Beginning of main content

Search over a million flights, hotels, packages, and more

No ebookers cancellation fee to change or cancel almost any holiday rental reservation


Holiday Rentals in The Berkshires

See all Holiday Rentals in The Berkshires
Vacation Village in the Berkshires

Vacation Village in the Berkshires

276 Brodie Mountain Rd, Hancock, MA
    3.0 out of 5.0
     
     

    Vacation Village in the Berkshires's great location gets high marks from our customers. During your stay, you're just a quick walk from Jiminy Peak Mountain ...

    Private Suite with Separate Entrance in a Quiet Berkshire Neighborhood

    Private Suite with Separate Entrance in a Quiet Berkshire Neighborhood

    75 Yorkshire Dr, Cheshire, MA
       
       

      Our customers tell us that they can't get enough of the overall value at this holiday home. During your stay, you'll be close to Mount Greylock State Reservation ...

      Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

      Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

      157 Excalibur Drive, Becket, MA
         
         

        The sightseeing around this cabin gets high marks from our customers. During your stay, you'll be close to Becket Land Trust Historic Quarry. The cabin includes ...

        Ashmere Lake Log Cabin With Privacy / 2 Bedrooms

        Ashmere Lake Log Cabin With Privacy / 2 Bedrooms

        80 Franklin Road, Hinsdale, MA
           
           

          Our customers tell us they can't get enough of this cabin's great beach location. During your stay, you'll be close to Bas Ridge Golf Course. Enjoy your stay ...

          Jiminy Peak Mountain Resort

          Jiminy Peak Mountain Resort

          37 Corey Rd, Hancock, MA
            3.0 out of 5.0
             
             
            4.0 out of 5 (1 reviews)

            Our customers tell us they can't get enough of Jiminy Peak Mountain Resort's great location. During your stay, you're just a quick walk from Jiminy Peak Mountain ...

            The Ponds at Foxhollow by Capital Vacations

            The Ponds at Foxhollow by Capital Vacations

            3 Foxhollow Drive Route 7, Lenox, MA
              3.0 out of 5.0
               
               

              The spacious condos at The Ponds at Foxhollow by Capital Vacations get good marks from our customers. During your stay, you'll be within walking distance of ...

              Garfield Guest House in the Office Complex

              Garfield Guest House in the Office Complex

              208 Main St, Lee, MA
                 
                 

                Our customers tell us that they enjoy the convenient parking at this apartment building. During your stay, you're just a quick walk from Animagic Museum of Animation. ...

                Beautiful 2 bedroom apartment in the Lenox Dale Ma.

                Beautiful 2 bedroom apartment in the Lenox Dale Ma.

                5 Crystal St, Lee, MA
                   
                   

                  During your stay at this apartment building, you'll be within walking distance of Wood's Pond. The apartment offers a TV and a microwave.

                  Honeysuckle Rose Cottage

                  Honeysuckle Rose Cottage

                  173 Barker Rd, Pittsfield, MA
                     
                     

                    During your stay at this holiday home, you'll be within walking distance of Colonial Theater. Enjoy your stay with amenities like a TV and a fridge in the holiday ...

                    Honeysuckle Rose Cottage€111

                    Honeysuckle Rose Cottage€111
                    New Listing! Berkshires Jiminy Peak Mountainside Condo

                    New Listing! Berkshires Jiminy Peak Mountainside Condo

                    9123 Mountainside Dr, Hancock, MA
                       
                       

                      During your stay at this condo building, you're just a quick walk from Jiminy Peak Mountain Resort. An outdoor pool is available. The condo includes amenities ...

                      Villa With Access to Pools, a Hot Tub, Mini Golf, and a Sauna! Great Location!

                      Villa With Access to Pools, a Hot Tub, Mini Golf, and a Sauna! Great Location!

                      190 Meadow Street, South Lee, MA
                         
                         

                        During your stay at this villa, you're just a quick walk from Beartown State Forest. Features include an indoor pool, outdoor tennis court and a spa tub. Enjoy ...

                        The Freckled Hen's Berkshire Nest

                        The Freckled Hen's Berkshire Nest

                        35 David Avenue, Lee, MA
                           
                           

                          The sightseeing around this holiday home gets high marks from our customers. During your stay, you'll be within walking distance of Animagic Museum of Animation. ...

                          Stunning Post & Beam Home Minutes From Lenox, Stockbridge and Tanglewood!

                          Stunning Post & Beam Home Minutes From Lenox, Stockbridge and Tanglewood!

