Massachusetts Vacation Rentals - 157 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 6, ~$365/night

    City : Marion
    Bedrooms : 4
    Bathrooms : 2.5

    Bright & sunny 4 bedroom, 2- 1/2 bath home with large well cared for...

  2. Sleeps 8, $135 to $215/night

    City : Charlestown
    Bedrooms : 3
    Bathrooms : 2

    We welcome you to enjoy our family cottage nestled in the woods and...

  3. Sleeps 8, ~$795/night

    City : Scituate
    Bedrooms : 4
    Bathrooms : 2.5

    Spectacular Colonial where you wake up to the sound of the waves and...

  4. Sleeps 12, $210 to $410/night

    City : Charlestown
    Bedrooms : 5
    Bathrooms : 2
    Pets OK

    This 5 bedroom, 2 bath home in the Charlestown Beach area will serve...

  5. Sleeps 8, $175 to $315/night

    City : Charlestown
    Bedrooms : 3
    Bathrooms : 2

    Begin making those vacation memories in this seaside cottage. Nicely...

  6. Sleeps 10, $240 to $430/night

    City : Charlestown
    Bedrooms : 5
    Bathrooms : 2

    This 5 bedroom, 2 bath gem has room for the whole family to vacation...

  7. Sleeps 6, $300 to $315/night

    City : Charlestown
    Bedrooms : 3
    Bathroom : 1.5

    A vacation spot where memories are made! Come and enjoy family time...

  8. Sleeps 10, ~$430/night

    City : Charlestown
    Bedrooms : 4
    Bathrooms : 2

    This spacious Colonial, located on a quiet dead end street, offers...

  9. Sleeps 8, $170 to $330/night

    City : Charlestown
    Bedrooms : 3
    Bathroom : 1.5

    Beach Pass to Blue Shutters and Charlestown Town Beach. Charming and...

  10. Sleeps 6, $470 to $570/night

    City : Charlestown
    Bedroom : 1
    Bathroom : 1.5

    Ocean views are captured by the sun-filled windows; waves lull you...

  11. Sleeps 8, $310 to $475/night

    City : Charlestown
    Bedrooms : 2
    Bathroom : 1.5

    Charlestown Beach. Sit on the deck and enjoy the beautiful views of...

  12. Sleeps 8, $120 to $590/night

    City : East Orleans
    Bedrooms : 4
    Bathrooms : 2.5

    Stepping into this 4-bedroom, 2.5-bath vacation rental in East...

  13. Sleeps 6, $570 to $785/night

    City : Charlestown
    Bedrooms : 3
    Bathroom : 1.5

    Ocean front on Charlestown Beach. Make a lifetime of memories at...

  14. Sleeps 12, $310 to $415/night

    City : Charlestown
    Bedrooms : 4
    Bathrooms : 2

    This two story cottage offers tons of sleeping and generous sized...

  15. Sleeps 8, $580 to $920/night

    City : Dennis
    Bedrooms : 3
    Bathrooms : 2
    Pool

    Central Cape Home with great Salt Water Pool! Inside this Colonial...

  16. Sleeps 6, $520 to $710/night

    City : North Truro
    Bedrooms : 3
    Bathrooms : 2
    Pets OK

    Picturesque water views await at this 3BR/2BA Beach Point home just...

  17. Sleeps 6, $255 to $535/night

    City : Charlestown
    Bedrooms : 3
    Bathrooms : 2.5
    Pets OK

    Beach: Central Cape located in the exclusive private beach community...

  18. Sleeps 10, $790 to $1155/night

    City : West Dennis
    Bedrooms : 4
    Bathrooms : 3
    Pool

    Property Overview Set on spectacular Grand Cove in Bass River with...

  19. Sleeps 9, $240 to $515/night

    City : Harwich Port
    Bedrooms : 3
    Bathroom : 1.5

    This classic 3BR/1.5BA cottage in Harwich, Massachusetts is tucked...

  20. Sleeps 6, $245 to $575/night

    City : Barnstable
    Bedrooms : 3
    Bathroom : 1

    Historic grandeur, quaint seaside energy and a friendly community...

  21. Sleeps 4, $275 to $685/night

    City : Provincetown
    Bedrooms : 2
    Bathrooms : 2
    Hot Tub Pets OK

    Enjoy show stopping views of the harbor and bay from the deck at...

  22. Sleeps 4, $395 to $575/night

    City : Chatham
    Bedrooms : 2
    Bathroom : 1.5
    Pets OK

    Property Overview Located just steps from family-friendly Ridgevale...

  23. Sleeps 8, $155 to $165/night

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

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

  24. Sleeps 8, $180 to $205/night

    City : Hancock
    Bedrooms : 2
    Bathrooms : 2
    Pool Hot Tub

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

  25. Sleeps 6, $890 to $1205/night

    City : Eastham
    Bedrooms : 2
    Bathrooms : 3

    Memorable beach trips begin at this elegant 2BR/3BA Eastham house....

  26. Sleeps 6, $105 to $690/night

    City : Truro
    Bedrooms : 3
    Bathrooms : 2

    Water surrounds you at our 3BR/2BA classic Cape Cod vacation rental!...

  27. Sleeps 8, $130 to $880/night

    City : Brewster
    Bedrooms : 4
    Bathrooms : 2.5

    Feel right at home in our spacious 4BR, 2.5BA vacation rental, just...

  28. Sleeps 7, $145 to $850/night

    City : Orleans
    Bedrooms : 4
    Bathrooms : 2.5

    This classic 4-bedroom, 2-bath Orleans, MA vacation rental is set so...

  29. Sleeps 6, $95 to $430/night

    City : East Falmouth
    Bedrooms : 3
    Bathroom : 1

    The beach is just steps away from this beautifully remodeled...

  30. Sleeps 6, $245 to $605/night

    City : North Chatham
    Bedrooms : 2
    Bathrooms : 2

    When only the best will do, head straight to this indulgent 2BR/2BA...