Best Vacation Homes in Great Barrington
850 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Cottage
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
£236/Night
For 7 Nights £1,655
291.53 ft²
26 Guests
13 Bedrooms
13 Bathrooms
Bed & Breakfast
- Parking
- Air Conditioner
- Internet
£124/Night
For 7 Nights £869
1 Bedroom
1 Bathroom
Ocean View
Bed & Breakfast
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
£165/Night
For 7 Nights £1,156
600 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Cottage
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
£182/Night
For 7 Nights £1,278
1636.11 ft²
8 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- View
- Parking
£333/Night
For 7 Nights £2,329
450 ft²
3 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cottage
- Private Pool
- Fireplace/Heating
- Pool
£218/Night
For 7 Nights £1,523
920 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
£336/Night
For 7 Nights £2,355
7535 ft²
5 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
£131/Night
For 7 Nights £917
Great Barrington Luxury Rentals
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cabin
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
Unlock the Best Price
16 Guests
6 Bedrooms
6 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
£3,662/Night
For 7 Nights £25,635
11000 ft²
16 Guests
10 Bedrooms
9 Bathrooms
Family Friendly
House
- Private Pool
- Hot Tub
- Fireplace/Heating
£2,790/Night
For 7 Nights £19,531
7500 ft²
14 Guests
6 Bedrooms
7 Bathrooms
Family Friendly
Cabin
- Spa
- Fireplace/Heating
- Balcony/Terrace
£1,445/Night
For 7 Nights £10,116
18 Guests
6 Bedrooms
6 Bathrooms
Family Friendly
House
- Private Pool
- Hot Tub
- Spa
£1,290/Night
For 7 Nights £9,031
1 Bedroom
1 Bathroom
Couples Retreat
House
- Fireplace/Heating
- Pool
- Parking
£1,224/Night
For 7 Nights £8,571
9500 ft²
15 Guests
6 Bedrooms
7 Bathrooms
Family Friendly
House
- Private Pool
- Fireplace/Heating
- Pool
£1,218/Night
For 7 Nights £8,528
20 Guests
7 Bedrooms
4 Bathrooms
Family Friendly
House
- Private Pool
- Fireplace/Heating
- Pool
£1,135/Night
For 7 Nights £7,943
Great Barrington Pet Friendly Vacation Rentals
1014 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
£300/Night
For 7 Nights £2,098
1097.92 ft²
5 Guests
2 Bedrooms
1 Bathroom
Free Cancellation
House
- Fireplace/Heating
- Pet Friendly
- Parking
£198/Night
For 7 Nights £1,386
5 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
£232/Night
For 7 Nights £1,624
753.47 ft²
2 Guests
1 Bedroom
1 Bathroom
Free Cancellation
House
- Spa
- Fireplace/Heating
- Pet Friendly
£186/Night
For 7 Nights £1,301
1000 ft²
4 Guests
2 Bedrooms
1 Bathroom
Ocean View
Cottage
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
£181/Night
For 7 Nights £1,268
2126 ft²
9 Guests
1 Bedroom
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
£196/Night
For 7 Nights £1,370
1100 ft²
5 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Cabin
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
£200/Night
For 7 Nights £1,403
300 ft²
2 Guests
1 Bedroom
1 Bathroom
Couples Retreat
Apartment
- Fireplace/Heating
- Pet Friendly
- Parking
£133/Night
For 7 Nights £934
Great Barrington Large Vacation Homes
7 Guests
5 Bedrooms
1 Bathroom
Family Friendly
Cottage
- Fireplace/Heating
- Pet Friendly
- Kitchen
£425/Night
For 7 Nights £2,973
1646.88 ft²
10 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
£299/Night
For 7 Nights £2,095
3000 ft²
16 Guests
5 Bedrooms
4 Bathrooms
Ocean View
House
- Hot Tub
- Skiing
- Fireplace/Heating
£793/Night
For 7 Nights £5,550
1496.18 ft²
10 Guests
3 Bedrooms
2 Bathrooms
Free Cancellation
House
- Fireplace/Heating
- View
- Pet Friendly
£478/Night
For 7 Nights £3,344
5000 ft²
12 Guests
5 Bedrooms
4 Bathrooms
Ocean View
House
- Hot Tub
- Fireplace/Heating
- Ocean View
£966/Night
For 7 Nights £6,764
4000 ft²
16 Guests
7 Bedrooms
4 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
£771/Night
For 7 Nights £5,397
15 Guests
7 Bedrooms
6 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
£680/Night
For 7 Nights £4,763
12 Guests
4 Bedrooms
3 Bathrooms
Ocean View
House
- Private Pool
- Hot Tub
- Spa
£631/Night
For 7 Nights £4,420
Why Choose Rent By Owner for your Great Barrington Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Great Barrington
When should you plan your Vacation Rentals stay?
