Massachusetts Vacation Rentals

Massachusetts Vacation Rentals & Vacation Homes!

Vacation Rentals | Massachusetts Luxury Rentals | Massachusetts Discounts | Massachusetts Pet Friendly Rentals
These Massachusetts vacation homes, condos, villas, cabins, cottages, chalets, and bed & breakfasts are presented by their owners or agents. Please contact them directly with your inquiries. Click on the underlined descriptions below for more details and property photos.
Click Here to review listings ordered by city and # of bedrooms.
 
Premium Listings
WT 101 SEVEN GATES FARM- WONDERFUL FIVE BEDROOM HOME IN PRIVATE AREA, ASSOCIATION BEACH,TENNIS
  • West Tisbury
  • House (single)
  • 5 bedrooms, sleeps 10
  • 4 bathrooms
     

    BEAUTIFUL ON THE POND HOME-SANDY BEACH AND CRYSTAL CLEAR WATERS
    • Falmouth
    • House (single)
    • 4 bedrooms, sleeps 8
    • 3.5 bathrooms
       

      Moor's Edge, Unit B, Closest to Herring Cove Beach - Cape Cod
      • Provincetown
      • Upside-down floor plan
      • 3 large, li bedrooms, sleeps 6
      • 2 bathrooms
         

        6000 sq. ft. Home With Fine Art And Furnishings That Sleeps Up To 10
        • Chilmark
        • House (single)
        • 5 bedrooms, sleeps 10
        • 5.5 bathrooms
           

          CHATHAM RETREAT Cottage Near the Beach, Scenic Views, and Tennis Courts
          • Chatham
          • very close to beach
          • 3 bedrooms, sleeps 5-6
          • 1 bathrooms
          • Weekly rates
            From 700 to 1700 USD
           

          Stunning New Vacation Home Located in National Seashore Park
          • Truro
          • House (single)
          • 5 bedrooms, sleeps 12
          • 3.5 bathrooms
             

            Cute Cape Cod Cottage - WEST HARWICH
            • Harwich
            • House (single)
            • 2 bedrooms, sleeps 6
            • 1 bathrooms
               

              Brand Spankin' New and Gorgeous in North Chatham
              • Chatham
              • House (single)
              • 5 bedrooms, sleeps 11
              • 5 bathrooms
              • Weekly rates
                From 3850 to 5850 USD
               

              One of a Kind Year Round Retreat - Plymouth, MA
              • Plymouth
              • Cottage Bungalow
              • 4 bedrooms, sleeps 10
              • 2.5 bathrooms
              • Weekly rates
                From 1440 to 3800 USD
               

              Luxurious Nantucket Vacation Home
              • Nantucket
              • House (single)
              • 7 bedrooms, sleeps 17
              • 9.5 bathrooms
                 

                Private Neighborhood In Prestigious New England Village - Private Beach, Dock, Mooring - Waterview Stage Harbor
                • Chatham
                • House (single)
                • 4 bedrooms, sleeps 7-8
                • 2.5 bathrooms
                • Weekly rates
                  From 2600 to 2900 USD
                 

                Wonderful Vacation Home Overlooking the Elizabeth Islands and Vineyard Sound - Martha's Vineyard
                • Chilmark
                • House (single)
                • 5 bedrooms, sleeps 10
                • 5 bathrooms
                   

                  Schoolhouse Cape - Edgartown, Massachusetts
                  • Edgartown
                  • House (single)
                  • 3 bedrooms
                  • 2 bathrooms
                     

                    Beautiful Vacation Home Located in the Longview area of West Tisbury
                    • West Tisbury
                    • House (single)
                    • 5 bedrooms, sleeps 10
                    • 3 bathrooms
                       

                       
                       
                      Rental Locations   (Listed alphabetically by City or Town)
                       
