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
    C389 Lorenzo

    C389 Lorenzo

    Charlestown, RI

    Enjoy panoramic views of Charlestown Beach and Ninigret Pond from the upstairs level of this well cared for home! The large open space and vaulted ceiling on this floor make up the well equipped kitchen, dining, living room and half bath. Lots of...

    $544/night

  2. HOUSE
    C164 Colby (3-Bedroom Home)

    C164 Colby (3-Bedroom Home)

    Charlestown, RI

    Bring your boat ( up to 19ft) and keep it at the dock in front of this peaceful 1960's cottage on Ningret Pond-( direct access to the Ocean). Ranch in private wooded setting on cul-de sac with wonderful water views of salt pond from kitchen/ living...

    $232 to $300/night

  3. COTTAGE
    Woods Hole Cottage by the Sea

    Woods Hole Cottage by the Sea

    Woods Hole, MA

    Follow the dirt road to our 2BR (sleeps 4) cottage by the sea. With charming yet modernized character as well as a private beach plus access to the Shining Sea Bikeway, our rental offers you the chance to truly explore Cape Cod. Walk or bike to...

    FREE CANCELLATION

    $337 to $622/night

  4. HOUSE
    C403 Orsini (4-Bedroom Home)

    C403 Orsini (4-Bedroom Home)

    Charlestown, RI

    Make your summer memories here at this well maintained home in Charlestown! Located roughly 1/2 mile from Charlestown Beach it has sleeping for 10 guests. There are two levels each with it's own kitchen,living,dining space which is ideal for two...

    $245 to $367/night

  5. HOUSE
    C402 Willow (2-Bedroom Home)

    C402 Willow (2-Bedroom Home)

    Charlestown, RI

    Lasting summer time memories are made here in this comfortable 2 bed room, 1.5 bth. An over-sized deck located on the south side of the house is large enough to grill and dine out on. A Charlestown town beach pass is provided . This pass allows you...

    $116 to $220/night

  6. CONDOMINIUM
    Alameda 2 at Weld Farm

    Alameda 2 at Weld Farm

    West Roxbury, MA

    Our Alameda 2 property in Boston features a vintage 1920’s floor plan and tall ceilings. The unit offers 2.5 bedrooms and an additional study for your comfort. The Alameda 2 hosts a large living room, dining room and renovated eat in...

    Pets OK

    $87 to $229/night

  7. COTTAGE
    C396 Schroeder

    C396 Schroeder

    Charlestown, RI

    Beach: West Beach *Classic Rhode Island beach cottage with full view of the ocean & Block Island * Located on private West Beach in Charlestown, RI *Rental comes with beach privileges * Porches on three sides for both shade and sun relaxing...

    Pets OK

    $202 to $458/night

  8. CONDOMINIUM
    Sawyer on Jones Hill

    Sawyer on Jones Hill

    Boston, MA

    Sawyer on Jones Hill Savin Hill - UMass Boston - Minutes from South End The Sawyer is what most travelers wish to find and rarely do. The Sawyer is walking distance to the subway for a direct line into downtown and the historic district of Boston....

    $99 to $343/night

  9. HOUSE
    Idyllic Mashpee 3BR on Lake

    Idyllic Mashpee 3BR on Lake

    Mashpee, MA

    Water, water everywhere you look at this fabulous 3BR/3.5BA lakefront home in scenic Mashpee, Cape Cod. Affectionately known as Point of View, this modern home is just a short drive (80-90 minutes) from downtown Boston and Providence and provides a...

    FREE CANCELLATION

    $440 to $782/night

  10. HOUSE
    4BR Pet-Friendly Cape Cod

    4BR Pet-Friendly Cape Cod

    East Falmouth, MA

    Picturesque views of Bournes Pond await at this quaint 4BR/2BA East Falmouth home. Enjoy a great location just minutes from downtown Falmouth and the Martha's Vineyard ferry and surrounded by opportunities to paddle board, fish, clam, and kayak....

    Pets OK
    FREE CANCELLATION

    $172 to $403/night

  11. HOUSE
    Walkable Falmouth Hts Beach Home

    Walkable Falmouth Hts Beach Home

    Falmouth, MA

    Bring the whole gang for a quintessential Cape Cod getaway at this adorable and spacious 5BR, 1.5BA (sleeps 10) bungalow. Park your car and leave it—you’re within walking distance of Falmouth Heights Beach, ferry to Martha’s Vineyard and Cape...

    Pets OK
    FREE CANCELLATION

    $204 to $592/night

  12. CONDOMINIUM
    Charming Cape Townhouse

    Charming Cape Townhouse

    Brewster, MA

    This charming 2-bedroom, 2-bath plus a loft townhouse promises a fantastic stay on the Cape! Newly renovated and filled with natural light, this rental features warm wood floors and modern marble-touched bathrooms. Brewster is famous for its...

    FREE CANCELLATION

    $263 to $345/night

  13. DUPLEX
    Spacious 4BR Close to Sea Street Beach

    Spacious 4BR Close to Sea Street Beach

    Dennis Port, MA

    Look no further, you’ve found the perfect Dennisport vacation rental! This delightful duplex is only an 8-minute walk from popular Sea Street Beach, and just a short stroll to ice cream, dining, and more. Sleeps 8. The 4BR/2BA duplex is...

