Williamstown vacation rentals

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Top-rated vacation rentals in Williamstown

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Guest favorite

Apartment in Williamstown

4.96 out of 5 average rating, 299 reviews

New Studio In Town, By the Water

★ New to Williamstown? Explore our interactive guidebook. Charming studio just steps away from shops, restaurants & few minutes’ walk to Williams College. Renovated and well-equipped, this home offers a wonderful view of Water Street. If you like the outdoors, descend on the Green River back of the property. The wooded riverbank with Adirondack chairs, and picnic tables is great for relaxing while enjoying your evening sundowners by the fire pit with the sound of the river in the background.

Feb 4 – 11

R3,495 ZAR per night

Guest favorite

Home in Williamstown

4.99 out of 5 average rating, 108 reviews

The Yellow Cottage at Williamstown | Four Bedrooms

Comfortable, charming and quirky Victorian cottage. Killer location by Williams College, The Clark, MassMOCA, Williamstown Theater Festival, Spring Street and wedding venues: Cricket Creek Farms, Bloom Meadows, Williams Inn and Mass MOCA. Regional ski resorts, Mount Greylock, trails, rivers, lakes, golf, are all close for the choosing. Tucked away in the upper west corner of the beautiful Berkshires, bordering NY and VT, adventure awaits in every direction...or doesn't. You get to choose.

Feb 12 – 19

R4,757 ZAR per night

Guest favorite

Cottage in Williamstown

4.9 out of 5 average rating, 165 reviews

Cute Cozy Comfy Cottage in the Berkshires

A cute cozy cottage sleeps 4 comfortably. One queensize bed and 1 full futon. Dog friendly for up to 2 dogs .More than two dogs will have to be an additional fee of 50.00 each pet. My cottage sits on 13 privately owned acres. Partially fenced in.3 miles down the road from Jiminy Peak ski resort & summer activities and a short drive to Ramblewild adventure park. Hiking, boating, museums, shopping, restaurants- all sorts of activities in the Berkshires. Two minute ride to Bloom Meadows!

Feb 7 – 14

R2,961 ZAR per night

Guest favorite

Guest suite in Williamstown

4.96 out of 5 average rating, 202 reviews

Berkshire Guest Suite

Welcome to our guest suite in the beautiful Northern Berkshires, home to many great cultural venues, including The Clark, Williamstown Theatre Festival and Mass MoCA. The newly updated private suite offers a queen pillow-top mattress, bathroom with stall shower, coffee bar and an outdoor seating area with mountain views. Located in a quiet neighborhood at the base of Mt. Greylock, we are a short walk to a local farm stand, and a few minutes drive to downtown Williamstown and North Adams.

Nov 30 – Dec 7

R1,850 ZAR per night

Guest favorite

Home in Williamstown

4.98 out of 5 average rating, 102 reviews

Quality, Comfort, Charm in Williamstown Center

Stay at this brand new old house in the center of Williamstown! Conveniently located in a quiet neighborhood within easy walking distance to the town center, Williams College and The Clark Art Institute. The house was fully renovated in 2021. All new everything including appliances, a luxurious tile shower, fresh sheets and towels and lovely furnishings, all to make your stay comfortable and cozy. The living room has a beautiful gas fireplace and smart tv and in the summer, central air.

Jan 6 – 13

R5,369 ZAR per night

Guest favorite

Guesthouse in Williamstown

4.93 out of 5 average rating, 219 reviews

Perfect Base for Your Berkshire Adventure

Charming private cottage with shared pool use. This newly renovated garden studio features high ceilings, a separate kitchenette with granite counters, mini fridge, microwave, queen sized bed, and rustic Arts & Crafts furniture. Located in a separate outbuilding, the cottage is close to woodland hikes, excellent biking, as well as many other attractions in the Berkshires. The beautiful in-ground pool is perfect for an afternoon dip - guest hours are usually between 3-5.

Aug 2 – 9

R2,812 ZAR per night

Guest favorite

Apartment in North Adams

4.97 out of 5 average rating, 409 reviews

See MoCA from your mansion+Sauna! Ski nearby!

20-30 mins to Jiminy Peak, East Mountain, Prospect Ski, 50 mins to Mount Snow. Situated on a hilltop oasis right above Mass MoCA, this apt is part of a private historic estate. 3 mins walk to MoCA. Steps to downtown’s restaurants. 5-10 mins drive to Williams, MCLA, Clark. Whimsically restored (yes, fast Wi-Fi & great water pressure). Home to the Floating Tower Artist Retreat. YOUR STAY ENABLES US TO HOST REFUGEE/IMMIGRANT ARTISTS PRO BONO!

