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Massachusetts Vacation Rentals - 95 Properties

When it comes to lobster rolls and New England clam chowder, nobody can touch Massachusetts. Shrouded in history, the Bay state is well known as the birthplace of the American revolution, the Freedom Trail, and the Boston Tea Party. Seafood, history, the Red Sox- Massachusetts has it all. RedAwning will help you find the perfect vacation rental to complete your East Coast experience. Browse your favorite Massachusetts region using the blue location links below, or filter your preferences using the panel on the side. With our simplified booking process, you'll have the most important part of your trip buttoned in no time.

Search results

  1. Sleeps 20, $1135 to $1930/night

    City : Scituate
    Bedrooms : 10
    Bathrooms : 7
    Hot Tub

    Gorgeous new home on the ocean near Boston and Cape Cod. The...

  2. Sleeps 8, ~$397/night

    City : Plymouth
    Bedrooms : 3
    Bathrooms : 2

    Charming lake front property in historic Plymouth Massachusetts. 4...

  3. Sleeps 3, ~$323/night

    City : Boston
    Bedrooms : 2
    Bathroom : 1.5

    The Bay State is an incredible hotel-style corporate condo in a...

  4. Sleeps 6, $130 to $273/night

    City : Charlestown
    Bedrooms : 3
    Bathroom : 1

    A delightful quintessential New England cottage. Views to Green Hill...

  5. Sleeps 9, $344 to $581/night

    City : Charlestown
    Bedrooms : 2
    Bathrooms : 2

    Enjoy your family vacation at this Green Hill Pond waterfront home....

  6. Sleeps 12, $207 to $332/night

    City : Charlestown
    Bedrooms : 5
    Bathrooms : 2

    Walk, bike or drive ¾ miles to Charlestown Beach from this 1800 sq...

  7. Sleeps 6, ~$770/night

    City : Charlestown
    Bedrooms : 2
    Bathroom : 1.5

    Oceanfront in Charlestown- walk directly out into the warm sand and...

  8. Sleeps 11, ~$663/night

    City : Falmouth
    Bedrooms : 5
    Bathrooms : 4

    Spectacular water views from this unique home, which sits directly...

  9. Sleeps 10, ~$790/night

    City : West Falmouth
    Bedrooms : 4
    Bathrooms : 3

    West Falmouth waterfront with dock! Spectacular views of West...

  10. Sleeps 6, ~$600/night

    City : Woods Hole
    Bedrooms : 3
    Bathrooms : 2
    Pets OK

    Located on a private peninsula overlooking Oyster Pond, this lovely...

  11. Sleeps 7, ~$585/night

    City : West Falmouth
    Bedrooms : 4
    Bathrooms : 2

    *West Falmouth Waterfront* Walk to Black Beach and Easy Access to...

  12. Sleeps 6, ~$474/night

    City : Falmouth
    Bedrooms : 3
    Bathrooms : 3

    Walk to Woods Hole Village & Stony Beach from this unique property....

  13. Sleeps 8, ~$434/night

    City : Falmouth
    Bedrooms : 4
    Bathrooms : 3

    *A Half Mile Walk to Surf Drive Beach* This home sits on a private...

  14. Sleeps 12, ~$1105/night

    City : Woods Hole
    Bedrooms : 5
    Bathrooms : 3

    Amazing Woods Hole waterfront home, with panoramic views of Buzzards...

  15. Sleeps 8, ~$711/night

    City : Falmouth
    Bedrooms : 5
    Bathrooms : 3.5

    Woods Hole- Stunning water views of Buzzards Bay! Tucked into a...

  16. Sleeps 8, $123 to $132/night

    City : Hancock
    Bedroom : 1
    Bathrooms : 2
    Pool Hot Tub

    Bentley Brook Ski-in and Ski-out your front door! Bentley Brook is...

  17. Sleeps 10, $277 to $378/night

    City : Plainfield
    Bedrooms : 3
    Bathrooms : 2
    Pets OK

    Both bathrooms are newly repainted. New carpeting. Wireless...

  18. Sleeps 6, $102 to $204/night

    City : Charlestown
    Bedrooms : 2
    Bathroom : 1

    Start making those summer vacation memories in this very sweet...

  19. Sleeps 6, $255 to $409/night

    City : Charlestown
    Bedrooms : 2
    Bathroom : 1

    Bright and cheerful well maintained beach cottage with partial ocean...

  20. Sleeps 8, $681 to $830/night

    City : Charlestown
    Bedrooms : 3
    Bathroom : 1

    Feel the ocean breezes and hear the waves from this wonderful three...

  21. Sleeps 8, $296 to $444/night

    City : Charlestown
    Bedrooms : 4
    Bathrooms : 2

    Enjoy great views of Green Hill Pond from this lovingly appointed...

  22. Sleeps 10, $172 to $344/night

    City : Charlestown
    Bedrooms : 5
    Bathrooms : 2

    Located just 1/2 mile from beautiful Charlestown Town Beach. This...

  23. Sleeps 8, ~$231/night

    City : Charlestown
    Bedrooms : 2
    Bathrooms : 2

    Great location to have a relaxing summer vacation where memories are...

  24. Sleeps 6, $178 to $296/night

    City : Charlestown
    Bedrooms : 3
    Bathroom : 1

    Walk to ocean beach from this ranch cottage located in charming Sea...

  25. Sleeps 6, $154 to $284/night

    City : Charlestown
    Bedrooms : 2
    Bathrooms : 2

    Close to the beach- less than a mile- with an association beach...

  26. Sleeps 5, $133 to $469/night

    City : Boston
    Bedrooms : 2
    Bathroom : 1
    Pets OK

    The Mayhew is a third floor, fully furnished 1200sf luxury apartment...

  27. Sleeps 9, $166 to $692/night

    City : Boston
    Bedrooms : 4
    Bathrooms : 2
    Pets OK

    Property Description 4 Queen Beds, 1 Single Bed 2 Bathrooms Fully...

  28. Sleeps 5, $140 to $494/night

    City : Boston
    Bedrooms : 2
    Bathroom : 1

    The Penthouse is a fourth floor, fully furnished 1200sf luxury...

  29. Sleeps 4, $105 to $466/night

    City : Jamaica Plain, Boston
    Bedroom : 1
    Bathroom : 1
    Pets OK

    All New for 2017! Wonderfully built brand new 820sq foot 1 bedroom/1...

  30. Sleeps 4, $99 to $441/night

    City : Jamaica Plain, Boston
    Bedroom : 1
    Bathroom : 1
    Pets OK

    The 206 at 3389 Washington St. is a recent addition to the Jamaica...