Determining the best time to visit here can enhance your stay, as seasonal changes influence the region's natural beauty and local events, making it essential to select a period that aligns with your vacation preferences for a memorable experience.
Peak Season Highlights
Summer (June to August)
During the summer months, this region experiences warm weather ideal for outdoor activities and exploring nearby natural scenery.
Average Temperature Daytime: 75°F to 85°F - Nighttime: 55°F to 65°F
Fall (September to November)
Autumn brings vibrant foliage and comfortable temperatures, making it a perfect time to enjoy the scenic beauty of the area.
Average Temperature Daytime: 60°F to 70°F - Nighttime: 40°F to 50°F
Off-Season Highlights
Late Fall to Early Winter (December to February)
The colder months see fewer visitors, offering a quieter experience and opportunities for cozy indoor relaxation.
Average Temperature Daytime: 35°F to 45°F - Nighttime: 20°F to 30°F
Spring (March to May)
Springtime gradually warms up the region, with blooming flora providing a picturesque setting before the busy summer season.
Average Temperature Daytime: 50°F to 60°F - Nighttime: 30°F to 40°F
Weekly Weather Forecast for Great Barrington
How to Book Your Great Barrington Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Great Barrington
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy a spacious outdoor patio or deck perfect for relaxing and dining al fresco.
- Take advantage of a private yard or garden area to unwind amidst nature.
- Make the most of outdoor grilling facilities for delicious barbecues with family and friends.
- Benefit from access to scenic hiking trails or nature walks right from your doorstep.
- Relax in a bubbling hot tub or jacuzzi under the stars after a day of exploring.
- Utilize outdoor recreation equipment such as bikes, kayaks, or paddleboards available for guests.
- Appreciate beautiful landscaped grounds or mountain views that showcase the area's natural beauty.
Top Attractions Around Great Barrington
What attractions are nearby?
Nearby, you can enjoy a variety of outdoor activities, explore charming local shops, or experience the region’s renowned dining scene, all just moments from your vacation rentals in this inviting destination.
Family Activities
- Norman Rockwell Museum: Explore the inspiring exhibitions and family-friendly activities that celebrate American art right in this charming town.
- Gilded Age Historic District: Take a leisurely stroll through the beautifully preserved historic neighborhood, offering educational opportunities for all ages.
- Mohawk Trail State Forest: Enjoy outdoor adventures like hiking, picnicking, and nature explorations amid the scenic landscapes of the region.
- Bartholomew's Cobble: Discover unique plant species and go on guided walks in this protected natural area, perfect for family nature outings.
Adult Activities
- Wine Tasting Experiences: Explore local vineyards and enjoy tasting tours that showcase the region's renowned wine selection, perfect for relaxing afternoons.
- Art Gallery Visits: Discover contemporary and traditional artworks at the area's vibrant galleries, offering a cultural escape in this scenic destination.
- Historical Walking Tours: Immerse yourself in the area's rich history by joining guided walks that highlight its fascinating past and architectural gems.
- Outdoor Recreation: Take advantage of hiking, biking, or outdoor excursions in nearby parks and scenic trails, embracing the natural beauty here.
Other Places to Stay in Great Barrington, MA
W.E.B. Du Bois Boyhood Homesite
Lake Mansfield Park
Mahaiwe Performing Arts Center
Housatonic River Walk
Art et Industrie
Ski Butternut
Alford
Dry Hill
New Marlborough
North Egremont
Egremont
Beartown State Forest
Great Barrington Travel Tips
How Can You Make the Most of Your Stay?
- Plan Your Visit Around Local Events: Check the area's event calendar to align your stay with festivals or gatherings that showcase the region’s vibrant culture.
- Explore Nearby Attractions: Take advantage of the proximity to natural parks and scenic vistas to enrich your experience in this charming destination.
- Choose Strategic Accommodation Locations: Opt for rental properties close to town centers or popular spots to maximize your time exploring and minimize commuting.
- Engage with the Local Community: Participate in local workshops, markets, or dining to gain authentic insights into the region’s unique character.
Transportation Options
- Great Barrington Municipal Airport: You can access regional flights and private charter services nearby, making travel to this part of Massachusetts convenient.
