Stockbridge Holiday Rentals from €200: Search Short-Term Rentals

Q: What are some of the best holiday rentals that Stockbridge has to offer?

Berkshire Village Carriage House - Super Private!! : This holiday home rental outside of Stockbridge is located in the mountains, and has a garden, a BBQ and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of books in this rental home to help you unwind.

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Holiday Rentals in Stockbridge

"We could not have been happier. The house was walking distance to all shops, restaurants and attractions of the town of Stockbridge. House was large enough to comfortably accommodate 9 adults. Thoroughly enjoyed "Christmas in Stockbridge"."

includes taxes & fees

4 Jan - 5 Jan

Indoor pool, outdoor pool, pool umbrellas

"Nice and quiet family get a way"

includes taxes & fees

5 Jan - 6 Jan

"It’s challenging to read the reviews and know what to expect for this hotel. One main reason for that is because each unit is owned by different owners. Some units may have been renovated more recently than other units. I booked 3 rooms. One unit had an old electric stove with coils while the other had a newer electric stove. 1 had a toaster oven while the others did not. We brought food to cook, but kept it simple because we didn’t know what cooking pots and utensils would be available. One...

includes taxes & fees

5 Jan - 6 Jan

"We loved the Freeman estate for our wedding!! Daniel and Anna were super helpful and the property was amazing! The house had so many amenities it was beyond our expectations. Our guests were astounded by the home and the surrounding property, would HIGHLY recommend to anyone and everyone. "

"We had a wonderful stay. The cabin was clean and comfortable! "

"A beautiful lodge nestled in the woods surrounded by an abundance of trails to hike. "

includes taxes & fees

5 Jan - 6 Jan

"Pristine can mean several different things. My interpretation was to be “like new”. This dwelling did not quite live up to that standard, but was clean, sans the “mud room” and what appeared to be mold on the peak of the ceiling above the living room. The original listing stated firewood was provided by the host. Then, the checkin instructions stated guests provided their own. Not huge, just misstated in the listing (since changed). There was a power outage while we were there, thus no...

"My family and I really enjoyed our stay at the lake. My kids enjoyed playing outside in the snow. We had such a quality family time playing board games, watching movies and drinking hot cocoa. Justin was such a great host and really helpful when needed. We’re definitely coming back!"

"The Cabin Had All The Amenities You Would Need and With A Quiet and Serene Area. For Me It Was Relaxing Stay!"

"Beautiful property, well-appointed, and comfortable for extended family of 12."

"Wonderful accommodation."

"The hosts were extremely responsive and helpful, providing us with hiking ideas, questions regarding the house and suggesting best shopping spots for incidentals. The living room was cozy, seating five comfortably. The kitchen was well stocked so cooking a Thanksgiving meal was a pleasure. We thoroughly enjoyed ourselves."

"We had expectations of a peaceful rustic cabin in the woods, and this rental checked almost all of the boxes! The quaint town of Great Barrington was just close enough for convenience, but the house was rural enough to help us all relax and enjoy the quiet. We loved the dock and the firepit, and the house was well-stocked with firewood, towels, and toiletries. "

"The house worked was exceptionally clean and worked great for us. The landowner was exceptionally helpful in providing suggestions. We loved visiting the Norman Rockwell Museum and walking around Lenox. Thanks for everything!"

"I'd describe the house as elegantly eclectic. The owner is clearly a collector of interesting items which they arrange in a way that enhance (rather than potentially clutter) the interior. The kitchen and living spaces are open and easy to mingle around. The four bedrooms and three bathrooms easily and comfortably accommodated two couples and two singles. Our stay could not have been better! "

"We had fun! Game room great! Spacious and comfortable. Never got to enjoy outdoors, so maybe another trip in the future!"

"The house was perfect for our group of couples and young kids. Large bedrooms and beautiful property "

"From beginning to end, could not have dreamed of a better island getaway, in the Berkshire’s none-the -less. Bill was a wonderful host. Very friendly, responsive and helpful. Super welcoming. The home was simple, quaint, and super cozy. Perfect for a nice long relaxing weekend for both the dogs and people. The views from the sun room were lovely. The deck/patio area had a beautiful view of the water. The fire pit was a nice perk in the evening. Surrounded by water, the place felt so private....

"We enjoyed it! Five of us stayed for a quiet weekend away. The house was clean, comfortable, and as advertised. There was plenty of space and beds for us to use. The hot tub was great. I would definitely recommend it to others! "

1 bedroom, iron/ironing board, WiFi, bed sheets

"House and grounds are large! Firepit is great! Local hiking and restaurants were fantastic! Enjoyed the large rooms and decor and artworks and prints."

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"Loved the location and the history of this property."

includes taxes & fees

14 Jan - 15 Jan

"Great location! Amazing view! "

includes taxes & fees

14 Jan - 15 Jan

"We love this property! We’ve stayed there two times so far and have had an great experience each time. The rooms are clean. The vibe is very sophisticated, and the food at the restaurant is out of this world. The staff is friendly and helpful. What more could you ask for in the Berkshires?!"

includes taxes & fees

16 Jan - 17 Jan

Find out more about Stockbridge

Everything you need to know about Stockbridge holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Stockbridge holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Stockbridge holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Stockbridge holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Stockbridge. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Stockbridge holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Stockbridge holiday rentals we have selected for you start as low as €200 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Stockbridge rentals

At Expedia, we put the best Stockbridge holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Stockbridge rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Stockbridge holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Stockbridge. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Recent reviews of Stockbridge properties

5/5 Excellent

"We love this property! We’ve stayed there two times so far and have had an great experience each time. The rooms are clean. The vibe is very sophisticated, and the food at the restaurant is out of this world. The staff is friendly and helpful. What more could you ask for in the Berkshires?!"

A verified traveller stayed at Life House Berkshires

Posted 20 hours ago

Frequently asked questions

Can I find a holiday rental in Stockbridge?

Yes, there are holiday rentals in Stockbridge close to Berkshire Botanical Garden, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers say Stockbridge has a good selection of bars. Make sure you have time to check out the gardens and museums during your trip.

What are some of the best holiday rentals that Stockbridge has to offer?

Berkshire Village Carriage House - Super Private!!: This holiday home rental outside of Stockbridge is located in the mountains, and has a garden, a BBQ and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of books in this rental home to help you unwind.

How many holiday rentals will I find in Stockbridge?

Choose from 29 Expedia holiday rentals in Stockbridge for a memorable holiday.

What’s there to see and do in Stockbridge?

Enjoy the outdoors at Naumkeag Museum and Beartown State Forest, or simply take in cultural attractions like Norman Rockwell Museum and Mission House. National Shrine of the Divine Mercy and Berkshire Theatre Festival are other places to visit while you're in town.

What’s a holiday rental in Stockbridge like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Stockbridge. Holiday rentals offer extras like WiFi and washers and dryers so you'll have all the conveniences of home. If you're concerned about cleanliness, a holiday rental can offer a sense of safety away from shared hotel lifts and busy front desks while still allowing you to travel. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental a popular choice for a small group gathering.

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Holiday Rentals in Stockbridge

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Check Stockbridge holiday rental availability

Holiday Rentals in Stockbridge

Find your Sanctuary at The Rectory at Stockbridge

Find your Sanctuary at The Rectory at Stockbridge

Vacation Village in the Berkshires

Vacation Village in the Berkshires

Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

The Freeman - Newly Renovated 14K SF Estate on 40 Acres

The Freeman - Newly Renovated 14K SF Estate on 40 Acres

Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!

Pristine Home In Becket Woods

Pristine Home In Becket Woods

Peace and quiet on the lake

Peace and quiet on the lake

Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

Private Estate, Heated Yearround Outdoor Pool

Private Estate, Heated Yearround Outdoor Pool

Serene Acreage - Pond - Hiking Trails Nearby

Serene Acreage - Pond - Hiking Trails Nearby

Berkshires Cabin 2 Mi to Appalachian Trail!

Berkshires Cabin 2 Mi to Appalachian Trail!

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

Berkshire Lake access

Berkshire Lake access

Antique Farmhouse Totally Restored

Antique Farmhouse Totally Restored

Beautiful 5-Star Private Estate! Inquire about our Early Booking Reduced Rates!

Beautiful 5-Star Private Estate! Inquire about our Early Booking Reduced Rates!

Quintessential 6-BR Berkshires Lodge

Quintessential 6-BR Berkshires Lodge

Private Island - Largest Fresh Water Reservoir in Mass....

Private Island - Largest Fresh Water Reservoir in Mass....

The Meadows House @ Otis Ridge w/ 7-person hot tub

The Meadows House @ Otis Ridge w/ 7-person hot tub

Peaceful, Post and Beam Loft, Sleeps 9

Peaceful, Post and Beam Loft, Sleeps 9

Other types of properties in Stockbridge you may be interested in

The Red Lion Inn

The Red Lion Inn

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

Life House Berkshires

Life House Berkshires

Find out more about Stockbridge

Find out more about Stockbridge

Recent reviews of Stockbridge properties

Recent reviews of Stockbridge properties

Life House Berkshires

Frequently asked questions