Apr 10 – 17

R2,995 ZAR per night

Guest favorite

Barn in Williamstown

4.97 out of 5 average rating, 261 reviews

Cozy barn apartment on the river

Private converted first floor barn apartment in a New England home next to the Green River. Comfortable with unique furnishings and back door to river patio. Sleeps 1-2 comfortably. Can accommodate 4 with the extra sleeper tri-fold mattress, (Best for 1-2 smaller children). Private full bath. Great for 1-2 adults or a family with smaller children. Due to Coronavirus we are doing extensive disinfecting and allowing for 72 hours between bookings.

Sep 3 – 10

R2,678 ZAR per night

Guest favorite

Apartment in Bennington

4.93 out of 5 average rating, 527 reviews

The Octopus's Garden

Welcome to the Octopus' Garden, a warm and cozy oasis located in the heart of Bennington, VT. This relaxing one bedroom suite, infused with amenities and much love, comfortably accommodates 2 people. This peaceful space is only a 10 minute walk to art, shops and dining and is the perfect hub for a variety of activities in Southern Vermont and Western Massachusetts.

Jul 30 – Aug 6

R1,855 ZAR per night

Guest favorite

Apartment in Pownal

4.94 out of 5 average rating, 180 reviews

The Shepherd's Retreat

This in-law apartment is on the first floor of our 2 level home and has its own separate entrances. It features an open floor plan with galley kitchen and breakfast bar. This location has a peaceful relaxing atmosphere but with easy access to shopping, site seeing, hiking, and is minutes away from historic Bennington, Vt and the Berkshires (Mass Moca Museum).

May 3 – 10

R2,071 ZAR per night

Guest favorite

Apartment in Williamstown

4.93 out of 5 average rating, 236 reviews

COLD SPRING

This cozy, quaint and quiet apartment offers the perfect Berkshire county getaway. Just a drive away from Mount Greylock National Park, Jiminy Peak Mountain Resort, and the Tony-Awarded Williamstown Theatre Festival. Enjoy the mountain views, in this two bedrooms 1 bath rental with fully equipped kitchen and skylight vaulted ceiling.

Sep 27 – Oct 4

R3,066 ZAR per night

Guest favorite

Guesthouse in Williamstown

4.97 out of 5 average rating, 146 reviews

Brookside Cottage

Drift off to the sound of a babbling brook outside the bay window in this cozy country cottage. Minutes from Downtown Williamstown, North Adams and Bennington, VT. We are about 20 minutes away from Jiminy Peak for downhill skiing. The trails behind our house are ideal for snowshoeing, nordic skiing, and snowman building.

Aug 25 – Sep 1

R2,513 ZAR per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Williamstown vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Stay near Williamstown's top sights

Mount Greylock213 locals recommend

The Clark Art Institute329 locals recommend

Williams College42 locals recommend

Stop & Shop61 locals recommend

Water Street Grill21 locals recommend

Coyote Flaco44 locals recommend

Other great vacation rentals in Williamstown

Guest favorite

Apartment in Bennington

4.96 out of 5 average rating, 139 reviews

Cooper's Place

Sep 14 – 21

R2,278 ZAR per night

Guest favorite

Bungalow in Williamstown

4.89 out of 5 average rating, 202 reviews

Hollywood Bungalow in the Berkshires

Jan 25 – Feb 1

R4,460 ZAR per night

Superhost

Apartment in Williamstown

4.86 out of 5 average rating, 198 reviews

Williamstown Apt. on Green River Walk to Williams!

May 23 – 30

R3,242 ZAR per night

Guest favorite

Cabin in Pownal

4.97 out of 5 average rating, 174 reviews

Historic Cozy Cabin Six

Aug 23 – 30

R2,525 ZAR per night

Guest favorite

Guest suite in Hancock

4.83 out of 5 average rating, 154 reviews

Cozy apartment near Jiminy Peak

May 6 – 13

R1,298 ZAR per night

Guest favorite

Apartment in Bennington

4.91 out of 5 average rating, 163 reviews

Scenic Vermont Studio

Aug 23 – 30

R1,919 ZAR per night

Superhost

Condo in North Adams

4.91 out of 5 average rating, 209 reviews

Downtown Flat Iron Condo - walk to MoCA #12

Aug 23 – 30

R2,116 ZAR per night

Guest favorite

Home in Pownal

4.99 out of 5 average rating, 212 reviews

Cozy Vermont mini-house

Oct 27 – Nov 3

R4,077 ZAR per night

Show all

Other great vacation rentals in Williamstown

Guest favorite

Cabin in Savoy

4.98 out of 5 average rating, 186 reviews

The Camp - 20 Minutes to Berkshire East!

