126 Properties in The Berkshires, Massachusetts, United States of America. November 29, 2026 through November 30, 2026

Where to?

Dates

Travelers

Room 1

Adults

ChildrenAges 0 to 17

Need to book 9 or more rooms?

Sort & Filter

Compare properties

Get a side-by-side view of up to 5 properties.

Search by property name

e.g. Marriott

Filter by

Star rating

1 star

2 stars

3 stars

4 stars

5 stars

Guest rating

Making a selection from this group results in this page refreshing to show relevant results

Good 7+

Very good 8+

Wonderful 9+

Any

Traveler experience

Eco-certifications

LGBTQ welcoming

Business friendly

Family friendly

Adults only

Luxury

Wedding

Romantic

Budget

Property amenities

Pool

Pet friendly

Wifi Included

Air conditioned

Airport shuttle included

Hot tub

Spa

Washer and dryer

Kitchen

Electric car charging station

Gym

Cribs

Parking

Outdoor space

Restaurant

Indoor pool

Bed linens provided

Balcony or patio

Indoor fireplace

Grill

Kids' high chair

Heated pool

Property type

Ryokan

Residence

Lodge

Inn

Palace

Cabin

Cruise

Villa

Hotel

Bed & breakfast

Hostal

Private vacation home

Castle

Pousada (Brazil)

Country House

Motel

Holiday Park

Pension

Hostel/Backpacker accommodation

Ranch

Pousada

Guesthouse

Chalet

Camping

Riad

Houseboat

Condo resort

Farm

Safari

TownHouse

Cottage

Aparthotel

Tree house

Resort

Capsule Hotel

Boat

Property cancellation options

Fully refundable property

Meal plans available

Breakfast included

Dinner included

Lunch included

All inclusive

Payment type

Pay over time with Affirm

Reserve now, pay later

One Key benefits and discounts

VIP Access properties

Top-rated stays with member perks

Member Prices

Discounted properties

Major discounts on selected stays

Accessibility

In-room accessibility

Elevator

Accessible bathroom

Wheelchair accessible parking

Roll-in shower

Stair-free path to entrance

Service animals allowed

Sign language-capable staff

Accessible pool

Handrail in stairway or hallway

Single-level property

Entrance ramp

Accessible path of travel

Accessible van parking

Room views

Ocean view

Lagoon view

Pool view

City view

Canal view

Bay view

Valley view

Resort view

Hill view

Water view

Marina view

Vineyard view

Courtyard view

River view

Mountain view

Golf course view

Desert view

Park view

Garden view

Lake view

Harbor view

Popular filters

Popular

Room amenities

Porch or lanai

Private bathroom

Blackout curtains

Air conditioning

Top floor

Accessibility features

Jetted or soaking bathtub

Private hot tub

In-room entertainment

Yard

Personal safe

Fireplace

WiFi

Refrigerator

Coffee/tea maker

Private sauna

Swim-up room

Kitchen or kitchenette

Private pool

Ground floor

Balcony or patio

Iron and board

Microwave

Oven

Dishwasher

Beach access

On the beach

Nothing between you and the sand

Near the beach

Stays within a 15-minute walk to the beach

Availability

Only show available properties

Popular locations

Making a selection from this group results in this page refreshing to show relevant results

Tanglewood Music Center

Catamount Ski Area

Massachusetts Museum of Contemporary Art

Mount Greylock

Williams College

Norman Rockwell Museum

Naumkeag Museum

Lee Premium Outlets

Ski Butternut

Mohawk Trail State Forest

Jiminy Peak Mountain Resort

National Shrine of the Divine Mercy

Bash Bish Falls State Park

Taconic State Park

Jacob's Pillow

Bousquet Ski Area

Brodie Mountain

Wyndhurst Golf & Club

Clarksburg State Park

North Adams Public Library

Neighborhood

Making a selection from this group results in this page refreshing to show relevant results

