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
    W531 Manente

    W531 Manente

    Charlestown, RI

    Large, well-appointed home within walking distance to the beach plus beach parking pass at Charlestown Town beach. Home has 4 bedrooms, one on the first floor, with master suite. It is located on a quiet road with pond views from second and third...

    $350 to $526/night

  2. 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

  3. 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

  4. HOUSE
    C291 Reeb (1-Bedroom Home)

    C291 Reeb (1-Bedroom Home)

    Charlestown, RI

    Ocean views are captured by the sun-filled windows; waves lull you to sleep, miles of fabulous wide sandy beach steps from the front door. Bright, light and all refurbished in 09-new kitchen. Seafood dining "al fresco" around the corner... fishing,...

    $507 to $605/night

  5. HOUSE
    C047 Sol (2-Bedroom Home)

    C047 Sol (2-Bedroom Home)

    Charlestown, RI

    Charlestown Beach. Sit on the deck and enjoy the beautiful views of the ocean and Block Island. There are no houses in front of you to block the views. There is a private walkway across the sand dune that takes you to the beach where you can jump...

    $367 to $489/night

  6. 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 $553/night

  7. HOUSE
    75 Lake Home at Cotuit

    75 Lake Home at Cotuit

    Cotuit, MA

    A quintessential Cape Cod getaway awaits your crew of six at this newly remodeled 3BR/2BA Cotuit home. A cool color palette and coastal details set the scene for a memorable stay. Settle into the sectional sofa on the deck with your new vacation...

    FREE CANCELLATION

    $237 to $676/night

  8. HOUSE
    41 Quivet Home at Dennis

    41 Quivet Home at Dennis

    Dennis, MA

    Classic New England charm awaits at this 4BR/2BA Dennis rental, with cedar shingles and a quaint nautical vibe. Spacious interiors and an expansive backyard offer lots of room for nine people to spread out. Throw a frisbee on the lush green lawn,...

    FREE CANCELLATION

    $405 to $603/night

  9. HOUSE
    12 Bayberry Lane Home

    12 Bayberry Lane Home

    Eastham, MA

    Memorable beach trips begin at this elegant 2BR/3BA Eastham house. With a private master bedroom and separate family suite, there’s plenty of room to spread out. Watch the sun set over Cape Cod Bay from the upper deck, or follow the walking path...

    FREE CANCELLATION

    $869 to $1,149/night

  10. HOUSE
    158 Long Beach Road Home

    158 Long Beach Road Home

    Centerville, MA

    Property Overview  Overlooking the Centerville River, this brand-new 3BR/1.5BA home affords an amazing location for your next Cape Cod getaway. Situated right on the water, an expansive deck provides a fantastic spot to relax, grill up dinner, and...

    FREE CANCELLATION

    $282 to $836/night

  11. 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 $610/night

  12. 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 $467/night

  13. 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 $732/night

  14. HOUSE
    C129 Albert (3-Bedroom Home)

    C129 Albert (3-Bedroom Home)

    Charlestown, RI

    A Vacation spot where memories are made! Come and enjoy family time at this spacious 1700 SQFT home by the beach. The house is newly remodeled; features hardwood flooring, newly carpeted bedrooms, and renovated baths, new kitchen that has granite...

    $306 to $324/night

  15. HOUSE
    Countryside House 21

    Countryside House 21

    Harwich, MA

    Property Overview  Surrounded by well-tended landscape and lush gardens, this two-story 4BR/2BA home offers the ultimate home base to explore the Cape’s tranquil countryside. Beautiful hardwood floors and coastal-inspired decor are sprinkled...

    Hot Tub
    FREE CANCELLATION

    $191 to $468/night

  16. HOUSE
    C368 Dudek (3-Bedroom Home)

    C368 Dudek (3-Bedroom Home)

    Charlestown, RI

    Beach Pass to Blue Shutters and Charlestown Town Beach. Charming and spacious three bedroom Cape with central air and nice hardwood floors thru out. Large spacious bright living room with wall of atrium doors and windows that welcomes in the gardens...

    $183 to $330/night

  17. APARTMENT
    Brookline Brownstone

    Brookline Brownstone

    Brookline, MA

    This 3 BR 2 BA apartment is fully updated and has in unit laundry. Good for couples, solo adventurers, traveling nurses, doctors, business travelers, families (with kids), and big groups. The apartment is minutes from Longwood Medical Area, home of...