Jul 29 – Aug 5

R2,172 ZAR per night

Guest favorite

Guesthouse in North Adams

4.92 out of 5 average rating, 181 reviews

"Worker's" Cottage (circa 1860).

May 24 – 31

R3,070 ZAR per night

Guest favorite

Apartment in North Adams

4.92 out of 5 average rating, 155 reviews

#7 Downtown Historic Flatiron building getaway.

Feb 7 – 14

R2,931 ZAR per night

Guest favorite

Loft in East Nassau

4.99 out of 5 average rating, 153 reviews

Dog Friendly Farm Spring bird watching

Aug 29 – Sep 5

R3,045 ZAR per night

Guest favorite

Apartment in Williamstown

4.94 out of 5 average rating, 71 reviews

Quiet Williamstown Apartment close to town & Moca.

Sep 25 – Oct 2

R2,628 ZAR per night

Guest favorite

Vacation home in Williamstown

4.97 out of 5 average rating, 69 reviews

ALL welcome: Lovely 1 BR studio, Berkshires beauty

Dec 3 – 10

R2,961 ZAR per night

Guest favorite

Apartment in Williamstown

4.94 out of 5 average rating, 52 reviews

Walk to College and Town; Sunny Spacious Apartment

May 24 – 31

R3,596 ZAR per night

Guest favorite

Cottage in Williamstown

4.97 out of 5 average rating, 72 reviews

Artistic Nature Cottage

Jan 14 – 21

R4,670 ZAR per night

Show all

Quick stats about vacation rentals in Williamstown

Total rentals
130 properties
Rentals with dedicated workspaces
60 properties have a dedicated workspace
Pet-friendly rentals
40 properties allow pets
Family-friendly rentals
90 properties are a good fit for families
Total number of reviews
6.4K reviews
Nightly prices starting at
R1,142 ZAR before taxes and fees

Frequently Asked Questions

Are there pet-friendly vacation rentals in Williamstown?
Four-legged friends are welcome in Williamstown. Choose from more than 40 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Williamstown?
Yes! Work meets play with ease at over 60 vacation rentals in Williamstown featuring dedicated workspaces. Stay connected and productive in your home away from home.
How much does it cost to stay in bed and breakfast rentals in Williamstown?
Experience the best of Williamstown with our bed and breakfast rentals, starting at about $110 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do hotel rentals in Williamstown have wifi?
Absolutely! We offer over 10 hotel rentals with wifi in Williamstown. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Williamstown have air conditioning?
Absolutely! We offer over 10 apartment rentals with air conditioning in Williamstown. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly apartment rentals in Williamstown?
Williamstown has more than 10 family-friendly apartment rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Williamstown have a bbq area?
Absolutely! We offer over 20 house rentals with a bbq area in Williamstown. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for Apartment Rentals in Williamstown?
Enhance your stay in our Apartment Rentals with the most popular amenities: over 20 homes with wifi, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

Williamstown vacation rentals

Top-rated vacation rentals in Williamstown

Vacation rentals for every style

Houses

Hotels

Unique stays

Popular amenities for Williamstown vacation rentals

Stay near Williamstown's top sights

Other great vacation rentals in Williamstown

Apartment in Bennington

Bungalow in Williamstown

Apartment in Williamstown

Cabin in Pownal

Guest suite in Hancock

Apartment in Bennington

Condo in North Adams

Home in Pownal

Other great vacation rentals in Williamstown

Cabin in Savoy

Guesthouse in North Adams

Apartment in North Adams

Loft in East Nassau

Apartment in Williamstown

Vacation home in Williamstown

Apartment in Williamstown

Cottage in Williamstown

Quick stats about vacation rentals in Williamstown

Total rentals

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Are there pet-friendly vacation rentals in Williamstown?

Are there vacation rentals with a dedicated workspace in Williamstown?

How much does it cost to stay in bed and breakfast rentals in Williamstown?

Do hotel rentals in Williamstown have wifi?

Do apartment rentals in Williamstown have air conditioning?

Are there family-friendly apartment rentals in Williamstown?

Do house rentals in Williamstown have a bbq area?

What are the most popular amenities for Apartment Rentals in Williamstown?

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