Are you craving the green landscapes in Massachusetts? Vacation rentals in Great Barrington range from romantic cottages with beautiful views, to lakefront cabins, and even rustic log homes.

Choose the perfect vacation rental
Best Vacation Home Deals in Great Barrington
Save up to 67%
Compare and find a dreamlike property from $83 per night by searching among the 208 properties being offered in Great Barrington. By comparing these vacation rentals, HomeToGo brings you the most economical offers as well as the highest rated properties in Great Barrington.
Top-Rated Rentals and Accommodations in Great Barrington
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Recommended Vacation Rentals in Great Barrington
Find your perfect vacation rental in Great Barrington: from $83 per night
Budget-friendly Vacation Rentals in Great Barrington
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Vacation Rentals With Fireplaces
Get warm and cozy on cold winter nights in Great Barrington by booking a vacation home with a fireplace.
Vacation rentals and apartments with air conditioning
Keep cool during your trip to Great Barrington and book a vacation rental with air conditioning.
Best vacation rentals with a balcony
Looking for a home with a balcony? Check out these vacation homes in Great Barrington with their own private patios and balconies.

Popular Rental Amenities in Great Barrington
Accommodations can be narrowed down based on the amenities they offer. Above, you can see the number of properties that include a specific amenity in Great Barrington. Great Barrington is the perfect place to book a rental if you travel with your pet or you need internet access during your vacation, as the most common amenities are "Pets allowed" and "Internet." Three features that are not often provided are "Detached," "Fenced," and "Crib."
The Weather in Great Barrington
Check out our climate diagram to find the perfect month for your vacation. July is the warmest month in Great Barrington with average maximum temperatures of 81°. January is the coolest month, with average minimal temperature reaching 16°. The rainiest month is December while the driest month is August.
7-Day Weather Forecast in Great Barrington
Accommodations for your vacation in Great Barrington
The best local eats in Great Barrington
One of the highlights of Great Barrington is the Barrington Brewery & Restaurant, which not only offers you American bar food, but also a wide selection of delicious home brews. What better way to start off your vacation than by enjoying food and famous, local craft beer? Once you've sated your appetite, you must visit SoCo Creamery for the best ice cream in the Berkshires - there are lots of flavors to choose from, but the coconut and ginger are to die for!
Entertaining the kids: family fun in Great Barrington
If you are a family of skiiers, look no further than Ski Butternut, one of the most famous ski resorts in Great Barrington, located on Warner Mountain in the Berkshires. Offering stunning views of the alpine landscape, ski lessons, 2 terrain parks, and 22 trails, this is the best destination for winter family fun. Children who love hiking will enjoy Monument Mountain, which offers easy hikes through gorgeous terrain (particularly when the fall leaves are changing color). At Beartown State Forest, a scenic park with a fishing pond, you can see wildlife, enjoy winter sports, or take advantage of year-round hiking trails whenever you decide to visit.
Renowned Berkshire festivals
The Annual Berkshires Arts Festival has been presenting art and fine crafts for over 30 years. Located right in Great Barrington, this festival has been consistently rated as one of the 10 Great Cultural Hotspots in Western Massachusetts. Travelers will find great food, exquisite arts & crafts, and a relaxed atmosphere for the whole family to enjoy. Great Barrington also proudly hosts the world-class Berkshire International Film Festival every year, featuring premier feature films, documentaries, shorts, and family films.
Information about vacation rentals in Great Barrington
🏡 Vacation rentals available | 208 homes |
---|---|
💳 Possible discounts | up to 67% |
🌙 Nightly prices starting at | $83 |
⭐ Popular amenities | Pets allowed, Internet and Pool |
🐾 Pet friendly homes | 42 homes |
🏊 Vacation rentals with pools | 64 homes |
Frequently Asked Questions
What is the typical nightly price for a vacation rental in Great Barrington?
The nightly price of accommodations in Great Barrington starts at $83. If you would like to stay in a house rental, the average price is $753 per night. A bed and breakfast rental Great Barrington will cost $375 per night on average.
How many vacation homes are available to book in Great Barrington?
Currently there are 208 vacation homes in Great Barrington to choose from and rent for your upcoming trip.
What are the most popular amenities for vacation rentals in Great Barrington?
If you're looking to book a vacation rental in Great Barrington, others search for accommodation with Pets allowed, Internet and Pool.
How many vacation rentals with a pool are there in Great Barrington?
There are 64 vacation rentals across 5 providers in Great Barrington.
Are dogs allowed in vacation rentals in Great Barrington?
Finding a vacation rental in Great Barrington that allows dogs is easy, with 42 pet-friendly available.
What's the best month to travel to Great Barrington?
If booking a vacation rental in Great Barrington, consider that rainy season is usually in December or February, with August often being the driest.
Find the perfect Great Barrington home to match your style
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