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.

Filter by Region:


Filter by Amenities:


Filter by Entertainment:


Close Filters
  1. HOUSE
    Colbyco Sand Hills Beach- Scituate

    Colbyco Sand Hills Beach- Scituate

    Scituate, MA

    Gorgeous new home on the ocean near Boston and Cape Cod. The Lions’ Den is a 4800 square foot gorgeous new home located in Scituate, MA – close to both Boston and Cape Cod. It features incredible views of the ocean with 6 decks and a widow's...

    Hot Tub

    $1,740 to $1,972/night

  2. HOUSE
    Beachfront 5BR w/ Cape Cod Bay View, Near Downtown

    Beachfront 5BR w/ Cape Cod Bay View, Near Downtown

    Provincetown, MA

    Plan a beachfront getaway for twelve guests at this 5BR/3BA home, where generous picture windows afford water views from almost every room. Spend leisurely vacation days on the two-story patio overlooking Cape Cod Bay. With lounge seating, a gas...

    Pool Pets OK
    FREE CANCELLATION

    $1,168 to $2,145/night

  3. HOUSE
    Colbyco CitySide

    Colbyco CitySide

    Boston, MA

    Rare large and comfortable Boston single family home available for vacation or short term rental. It is located in South Boston near the Beach, Convention Center, Seaport District and Downtown Boston. Huge deck with views of city skyline. This home...

    $1,044/night

  4. 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 $1,037/night

  5. HOUSE
    C347 Wilson (2-Bedroom Home)

    C347 Wilson (2-Bedroom Home)

    Charlestown, RI

    Oceanfront in Charlestown - walk directly out into the warm sand and enjoy swimming, sun bathing, surf fishing, building a sandcastle; or, a stroll on the beautiful beach. For those that want to reserve their energy, there's "people watching" from a...

    $825/night

  6. HOUSE
    Colbyco Murphys House

    Colbyco Murphys House

    Scituate, MA

    South Shore Beach Vacation in Quaint New England Fishing Village Experience the sound of crashing waves and smell of the ocean along with a sweeping vista of the sea and lighthouses in this 1925 cobblestone exterior, newly redecorated, luxury...

    $754 to $986/night

  7. HOUSE
    C392 Charlestown on the Beach

    C392 Charlestown on the Beach

    Charlestown, RI

    Feel the ocean breezes and hear the waves from this wonderful three bedroom home on Charlestown Beach. Watch the sun rise and set from the large comfortable deck that has multiple tables with umbrellas and seating all around. A few steps down the...

    $734 to $874/night

  8. HOUSE
    Colbyco Oceanside- Scituate

    Colbyco Oceanside- Scituate

    Scituate, MA

    Spectacular Colonial where you wake up to the sound of the waves and unobstructed ocean views! Wake up to the sound of the waves as you take in the unobstructed ocean views! This spectacular newer (2013) colonial features the best in craftsmanship,...

    $696 to $986/night

  9. 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 $1,000/night

  10. 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

  11. HOUSE
    Colbyco Veira Park- Martha's Vineyard

    Colbyco Veira Park- Martha's Vineyard

    Martha's Vineyard, MA

    Located in the Oaks Bluff section of Martha's Vineyard, our single family home was Built in 1870, and renovated in 1973, and then again in 2017. The home is approximately 1,700 Sq. Ft., and there are three entryways.  Walk to beach, town (Circuit...

    $580 to $812/night

  12. 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

    $578 to $1,400/night

  13. 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

  14. HOUSE
    Waterfront 3BR w/ Deck & Dock

    Waterfront 3BR w/ Deck & Dock

    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

    $536 to $929/night

  15. HOUSE
    Charming 4BR- Walk to 3 Beaches!

    Charming 4BR- Walk to 3 Beaches!

    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

    $533 to $916/night

  16. 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

    $509 to $934/night

  17. 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

  18. HOUSE
    Scenic Bourns Pond 4BR w/ Waterfront Deck

    Scenic Bourns Pond 4BR w/ Waterfront Deck

    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

    $473 to $714/night

  19. HOUSE
    C409 Tricarico

    C409 Tricarico

    Charlestown, RI

    Bright and cheerful well maintained beach cottage with ocean and Ninigret pond views! Nice open kitchen,dining ,living room area with two sliders that take you out onto the wrap around deck for summer enjoyment on those sunny days and moonlit...

    $471/night

  20. 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

  21. 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

  22. 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

  23. 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

  24. HOUSE
    Remodeled 4BR on River w/ Kayaks

    Remodeled 4BR on River w/ Kayaks

    Falmouth, MA

    Perched on a hill overlooking the tidal Moonakis River, Osprey Point is a 4BR/2.5BA remodeled builder’s home offering a peaceful retreat for eight. With three living areas and a sprawling backyard, there’s plenty of room to gather and have fun....

    FREE CANCELLATION

    $418 to $771/night

  25. 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

  26. HOUSE
    Colbyco Morton Park- Plymouth

    Colbyco Morton Park- Plymouth

    Plymouth, MA

    Charming lake front property in historic Plymouth Massachusetts. 4 Bedrooms, 2 full bathroom, sleeps 8 Charming four bedroom lake front vacation rental in historic Plymouth Massachusetts. Close to Cape Code and Boston, MA. Plymouth holds a place of...

    $406/night

  27. HOUSE
    Colbyco Dana Park- Cambridge

    Colbyco Dana Park- Cambridge

    Cambridge, MA

    Three story residential Townhouse. The structure was built in 1977, and the home is made up of approximately 1,360 square feet of livable space, and sits on about 1,632 square foot lot.While close to the MBTA Redline train station (Central Square),...

    $406/night

  28. 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

    $405 to $603/night

  29. 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

  30. 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