Berkshires Luxury Rentals. If you are a resident of another country or region, please select the appropriate version of Tripadvisor for your country or region in the drop-down menu. A dining room that can comfortably seat 12, with a bonus eat-in kitchen that seats six. There are 0 vacation homes in Berkshires resorts. Warm-up in our fitness room, then cool off in our large swimming pool. Booking for fall, winter & 2021! Walking distance to town. Modern home with all amenities + sep. cabin on 10+ wooded acres. Save time searching for Berkshires rental vacations and Berkshires accommodations! Spacious with mountain views on 47 acre estate, convenient to culture & recreation. Price per night. $1,000+ Suitability. Bathrooms. Your family vacation awaits in Berkshire! Owner log in. Stunning Post & Beam home minutes from Lenox, Stockbridge and Tanglewood! From 84 cabin rentals to 563 house rentals, find unique vacation rental for you to enjoy a memorable holiday or a weekend with your family and friends. This luxurious and newly renovated home in the heart of a beautiful community offers all the charm of New England, along with the modern amenities you desire. 0+ rooms, 2+ guests. 300+ point inspection. Great Barrington Retreat ! We understand what attracts you to the Berkshires. Create awesome memories for you and your loved ones at one of these rustic mountain cabins near the Berkshires, Massachusetts! Stay two nights get one free for March and April! Let us be your home away from home! February 30°F           August 67°F Luxury amenities. Choose from more than 1,000 properties, ideal house rentals for families, groups and couples. Beautiful +Family Friendly - W Tree House & Tennis Court, New Rates! Fiber optic internet. Custom itineraries. Browse all rentals currently on the market in the Berkshires. Amenities. 4 BR home w/ beautiful gardens on pond in Berkshires. Features include a picnic and children’s play area and big-screen TV, perfect for movie nights. Booking for the Fall & Winter Now! Owner log in. #11-Apartment at the Rose and Goat Retreat. Stay at one of the many vacation home rentals throughout the Berkshires. Each property is verified for pristine condition and meticulously maintained. Perfect for 2 families or 4 couples. Whether you’re looking for a log cabin to host your weekend of solitude or are curious about one of many luxury cabin rentals to host you and your special someone, Travelocity has everything you need for your next vacation. Berkshires Luxury Vacation Rentals. Room to Roam. The perfect getaway: 5 bd, 3 ba, 3 acres. Whether you're getting cozy inside your fairytale luxury cottage or enjoying the views from your modern cabin, this collection of rentals is sure to make your vacation to the Berkshires one you'll never forget. Birchwood Inn offers you and your loved ones the chance to get away from it all. Call Berkshire Property Agents today for more information. On your next trip, consider a Berkshires vacation home rental for your accommodations. Price per night. January 27°F              July 69°F Minutes to Tanglewood, golfing, skiing, hiking, lakes, fine arts and more. Paddleboard, kayak, or take a rowboat for an easy-going float on the water. Mountain . Huge Luxe Williamstown Updated Victorian, All Ensuite Baths, Walk to Spring St! Exclusive Properties Search Homes for Sale Search Rentals Search Waterfront Homes Search Land for Sale Search Commercial for Sale. 15 minutes to Great Barrington, Tanglewood, and Jacob’s Pillow. Apartment Rentals in Berkshires: View Tripadvisor's 3,436 unbiased reviews, 11,444 photos and great deals on Berkshires Apartment Rentals Sleeps a total of 12 people; pet friendly! RANKED #1 for 5 STAR REVIEWS covering 355 properties. View Map. 2 BED/BATHS ; CENTRAL AC; FIREPL; ROMANTIC 'SKI LODGE' FEEL. View our map to find vacation home rentals in the Northern Berkshires, Central Berkshires and Southern Berkshires. Best Luxury Hotels in Berkshires on Tripadvisor: Find traveller reviews, candid photos, and prices for 9 luxury hotels in Berkshires, Massachusetts. Contact us for Monthly Specials! Distance from. 0+ rooms, 2+ guests. 