    FREE CANCELLATION

    $146 to $439/night

  14. HOUSE
    Orleans Home On 7 Waterfront Acres

    Orleans Home On 7 Waterfront Acres

    Orleans, MA

    Kayakers and nature lovers take note! This 4BR, 2BA (sleeps 8) house sits on 7+ waterfront acres in Orleans, offering extraordinary privacy with exquisite water views of historic Arey's Pond, part of Pleasant Bay. Note: this is a salt water pond....

    FREE CANCELLATION

    $193 to $454/night

  15. HOUSE
    Wooded Chatham Home on the Monomoy

    Wooded Chatham Home on the Monomoy

    Chatham, MA

    This peaceful 3BR, 2BA woodland Chatham home (sleeps 6) is located right on the Monomoy River. Patio doors open to the travertine stone terrace, where a hot tub overlooks the water. Large windows, cathedral ceilings, soft colors, and modern...

    Hot Tub
    FREE CANCELLATION

    $275 to $497/night

  16. HOUSE
    C323 Kahn (3-Bedroom Home)

    C323 Kahn (3-Bedroom Home)

    Charlestown, RI

    Privacy by the beach…this spacious, comfortable 3 bedroom, 4 bath home sleeps 10. There is a fourth room over the garage which is a great sleeping area for the kids and their friends. There are many areas to hang out with friends and family or...

    $300 to $422/night

  17. HOUSE
    Historic Downtown 4BR Near Harbor

    Historic Downtown 4BR Near Harbor

    Wellfleet, MA

    Gaze out at the charms of downtown Wellfleet from your second-floor balcony in this 4BR/3BA home. Restaurants, shops, and the coastal town’s famous galleries are just steps away. Head down Main Street towards the Town Pier, Mayo Beach, and...

    FREE CANCELLATION

    $292 to $718/night

  18. HOUSE
    5BR Multi-Level with 3 Decks

    5BR Multi-Level with 3 Decks

    Wellfleet, MA

    Welcome to this ideal 5BR/2.5BA Wellfleet getaway in a quiet, residential cul-de-sac less than 2 miles from the town pier and Cahoon Hollow Beach on the Cape Cod National Seashore. With three decks for breathing in the salty sea air, three levels...

    FREE CANCELLATION

    $189 to $580/night

  19. HOUSE
    4BR w/ Sunroom & BBQ, Walk to Beach

    4BR w/ Sunroom & BBQ, Walk to Beach

    Harwich Port, MA

    Harwich Port is a wonderful, fun-filled village that offers the beaches, boating, beauty and charm that make Cape Cod simply irresistible. Located on the Cape's south ocean coast, directly on spectacular Nantucket Sound, a visit here can be whatever...

    FREE CANCELLATION

    $354 to $783/night

  20. 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

    $266 to $664/night

  21. 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

    $137 to $281/night

  22. HOUSE
    5BR on 3 Acres w/ Deck, Near Beaches

    5BR on 3 Acres w/ Deck, Near Beaches

    Wellfleet, MA

    You'll love spending your time outdoors at this large 5BR/2BA Wellfleet home, located on three wooded acres with a 50’ wraparound deck. Fire up the grill for an afternoon barbeque and enjoy views of the vernal pools and wildlife. Pack for the...

    Pets OK
    FREE CANCELLATION

    $219 to $629/night

  23. 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

    $322 to $528/night

  24. HOUSE
    3BR w/ Patio & 2 Decks – Near Beach

    3BR w/ Patio & 2 Decks – Near Beach

    Hyannis, MA

    Unparalleled charm and craftsmanship await at this 3BR/2BA single-story home. Originally built in 1937, your Cape Cod getaway boasts classic features including hardwood floors, arched doorways, gorgeous beam ceilings, and nautically inspired decor....

    FREE CANCELLATION

    $158 to $405/night

  25. HOUSE
    3BR on Private Half-Acre, Near Beach

    3BR on Private Half-Acre, Near Beach

    Harwich, MA

    Situated on the desirable Harwich/Chatham line, this charming 3BR/3BA home affords a prime locale on a quiet street just off Route 28. Spanning three floors, your spacious retreat sits on a private half-acre of land and includes a beautifully...

    FREE CANCELLATION

    $189 to $404/night

  26. 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

  27. HOUSE
    Cape Cod Home Near the Beach

    Cape Cod Home Near the Beach

    Eastham, MA

    Have a classic American beach trip at this 4-bed, 2-bath Eastham Cape Cod style house with room for 8. With a charming wood-burning fireplace, huge back deck, horseshoe toss, and a great location within biking distance to the beach, your group will...

    FREE CANCELLATION

    $264 to $371/night

  28. 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 $509/night

  29. HOUSE
    C413 Alper (2-Bedroom Home)

    C413 Alper (2-Bedroom Home)

    Charlestown, RI

    This delightful home is located just a short walk to Green Hill Pond and 1.5 miles to Charlestown Town Beach. With two lovingly furnished bedrooms, one with full master bath and a full bath with laundry to accommodate the second bedroom, spacious...

    Pets OK

    $220/night

  30. HOUSE
    C021 Howard (3-Bedroom Home)

    C021 Howard (3-Bedroom Home)

    Charlestown, RI

    Charlestown Ocean Ridge South. This comfortable home is yours to enjoy on your vacation. It has an open living, dining and kitchen areas. There are three nice sized bedrooms, the master bedroom with it's own bath and two additional bedrooms with a...

    $202/night