                       
                        City BR(s) BA(s) Sleeps Description
                      Aquinnah3 BR2 BA6Beautiful Home In A Country Setting.
                      Aquinnah3 BR2 BA7The "Literary House" on a hillside with waterviews over Menemsha Pond and the Atlantic Ocean
                      Aquinnah3 BR2 BA6AQ602-Aquinnah 3 Bedroom Home w/waterviews overlooking Vineyard Sound and the Elizabeth Islands
                      Aquinnah3 BR2 BA6AQ603- Contemporary On The Cliffs Waterview with Private Beach
                      Aquinnah4 BR BAMartha's Vineyard's Aquinnah / Gay Head House
                      Aquinnah4 BR3 BA8Spectacular water views over Vineyard!
                      Aquinnah4 BR2 BA8Aq604- Southern views of the Atlantic Ocean from this bright and breezy home in Aquinnah.
                      Aquinnah6 BR3.5 BA9-11Aq601- Aquinah Waterview Vacation Home!
                      Barnstable2 BR1 BACAPE COD RENTAL - BEACH HOUSE, 2nd floor loft
                      Barnstable5 BR3 BA10Inviting Family Home Located in Barnstable Village Across from Private Beach
                      Becket3 BR2 BA6-8Colesbrook Manor Berkshire Cottage
                      Boston3 BR3.5 BA6-8Georgia Hill Garden Condominium
                      Boston3 BR2 BA8-10Luxurious Summer 3 Bedroom Vacation Home with Ocean Views
                      Boston4 BR3 BA12Luxurious Ocean View 4 Bedroom Vacation Home
                      Boston4 BR2.5 BA8-10Completely Renovated Holman Apartment Near Harvard Square
                      Bourne4 BR2 BA15Cape Cod Canal Waterfront Home - Sagamore Beach
                      Brewster2 BR2 BA6Cape Cod Ocean Edge Resort Condo
                      Brewster2 BR2 BA6completely renovated
                      Brewster2 BR2 BA6Ocean Edge Resort Condo-Very Nice-Pondview Location
                      Brewster3 BR1.5 BA6-7Cape Cod Summer on Elbow Pond
                      Brewster3 BR1.5 BA8Historic Brewster Summer House
                      Brewster3 BR2 BA8Beautiful Brewster Home - Great Views!
                      Brewster5 BR3 BA10Wonderful Cape Cod family 5 bedroom Air Conditioned Home
                      Buzzards Bay2 BR1 BA4Quiet, friendly neighborhood on Mark's Cove.
                      Centerville1 BR1.5 BA3-4Immaculate Salt Water Cottage - 100 Steps to Craigville Beach
                      Centerville5 plus pull BR2.5 +ext s BA12-14WATERFRONT- Craigville Beach Area.Fabulous 4-5 bedroom home, 2.5 bath on waterfront penninsula. 2 docks, small sandy beach and just 2 blocks to fabulo
                      Centerville5 BR1.5 BA10Summer House in Craigville Village under the Stars
                      Chappaquiddick3+ BR2 BA9Chappy on the Beach - Chappaquiddick
                      Chappaquiddick10 BR BA19Wasque Watch - Chappaquiddick
                      Chatham2 BR2 BA6BEAUTIFUL CHATHAM VACATION BEACH HOUSE!
                      Chatham2 BR1 BA6Breathtaking Views From This Vacation Rental In Chatham
                      Chatham2 BR1 BA4Post and Beam Retreat in Downtown Chatham
                      Chatham2 BR1.5 BA6Oceanfront Condo with Beautiful Views Steps to Beach - Chatham, MA
                      Chatham2 BR2 BA6Marshviews, 3/10 mile from beach - South Chatham
                      Chatham2 BR1 BA4West Chatham Cape Cod Cottage
                      Chatham3 BR2 BA5On The Beach, Sink your toes in the sand!
                      Chatham3 BR1.5 BA63 BR Cottage near Ridgevale Beach with Central Air Condition
                      Chatham3 BR2 BA6Oyster Pond Vacation Home
                      Chatham3+ BR2 BA9Chatham Vacation Home Walk to Ridgevale Beach
                      Chatham3 BR3 BA6Gorgeous Harding's Hills Home with Stunning Waterviews
                      Chatham3 BR3 BA6Scenic Salt Marsh Views on a quiet street near Hardings Beach
                      Chatham3 BR2.5 BA6Close to Downtown Chatham: Beautifully decorated home with serene Marsh Views
                      Chatham3 BR2 BA8Waterfront onTaylor's Pond
                      Walk to Cockle Cove Beach
                      Chatham3 BR2 BA8Charming Cape Style home just a short walk to the ballfield, park and downtown Chatham
                      Chatham3 BR2 BA6Nice cape with great backyard - park-like setting. Walk to town and ballfield, playground
                      Chatham3 BR2 BA6Light and bright post and beam home 1 mile from Hardings Beach
                      Chatham3 BR1 BA5-6CHATHAM RETREAT Cottage Near the Beach, Scenic Views, and Tennis Courts
                      Chatham3 BR2.5 BA6Peaceful Pond View with Central A/C right on the water
                      Chatham3 BR2 BA6Expansive Water Views of Hardings Beach and Nantucket Sound
                      Chatham4 BR3 BA6-8Shore Road Location -- Lovely 4 BR 3 BA Luxury Home
                      Chatham4 BR5 BA8Massachusetts - Chatham Vacation Rental
