Stephentown vacation rentals

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July 2025

August 2025

Discover a selection of 6 homes and other vacation rentals in Stephentown that are perfect for your trip. Vacation homes offer the best amenities for your family, friends, or furry companion, such as a hot tub and garden. At the end of the day, you'll be sure to find a rental that has what everyone needs, including a place that's non-smoking or offers accessibility.

Vacation rentals with weekly discounts - Stephentown

Showing deals for:Oct 3 - Oct 10

55” smart TV to watch all your streaming favorites like Netflix and Disney Plus

Exceptional

(10 reviews)

3bd 2ba Townhouse. Walkable to College and walking paths. Longer stays welcome

Williamstown, MA

17% off

Fees included upfront

Exceptional

(5 reviews)

Country living close to the capital region 100 acres of nature to explore

Nassau, NY

8% off

Fees included upfront

Exceptional

(24 reviews)

11 acre mid-century estate, newly renovated, seasonally available pool.

Williamstown, MA

8% off

Fees included upfront

Front Lawn, stone walkway, Front Door behind tree.

Exceptional

(55 reviews)

Berkshire Gorge House, 15 minutes to Williamstown, 15 minutes to Jiminy Peak.

New Ashford, MA

18% off

Fees included upfront

Exceptional

(68 reviews)

Secluded Beautiful House w/16 Acres-fits 8 - Low rates- 2 min to Jiminy Peak

Williamstown, MA

20% off

Fees included upfront

Our private dock on Richmond Pond has a spectacular view, especially at sunset.

Exceptional

(98 reviews)

Spacious Berkshire Summer Rental, Private Dock on Lake 3 BR/2b

Richmond, MA

9% off

Fees included upfront

Excellent

(10 reviews)

In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants

Hancock, MA

9% off

Fees included upfront

The living room is open and airy. Double doors to the deck and internet ready TV

Exceptional

(6 reviews)

Beautiful Jiminy Peak Mountainside Condo Near Lifts - Just Remodeled

Hancock, MA

7% off

Fees included upfront

Comfortable New Decor in Living Room Equipped w Smart TV and Deck

Exceptional

(70 reviews)

Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

Hancock, MA

8% off

Fees included upfront

Find spaces that suit your style

House

Condo/Apartment

Find the best place to stay - Stephentown

Showing deals for: Oct 1 - Oct 4

A MAGIC SPOT: Booking all year Weekly, monthly discounts available

Sleeps 8 · 4 bedrooms · 2 bathrooms

Fees included upfront

Family-Friendly Home With Incredible Berkshire Views And A Private Swim Pond

Sleeps 8 · 3 bedrooms · 1+ bathroom

Fees included upfront

Kitchen comes fully stocked with all essentials. Gas stove, double side fridge, dishwasher, Keurig machine, etc.

5 Bed / 3 bath Apt Near Jiminy Peak Berkshires

Sleeps 12 · 5 bedrooms · 3 bathrooms

Fees included upfront

WE'RE OPEN AGAIN FOR IMMUNIZED FOLKS AND THEIR PETS

Sleeps 12 · 4 bedrooms · 4 bathrooms

Fees included upfront

Apt 1: Living room with (x2) sleeper sofas + (x2) full size arcade games!

2 Bed Berkshire Apt minutes to Jiminy Peak Ski

Sleeps 6 · 2 bedrooms · 1 bathroom

Fees included upfront

Top rated rentals - Stephentown

Premier Host

Repeat Customers!

This was our second time staying here. Great, relaxing way to spend a weekend. Supplied with everything you could need and a host who goes above and beyond to make sure you have everything you need!

Tonya R.

Stayed Jun 2025

Premier Host

Perfect Cabin

A lovely cabin centrally located in the Berkshires! Had everything we needed for our stay, including air conditioning during a heat wave!

Nicholas S.

Stayed Jun 2025

Weekend Stop Before Camp

This was the perfect little spot for our family to stop and stay on our way to dropping our daughter at camp and enjoy Williamstown. Our hike at the Clark Institute was a highlight along with the proximity to downtown’s great restaurants.We were talking about how gorgeous it must be in the fall… when it must be even more scenic and amazing.

