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
    C222 Shafer (4-Bedroom Home)

    C222 Shafer (4-Bedroom Home)

    Charlestown, RI

    This spacious Colonial, located on a quiet dead end street, offers large, sun-filled rooms that are nicely furnished and ideal for a large group of up to 10 guests. Gather in the open kitchen/dining/family room or have quiet conversation in the den....

    $440/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
    W091 Vaccaro

    W091 Vaccaro

    Charlestown, RI

    We welcome you to enjoy our family cottage nestled in the woods and just a 10 minutes from the beach. Our place has a large backyard with plenty of shade and privacy. Take advantage of our deck and patio on our one acre lot. Feel free to gather...

    $134 to $210/night

  7. 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

  8. HOUSE
    2BR Garden Cottage, Near Beach

    2BR Garden Cottage, Near Beach

    Wellfleet, MA

    Enjoy the peaceful surroundings of this 2BR/2BA cottage, less than a mile from the heart of Wellfleet. Those who love the great outdoors will be right at home in the artist’s garden. Indoors, high ceilings and natural light complement an...

    FREE CANCELLATION

    $158 to $372/night

  9. 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

  10. 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

  11. 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

  12. HOUSE
    Barnstable Village 4BR w/ Yard

    Barnstable Village 4BR w/ Yard

    Barnstable, MA

    With a quiet location in an historic Barnstable neighborhood, this 4BR/2BA 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 along Main Street....

    FREE CANCELLATION

    $132 to $377/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
    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

  15. HOUSE
    C315 Broccoli 676

    C315 Broccoli 676

    Charlestown, RI

    Ocean front on Charlestown Beach. Make a lifetime of memories at this newly built beach house. Relax on the deck overlooking the Atlantic Ocean, Block Island, the Breachway and miles of one of South County’s most sought after beaches. Enjoy your...

    $581 to $844/night

  16. HOUSE
    C384 Buckley

    C384 Buckley

    Charlestown, RI

    Begin making those vacation memories in this seaside cottage . Nicely furnished , this one level home has open kitchen & living area , large deck and an outside shower to rinse off that beach sand . Sleeping accommodations for 6 . Master bedroom has...

    $293 to $324/night

  17. 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

  18. 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

  19. 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

  20. 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

  21. HOUSE
    Woodsy Cape Cod Home in Wellfleet

    Woodsy Cape Cod Home in Wellfleet

    Wellfleet, MA

    Get in touch with the wildlife of Cape Cod at this 3BR, 2.5BA home (sleeps 8) just across from a tidal creek flowing into Cape Cod Bay. Travel the gorgeous trails of the Audubon Sanctuary, or drive 20 minutes to Provincetown. The marshes are...

    FREE CANCELLATION

    $172 to $462/night

  22. HOUSE
    C359 Matos (5-Bedroom Home)

    C359 Matos (5-Bedroom Home)

    Charlestown, RI

    This 5 bedroom, 2 bath gem has room for the whole family to vacation in comfort. A recent interior renovation offers updates everywhere. An extra large deck overlooking the acre of back yard lends itself to summer fun and entertaining. New outside...

    $263 to $458/night

  23. 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

  24. 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

  25. 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

  26. HOUSE
    C024 Broccoli

    C024 Broccoli

    Charlestown, RI

    This two story cottage offers tons of sleeping and generous sized rooms. Fresh, immaculate and cute. Large dining/sun bathing deck. 1 acre of yard, shed for the bikes. .75 of a mile to beach, 1/4 mile to ice cream, bakery & deli shops. "Sea Breeze...

    $318 to $440/night

  27. HOUSE
    Spacious Waterfront Home in Hyannis

    Spacious Waterfront 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

    $190 to $459/night

  28. 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

  29. 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

  30. 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