1-844-934-1851 . COUPLE(S) PERFECT!! From vacation homes for rent to vacation apartment and condo rentals, each vacation rental offers a truly unique lodging experience. Bathrooms. Explore an array of The Berkshires, US vacation rentals, including houses, cabins & more bookable online. 413–528–6800 info@bpagents.com. Berkshire Mountain Lodge New one bedroom suites. 413–528–6800 info@bpagents.com. Luxury Cabin in the Berkshires Woods A clean, safe, luxury cabin smack in the middle of the Berkshire woods. This is the version of our website addressed to speakers of English in the United States. Rent a whole home for your next weekend or holiday. June 64°F                   December 31°F. Check in — / — / — Check out — / — / — Guests. Any. Lake . Barrington Compound w/ Scenic Mountain View(s) Distance from. Full kitchens, WiFi, indoor pool, hot tub. Our luxury Berkshires rental sleeps 12. The breathtaking view of the lake, forests, and Appalachian trail can be enjoyed all four seasons. Close to everything. No matter what activities you have in mind for your vacation or what time of year you plan to visit the Berkshires, you'll find endless things to do here, and the best way to enjoy it all is with your own private vacation rental. Elegant 19th Century New England 2BR Vacation Rental at Garfield House. Vacation Rentals in the Berkshires. from $209. Beautiful 1920's Colonial 20 Minutes from Tanglewood, Charming Downtown Williamstown Cottage - 5 Min Walk to Campus. May 56°F                    November 44°F Berkshire Pontoosuc Lake Beauty Too-Brand new construction on the lake, Lovingly restored Victorian in Lee's Historic District **Spring:3rd nt 1/2 off, PRIVATE LAKEFRONT BEACH PROPERTY ON GOOSE POND near TANGLEWOOD. Take in the Berkshires’ bucolic scenery from this lakefront haven. Great Barrington Lenox Monterey … Most popular short term rental in Berkshires is Yankee Inn; Cheapest place to stay in Berkshires is Weathervane Motel Lanesboro; Most expensive holiday rental in Berkshires is Gt. Unplug and reconnect with nature and the outdoor adventures unique to the Berkshires. Spring Break Special! All other days are non-selectable. BEAUTIFUL Ski-In/Ski-Out - Jiminy Peak Mountain Resort - Berkshires. more, InterContinental (IHG) Hotels in Berkshires. Communities. Berkshires' Award-Winning Fairfield by Marriott Relax and Rejuvenate this winter at one of Marriott’s 4.8 out of 5 guest rated hotels. Your trip designer can plan every last detail and make sure everything is just right. Four courts offer ample space for a few leisurely matches. Thoughtfully curated for desirability, location, and great amenities, BRP listings are a step above the typical offerings. Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table. Luxury 5-bedroom vacation rental in the Berkshires makes for a memorable vacation. Routines are important, even on vacation. Lenox, Massachusetts, United States . Berkshire County, located in the far western region of Massachusetts, is one of the premier destination spots in all of New England.Abutting New York to the West, Vermont to the North and read … Cozy Monterey Family Chalet, Minutes From Lake & 10 Minutes From Butternut! Situated on the pristine waters of Pontoosuc Lake in Lanesborough, Massachusetts at the foothills of the Berkshire Mountains, The Lake House is a waterfront, boutique-style cottage resort; offering an all-season charming and tranquil escape with a touch of luxury in the heart of The Berkshires- meaning you can get to any part of the Berkshires within 30 minutes! Sign Up; Login ; Find Real Estate. You can only select check-in or check-out days (Thursday/Friday). Stay. Birchwood Inn . 'Too Good' With 11 Private Acres. A serene a-frame deck provides the perfect lookout and grill spot. 'The Mill River Cabin’ w/ Fireplace & River View! List your property. March 34°F                September 65°F Communities. 