                      Chatham4 BR2.5 BA8West Chatham 4 Bedroom Cape
                      Chatham4 BR2.5 BA7-8Private Neighborhood In Prestigious New England Village - Private Beach, Dock, Mooring - Waterview Stage Harbor
                      Chatham4 BR3.5 BA8Beautiful Brand New Home in Chatham with Exquisite Decor!!
                      Chatham4 BR3 BA10Spacious newer home close to Cockle Cove Beach with a private back deck
                      Chatham4 bedrooms BR5 full bat BA10+Stunning and Upscale home with views of Nantucket Sound
                      Chatham5 BR5 BA12Wowing waterviews of Stage Harbor- Amazing Cape Cod Ocean View Vacation Home
                      Chatham5 BR4 BA10Stage Harbor / Mill Pond / Crocker Rise - Great Water Views!
                      Chatham5 BR2 BA10Sprawling Shore Road Rental - Chatham
                      Chatham5 BR3.5 BA10Spectacular Waterfront Home on Oyster River - Massachusetts
                      Chatham5 BR3 BA9Nice antique cape; walk to town and lighthouse beach
                      Chatham5 BR5 BA11Brand Spankin' New and Gorgeous in North Chatham
                      Chatham6 BR2 BA12Cape Cod Vacation Home - Stage Harbor Beach - Water Views
                      Chilmark1 BR2 BA2Great for a couple seeking a romantic get-away.
                      Chilmark2 BR1 BA4Ch210- Lovely, two bedroom, private Chilmark cottage. Fabulous location, access to Lucy Vincent and Squibnocket beaches.
                      Chilmark2 BR1 BA4ch213- Up-Island Chilmark Cottage with-in walking distance to Menemsha Village
                      Chilmark3 BR2 BA6A newly built contemporary home that has style and flair.
                      Chilmark3 BR2 BA8CH 201- Kayak To Beach Across Chilmark Pond For Swimming & Picinicking
                      Chilmark3 BR2 BA6CH205- This bright and cheerful, wooded retreat is truly tranquil.
                      chilmark3 BR1 BA5Ch202- Charming waterview Chilmark Vacation home just minutes to Lucy Vincent Beach and Chilmark Store
                      Chilmark4 BR4 BA12Modern Comforts and Unforgettable Views From This Waterfront Vacation Home
                      Chilmark4 BR2.5 BA8
                      Chilmark4 BR2 BA7
                      Chilmark4 BR3 BA8CH204- Menemsha Sunsets - Chilmark Home with Water Views
                      Chilmark4 BR3 BA8CH207- Panoramic Up Island Waterview
                      Chilmark4 BR2 BA8CH208- Secluded Chilmark Vacation Home
                      Chilmark4 BR2 BA10Ch209- Fantastic Chilmark Vacation Rental. Enjoy this outrageous view of the south shore
                      Chilmark5 BR5 BA10Wonderful Vacation Home Overlooking the Elizabeth Islands and Vineyard Sound - Martha's Vineyard
                      Chilmark5 BR5.5 BA106000 sq. ft. Home With Fine Art And Furnishings That Sleeps Up To 10
                      Chilmark5 BR2 BA9CH 203- Menemsha Bright & Spacious Contemporary Four Bedroom Home With Waterview
                      Chilmark5 BR3 BA9CH206- The Best Chilmark has to Offer - Breathtaking Views!
                      Chilmark6 BR3 full BA12ch212- Boat across Chilmark Pond to beach from this wonderful Chilmark vacation home.
                      Chilmark10 BR6 full BA18ch211- Spring Point Waterfront House and Guest House with Fabulous views of the North Shore
                      Dennis2 BR1.5 BA6Seawinds Condo with Ocean Views
                      Dennis3 BR2 BA8A few feet along the sandy path brings you to beautiful private beach overlooking Nantucket Sound.
                      Dennis3 BR2.5 BA11Breathtaking Ocean Views - West Dennis
                      Dennis4 BR2 BA12Beautiful Ranch Style Home with the Cape's Best Beaches
                      Dennis4 BR2 BA8-9Cape Cod Vacation Home - Walk to a small beach
                      Dennisport1-2 BR1 BA4 - 6'By The Sea' Guests Suites
                      Dennisport5 BR2 BA12Spacious Cape Home-location, location, location!
                      Eastham BR BAInformation Coming soon!!!
                      Eastham2 BR1 BA1-4Adorable Immaculate Cottage - Private 1/2 Acre on Dirt Road
                      Eastham4 BR2 BA8Newly Renovated Cape ***Reduced Rates August***
                      Eastham5 BR3 BA10Classic Cape Colonial near National Seashore Beaches
                      Eastham6 BR4 BA2-12Great private spot for Family Fun in North Eastham
                      Edgartown1 BR1 BA2ED304- COZY COTTAGE NESTLED ON EDGARTOWN GREAT POND
                      Edgartown2 BR1 BA7BIKE TO EDGARTOWN AND SOUTH BEACH
                      Edgartown2 BR1 BA4ed307- THIS EDGARTOWN VACATION HOME IS A TWO BEDROOM BUNGALOW WITH SHARED POOL AND TENNIS.WALK TO TOWN, BIKE TO SOUTH BEACH.
                      Edgartown3 BR2 BA6In A Neighborhood Of Quietude And Charm
                      Edgartown3 BR1.5 BA6Comfortable Vacation Rental Home On Martha's Vineyard
                       
