviews)

10/10

Exceptional

(13 reviews)

"Absolutely wonderful place to stay. Quiet, clean, comfortable and close to a lot of things while feeling secluded. Owner communicated quickly and entry was easy. Loved every minute of our stay."

Jeri R.

The price is AU$292

AU$292

includes taxes & fees

1 Nov - 2 Nov

Cozy Home in Pownal VT

A two-story house with a porch, surrounded by trees and snow.

A red house with a porch, a fire pit, and a car parked nearby.

A house with a porch, a small pond, and surrounding trees.

A kitchen with white cabinets, a microwave, a refrigerator, and a dishwasher. There is a window with a view of greenery outside.

3. Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat

Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat

Bennington

8.6 out of 10, Excellent, (36 reviews)

8.6/10

Excellent

(36 reviews)

"The location was quite and peaceful. We enjoyed our stay and were suprised how great the wifi was for the location."

Malika R.

The price is AU$416

AU$416

includes taxes & fees

1 Nov - 2 Nov

Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat

A kitchen with white cabinets, a wooden dining table, and pendant lights.

A room with a wooden bench, a table, and a door with glass panels.

A narrow hallway with a wooden floor, a black door at the end, and a wall with floral wallpaper.

A cozy room with a wooden bench, a small table, and a chair.

4. A roomy remodeled retreat close to MassMoCA

A roomy remodeled retreat close to MassMoCA

North Adams

10.0 out of 10, Exceptional, (61 reviews)

10/10

Exceptional

(61 reviews)

"Cute and comfy home. We enjoyed the unique decor and lack of TVs everywhere. It was a great break from all the crazy. Lots of conversation and togetherness."

Diane

The price is AU$666

AU$666

includes taxes & fees

31 Oct - 1 Nov

A roomy remodeled retreat close to MassMoCA

A snow-covered landscape with a cabin surrounded by trees.

A rustic cabin with a stone chimney, a porch with steps, and a view of a lake.

A rustic cabin surrounded by a forest with autumn foliage.

A modern kitchen with a stone wall, a fireplace, and a dining area with red stools.

5. Bright Modern Secluded Vermont Home: Fish Pond + Trails, 5 Mins to Williamstown

Bright Modern Secluded Vermont Home: Fish Pond + Trails, 5 Mins to Williamstown

Pownal

10.0 out of 10, Exceptional, (41 reviews)

10/10

Exceptional

(41 reviews)

"We enjoyed our stay! The home was clean, well-stocked, and very comfortable. I loved the serenity of the location. We took walks on trails through the forest and enjoyed the peace and quiet."

Claudette R.

The price is AU$819

AU$819

includes taxes & fees

2 Nov - 3 Nov

Bright Modern Secluded Vermont Home: Fish Pond + Trails, 5 Mins to Williamstown

A kitchen with dark cabinets, a stainless steel stove, a microwave, and a coffee maker.

A wooden deck with a grill, a table, and chairs.

A wooden bear statue with a 'WELCOME' sign in front of a garden with various plants and a stone pathway.

A living room with a fireplace, a television, a ceiling fan, a clock, and a window with curtains.

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

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

Hoosick Falls

9.8 out of 10, Exceptional, (117 reviews)

9.8/10

Exceptional

(117 reviews)

"enjoyed our week at this property"

cory p.

The price is AU$546

AU$546

includes taxes & fees

30 Oct - 31 Oct

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

A two-story house with a red roof, a front porch with a railing, and a gravel driveway.

A cozy cabin interior with a sectional sofa, a coffee table, a small cabinet, and a window with a view of the outdoors.

A kitchen with wooden floors, white cabinets, a central island, and stainless steel appliances.

A modern living room with a flat-screen TV, wooden flooring, a gray sofa, and a kitchen in the background.

7. The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont

The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont

Woodford

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

"Enjoyed our stay! Very clean and comfortable."

Dana W.

The price is AU$787

AU$787

includes taxes & fees

1 Nov - 2 Nov

The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont

A log cabin with a balcony, surrounded by snow-covered trees and a wind turbine in the background.

An outdoor seating area with a wooden table and chairs, a small fire pit, and string lights.

A cozy cabin interior with a kitchen, dining area, and living room.

A modern kitchen with wooden floors, stainless steel appliances, and grey cabinets.

8. Greylock Cabin

Greylock Cabin

Florida

10.0 out of 10, Exceptional, (7 reviews)

10/10

Exceptional

(7 reviews)

"This is a beautiful cabin on an amazing property with a great view of Mt Greylock! Clean, comfortable, great location, communication with the owner was outstanding and questions were answered quickly. It all went smoothly and we highly recommend this property!"

Margaret M.

The price is AU$650

AU$650

includes taxes & fees

1 Nov - 2 Nov

Greylock Cabin

A two-story house with a front porch, a small garden with autumn leaves, and a clear blue sky.

