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.

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  1. HOUSE
    Beachfront 5BR w/ Cape Cod Bay View, Near Downtown

    Beachfront 5BR w/ Cape Cod Bay View, Near Downtown

    Provincetown, MA

    Plan a beachfront getaway for twelve guests at this 5BR/3BA home, where generous picture windows afford water views from almost every room. Spend leisurely vacation days on the two-story patio overlooking Cape Cod Bay. With lounge seating, a gas...

    Pool Pets OK
    FREE CANCELLATION

    $1,168 to $2,145/night

  2. CONDOMINIUM
    Bentley Brook 1 Bedroom

    Bentley Brook 1 Bedroom

    Hancock, MA

    Bentley Brook Surround yourself with the natural beauty of Massachusetts at Bentley Brook. Situated at the bottom of Jiminy Peak in the stunning Berkshires, Bentley Brook is the ski enthusiast dream come true. Ski out your door and straight to the...

    Pool Hot Tub

    $159/night

  3. HOUSE
    Colbyco Sand Hills Beach- Scituate

    Colbyco Sand Hills Beach- Scituate

    Scituate, MA

    Gorgeous new home on the ocean near Boston and Cape Cod. The Lions’ Den is a 4800 square foot gorgeous new home located in Scituate, MA – close to both Boston and Cape Cod. It features incredible views of the ocean with 6 decks and a widow's...

    Hot Tub

    $1,740 to $1,972/night

  4. HOUSE
    Colbyco Dana Park- Cambridge

    Colbyco Dana Park- Cambridge

    Cambridge, MA

    Three story residential Townhouse. The structure was built in 1977, and the home is made up of approximately 1,360 square feet of livable space, and sits on about 1,632 square foot lot.While close to the MBTA Redline train station (Central Square),...

    $406/night

  5. HOUSE
    Woodsy Haven- Near Sandy Neck & Boardwalk Beach

    Woodsy Haven- Near Sandy Neck & Boardwalk Beach

    East Sandwich, MA

    Just 3 miles from Sandy Neck and 6 miles to stunning Boardwalk Beach, this lovely 4BR/2.5BA home is tucked away on a private, wooded lot. From the open-concept main floor to the spacious deck and master balcony, there's plenty of space indoor and...

    Pets OK
    FREE CANCELLATION

    $262 to $537/night

  6. HOUSE
    Remodeled 4BR on River w/ Kayaks

    Remodeled 4BR on River w/ Kayaks

    Falmouth, MA

    Perched on a hill overlooking the tidal Moonakis River, Osprey Point is a 4BR/2.5BA remodeled builder’s home offering a peaceful retreat for eight. With three living areas and a sprawling backyard, there’s plenty of room to gather and have fun....

    FREE CANCELLATION

    $418 to $765/night

  7. CONDOMINIUM
    Mayhew at Upham's Corner

    Mayhew at Upham's Corner

    Boston, MA

    The Mayhew is a third floor, fully furnished 1200sf luxury apartment centrally located in Boston near the historic South End. Part of a meticulous building restoration, the Mayhew combines characteristic turn-of-the-century Boston area architecture...

    Pets OK

    $95 to $370/night

  8. CONDOMINIUM
    Roseclair at Upham's Corner

    Roseclair at Upham's Corner

    Boston, MA

    AMENITIES Fully furnished luxury apartment centrally located in Boston near the historic South End 3 Bedrooms/1 Bathroom Bedrooms have queen beds Full Kitchen Free Wifi Designer furnishings create an elegant coziness throughout The Roseclair is a...

    Pets OK

    $93 to $383/night

  9. CONDOMINIUM
    Penthouse at Upham's Corner

    Penthouse at Upham's Corner

    Boston, MA

    The Penthouse is a fourth floor, fully furnished 1200sf luxury apartment centrally located in Boston near the historic South End. Part of a meticulous building restoration, the Penthouse combines characteristic turn-of-the-century Boston area...

    Pets OK

    $95 to $390/night

  10. HOUSE
    C390 Hall (2-Bedroom Home)

    C390 Hall (2-Bedroom Home)

    Charlestown, RI

    Start making those summer vacation memories in this very sweet cottage. This charmer was tastefully redone to include hardwood floors, stainless steel appliances and large outside shower. Home offers a private backyard for enjoying grilling and al...

