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
    Colbyco Oceanside- Scituate

    Colbyco Oceanside- Scituate

    Scituate, MA

    Spectacular Colonial where you wake up to the sound of the waves and unobstructed ocean views! Wake up to the sound of the waves as you take in the unobstructed ocean views! This spectacular newer (2013) colonial features the best in craftsmanship,...

  2. CONDOMINIUM
    Bentley Brook Studio

    Bentley Brook Studio

    Hancock, MA

    The town of Hancock is off the beaten path near the Taconic Mountains, which are part of the Appalachians. Hancock is 14 miles northwest of Pittsfield, MA, and 28 miles east of Albany, NY. Bentley Brook is tucked away in a peaceful rural setting...

    Pool Hot Tub

    $87 to $106/night

  3. 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

    $195 to $227/night

  4. HOUSE
    Spacious Home in Hyannis

    Spacious Home in Hyannis

    Hyannis, MA

    INSIDE THE HOUSE The homey living room features polished hardwood floors throughout. A comfy love seat and couch offer seating for 6, and there’s a 32” TV with cable for your evening entertainment. A bright dining area offering seating for...

    FREE CANCELLATION

    $158 to $587/night

  5. HOUSE
    South Chatham Home 103

    South Chatham Home 103

    South Chatham, MA

    Bring the whole family to Cape Cod! This sprawling 4BR, 4.5BA home sleeps 10 in comfort. Kids will love the basement entertainment and sleep area, and you’ll adore the 3-season room. Walk to Forest Beach, and drive to downtown Chatham in 10...

    FREE CANCELLATION

    $255 to $865/night

  6. 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

    $115 to $545/night

  7. HOUSE
    361 Shore House at North Truro

    361 Shore House at North Truro

    North Truro, MA

    Picturesque water views await at this 3BR/2BA Beach Point home just across the street from Cape Cod Bay. Make the quick walk to the beach or take a short drive to the stunning National Seashore beaches. Provincetown is just 2 miles away, offering...

    Pets OK
    FREE CANCELLATION

    $392 to $690/night

  8. HOUSE
    312 Carriage Lane Home

    312 Carriage Lane Home

    Barnstable, MA

    With a quiet location in an historic Barnstable neighborhood, this 4 Bedroom / 2 Bathroom home offers a wonderful sense of seclusion, though countless local attractions sit right on your doorstep. Walk 1.2 miles to unique shops and restaurants...

    FREE CANCELLATION

    $162 to $571/night

  9. 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

    $111 to $349/night

  10. 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

    $217 to $556/night

  11. HOUSE
    49 Winthrop Drive Home

    49 Winthrop Drive Home

    East Falmouth, MA

    The beach is just steps away from this beautifully remodeled 3-bedroom cottage! We’re 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...

    FREE CANCELLATION

    $113 to $410/night

  12. 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

    $476 to $680/night

  13. 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

    $385 to $705/night

  14. 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

    $195 to $1057/night

  15. HOUSE
    112 Ocean Drive Home

    112 Ocean Drive Home

    West Hyannis Port, MA

    Climb to the roof deck on the third floor of your 3BR/3.5BA classic Cape retreat for a peek at idyllic water views. Decorated in classic Cape Cod style, this newly constructed rental provides the comfort and nostalgia of a traditional beachside...

    FREE CANCELLATION

    $597 to $946/night

  16. HOUSE
    22 Sunrise Lane Home

    22 Sunrise Lane Home

    Harwich, MA

    Completely renovated, this beautiful 4BR/2BA Harwich home features a welcoming open floor plan with high ceilings, hardwood floors, and central AC throughout. Whip up tasty dishes in the gourmet kitchen, relax in one of three living areas, or spend...

    FREE CANCELLATION

    $368 to $682/night

  17. 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

    $829 to $1174/night

  18. 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

    $166 to $780/night

  19. 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

    $601 to $1140/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

    $303 to $583/night

  21. 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

    $119 to $557/night

  22. HOUSE
    Cape Cod House at Truro 599

    Cape Cod House at Truro 599

    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

    $191 to $559/night

  23. DUPLEX
    460 Lower County Road Duplex Left Side Unit

    460 Lower County Road Duplex Left Side Unit

    Dennis Port, MA

    This single-story 3BR cottage is a quaint getaway offering superb outdoor space. Relax on the front porch and host a fun cookout in the large backyard. An outdoor shower is great for rinsing sandy toes after a fun beach day. Walk across the street...

    FREE CANCELLATION

    $106 to $260/night

  24. HOUSE
    73 Sequat House at Harwich

    73 Sequat House at Harwich

    Harwich, MA

    Business : nearby atm, nearby post office, nearby internet cafe, nearby bank Living : central air, air conditioning, ceiling fans, linens, washer & dryer, ironing board, high speed internet, fireplace, iron, hair dryer, cable, dvd, games, heat Local...

    Pets OK
    FREE CANCELLATION

    $488 to $1473/night

  25. 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

    $252 to $561/night

  26. 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

    $164 to $475/night

  27. APARTMENT
    506 on Parker Hill Apartment

    506 on Parker Hill Apartment

    Boston, MA

    525 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

    $243 to $486/night

  28. HOUSE
    Cape Cod Beach Rental

    Cape Cod Beach Rental

    Wellfleet, MA

    Total relaxation and comfort in a house that feels like home, not a rental. Just a 3 min. walk to Wellfleet's Chipman's Cove, 6-12min. more to Indian Neck bay beach or a 25 min. nature walk around the cove and over famous Uncle Tim's Bridge to...

    Pets OK
    FREE CANCELLATION

    $237 to $609/night

  29. 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

    $318 to $707/night

  30. 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

    $170 to $684/night