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
    3BR on Wakeby Pond w/ Private Dock

    3BR on Wakeby Pond w/ Private Dock

    Mashpee, MA

    PROPERTY OVERVIEW Mashpee Heaven provides rare access to one of Cape Cod's largest freshwater lakes. Enjoy swimming from a private pier and exploring the lake’s three islands, two beaches, and miles of trails. Centrally located, the 3BR/2BA...

    FREE CANCELLATION

    $214 to $414/night

  2. HOUSE
    3BR Coastal Getaway- Walk to Beach

    3BR Coastal Getaway- Walk to Beach

    Dennis Port, MA

    PROPERTY OVERVIEW Within walking distance of the local beaches and downtown Dennis Port, this 3BR/2BA home provides the ultimate coastal getaway. Freshly updated, your inviting retreat includes all-new furniture, new LED TVs with cable, and central...

    FREE CANCELLATION

    $217 to $471/night

  3. HOUSE
    Near Coast & Bay- 3BR w/ Fire Pit

    Near Coast & Bay- 3BR w/ Fire Pit

    Dennis, MA

    PROPERTY OVERVIEW Soak up the sun on nearby beaches, play games in the backyard, and gather around a fire pit in the evening at this welcoming two-level 3BR/2BA home. Crafted with hardwood floors and a gorgeous kitchen, you’ll find lots of...

    FREE CANCELLATION

    $202 to $377/night

  4. 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 $534/night

  5. 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

    $203 to $358/night

  6. 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

  7. HOUSE
    C392 Charlestown on the Beach

    C392 Charlestown on the Beach

    Charlestown, RI

    Feel the ocean breezes and hear the waves from this wonderful three bedroom home on Charlestown Beach. Watch the sun rise and set from the large comfortable deck that has multiple tables with umbrellas and seating all around. A few steps down the...

    $734 to $874/night

  8. 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

  9. HOUSE
    4BR Eastham Gem, Minutes to Beach

    4BR Eastham Gem, Minutes to Beach

    Eastham, MA

    This welcoming 4BR/1.5BA cottage in Eastham offers the ultimate coastal getaway. Supremely located between the tranquil bay-side beaches and invigorating dunes and ocean waves of Nauset Light Beach, this home has it all, including a gourmet kitchen,...

    FREE CANCELLATION

    $268 to $487/night

  10. HOUSE
    Waterfront 3BR w/ Deck & Dock

    Waterfront 3BR w/ Deck & Dock

    Chatham, MA

    Overlooking the saltwater inlet of Bucks Creek Marsh, this stunning 3BR/3BA waterfront home affords the quintessential Cape Cod experience. Vaulted ceilings with exposed beams and intriguing artwork create a sophisticated style, while large windows...

    FREE CANCELLATION

    $536 to $929/night

  11. 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

    $322 to $665/night

  12. 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

  13. 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

  14. 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

    $199 to $459/night

  15. 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

    $243 to $450/night

  16. APARTMENT
    404 on Parker Hill

    404 on Parker Hill

    Boston, MA

    540 Sq Ft. Mission Hill Apartment, 1 bedroom, 1 bathroom, in unit washer dryer, central air/heating on Parker Hill in the Mission Hill Neighborhood. Full kitchen including dishwasher, disposal, coffee maker and pots and pans, Unit is brand new for...

    Pets OK

    $92 to $217/night

  17. APARTMENT
    3399 Washington Unit 2

    3399 Washington Unit 2

    Jamaica Plain, Boston, MA

    Wonderfully built brand new 3 bed / 2 bath apartment in Jamaica Plain with patio! Minutes walk to gorgeous Jamaica Pond and the night life on Centre Street, 5 min walk to Subway! Dedicated parking, central air, gas heat, in unit washer/dryer! Unit...

    $112 to $367/night

  18. 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

    $93 to $380/night

  19. HOUSE
    C371 Garro (3-Bedroom Home)

    C371 Garro (3-Bedroom Home)

    Charlestown, RI

    Walk to ocean beach from this ranch cottage located in charming Sea Lea Colony. Also, for a change of pace, you can sit on the viewing deck located on the roof & enjoy the view along with your summer cocktail and watch the beautiful sunsets. In...

    $183 to $306/night

  20. 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

    $256 to $392/night

  21. 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

  22. 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

    $271 to $542/night

  23. 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

    $305 to $504/night

  24. 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

    $226 to $438/night

  25. 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

    $292 to $577/night

  26. 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 $714/night

  27. HOUSE
    C037 Pape (2-Bedroom Home)

    C037 Pape (2-Bedroom Home)

    Charlestown, RI

    Great location to have a relaxing summer vacation where memories are made. The kitchen is fully equipped. Lounge in Living room or grill on deck. This two bedroom with loft sleeps eight people. One bedroom has a queen bed and the other bedroom has 2...

    $245/night

  28. HOUSE
    Charming 4BR- Walk to 3 Beaches!

    Charming 4BR- Walk to 3 Beaches!

    West Harwich, MA

    PROPERTY OVERVIEW Nestled on a peaceful oceanside road, this single-story 4BR/3BA home features vaulted beam ceilings, a gourmet kitchen, and brick fireplace. Dine al fresco on the private patio or relax in the sunroom with a good book. Enjoy a...

    Pets OK
    FREE CANCELLATION

    $533 to $916/night