    $110 to $214/night

  11. HOUSE
    Water Views on Monomoscoy Island

    Water Views on Monomoscoy Island

    Mashpee, MA

    Our 3-bedroom, 2-bath Cape Cod on Monomoscoy Island, with ample back deck, enjoy water views and use of a small private beach, perfect for families. You’re just steps from the great swimming, clamming, and fishing that make for the quintessential...

    FREE CANCELLATION

    $161 to $473/night

  12. HOUSE
    Delightful West Harwich House

    Delightful West Harwich House

    West Harwich, MA

    This charming 3BR/2BA West Harwich House is less than a mile from Pleasant Road Beach and its gentle waves and wide, sandy shoreline. Recently remodeled with cathedral ceilings, an open-concept design, and big bright windows -- this rental also...

    FREE CANCELLATION

    $264 to $366/night

  13. HOUSE
    Cape Cod Cottage on the Bay

    Cape Cod Cottage on the Bay

    East Falmouth, MA

    Feel the ocean breeze from this 3BR/1.5BA rustic beach home. Spacious and roomy, you and your guests can stretch out in the sun-dappled living room, the screened-in porch and even in the updated, oversized kitchen. Waquoit Bay's mild waters and...

    FREE CANCELLATION

    $135 to $324/night

  14. CONDOMINIUM
    Coastline Cheer in Provincetown

    Coastline Cheer in Provincetown

    Provincetown, MA

    Teeming with coastal cheer, this bright 3BR/2.5BA condo is the quintessential Cape Cod vacation rental. Sweeping ocean vistas, seashore hues, and a location in the heart of the historic west end allow you to truly experience the charm and beauty of...

    FREE CANCELLATION

    $227 to $668/night

  15. HOUSE
    Cape Cod Bay 4BR, Walk to Campground Beach!

    Cape Cod Bay 4BR, Walk to Campground Beach!

    Eastham, MA

    With 2,785 square feet of living space, this two-story Eastham home offers abundant social space with two living areas and a large deck. A huge, open kitchen makes it easy to prep meals for your entire group. In a prime location, you’ll be within...

    FREE CANCELLATION

    $211 to $570/night

  16. HOUSE
    Oceanview Buzzards Bay Getaway

    Oceanview Buzzards Bay Getaway

    Bourne, MA

    This family-friendly 3BR/2.5BA beach house offers beautiful views of the ocean from the wraparound deck. Enjoy a relaxing stay in a peaceful and secluded neighborhood while still being steps away from beautiful beaches situated on either side of the...

    FREE CANCELLATION

    $156 to $491/night

  17. HOUSE
    Newly Renovated Home in New Seabury

    Newly Renovated Home in New Seabury

    Mashpee, MA

    This newly renovated 3BR/3BA New Seabury home offers classic New England charm with its beachy decor and cathedral ceilings. The ideal place from which to adventure into the outdoors, it’s just a stroll away from Jim Pond and 5 minutes from South...

    FREE CANCELLATION

    $193 to $542/night

  18. HOUSE
    3BR “Perfect Moments” on Swan Pond

    3BR “Perfect Moments” on Swan Pond

    Dennis Port, MA

    Situated on Swan Pond, this newly remodeled home enjoys the privacy of a wooded lot and includes a large deck and an outdoor shower. Launch your own kayak from the backyard during high tide, and enjoy some of the best paddling on the Cape. When...

    FREE CANCELLATION

    $211 to $376/night

  19. HOUSE
    Falmouth Family Getaway

    Falmouth Family Getaway

    Falmouth, MA

    INSIDE THE HOUSE Park up to 4 cars in the roomy driveway, then make your way up the stone walk to the front entrance. Step onto beautifully tiled floors and into the kitchen and sitting area. The sitting area has a sofa and 2 wicker armchairs, a...

    FREE CANCELLATION

    $219 to $597/night

  20. HOUSE
    3BR Near Bike Trail & Beach

    3BR Near Bike Trail & Beach

    Orleans, MA

    This 3BR/2BA Orleans home is within walking distance to virtually everything, including downtown Orleans, local restaurants, cafes, shops, parks, and art galleries. There’s also a convenient public transport service nearby. Feel like a day on...

    FREE CANCELLATION

    $158 to $360/night

  21. HOUSE
    Designer Beach Home; Steps to Ocean

    Designer Beach Home; Steps to Ocean

    Hyannis, MA

    This stunning Cape Cod colonial with beach access and ocean views can be all yours! Located in the Waterfront District, it’s less than a mile to downtown Hyannis for dining, shopping, and sightseeing. ABOUT THE HOUSE Situated in a quiet...

