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. DUPLEX
    Walk to Beach & Downtown! 6BR Duplex w/ Huge Yard

    Walk to Beach & Downtown! 6BR Duplex w/ Huge Yard

    Dennis Port, MA

    Host your next family get together at this quaint 6BR/2BA duplex cottage. This rental includes two identical side-by-side units -- each with a full-size kitchen, living area, and awesome outdoor space. Hang out on comfy furniture on the front porch...

    FREE CANCELLATION

    $422 to $528/night

  2. DUPLEX
    3BR w/ Yard & Porch, Walk to Beach & Downtown!

    3BR w/ Yard & Porch, Walk to Beach & Downtown!

    Dennis Port, MA

    Walk everywhere from this cute 3BR cottage! Enjoy an amazing outdoor space, including a quintessential front porch with lounge furniture and a shared yard that has an outdoor shower, grill, and shaded al fresco dining. Your rental commands a prime...

    FREE CANCELLATION

    $211 to $241/night

  3. COTTAGE
    Classic Lakefront 2BR w/ Screened Porch

    Classic Lakefront 2BR w/ Screened Porch

    Mashpee, MA

    PROPERTY OVERVIEW Tucked away in a charming Cape Cod neighborhood, this classic 2BR cottage sits on the lovely Mashpee-Wakeby Pond, which is the largest pond on the Cape and has phenomenal Bass fishing (contests are held here). It is also a...

    FREE CANCELLATION

    $168 to $295/night

  4. HOUSE
    5BR Eastham Home w/ Large Deck & Yard

    5BR Eastham Home w/ Large Deck & Yard

    Eastham, MA

    PROPERTY OVERVIEW Featuring miles of unspoiled shoreline and warmer bay beaches, Eastham is a sure bet for your next Cape Cod getaway. An ideal place to relax, this two-story 5BR/2.5BA home offers 2,274 square feet of comfortable living space --...

    FREE CANCELLATION

    $392 to $714/night

  5. HOUSE
    Quiet 3BR – Walk to Old Silver Beach

    Quiet 3BR – Walk to Old Silver Beach

    Falmouth, MA

    Plan the ultimate beach vacation at this 3BR/3BA (plus bonus sleeping space) retreat in the Old Silver Beach neighborhood of West Falmouth. The house comes stocked with beach chairs and gear, so it’s simple to make the quick walk to the bayside....

    FREE CANCELLATION

    $386 to $528/night

  6. 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 $517/night

  7. 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 $620/night

  8. 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

  9. 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

  10. 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 $463/night

  11. 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

    $196 to $436/night

  12. HOUSE
    Updated 4BR Family Home in Harwich

    Updated 4BR Family Home in Harwich

    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

    $390 to $627/night

  13. HOUSE
    3BR Gem at Cape Cod Bay w/ Water Views

    3BR Gem at Cape Cod Bay w/ Water Views

    Eastham, MA

    Memorable beach trips begin at this elegant 3BR/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 $1,061/night

  14. HOUSE
    Remodeled 4BR Near Beaches & Golf

    Remodeled 4BR Near Beaches & Golf

    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

    $425 to $606/night

  15. HOUSE
    Classic 4BR on Oyster Pond w/ Dock & Boat Fleet

    Classic 4BR on Oyster Pond w/ Dock & Boat Fleet

    Falmouth, MA

    Situated on the shores of Oyster Pond, this 4BR/3BA 1930s-era summer home radiates classic Cape Cod charm. Amenities include a private dock with rowboats (with sails), a kayak, and canoe for your use. The lake is ideal for swimming and fishing, and...

    Pets OK
    FREE CANCELLATION

    $325 to $616/night

  16. HOUSE
    Big 4BR Gem w/ Fenced Yard & Private Beach Access

    Big 4BR Gem w/ Fenced Yard & Private Beach Access

    Hyannis, MA

    This spacious 4BR/2.5BA 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 $686/night

  17. HOUSE
    4BR w/ Private Beach Access

    4BR w/ Private Beach Access

    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...

    FREE CANCELLATION

    $275 to $571/night

  18. DUPLEX
    3BR w/ Yard & Outdoor Shower- Walk Everywhere!

    3BR w/ Yard & Outdoor Shower- Walk Everywhere!

    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

    $211 to $241/night

  19. HOUSE
    New 2BR on Nature Conserve w/ Sun Deck

    New 2BR on Nature Conserve w/ Sun Deck

    Wellfleet, MA

    PROPERTY OVERVIEW Nestled on 24 acres of Massachusetts Audubon and Wellfleet Conservation Trust Land, this brand-new 2BR/1.5 offers a sunroom, expansive balcony, and miles of lovely hiking trails. Spend sun-dappled afternoons in the enormous yard...

    FREE CANCELLATION

    $260 to $408/night

  20. HOUSE
    4BR w/ Fenced Yard- Walk to Beach & Commercial St

    4BR w/ Fenced Yard- Walk to Beach & Commercial St

    Provincetown, MA

    PROPERTY OVERVIEW Tucked away off a quiet residential street in the center of Provincetown, this 4BR/3BA home offers a peaceful retreat along with a convenient location -- just steps away from the pier, ferry, and all the charming boutique shops...

    Pets OK
    FREE CANCELLATION

    $509 to $944/night

  21. HOUSE
    New Seaside 3BR w/ Water Views & Deck

    New Seaside 3BR w/ Water Views & Deck

    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

    $446 to $788/night