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 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

    $143/night

  2. HOUSE
    Windmill Home Overlooking Marsh

    Windmill Home Overlooking Marsh

    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

  3. HOUSE
    Spacious 5BR Long Pond Home- Private Beach & Dock

    Spacious 5BR Long Pond Home- Private Beach & Dock

    Harwich, MA

    From an abundance of outdoor space to a welcoming interior with breathtaking lake views and fireplaces, this three-story 5BR/4BA home is a sure bet for your Cape Cod getaway. Overlooking Long Pond, this stunning home features a private beach and...

    Pets OK
    FREE CANCELLATION

    $521 to $1,400/night

  4. 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

    $211 to $448/night

  5. 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

    $193 to $568/night

  6. 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

    $211 to $378/night

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

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

    Provincetown, MA

    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 and restaurants along...

    Pets OK
    FREE CANCELLATION

    $422 to $934/night

  8. CONDOMINIUM
    2BR Condo at Ocean Edge Resort

    2BR Condo at Ocean Edge Resort

    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...

    Pool
    FREE CANCELLATION

    $115 to $332/night

  9. 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

    $739 to $1,037/night

  10. 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 alfresco meals on the patio in the big fenced yard. Spend...

    FREE CANCELLATION

    $261 to $653/night

  11. HOUSE
    Quaint 4BR Cottage in the Woods

    Quaint 4BR Cottage in the Woods

    Wellfleet, MA

    The tranquil setting at this 4BR/3BA Cape Cod home will put you in full vacation mode. Set on 1.5 acres of land with soaring pine trees, the house is less than 10 minutes from beaches on the ocean and bay. Visit nearby Bound Brook Island Beach for...

    FREE CANCELLATION

    $286 to $506/night

  12. 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

  13. HOUSE
    3BR on Buck’s Pond w/ Beach Access

    3BR on Buck’s Pond w/ Beach Access

    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...

    FREE CANCELLATION

    $183 to $421/night

  14. 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 $658/night

  15. HOUSE
    Moonakis River 4BR w/ Pool & Spa- Near Downtown

    Moonakis River 4BR w/ Pool & Spa- Near Downtown

    East Falmouth, MA

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

    Pool Hot Tub
    FREE CANCELLATION

    $672 to $991/night

  16. HOUSE
    Serene 4BR w/ Large Deck & Trail Access

    Serene 4BR w/ Large Deck & Trail Access

    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

    $211 to $488/night

  17. HOUSE
    Spacious S. Chatham Home Near Beach

    Spacious S. Chatham Home Near Beach

    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

    $261 to $652/night

  18. HOUSE
    Charming Ocean View Beach House

    Charming Ocean View 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...

    FREE CANCELLATION

    $287 to $742/night

  19. 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

    $317 to $627/night

  20. 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

    $156 to $462/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

    $197/night

  22. HOUSE
    Sunny 3BR w/ Views of Cape Cod Bay

    Sunny 3BR w/ Views of Cape Cod Bay

    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

    $407 to $607/night

  23. HOUSE
    Countryside 4BR, 1 Mile to Beach

    Countryside 4BR, 1 Mile to Beach

    Harwich, MA

    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 throughout the updated...

    FREE CANCELLATION

    $146 to $442/night

  24. 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

    $167 to $459/night

  25. 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

    $214 to $469/night

  26. HOUSE
    Oceanfront 3BR w/ Huge Deck & Private Dock

    Oceanfront 3BR w/ Huge Deck & Private Dock

    Centerville, MA

    Overlooking the Centerville River, this 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 enjoy spectacular sunsets. A...

    FREE CANCELLATION

    $321 to $696/night

  27. HOUSE
    Corner Lot 4BR w/ Canoe & Bikes, Walk to Long Pond

    Corner Lot 4BR w/ Canoe & Bikes, Walk to Long Pond

    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

    $156 to $369/night

  28. HOUSE
    Remodeled 3BR, Walk to Cotuit Village

    Remodeled 3BR, Walk to Cotuit Village

    Cotuit, MA

    A quintessential Cape Cod getaway awaits your crew of eight 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

    $229 to $549/night

  29. 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

  30. HOUSE
    Charming 4BR Cottage-- Steps to Long Pond

    Charming 4BR Cottage-- Steps to Long Pond

    Harwich, MA

    Boasting classic Cape Cod style and a prime location just 200 steps from Long Pond, this 4BR/2BA cottage offers the perfect home base for your vacation. Spend your days fishing, swimming, and boating on Long Pond, the largest freshwater lake on...

    FREE CANCELLATION

    $238 to $475/night