Kevin R.

Stayed Jun 2025

Premier Host

An amazing getaway!

We had a getaway for four couples at Fox Hollow Estate, and it was amazing! We did a little bit of work, a little bit of team-building exercises, and a lot of rest. The property let us do all of that and more. It has a Victorian feel with many modernized upgrades! The master bathroom with a claw-foot tub, a steam/aromatherapy shower, and dark walnut was spectacular. The kitchen, with its beautiful cabinetry, hidden appliances (microwave, dishwasher), built-in wine cellar, and amazing range stove, made the slow mornings very enjoyable. The entire place was very clean and had a character that made you feel you were staying in a Victorian estate. But the hospitality and communication provided by the host, Ken exceeded everything! He was prompt in getting back to me when I had questions and was very intentionaly to ensure we had a great stay! We will definately stay again in the future!

Jesse K.

Stayed Mar 2025

Beautiful yard with wrap around deck right on the lake.

Premier Host

Great location near Jiminy peak

We had a very nice time, the house has lots of room for a large group and had what we needed for a nice short ski vacation. The frozen lake was a very fun experience as well. Owner was responsive helpful and informative. The house is in a great condition, everything is new and updated. Thanks for the stay we hand a very nice time

Tomer M.

Stayed Jan 2025

Premier Host

Everything you need in Stephentown

This unit in the Stephentown is truly a gem. The space is beautiful, beds were comfy and they provide all the amenities you could need!….even extra toothpaste, toothbrushes, makeup remover, etc. The host reached out immediately after booking with tons of info about local restaurants and attractions - all of which were excellent. The property is less than 10 mins from Jiminy Peak as well as plenty of great restaurants and shops. My only heads up is that the stairs are somewhat narrow (it’s an old bldg so that’s not a big surprise). But be aware of it. Even still, it deserves 5 stars.

Amanda J.

Stayed Dec 2024

Premier Host

Reunion with friends

We got 7 families to all stay on the property. Lots of fun. Clean and comfortable sleeping accommodations.

Ken H.

Stayed Nov 2024

Premier Host

Great Stay Beautiful Views!

We had a wonderful time at this property! It was perfect for what we wanted- a place to ourselves in nature with beautiful views. Host was great! Would definitely recommend!

Michelle K.

Stayed Nov 2024

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A place for everyone
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Find out more about Stephentown

The charming area of Stephentown awaits your stay

Learn about the unique charm of Stephentown with a stay in a private vacation home. This romantic city allures visitors with its skiing and restaurants. If you need more space to accommodate a family vacation or friends trip, rental homes often come with separate dining areas and spacious living rooms.

Activities and attractions in and around Stephentown

Do you want to discover things to do in the city? Although it can be tempting to stay in your comfortable vacation rental, you'll want to experience everything that Stephentown has to offer. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city center:

Jiminy Peak Mountain Resort (5.2 mi / 8.4 km)
Furnace Brook Winery at Hilltop Orchards (11 mi / 17.7 km)
Bousquet Ski Area (11.2 mi / 18.1 km)
Kennedy Park (13.4 mi / 21.6 km)
Wyndhurst Golf & Club (15.9 mi / 25.7 km)
Zema's Nursery (2 mi / 3.1 km)

Exploring the natural features in Stephentown

Whether you're an active traveler or just want to spend some time taking in the scenery, Stephentown is a great place to spend some time outside. Here are a few of the area's most stunning natural features, all within 30 miles (48.2 km) of the city center:

Mount Greylock State Reservation Visitor Center (9.2 mi / 14.8 km)
Brodie Mountain (9.5 mi / 15.3 km)
Queechy Lake (10.2 mi / 16.4 km)
Lenox Mountain (11.5 mi / 18.4 km)
Lenox Mountain Reserve (11.9 mi / 19.1 km)
Pleasant Valley Wilderness Sanctuary (12.2 mi / 19.6 km)

Transportation to and around Stephentown

The nearest airport is in Pittsfield, MA (PSF-Pittsfield Municipal), located 10.3 mi (16.6 km) from the city center. If you can't find a flight that's convenient for your trip, you could book a flight to Hudson, NY (HCC-Columbia County), which is 24.2 mi (38.9 km) away.

Frequently asked questions

What is the most popular type of vacation rental accommodation in Stephentown?

Based on our research, apartments are the most in-demand property type in Stephentown. But having said that, everyone's idea of an epic trip will differ. Vrbo has vacation rentals of all sizes and shapes, and we'll help you find your ideal match.

How much does it cost to rent a vacation rental in Stephentown?

A range of factors affect how much you pay for a vacation rental in Stephentown, like the length of stay, season and type of property. But, all of our vacation homes have one thing in common --- excellent value. Just add your travel dates to find your dream escape.

How much does it cost to rent a beach house in Stephentown?

When you travel and the size and style of the property will influence how much you'll pay for your beachside escape. Enter your Stephentown travel dates to view your options on Vrbo. Did someone just say "hot tub"? Use the filters to pick the amenities and features you need.

Are there pet-friendly vacation rentals in Stephentown?

Pack a travel bag for the pooch in your life because Stephentown has nine stays that put out the welcome mat to pets. Let your four-legged buddy join in with the family fun at one of our pet-friendly vacation rentals on Vrbo. Simply enter your dates then check our "Pets allowed" filter box.

Can I rent a house with a pool in Stephentown?

Add another level of fun to your adventure by staying in one of the two houses with a private pool in Stephentown. Use our search filter to find the kind of property you want on Vrbo, and then spend leisurely days splishing and splashing in a swimming pool that's all yours.

What are popular rental amenities in Stephentown?

When it comes to rental amenities that people search for in Stephentown, a barbecue grill, a garden and ski-in/ski-out facilities are the most popular. With Vrbo vacation homes, you'll enjoy options to fit your taste and style, whether you're going away with family members, friends or even pets.

Are there large group vacation rentals in Stephentown?

You can choose from two properties in Stephentown that can accommodate 10 or more guests. Whether you're organizing a get-together with extended family or an event like a party, there's plenty of space to get your favorite people together under one roof.

Are there vacation rentals in Stephentown that welcome kids?

With nine family-friendly vacation homes to choose from in Stephentown, now is a great time to introduce the little ones to the excitement of travel. Simply check our "Properties good for families" filter to browse stays that come with conveniences perfect for traveling families, such as full kitchens, pools, hot tubs and bunk beds.

Can I find two-bedroom vacation rentals in Stephentown?

You can select from three two-bedroom vacation rentals in Stephentown. Settle the kids into the second room or maybe fill it with a couple of your favorite people. There's a comfy spot for whoever's lucky enough to be joining in on the fun.

Are there vacation rentals with WiFi in Stephentown?

Whether you'd like to stay in touch with world events, reply to emails or surf social media, there are six vacation homes with WiFi in Stephentown. Check the "WiFi" box when searching on Vrbo and stay connected on your getaway.

How can I find vacation rentals with air conditioning in Stephentown?

Stephentown has eight vacation rentals where you can kick back in air-conditioned comfort. To locate a property on Vrbo that offers this perk, enter your desired travel dates and use the filter tool to select the "air conditioning" box.

How old do you have to be to rent a vacation rental in Stephentown?

The minimum age allowed can vary across properties on Vrbo, so look at the rules of the vacation home in Stephentown you want to book. But typically, it's 16, 18 or 21.

How long can I rent a vacation rental in Stephentown for?

The amount of time you can rent a Stephentown vacation rental for is up to the property. Simply put in your dates of travel to see options that offer extended stays. They have all the things you need to make your extended getaway more comfortable and convenient, such as kitchens and laundries. Some properties may also offer weekly or monthly discounted prices, so you can stay even longer for less.

Does Vrbo offer discounts for vacation homes in Stephentown?

In Stephentown, you'll find some fantastic discounts and deals for weekly and monthly discounts on vacation rentals, as well as newly listed homes on Vrbo. Whether it's a weekend escape or a much longer stay, we offer a variety of options to match your style.