    Pool Hot Tub Pets OK
    FREE CANCELLATION

    $294 to $541/night

  18. APARTMENT
    110 on Parker Hill

    110 on Parker Hill

    Boston, MA

    Mission Hill Apartment, 2 bedroom, 1.5 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 2018 and...

    Pets OK
    FREE CANCELLATION

    $227 to $392/night

  19. APARTMENT
    201 on Washington

    201 on Washington

    Jamaica Plain, Boston, MA

    Wonderfully built brand new 990sq foot 2 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...

    Pets OK
    FREE CANCELLATION

    $193 to $392/night

  20. HOUSE
    97 Pheasant Cove Cir Home

    97 Pheasant Cove Cir Home

    Yarmouth Port, MA

    Take in incredible, ever-changing marsh views from this traditional 4BR home (sleeps 8) in a quiet Yarmouth Port neighborhood. Enjoy the convenience of 2.5 bathrooms in addition to an oversized outdoor shower for rinsing off after the beach. A...

    FREE CANCELLATION

    $319 to $555/night

  21. 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

  22. HOUSE
    Serene Chatham House by Oyster Pond

    Serene Chatham House by Oyster Pond

    Chatham, MA

    The far reaches of Cape Cod are easily discovered from this quaint 3BR, 2BA house hidden in the woods. Just steps from Oyster Pond, our rental sleeps 6 and will delight any kayaker or fisherman. Spend evenings listening to the birds on the porch - a...

    FREE CANCELLATION

    $203 to $462/night

  23. HOUSE
    Coastal/Beach Access Cottage in Centerville

    Coastal/Beach Access Cottage in Centerville

    Barnstable, MA

    Historic grandeur, quaint seaside energy and a friendly community bring visitors from near and far to the shores of Cape Cod. This renovated 3-bedroom, 1-bath cottage embodies the best of this town by the sea, on a lakefront property in a tranquil...

    FREE CANCELLATION

    $231 to $465/night

  24. HOUSE
    Cape Cod Home at Falmouth Harbor

    Cape Cod Home at Falmouth Harbor

    Falmouth, MA

    This charming 3BR/2BA Cape Cod home with room for 6 is just steps away from Falmouth Harbor. With new furnishings, a large deck, and an ideal location just a quarter-mile to the beach and a 15-minute walk to Main Street, all you need for a perfect...

    FREE CANCELLATION

    $251 to $469/night

  25. HOUSE
    Charming 3BR Beach Cottage

    Charming 3BR Beach Cottage

    East Falmouth, MA

    The beach is just steps away from this beautifully remodeled 3-bedroom cottage (just 7 houses from the path to the private association beachfront)! A true Cape Cod home with a high-end kitchen, hardwood floors, a lovely tiled bathroom, and an...

    FREE CANCELLATION

    $126 to $315/night

  26. CONDOMINIUM
    Bentley Brook 2 Bedroom

    Bentley Brook 2 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
  27. HOUSE
    6 Mockingbird Lane House

    6 Mockingbird Lane House

    Harwich, MA

    Look out over Buck's Pond from this 3BR/2BA Cape Cod house with water views from almost every room. Your own private beach is just steps away, where you can fish, swim, sail, or just stroll the sandy shore. This home is located in the idyllic family...

    FREE CANCELLATION

    $214 to $466/night

  28. HOUSE
    62 Crowell Road Home

    62 Crowell Road Home

    East Falmouth, MA

    Set on three scenic acres beside the glittering waters of Bourne’s Pond, this 4 Bedroom / 2 Bathroom home offers a tranquil haven with fabulous sunrises, its own private beach, dock and a sunny screened-in porch. Feel like a day on the water?...

    Pets OK
    FREE CANCELLATION

    $291 to $563/night

  29. HOUSE
    Oceanside Hyannis Beach House

    Oceanside Hyannis Beach House

    Hyannis, MA

    This 4BR, 2BA Hyannis beach house sleeps 9. Relax on the deck with spectacular views of both sunrise and sunset, and watch the island ferries shuttling passengers to Nantucket and Martha’s Vineyard. You are a 3 minute walk from Kalmus Beach and...

    Hot Tub
    FREE CANCELLATION

    $314 to $742/night

  30. CONDOMINIUM
    232 Billington Ln Condo

    232 Billington Ln Condo

    Brewster, MA

    You can have it all at Ocean Edge Resort & Golf Club. Step out from your 2BR/1.5BA condo and onto the beautiful fairway—the course was designed by Jack Nicklaus and makes for an incredible backdrop for an afternoon game or a bike ride. Ocean Edge...

    Pool
    FREE CANCELLATION

    $143 to $332/night