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. 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

    $110 to $124/night

  2. HOUSE
    Eastham Gem Home 190

    Eastham Gem Home 190

    Eastham, MA

    Property Overview  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,...

    FREE CANCELLATION

    $250 to $559/night

  3. HOUSE
    Woodsy Haven Home

    Woodsy Haven Home

    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

    $168 to $564/night

  4. 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

    $518 to $872/night

  5. HOUSE
    Scenic Bourns Pond House

    Scenic Bourns Pond House

    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

    $600 to $633/night

  6. 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

    $172 to $628/night

  7. CONDOMINIUM
    26 Pleasant St Condo Unit 1

    26 Pleasant St Condo Unit 1

    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

    $289 to $600/night

  8. HOUSE
    32 Crosby Lane House

    32 Crosby Lane House

    Falmouth, MA

    Perched on a hill overlooking the tidal Moonakis River, Osprey Point is a 3BR/2.5BA remodeled builder’s home offering a peaceful retreat for six. With three living areas and a sprawling backyard, there’s plenty of room to gather and have fun....

    FREE CANCELLATION

    $394 to $498/night

  9. HOUSE
    35 Timberlane Drive Home

    35 Timberlane Drive Home

    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

    $189 to $557/night

  10. HOUSE
    16 East Falmouth Home

    16 East Falmouth Home

    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

    $238 to $666/night

  11. HOUSE
    5 Third Home in Harwich

    5 Third Home in Harwich

    Harwich, MA

    Your 3BR/2BA is just a block away from Long Pond—swim, float, splash, paddle, and sail on Cape Cod’s largest lake, named one of the best swimming spots by Boston Magazine. Hop on your bikes and ride the 25-mile Rail Trail that runs from Dennis...

    FREE CANCELLATION

    $247 to $557/night

  12. HOUSE
    25 Doane Home at Harwich Port

    25 Doane Home at Harwich Port

    Harwich Port, MA

    Enjoy a peaceful Cape Cod country setting at this newly remodeled 3BR/2BA home, featuring hardwood floors and vibrant interior design elements. Entertain on the private deck in the fenced yard, equipped with a fire pit and a grill as well as an...

    Pets OK
    FREE CANCELLATION

    $166 to $436/night

  13. HOUSE
    356 Deer Meadow Lane Home

    356 Deer Meadow Lane Home

    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

    $173 to $502/night

  14. HOUSE
    29 Shore Road Ext Home

    29 Shore Road Ext Home

    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

    $513 to $874/night

  15. HOUSE
    85 Cynthia Lane Home

    85 Cynthia Lane Home

    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...

    FREE CANCELLATION

    $161 to $485/night

  16. HOUSE
    34 Salt Spray Home

    34 Salt Spray Home

    South Chatham, MA

    With two levels of living space, this completely remodeled 3BR/2BA home features radiant heating, high-end appliances, and custom cabinetry. Abundant natural light abounds with large windows, French glass doors, and a multitude of skylights....

    FREE CANCELLATION

    $264 to $459/night

  17. HOUSE
    56 S Yarmouth Rd Home

    56 S Yarmouth Rd Home

    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

    $131 to $473/night

  18. 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

    $121 to $534/night

  19. 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

    $121 to $775/night

  20. 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

  21. 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

  22. 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

  23. 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

  24. 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 $1,142/night

  25. 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

  26. 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

  27. 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

  28. 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

    $135 to $475/night

  29. 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

  30. HOUSE
    90 Lieutenant Island Rd Home

    90 Lieutenant Island Rd Home

    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

    $245 to $445/night