                          275 Spring St, Lee, MA
                             
                             

                            The clean holiday homes at this holiday home get high marks from our customers. During your stay, you'll be within walking distance of Greenock Country Club. ...

                            Craftsman Home In The Berkshire Forest

                            Craftsman Home In The Berkshire Forest

                            148 Middlefield Rd., Washington, MA
                               
                               

                              Our customers tell us that they can't get enough of the comfortable holiday homes at this holiday home. During your stay, you'll be close to Iroquis Waterfront. ...

                              Spend Summer in the Bershires!

                              Spend Summer in the Bershires!

                              37 Corey Rd, Hancock, MA
                                 
                                 

                                Our customers tell us they can't get enough of this condo's great location. During your stay, you're just a quick walk from Jiminy Peak Mountain Resort. You'll ...

                                Beautiful log cabin with all the major amenities.

                                Beautiful log cabin with all the major amenities.

                                767 Algerie Rd, Otis, MA
                                   
                                   

                                  During your stay at this holiday home, you'll be close to County Beach. A kitchen and 3 bathrooms are available in the holiday home.

                                  Walk to Tanglewood -luxury Dream Home - Htd Pool, Hot Tub, Stckbrdg Bowl W/boats

                                  Walk to Tanglewood -luxury Dream Home - Htd Pool, Hot Tub, Stckbrdg Bowl W/boats

                                  7 Hawthorne Rd, Lenox, MA
                                     
                                     

                                    During your stay at this holiday home, you're just a quick walk from Frelinghuysen Morris House and Studio. Features include outdoor tennis court, a spa tub ...

                                    Spacious Country Retreat With Secluded Tree Top Mountain Views

                                    Spacious Country Retreat With Secluded Tree Top Mountain Views

                                    301 Shunpike Rd, Sheffield, MA
                                       
                                       

                                      This holiday home's great location gets high marks from our customers. During your stay, you'll be close to Umpachene Falls Park. The holiday home offers a private ...

                                      Walk to Downtown Lenox and Tanglewood in This Super Charming Home

                                      Walk to Downtown Lenox and Tanglewood in This Super Charming Home

                                      68 Old Stockbridge Rd, Lenox, MA
                                         
                                         

                                        This holiday home's great location gets high marks from our customers. During your stay, you're just a quick walk from Lenox Library. A kitchen and 2 bathrooms ...

                                        Elegant 19th Century New England Newly Renovated 1BR Vacation Rental

                                        Elegant 19th Century New England Newly Renovated 1BR Vacation Rental

                                        192 Main St, Lee, MA
                                           
                                           

                                          Our customers tell us that they enjoy the shopping around this apartment building. During your stay, you're just a quick walk from Animagic Museum of Animation. ...

                                          Map

                                          Holiday Rentals in The Berkshires

                                          Thinking of a holiday to The Berkshires? While it may be tempting to simply go traditional and stay in a hotel, you could have a new kind of adventure by booking your own holiday rental in The Berkshires. Top of the list of perks may well be the cost advantage. After all, with holiday homes, from sleek apartments and villas to cosy cottages, you can expect significantly lower nightly rates compared to a hotel. Which is great news if you’re keeping an eye on your holiday budget, or simply prefer the idea of having more to spend while you’re there.

                                          As well as making your money go further, you’ll also get the pleasurable feeling of being far more than a “tourist”. Whether you’re visiting for a long break, or are just stopping over for a few days, a holiday home in The Berkshires will allow you to settle in like a true local. You can expect large living spaces to chill out in, as well as a fully-equipped kitchen where you can make use of locally-sourced ingredients from food markets and artisan shops.

                                          There’s also an unbeatable sense of privacy when you stay in a holiday apartment, villa or cottage. No more interruptions from hotel staff, or feeling like you have to adhere to someone else’s schedule. This will be your own space, where you can allow a holiday to unfold at a natural pace that suits you. From relaxed breakfasts at the kitchen table, to languid siestas on lazy afternoons, in between sightseeing excursions, your holiday home will feel like your real home.

                                          With ebookers, picking the right place is easy. We have a wide variety of potential pads on offer, from contemporary apartments that will suit holidaying couples, to larger family villas where the kids can play and grown-ups can bask. If you have particular attractions or districts you are eager to see, you can use ebookers to see which rentals are close by.

                                          By using our map of the area, you can check where the properties are in relation to sought-after areas, and opt to be in the heart of the action, or in a more tranquil outlying district which will ensure peace and quiet. All you have to do is select your travel dates and the most up-to-the-minute offers on The Berkshires holiday homes will be ready and waiting to be discovered.


                                          *Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.