- Amtrak Train Service: The train station in nearby Pittsfield offers rail connections that make exploring the area or traveling further afield straightforward.
- Local Bus Services: Public bus routes provide economical transportation options within the region, connecting you seamlessly to local attractions and amenities.
- Car Rental Services: Renting a vehicle here offers flexibility, allowing you to explore the natural beauty and scenic spots around this destination at your own pace.
Local Customs Options
- Local Arts and Crafts: You’ll notice a strong appreciation for handcrafted goods and local art, reflecting the area's rich cultural heritage.
- Farmers’ Market Traditions: Visiting the community farmers’ markets offers a glimpse into the region’s agricultural roots and commitment to fresh, local produce.
- Seasonal Festivals: The region hosts vibrant festivals that celebrate its natural beauty and community spirit throughout the year.
- Historical Preservation: Respect for historic buildings and landmarks underscores the area's dedication to maintaining its charming character for visitors staying in here.
Frequently Asked Questions About Great Barrington?
1. What are the top vacation rentals in Great Barrington?
There are a lot of options in Great Barrington. If you plan on staying in the Great Barrington area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Great Barrington:
- Waterfront Cottage 10 Min From Great Barrington
- Charming Cottage, New Marlborough Village Green in the Berkshires
- Romantic Berkshires Cottage - Stunning Views, Pool
- The Great Escape Ski Cottage w/HOT TUB @ Great Barrington
- Stunning Renovated Victorian
- Incredible Ski Lodge - 7500 Square ft - Log Cabin - Moose Lodge
- Twin Maple Farm: Charming Modern Farmhouse
- NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE
- Beautiful Berkshire Farm House on 160+ Acres
- Converted Berkshire schoolhouse on a quiet river
2. How many vacation rentals have private pools in Great Barrington?
There are 25 vacation rentals with private pools near Great Barrington. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Great Barrington are best for families?
If you are looking for a family-friendly vacation home in Great Barrington, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Great Barrington:
4. How many Rentbyowner vacation rentals are available in Great Barrington?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 310 in the Great Barrington area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Great Barrington.
5. What is the cancellation policy for vacation rentals in this area?
Cancellation policies vary by property, so it's important to review the specific listing details or contact the owner directly to understand the terms and any applicable fees before booking.
6. How do I know if a vacation rental in Massachusetts is available on my preferred dates?
Availability is shown in real-time on the listing page; however, if your dates are not visible or appear unavailable, reaching out to the property owner can provide additional options or updates.
7. Are there any additional fees or charges associated with booking a vacation rental here?
Additional fees such as cleaning, service charges, or security deposits are typically outlined in the listing details, but confirming these directly with the host ensures clarity before completing your reservation.
8. Can I find pet-friendly vacation rentals in Great Barrington?
Many properties in the region accommodate pets, but availability varies. Check the listing filters or contact the owner directly to confirm pet policies and any extra charges.
9. What amenities should I expect when staying at vacation rentals in this destination?
Amenities range from fully equipped kitchens to Wi-Fi and outdoor spaces. Review each listing thoroughly or contact the owner for detailed information about specific features available during your stay.
Great Barrington Top Rated Vacation Rentals
2320 ft²
8 Guests
4 Bedrooms
3 Bathrooms
Ocean View
House
- Private Pool
- Spa
- Fireplace/Heating
£329/Night
For 7 Nights £2,301
3000 ft²
8 Guests
4 Bedrooms
2 Bathrooms
Ocean View
House
- Private Pool
- Hot Tub
- Fireplace/Heating
£964/Night
For 7 Nights £6,752
11 Guests
5 Bedrooms
3 Bathrooms
Ocean View
Other
- Private Pool
- Hot Tub
- Fireplace/Heating
£514/Night
For 7 Nights £3,595
8 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Private Pool
- Fireplace/Heating
- Pool
£747/Night
For 7 Nights £5,226
3000 ft²
10 Guests
5 Bedrooms
4 Bathrooms
Family Friendly
House
- Private Pool
- Fireplace/Heating
- Pool
£1,025/Night
For 7 Nights £7,176
8 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Private Pool
- Fireplace/Heating
- Pool
£600/Night
For 7 Nights £4,199
8 Guests
5 Bedrooms
2 Bathrooms
Family Friendly
House
- Private Pool
- Hot Tub
- Fireplace/Heating
£413/Night
For 7 Nights £2,893
4 Guests
2 Bedrooms
1 Bathroom
Ocean View
Apartment
- Oceanfront
- Fireplace/Heating
- Pool
£183/Night
For 7 Nights £1,284
