Compare Great Barrington Vacation Rentals

Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels

Save 10% or more on select hotels with Insider Prices

Book on the app to instantly earn 5% on 350,000+ hotels

Great Barrington Rentals

Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat

Great Barrington MA
3.38 mi from city center
$306 nightly
The price is $342 total per night
$342 total
Sep 8 - Sep 9
Total with taxes and fees
At this vacation home, guests have access to features like laundry facilities. This smoke-free vacation home also has 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
At this vacation home, guests have access to an outdoor pool, laundry facilities, and a garden. Helpful staff is there to provide concierge services, as well as offer insight about the area. This smoke-free vacation home also has barbecue grills.
Hotel-like Balcony Suite—View—Private Wing&Entry—Ensuite Bath—Walk to Town, Lake

Hotel-like Balcony Suite—View—Private Wing&Entry—Ensuite Bath—Walk to Town, Lake

Great Barrington MA
0.67 mi from city center
$238 nightly
The price is $265 total per night
$265 total
Aug 11 - Aug 12
Total with taxes and fees
At this apartment, guests have access to features like laundry facilities. This smoke-free apartment building also has a garden.
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
Great Barrington, Cabin Sleeps 14, Walk To Town

Great Barrington, Cabin Sleeps 14, Walk To Town

Great Barrington MA
0.13 mi from city center
$1,601 nightly
The price is $1,788 total per night
$1,788 total
Aug 10 - Aug 11
Total with taxes and fees
Guests staying at this vacation home have access to laundry facilities, barbecue grills, and a garden.
Kitchen
Washer
5 Minutes from The Appalachian Trail and Mount Washington. In the Berkshires!

5 Minutes from The Appalachian Trail and Mount Washington. In the Berkshires!

Egremont MA
4.36 mi from city center
This vacation home features a hot tub and a garden.
Hot Tub
Kitchen
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.
Luxury Fox Hollow Estate Home on Laurel Lake - Dream Location, Hot Tub, Kayaks++

Luxury Fox Hollow Estate Home on Laurel Lake - Dream Location, Hot Tub, Kayaks++

Lenox MA
9.72 mi from city center
Guests of this vacation home enjoy features like an indoor pool, a hot tub, and an arcade/game room. Other amenities at this family-friendly vacation home include laundry facilities, local meal delivery service, and a garden.
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. Helpful staff is there to provide a safe deposit box at the front desk, as well as offer insight about the area. Additional amenities include a sauna, free WiFi in public areas, and an outdoor tennis court.
Private Island - Largest Fresh Water Reservoir in Mass

Private Island - Largest Fresh Water Reservoir in Mass

Otis MA
16.32 mi from city center
Guests staying at this cottage can enjoy a gym, a garden, and barbecue grills.
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
15.76 mi from city center
$138 nightly
The price is $155 total per night
$155 total
Aug 30 - Aug 31
Total with taxes and fees
At Berkshire Mountain Lodge, guests have access to an indoor pool, free WiFi in public areas, and a hot tub. If you decide to drive, there's free parking. Front-desk staff can help secure valuables, and provide local restaurant recommendations. Other amenities at this golf aparthotel include a business center, an arcade/game room, and laundry facilities.
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
Aug 9 - Aug 10
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 garden, a picnic area, and barbecue grills.
Don't see what you're looking for?
See all available properties in Great Barrington
View all properties
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.