Dalton

Williamstown

Lee

Lenox

North Adams

Pittsfield

Great Barrington

Hancock

New Marlborough

Sheffield

Stockbridge

West Stockbridge

South Lee

Adams

Becket

Hinsdale

Lanesborough

Otis

Sandisfield

Egremont

Property brand

Courtyard

BedandBreakfast.com

Hilton Garden Inn

TravelStaytion

Residence Inn

Tribute Portfolio

Ascend Collection

InnRoad

Hampton Inn

Quality

Tru by Hilton

Homewood Suites

Marriott Hotels & Resorts

voco

HYATT house

Holiday Inn Express

Preferred

Red Roof Plus+

Sheraton Hotel

La Quinta Inn & Suites

Fairfield Inn and Suites

Magnuson Managed

eviivo NORAM

Knights Inn

Best Western Plus

CR Managers LLC

Doubletree

Econo Lodge

element

Comfort

Howard Johnson

Holiday Inn

Motel 6

TownePlace Suites

Ramada

Best Value Inns

Days Inn

AMEX

Holiday Inn Club Vacations

Best Western

Rocket Fuel

Travelodge

Red Carpet Inn

Baymont Inns & Suites

Trademark

SpringHill Suites

Rodeway Inn

SureStay Collection

Red Roof Inn

Spark by Hilton

Candlewood Suites

MGM

Nearby activities

Museums

Golfing

Rock or mountain climbing

Spa and wellness

Cycling

Wineries or breweries

Theme parks

Skiing or snowboarding

Winter activities

Enjoy the season with activities like ice skating, snowmobiling, or sledding.

Scuba diving or snorkeling

Fishing

Zoo or wildlife viewing

Horseback riding

Hiking

Shopping

Watersports

Tennis

Casino

Nightly price

Min

Max

$0, Minimum, Nightly price

$1,000 and above, Maximum, Nightly price

All stays

Hotels

Homes

How our sort order works

126 properties

Search results

A two-story building with a symmetrical facade, a central entrance, and a well-maintained lawn.

A spacious lobby with a patterned carpet, multiple seating areas including sofas and armchairs, two chandeliers, and large windows providing natural light.

VIP Access

Vacation Village in the Berkshires

Williamstown

Pool

8.88.8 out of 10

Excellentexcellent

2,545 reviews(2,545 reviews)

$118 nightly

The current price is $143 total

$143 total

Total with taxes and fees

More information about Vacation Village in the Berkshires, opens in a new tab

A park with a picnic table and benches, surrounded by trees with autumn foliage.

A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.

The Yankee Inn

Lenox

Breakfast included
Pool
Hot tub

Fully refundable

Reserve now, pay later

9.29.2 out of 10

Wonderfulwonderful

1,008 reviews(1,008 reviews)

$129 nightly

The current price is $144 total

$144 total

Total with taxes and fees

More information about The Yankee Inn, opens in a new tab

A reception area with a large landscape painting, a dark reception desk, and a potted plant.

A hotel room with a bed, a sofa, a TV, and a bathroom visible through an open door.

Hotel Downstreet, an Ascend Collection Hotel

North Adams

Breakfast included
Pool
Hot tub

8.88.8 out of 10

Excellentexcellent

1,006 reviews(1,006 reviews)

$136 nightly

The current price is $152 total

$152 total

Total with taxes and fees

We have 1 left at this price

More information about Hotel Downstreet, an Ascend Collection Hotel, opens in a new tab

Sort & Filter

Search by property name

Filter by

Star rating

Guest rating

Traveler experience

Property amenities

Property type

Property cancellation options

Meal plans available

Payment type

One Key benefits and discounts

Accessibility

Room views

Popular filters

Room amenities

Beach access

Availability

Popular locations

Neighborhood

Property brand

Nearby activities

Nightly price

Search results

Photo gallery for Vacation Village in the Berkshires

Vacation Village in the Berkshires

Photo gallery for The Yankee Inn

The Yankee Inn

Photo gallery for Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel