Compare Great Barrington Vacation Rentals

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Great Barrington Rentals

Family Ski Getaway in the Berkshires

Family Ski Getaway in the Berkshires

Great Barrington MA
3.38 mi from city center
$249 nightly
The price is $278 total per night
$278 total
Jan 14 - Jan 15, 2026
Total with taxes and fees
At this vacation home, guests have access to an arcade/game room, laundry facilities, and a garden.
Kitchen
Washer
Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!

Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!

Great Barrington MA
2.71 mi from city center
Guests staying at this vacation home have access to laundry facilities, a garden, and barbecue grills.
Kitchen
Washer
The Great Escape Ski Cottage w/HOT TUB @ Great Barrington

The Great Escape Ski Cottage w/HOT TUB @ Great Barrington

Great Barrington MA
2.05 mi from city center
Guests staying at this vacation home enjoy access to ski-in/ski-out access, a gym, and a hot tub. Other amenities at this ski vacation home include an arcade/game room, laundry facilities, and barbecue grills.
Hot Tub
Kitchen
Great Barrington Get Away

Great Barrington Get Away

Great Barrington MA
0.62 mi from city center
$496 nightly
The price is $554 total per night
$554 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
Guests staying at this vacation home have access to laundry facilities, barbecue grills, and a garden.
Kitchen
Washer
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Great Barrington MA
2.21 mi from city center
$1,193 nightly
The price is $1,332 total per night
$1,332 total
Dec 25 - Dec 26
Total with taxes and fees
Guests of this vacation home enjoy features like a gym, a hot tub, and laundry facilities. Additional amenities include a garden and barbecue grills.
Hot Tub
Washer
Half Moon by AvantStay | 4BR Cabin w/ Large Deck & Yard

Half Moon by AvantStay | 4BR Cabin w/ Large Deck & Yard

Great Barrington MA
3.52 mi from city center
At this cabin, guests have access to features like laundry facilities. This smoke-free cabin also has a garden.
Kitchen
Washer
Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!

Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!

New Marlborough MA
4.68 mi from city center
Guests staying at this cottage enjoy a gym, laundry facilities, and local meal delivery service. Other amenities at this family-friendly cottage include barbecue grills and a garden.
Kitchen
Washer
Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!

Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!

Great Barrington MA
1.63 mi from city center
This vacation home offers a water park, an outdoor pool, and laundry facilities. Helpful staff is there to provide concierge services, as well as offer insight about the area. Additional amenities include a garden and barbecue grills.
Pool
Kitchen
Stunning Renovated Victorian

Stunning Renovated Victorian

Great Barrington MA
0.67 mi from city center
This vacation home features a hot tub, an arcade/game room, and laundry facilities. Other amenities at this family-friendly vacation home include a garden and barbecue grills.
Hot Tub
Kitchen
The Ponds at Foxhollow

The Ponds at Foxhollow

3 out of 5
3 Foxhollow Drive Route 7 Lenox MA
9.67 mi from city center
The Ponds at Foxhollow features an indoor pool, an outdoor pool, and a gym. Free parking is available if you drive. The front desk is staffed 24/7 to help secure valuables, and answer any questions about the accommodations. Additional amenities include a sauna, free WiFi in public areas, and a hot tub.
Pool
Hot Tub
Peace and quiet on the lake

Peace and quiet on the lake

Becket MA
15.73 mi from city center
Guests staying at this vacation home have access to laundry facilities, a garden, and barbecue grills.
Kitchen
Washer
Micosta Leisure Inn

Micosta Leisure Inn

3 out of 5
3007 County Rd 20 Hudson NY
Free Cancellation
Reserve now, pay when you stay
19.98 mi from city center
$133 nightly
The price is $150 total per night
$150 total
Jan 10 - Jan 11, 2026
Total with taxes and fees
Guests of Micosta Leisure Inn enjoy free WiFi in public areas, a terrace, and laundry facilities. If you drive, put free parking to good use. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Additional amenities include a picnic area, barbecue grills, and a garden.
Kitchen
Pet friendly
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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.

Great Barrington Large Group Rentals

How to Book Vacation Rentals in Great Barrington



🏠 What is the best price for Great Barrington vacation rentals?

Great Barrington vacation rentals range in price, starting at $150 per night.


🏠 What types of vacation rentals in Great Barrington can I rent?

Orbitz offers a wide range of Great Barrington rentals so you can plan the perfect vacation. Whether you're on a budget or looking for luxury, our rentals include spots for families, couples, activities, leisure, summer, winter, and more. Explore unique property types available such as cabins, cottages, private vacation homes, and Great Barrington condo rentals.


🏠 Is it free to cancel my Great Barrington vacation rental with Orbitz?

Most vacation rentals are free to cancel when you do so before the cancellation deadline. However, cancellation policies vary by property. Non-refundable bookings will not receive a refund. We recommend booking with free cancellation in case your plans change.


🏠 How do I find the best deals to rent a Great Barrington vacation rental with Orbitz?

There are many different options for finding the best deal to suit your needs. Choose exclusive offers on rentals in various locations in Great Barrington. You can filter by price range, guest rating, property type, neighborhood, and more to customize your search and view the best deals for you.


🏠 How can I cancel my vacation rental booking through Orbitz?

Change of plans? We get it. You can cancel most vacation rentals bookings by getting in touch with the property manager. Sign in to your account and navigate to ‘My Trips’. Choose ‘Itinerary’ to view the property’s contact details. For questions and concerns, you can always visit our customer service portal.


🏠 What are the advantages of booking a vacation rental in Great Barrington?

Vacation rentals are your home away from home, offering a different kind of experience than traditional hotels. They’re often the best option if you're looking for more space, more privacy, and a place to make your own. Find homes for all kinds of stays with Orbitz. Plan group vacations with short-term rentals or choose from our Great Barrington apartments and enjoy an extended stay.


🏠 Why should I book my vacation rental with Orbitz in Great Barrington?

Orbitz offers incredible deals and offers on a large selection of vacation rentals as your one-stop-shop for travel. You’ll get rewards back with every booking, and when you book your stay along with a rental car, flight, or activity, our Great Barrington package deals will get you even more savings.