A wooden deck with two Adirondack chairs and a railing, surrounded by trees with autumn foliage.

A kitchen with wooden cabinets, a microwave, stove, and a bar area with wooden chairs.

9. Comfortable Berkshires retreat on mtn resort, SISO

Comfortable Berkshires retreat on mtn resort, SISO

Hancock

8.8 out of 10, Excellent, (12 reviews)

8.8/10

Excellent

(12 reviews)

"Host was proactive in communication and answer each and every question."

Amit

The price is AU$749

AU$749

includes taxes & fees

30 Oct - 31 Oct

Comfortable Berkshires retreat on mtn resort, SISO

A rural landscape with a stone wall, grassy fields, and distant hills.

A compact kitchenette with a microwave, coffee maker, and a small sink.

A bedroom with a large bed, a sitting area with a chair, a small table, a television, and a window.

10. East Barn Suite at Hubbell Homestaead - Mountain Views & Jetted Tub

East Barn Suite at Hubbell Homestaead - Mountain Views & Jetted Tub

Bennington

The price is AU$572

AU$572

includes taxes & fees

30 Oct - 31 Oct

East Barn Suite at Hubbell Homestaead - Mountain Views & Jetted Tub

A modern kitchen with white cabinets, a stainless steel microwave, a stove, and a refrigerator.

A white house with a porch, surrounded by a grassy lawn and trees with autumn foliage.

A compact kitchen with a dining table and chairs, a microwave, and a refrigerator.

11. NEW RENO - Chalet-style farm loft near Tanglewood

NEW RENO - Chalet-style farm loft near Tanglewood

New Lebanon

8.6 out of 10, Excellent, (7 reviews)

8.6/10

Excellent

(7 reviews)

"We enjoyed our stay and the location. This rustic, spacious loft was great for our brief visit to the Berkshires. "

Joanna P.

The price is AU$297

AU$297

includes taxes & fees

2 Nov - 3 Nov

NEW RENO - Chalet-style farm loft near Tanglewood

A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

A spacious kitchen with a large island, built-in appliances, and a laundry area.

A dining area with a wooden table and chairs, a large wooden cabinet, and a kitchen in the background.

A modern living room with a fireplace, white cabinetry, a large flat-screen TV, and a cozy seating area with patterned cushions.

12. 8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

Stephentown

9.2 out of 10, Wonderful, (10 reviews)

9.2/10

Wonderful

(10 reviews)

"A lovely house! Very convenient for a Tanglewood weekend."

Robert B.

The price is AU$829

AU$829

includes taxes & fees

3 Nov - 4 Nov

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

A wooden deck with outdoor furniture, including chairs and a table, surrounded by a lush garden and trees.

A modern kitchen with wooden cabinets, a central island, a refrigerator, a sink, and pendant lighting.

A large white house with black shutters, surrounded by snow-covered trees and a fence.

A wooden cabinet with multiple compartments, including glass doors and drawers, likely used for storage.

13. Hancock Village Inn Near Jiminy Peak

Hancock Village Inn Near Jiminy Peak

Hancock

10.0 out of 10, Exceptional, (22 reviews)

10/10

Exceptional

(22 reviews)

"Amazing Inn. Cozy and everything we needed. "

Price F.

The price is AU$1,509

AU$1,509

includes taxes & fees

3 Nov - 4 Nov

Hancock Village Inn Near Jiminy Peak

A wooden deck with a table and chairs, surrounded by a white railing.

A modern kitchen with grey cabinets, a black refrigerator, a microwave, and a dishwasher.

A bedroom with a bed, a ceiling fan, a window with curtains, and a framed picture on the wall.

A living room with a sofa, a coffee table, and a television. There are curtains on the windows, and a lamp is on a side table.

14. 3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Pittsfield

8.6 out of 10, Excellent, (11 reviews)

8.6/10

Excellent

(11 reviews)

"Very comfortable and clean accommodations in a nice neighborhood, and a great deck to appreciate the view."

Stephen L.

The price is AU$681

AU$681

includes taxes & fees

31 Oct - 1 Nov

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

A spacious living room with a dining area, a kitchen, and a large window.

A bedroom with a bed, two bedside tables, a window, a skylight, and a door leading outside.

A living room with a glass coffee table, a sofa, a TV, and a dining area with chairs and a table.

A gazebo with a stone floor and a grassy area with trees in the background.

15. 1800s Carriage house in Berkshires / Hudson Valley

1800s Carriage house in Berkshires / Hudson Valley

New Lebanon

7.0 out of 10, Good, (2 reviews)

7.0/10

Good

(2 reviews)

"Lovely location with a view of the mountains from the deck.Both bedrooms- a master bedroom and a kids room are air conditioned. (The living room and kitchen are cooled with overhead fan)"

Leslie H.

The price is AU$325

AU$325

includes taxes & fees

16 Nov - 17 Nov

1800s Carriage house in Berkshires / Hudson Valley

A cozy living room with a fireplace, a large TV, a Christmas tree, and a leather sofa.

A hot tub on a wooden deck with wicker furniture and a view of trees.

A spacious kitchen with wooden cabinets, a stainless steel refrigerator, and a central island.

A bedroom with a bed, a nightstand, a lamp, a ceiling fan, and two windows.

16. 5BR Berkshire Home Mins To The Mountain

5BR Berkshire Home Mins To The Mountain

Charlemont

10.0 out of 10, Exceptional, (8 reviews)

10/10

Exceptional

(8 reviews)

"What an amazing house to stay at! Tons of room, well equipped kitchen and a great location! "

Jason F.

The price is AU$961

AU$961

includes taxes & fees

1 Nov - 2 Nov

5BR Berkshire Home Mins To The Mountain

A snow-covered landscape with a house surrounded by trees.

A house with a garage, surrounded by snow-covered trees and a mountain in the background.

A backyard with a campfire, two Adirondack chairs, and a house in the background.

A bedroom with a bed, bedside table, lamp, and a ceiling fan.

17. Mt Snow Ski Escape • Fire Pit • Arcade • Sleeps 11

Mt Snow Ski Escape • Fire Pit • Arcade • Sleeps 11

Whitingham

10.0 out of 10, Exceptional, (16 reviews)

10/10

Exceptional

(16 reviews)

"Great 2 family group vacation spot. Very clean and right in between great ski mountains"

Jonathan

The price is AU$714

AU$714

includes taxes & fees

2 Nov - 3 Nov

Mt Snow Ski Escape • Fire Pit • Arcade • Sleeps 11

A cozy interior with a wooden ceiling, a large window, and a table with chairs.

A cozy cabin interior with a wooden interior, a leather sofa, a pool table, and a large window offering a view of the outdoors.

A spacious kitchen with a built-in oven, a microwave, and a refrigerator. There is a dining area with a table set for four, and a loft area with a staircase.

A cozy cabin interior with a dining area, a sofa, and a large window.

18. VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!

VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!

Wilmington

10.0 out of 10, Exceptional, (21 reviews)

10/10

Exceptional

(21 reviews)

"Beautiful home and property with quick access to a clubhouse with a gym, indoor and outdoor pools, and hot tub. Great for our family trip (including two kids) and lots of games/entertainment for the kids. The house had everything we needed (including kitchenware needed for cooking and preparing food)."

Natalie

The price is AU$786

AU$786

includes taxes & fees

1 Nov - 2 Nov

VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!

A wooden cabin with a curved roof, two windows, and a door, surrounded by a garden and forest.

A modern bedroom with a large bed, a flat-screen TV on a tripod stand, a bedside table with a lamp, and several potted plants.

A kitchen with a black countertop, a gold faucet, a vase of white flowers, and two bottles of hand soap.

A modern kitchen with a central island, bar stools, and a window with a view of trees.

19. June Farms is like no place else on earth! "My New Happy Place" is a comment we hear quite often

June Farms is like no place else on earth! "My New Happy Place" is a comment we hear quite often

West Sand Lake

9.8 out of 10, Exceptional, (9 reviews)

9.8/10

Exceptional

(9 reviews)

"We loved our stay here - it was beautiful, well appointed, and relaxing!"

LauraS

The price is AU$725

AU$725

includes taxes & fees

2 Nov - 3 Nov

June Farms is like no place else on earth! "My New Happy Place" is a comment we hear quite often

A wooden interior with a sectional sofa, a coffee table, and large windows offering a forest view.

A modern living room with a sectional sofa, a flat-screen TV, and a wall-mounted air conditioning unit.

A house with a wooden front door, stone steps, and a porch with a railing.

20. Beautiful and Private Home Centrally Located in the Berkshires

Beautiful and Private Home Centrally Located in the Berkshires

West Stockbridge

The price is AU$1,814

AU$1,814

includes taxes & fees

9 Nov - 10 Nov

Beautiful and Private Home Centrally Located in the Berkshires

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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Top Williamstown Hotel Reviews

The Williams Inn

10/10 Excellent

"Clean, spacious rooms."

Linda 1-night trip

Posted 21 hours ago

The Williams Inn

Howard Johnson by Wyndham Williamstown

8/10 Good

"Better than basic. The owners are making an effort to keep up this property. They are trying with fresh paint and fashion accents in the rooms. I liked the nonsmoking policy and I liked the convenient location. A towel bar in the bathroom would be a plus."

Loring 1-night trip

Posted 21 hours ago

Howard Johnson by Wyndham Williamstown