1 km. Our 2020 vacation rental listings offer a large selection of 796 house rentals around The Berkshires. Effortless arrivals. Berkshire Rental Properties Whether you’re looking for a cute cozy cottage or a stunning multifamily estate Berkshire Rental Properties offers luxury at every level. $0. C$1,000+ Suitability. C$0. Check-in — / — / — Check-out — / — / — Guests. Cozy accommodations provide you with plenty of space to relax... more. Spacious, Modern House 5 Bedrooms, 2.5 Bathrooms, Sleep 12 on small horse farm. Simply click the "Inquire Now" button, complete a short inquiry form, and within minutes you will start receiving multiple offers from Berkshires vacation home rentals owners as well as from Berkshires resorts, Berkshires cabin rentals, and Berkshires vacation homes. Great Barrington Lenox Monterey … Kid friendly (188) Pet friendly (34) Elder access (33) Business Travel (30) Show more. The best place to stay around The Berkshires is … Browse all luxury homes currently on the market in the Berkshires. Beautiful home with all amenities. Recently renovated 4 bedroom lakefront house in The Berkshires. Many vacation rentals are located within a short distance to one of our wonderful Berkshire attractions such as Tanglewood, MASS MoCA, The Colonial Theatre, Norman Rockwell Museum, Barrington Stage Company, Williamstown Theatre Festival, Clark Art, Ski Areas, Colleges and more. Berkshires Luxury Vacation Rentals; Search. Fantastic Fall Stay at Berkshires Lake Home. A scenic four season playground, The Berkshires has something to offer everyone. Top rated vacation home in Berkshires is Recently renovated 4 bedroom lakefront house in The Berkshires. Tranquil 3BR Stockbridge House w/Private Deck, Unique People & Pet-Welcoming Country Haven, Berkshires: Romantic Cottage with spectacular view, Close To Skiing! Relax after dinner in the adjacent bar or in front of the fireplace. Travelers have always appreciated The Berkshires for its natural wonders, and now you can too. From night skiing to ice-skating to snowboarding, there are winter sports for all ages. Secluded Vacation Rentals in the Berkshires, Massachusetts Create awesome memories for you and your loved ones at one of these secluded vacation rentals in the Berkshires, Massachusetts! Book vacation rentals directly from owners of chalet, cabin, home, and condo accommodations at The Berkshires, MA, USA. Overlooking the majestic lake and woods; can you spell LOVE? Best Berkshires Resorts on Tripadvisor: Find traveller reviews, candid photos, and prices for resorts in Berkshires, Massachusetts. Luxury . Find a cabin or condo that offers all the luxury amenities you and your family need, then relax, unwind, and make great vacation memories. Warm your heart this holiday season in this cozy cottage next to downtown Lenox. Showing 1-15 of 15 Family Resorts. 1 mi. Amenities. Sign Up; Login; Find Real Estate. View Map. Any. Whether you're hanging out inside your secluded getaway or taking in the views from your stately cabin, this collection of rentals is sure to make your vacation to the Berkshires one you'll never forget. Jan 9, 2021 - View the Best 410 vacation rentals with Prices in Berkshires with Tripadvisor's 3,433 unbiased reviews for a great deal on cabin rentals in Berkshires, MA Fully equipped to meet your needs, with ample space and privacy. List your property. While at our country home, you’ll have access to the Clubhouse. Vacation home rentals are generally appealing for many reasons. Call Berkshire Property Agents today for more information. Exclusive Properties Search Homes for Sale Search Rentals Search Waterfront Homes Search Land for Sale Search Commercial for Sale. Vacation rentals in the Berkshires make for a memorable Berkshire vacation. Beautiful Waterfront home with deep water dock on Onota Lake, Historic Red Schoolhouse featured in the 2015 Home & Garden TV Special, Tranquil Lake House Getaway on Onota Lake, 2 bedroom Riverhouse in the Heart of the Berkshires. General Williams Estate House Lenox/Stockbridge, A Beautiful Log Cabin In The Woods, On A Lake (Pontoosuc), Yet Near Everything. Spotlight. Kid friendly (196) Pet friendly (34) Elder access (33) Business Travel (29) Show more. Some of the foremost being cost savings, more space, and no tips or service charges that are associated with hotel rooms. The Berkshires Travel Guide Flights to The Berkshires Things to do in The Berkshires Car Rentals in The Berkshires The Berkshires Vacation Packages Massachusetts may have travel restrictions in place, including self-quarantine, due to COVID-19. Large groups are welcome with three floors, five bedrooms, and three full baths. 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