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                      Select additonal pages to continue viewing the listings alphabetically by city/town
                       
                         Featured Property Managers  

                      www.OvertoomMV.com
                      By visiting our site, you have found your connection to all Martha's Vineyard real estate for sale as well as an extensive array of Martha's Vineyard rentals. Our outstanding team of exerienced sales and rental agents are uniquely qualified to help you meet your individual investment objectives and/or vacation dreams.

                      www.ChathamVillageRealty.com
                      Welcome to ChathamVillageRealty.com, your internet resource for property sales and summer vacation rentals in beautiful Chatham, Massachusetts and its surrounding communities.

                      ADMS Vacation Rentals by Design

                      Pine Acres Realty
                      Welcome to Pine Acres Realty
                      Chatham Real Estate & Vacation Rentals

                      MassCities.com
                      Need Massachusetts travel information? Well welcome to MassCities.com where you will find a complete list of local city guides full of Massachusetts travel information, local events and featured businesses.

                      www.CongdonandColeman.com
                      Nantucket Summer Rentals
                      Congdon & Coleman has been in the business providing Nantucket summer rentals to island visitors since 1931. We list the largest selection of homes, ranging from a simple beach cottage to an elaborate antique home in town. One of the best things about our site is that the availability showing with each property is "live," saving you time when booking.

                      Uppvall Associates Inc.
                      Specializing in the West Dennis and Dennisport area, we provide the friendly, efficient service that helps ensure an enjoyable vacation. Our large selection of one to four bedroom privately owned vacation homes, near warm beaches provides a wealth of options from which to choose.


                      Rooney & Company of Martha's Vineyard Inc.
                      We are a professional real estate office, featuring sales and vacation rentals. We invite you to explore Martha's Vineyard… an island that offers a little something for everyone.


                         Premium Listings  

                      WONDERFUL FIVE BEDROOM HOME IN PRIVATE AREA, ASSOCIATION BEACH,TENNIS


                      West Tisbury, House (single), 5 bedrooms, sleeps 10, 4 bathrooms.



                      BEAUTIFUL ON THE POND HOME-SANDY BEACH AND CRYSTAL CLEAR WATERS

                      Falmouth, House (single), 4 bedrooms, sleeps 8, 3.5 bathrooms.



                      Moor's Edge, Unit B, Closest to Herring Cove Beach - Cape Cod
                      Provincetown, Upside-down floor plan, 3 large, li bedrooms, sleeps 6, 2 bathrooms.



                      6,000 sq. ft. Home With Fine Art And Furnishings That Sleeps Up To 10
                      Chilmark, House (single), 5 bedrooms, sleeps 10, 5.5 bathrooms.



                      CHATHAM RETREAT Cottage Near the Beach, Scenic Views, and Tennis Courts
                      Chatham, very close to beach, 3 bedrooms, sleeps 5-6, 1 bathrooms. Weekly rates from 700 to 1700 USD



                      Stunning New Vacation Home Located in National Seashore Park
                      Truro, House (single), 5 bedrooms, sleeps 12, 3.5 bathrooms.



                      Cute Cape Cod Cottage - WEST HARWICH

                      Harwich, House (single), 2 bedrooms, sleeps 6, 1 bathrooms.



                      Brand Spankin' New and Gorgeous in North Chatham
                      Chatham, House (single), 5 bedrooms, sleeps 11, 5 bathrooms. Weekly rates from 3850 to 5850 USD



                      One of a Kind Year Round Retreat - Plymouth, MA
                      Plymouth, Cottage Bungalow, 4 bedrooms, sleeps 10, 2.5 bathrooms. Weekly rates from 1440 to 3800 USD



                      Luxurious Nantucket Vacation Home
                      Nantucket, House (single), 7 bedrooms, sleeps 17, 9.5 bathrooms.



                      Private Neighborhood In Prestigious New England Village - Private Beach, Dock, Mooring - Waterview Stage Harbor
                      Chatham, House (single), 4 bedrooms, sleeps 7-8, 2.5 bathrooms. Weekly rates from 2600 to 2900 USD



                      Wonderful Vacation Home Overlooking the Elizabeth Islands and Vineyard Sound - Martha's Vineyard
                      Chilmark, House (single), 5 bedrooms, sleeps 10, 5 bathrooms.



                      Schoolhouse Cape - Edgartown, Massachusetts
                      Edgartown, House (single), 3 bedrooms, 2 bathrooms.



                      Located in the Longview area of West Tisbury
                      West Tisbury, House (single), 5 bedrooms, sleeps 10, 3 bathrooms.


                        
                       

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