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Massachusetts Vacation Rentals - 176 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, ~$400/night

    City : Plymouth
    Bedrooms : 3
    Bathrooms : 2

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

  3. Sleeps 3, ~$325/night

    City : Boston
    Bedrooms : 2
    Bathroom : 1.5

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

  4. Sleeps 8, $685 to $830/night

    City : Charlestown
    Bedrooms : 3
    Bathroom : 1

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

  5. Sleeps 6, $255 to $500/night

    City : Charlestown
    Bedrooms : 2
    Bathroom : 1

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

  6. Sleeps 6, $105 to $205/night

    City : Charlestown
    Bedrooms : 2
    Bathroom : 1

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

  7. Sleeps 6, $155 to $285/night

    City : Charlestown
    Bedrooms : 2
    Bathrooms : 2

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

  8. Sleeps 6, $135 to $275/night

    City : Charlestown
    Bedrooms : 3
    Bathroom : 1

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

  9. Sleeps 10, $175 to $345/night

    City : Charlestown
    Bedrooms : 5
    Bathrooms : 2

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

  10. Sleeps 8, $300 to $445/night

    City : Charlestown
    Bedrooms : 4
    Bathrooms : 2

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

  11. Sleeps 8, ~$235/night

    City : Charlestown
    Bedrooms : 2
    Bathrooms : 2

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

  12. Sleeps 6, $180 to $300/night

    City : Charlestown
    Bedrooms : 3
    Bathroom : 1

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

  13. Sleeps 12, $210 to $335/night

    City : Charlestown
    Bedrooms : 5
    Bathrooms : 2

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

  14. Sleeps 11, $605 to $665/night

    City : Falmouth
    Bedrooms : 5
    Bathrooms : 4

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

  15. Sleeps 10, ~$795/night

    City : West Falmouth
    Bedrooms : 4
    Bathrooms : 3

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

  16. Sleeps 6, $635 to $715/night

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

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

  17. Sleeps 7, ~$585/night

    City : West Falmouth
    Bedrooms : 4
    Bathrooms : 2

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

  18. Sleeps 6, ~$475/night

    City : Falmouth
    Bedrooms : 3
    Bathrooms : 3

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

  19. Sleeps 8, ~$435/night

    City : Falmouth
    Bedrooms : 4
    Bathrooms : 3

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

  20. Sleeps 12, ~$1105/night

    City : Woods Hole
    Bedrooms : 5
    Bathrooms : 3

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

  21. Sleeps 8, ~$715/night

    City : Falmouth
    Bedrooms : 5
    Bathrooms : 3.5

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

  22. Sleeps 6, $335 to $885/night

    City : Provincetown
    Bedrooms : 3
    Bathrooms : 2.5

    Teeming with coastline cheer, this bright 3-bedroom, 2.5 bath condo...

  23. Sleeps 10, $180 to $735/night

    City : Bourne
    Bedrooms : 3
    Bathrooms : 2.5

    This tranquil 3-bedroom, 2.5-bath beach house offers beautiful views...

  24. Sleeps 8, $250 to $620/night

    City : Mashpee
    Bedrooms : 3
    Bathrooms : 2
    Pets OK

    Our 3-bedroom, 2-bath Cape Cod on Monomoscoy Island, with ample back...

  25. Sleeps 12, $225 to $470/night

    City : Dennis Port
    Bedrooms : 4
    Bathrooms : 2
    Pets OK

    A short walk from Dennisport’s Sea Street Beach, this 4BR, 2BA...

  26. Sleeps 8, $260 to $600/night

    City : Dennis Port
    Bedrooms : 4
    Bathrooms : 2

    Beach, biking, and family—a recipe for a great vacation. This...

  27. Sleeps 8, $205 to $785/night

    City : Falmouth
    Bedrooms : 4
    Bathrooms : 3.5

    INSIDE THE HOUSE Park up to 4 cars in the roomy driveway, then make...

  28. Sleeps 7, $130 to $385/night

    City : Boston
    Bedrooms : 3
    Bathroom : 1
    Pets OK

    Property Description Fully furnished luxury apartment centrally...

  29. Sleeps 5, $135 to $410/night

    City : Boston
    Bedrooms : 2
    Bathroom : 1
    Pets OK

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

  30. Sleeps 9, $165 to $600/night

    City : Boston
    Bedrooms : 4
    Bathrooms : 2
    Pets OK

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