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.

Filter by Region:


Filter by Amenities:


Filter by Entertainment:


Close Filters
  1. HOUSE
    W091 Vaccaro

    W091 Vaccaro

    Charlestown, RI

    We welcome you to enjoy our family cottage nestled in the woods and just a 10 minutes from the beach. Our place has a large backyard with plenty of shade and privacy. Take advantage of our deck and patio on our one acre lot. Feel free to gather...

    $134 to $210/night

  2. HOUSE
    63 Harbor Road House

    63 Harbor Road House

    Hyannis, MA

    This spacious 4BR/3BA classic Cape Cod abode is located just a 3-minute walk from a private beach. Enjoy quality time with friends and family in three inviting living spaces, or savor al fresco meals on the patio in the big fenced yard. Spend...

    FREE CANCELLATION

    $274 to $664/night

  3. HOUSE
    50 Sea Pine Road House

    50 Sea Pine Road House

    Wellfleet, MA

    This quaint 4BR/3BA is surrounded by tall trees and lush greenery. The Cape Cod Rail Trail (a 22-mile scenic path from Wellfleet to Dennis) is quite literally in your backyard. Just wander past the vegetable patch and hop on the trail! Enjoy a...

    FREE CANCELLATION

    $271 to $488/night

  4. HOUSE
    Corner Lot Home

    Corner Lot Home

    South Yarmouth, MA

    Situated on a corner lot with views of James Pond from nearly every room, this 4BR/2BA house offers a tranquil retreat. Affording a walkable locale, you’ll love being a pleasant stroll from Long Pond as well as local restaurants and attractions....

    FREE CANCELLATION

    $177 to $401/night

  5. HOUSE
    120 Boreen Home at Eastham

    120 Boreen Home at Eastham

    Eastham, MA

    Situated on a forested property in the highly desirable Dunes Beach Association, your 4BR getaway offers a serene location between the woods and sea. Follow a sandy pathway to enjoy direct access to a glorious semi-private Cape Cod beach. This newly...

    FREE CANCELLATION

    $236 to $568/night

  6. HOUSE
    75 Red Brook Rd Home

    75 Red Brook Rd Home

    East Falmouth, MA

    Enjoy the magnificent water views from inside or out. Beautiful gardens with a waterfall, gunite heated saltwater pool with spa, outdoor shower and pool house w/half bath make this home perfect for outdoor and indoor fun. Launch our 2 kayaks or...

    Pool Hot Tub
    FREE CANCELLATION

    $635 to $1,120/night

  7. HOUSE
    112 Ransom Home at Falmouth

    112 Ransom Home at Falmouth

    Falmouth, MA

    Sitting directly on Oyster Pond with a view of Vineyard Sound, tucked away on a private wooded peninsula, this 1930s summer home radiates charm and comfort with its own dock, two rowboats (with sails), a large canoe, and a kayak. Oyster Pond...

    Pets OK
    FREE CANCELLATION

    $309 to $596/night

  8. HOUSE
    Classic Cape Cod House

    Classic Cape Cod House

    Truro, MA

    Water surrounds you at our 3BR/2BA classic Cape Cod vacation rental! Watch the sun rise and sink over two different bodies of water. At first light, bring your coffee to the home’s back deck and watch the sunrise on Pilgrim Lake, which is also...

    FREE CANCELLATION

    $206 to $472/night

  9. HOUSE
    Colbyco Morton Park- Plymouth

    Colbyco Morton Park- Plymouth

    Plymouth, MA

    Charming lake front property in historic Plymouth Massachusetts. 4 Bedrooms, 2 full bathroom, sleeps 8 Charming four bedroom lake front vacation rental in historic Plymouth Massachusetts. Close to Cape Code and Boston, MA. Plymouth holds a place of...

  10. 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

  11. 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),...

  12. HOUSE
    C347 Wilson (2-Bedroom Home)

    C347 Wilson (2-Bedroom Home)

    Charlestown, RI

    Oceanfront in Charlestown - walk directly out into the warm sand and enjoy swimming, sun bathing, surf fishing, building a sandcastle; or, a stroll on the beautiful beach. For those that want to reserve their energy, there's "people watching" from a...

  13. HOUSE
    C354 Munier (2-Bedroom Home)

    C354 Munier (2-Bedroom Home)

    Charlestown, RI

    Close to the beach - less than a mile - with an association beach parking pass and plenty of room. This house has window air conditioners and internet access. There is an amazing and very private back yard with deck and large, enclosed outdoor...

    $202 to $293/night

  14. HOUSE
    66 Indian Trail Home

    66 Indian Trail Home

    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 $819/night

  15. 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
    FREE CANCELLATION

    $93 to $405/night

  16. APARTMENT
    206 on Washington Apartment

    206 on Washington Apartment

    Jamaica Plain, Boston, MA

    The 206 at 3389 Washington St. is a recent addition to the Jamaica Plain neighborhood where the original Sam Adams Brewery is located. Each unit is brand new and features a washer/dryer, private patio access, full kitchen including dishwasher,...

    Pets OK
    FREE CANCELLATION

    $69 to $226/night

  17. APARTMENT
    3399 Washington Unit 2

    3399 Washington Unit 2

    Jamaica Plain, Boston, MA

    All New for March 2018! 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...

    FREE CANCELLATION

    $112 to $359/night

  18. CONDOMINIUM
    Grand View on Jones Hill

    Grand View on Jones Hill

    Boston, MA

    Property Description4 Queen Beds, 1 Single Bed 2 Bathrooms Fully furnished Free WIFI through a secure, password-protected router. Laundry room on the bedroom level with full washer/dryer Kitchen equipped with refrigerator, dishwasher, stove,...

    Pets OK
    FREE CANCELLATION

    $93 to $407/night

  19. APARTMENT
    404 on Parker Hill Apartment

    404 on Parker Hill Apartment

    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
    FREE CANCELLATION

    $92 to $212/night

  20. APARTMENT
    Roseclair at Upham's Corner

    Roseclair at Upham's Corner

    Boston, MA

    Property Description 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...

    Pets OK
    FREE CANCELLATION

    $93 to $393/night

  21. 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
    FREE CANCELLATION

    $93 to $384/night

  22. APARTMENT
    306 on Washington Apartment

    306 on Washington Apartment

    Jamaica Plain, Boston, MA

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

    Pets OK
    FREE CANCELLATION

    $75 to $226/night

  23. HOUSE
    74 Harbor Road House

    74 Harbor Road House

    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

    $350 to $557/night

  24. 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 larger...

    Pets OK
    FREE CANCELLATION

    $203 to $410/night

  25. 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

    $232 to $473/night

  26. 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

    $360 to $398/night

  27. 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
  28. HOUSE
    87 West Pond Rd Home

    87 West Pond Rd Home

    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

    $227 to $450/night

  29. HOUSE
    5 Redgate Lane Home

    5 Redgate Lane Home

    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

    $209 to $597/night

  30. HOUSE
    17 Finway House in New Seabury

    17 Finway House 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

    $251 to $542/night