    FREE CANCELLATION

    $373 to $513/night

  22. HOUSE
    Historic Home on Bourne Pond

    Historic Home on Bourne Pond

    East Falmouth, MA

    Set on a scenic 4-acre plot, this historic (newly renovated) 5BR + bonus room, 2BA East Falmouth home is nestled on Bourne Pond. Kayak out on the water, relax between private decks and indoor sitting areas, and drive 5-10 min to dining/beaches....

    FREE CANCELLATION

    $239 to $577/night

  23. DUPLEX
    Beach-Central Cape Cod Duplex

    Beach-Central Cape Cod Duplex

    Dennis Port, MA

    A short walk from Dennisport’s Sea Street Beach, this 4BR, 2BA duplex (sleeps 10) is perfect for extended families or large groups. Have your own space, then gather together on the deck. Walk or drive to ice cream, dining, and more! Have a...

    Pets OK
    FREE CANCELLATION

    $156 to $394/night

  24. HOUSE
    Scenic Bourns Pond 4BR w/ Waterfront Deck

    Scenic Bourns Pond 4BR w/ Waterfront Deck

    East Falmouth, MA

    This classic Cape-style 4BR/2BA is perched on the shore of the saltwater Bourns Pond, offering 180-degree water views from your own backyard. With west-facing windows, you can end every evening with a view of the sunset over the water. On lazy...

    FREE CANCELLATION

    $473 to $707/night

  25. HOUSE
    3BR w/ Yard & Deck- Close to Schoolhouse Pond & Bike Path

    3BR w/ Yard & Deck- Close to Schoolhouse Pond & ...

    Chatham, MA

    PROPERTY OVERVIEW Nestled in a quaint Cape Cod enclave, this 3BR/2BA home is less than one mile to pristine Goose Pond, a local favorite for swimming, canoeing, and kayaking. Enjoy bike paths, hiking trails, and Volunteer Park - all within walking...

    FREE CANCELLATION

    $167 to $450/night

  26. HOUSE
    Family-Friendly 3BR, Steps to Long Pond

    Family-Friendly 3BR, Steps to Long Pond

    Harwich, MA

    Your 3BR/2BA is just a block away from Long Pond—swim, float, splash, paddle, and sail on Cape Cod’s largest lake, named one of the best swimming spots by Boston Magazine. Hop on your bikes and ride the 25-mile Rail Trail that runs from Dennis...

    FREE CANCELLATION

    $307 to $461/night

  27. HOUSE
    Bright 3BR w/ Sunroom & Deck – Minutes to Beaches

    Bright 3BR w/ Sunroom & Deck – Minutes to Beaches

    Chatham, MA

    Six beaches are within a 10-minute drive of this recently renovated 3BR/2.5BA Chatham home, tucked in a quiet neighborhood ideal for morning walks and bike rides. The light-filled interior includes a peaceful master suite and a sunroom, and the...

    FREE CANCELLATION

    $189 to $459/night

  28. HOUSE
    3BR w/ Kayaks on Santuit Pond

    3BR w/ Kayaks on Santuit Pond

    Mashpee, MA

    Nestled right on Santuit Pond, this charming 3BR/3BA home is the perfect Cape Cod getaway for a family or group of friends. Stairs lead down to a private floating dock where you can launch the provided kayaks. Rent jet skis or sailboats for even...

    FREE CANCELLATION

    $177 to $438/night

  29. CONDOMINIUM
    Newly Remodeled 2BR at Cape Cod Bay

    Newly Remodeled 2BR at Cape Cod Bay

    Provincetown, MA

    Live in luxury at this 2BR/2BA Provincetown condo with beautifully remodeled interiors, all-new furnishings, and comfortable accommodations for four guests. Enjoy coastal breezes on your own private patio. The apartment is peacefully tucked away in...

    FREE CANCELLATION

    $253 to $504/night

  30. HOUSE
    3BR Near Main Street & Beach

    3BR Near Main Street & Beach

    Harwich Port, MA

    Enjoy a peaceful Cape Cod country setting at this newly remodeled 3BR/2BA home, featuring hardwood floors and vibrant interior design elements. Entertain on the private deck in the fenced yard, equipped with a fire pit and a grill as well as an...

    FREE CANCELLATION

    $132 to $403/night