Holiday houses in Brookline

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Top-rated holiday rentals in Brookline

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite

Rental unit in Winthrop

4.96 out of 5 average rating, 298 reviews

Cody's Place Boston Airport Pool/Beaches ParkFree

Retreat, relax, & refresh in your own private entry basement in law apartment of our well bunkered Beach House. BEST LOCATION across from the mighty Atlantic & Iconic Winthrop Arms Hotel/Restaurant. Take in the salty air & breathtaking sunrises. Steps from Ocean Sunrise & Sandy Beach Surf. Walking distance to public transport, restaurants, parks, or Uber/Walk to the center bars & other attractions. Vacation living. Ferry minutes to downtown Boston. 1 of 3 officially licensed AirBnB's in town.

Guest favourite

Rental unit in Salem

4.85 out of 5 average rating, 104 reviews

Historic House by the Gables

Historic home off Derby street in Old Town Salem, and just a short walk to all the best that Salem has to offer. This 3rd flr apt has water views from most rooms, and is just across the st from The House of Seven Gables. A spacious feel to this apt and has a open layout, and beautiful kitchen for those that like to cook. If you prefer to eat out, there are at least a dozen restaurants within a short 5 to 10 minute walk. This home is truly located in one of the most desirable locations in Salem

Superhost

Home in Wayland

4.78 out of 5 average rating, 465 reviews

Tiny house experience steps from the water!

-Tiny house experience in quiet private neighborhood on its own lot with great backyard & fire pit on private secluded St. -prof cleaned after each guest -High speed internet/ expanded cable -Built in full bed with queen sleeper futon bed that can sleep 2 more -Just a few steps from beautiful Dudley Pond for swimming/fishing and great walking trails Wayland is one of nicest towns in MA yet only a min or two from anything you need and less than half hour from Boston. texts returned instantly

Superhost

Condo in Cambridge

4.89 out of 5 average rating, 136 reviews

#1A-Cambridge Harvard MIT with In unit W/D!

WALK to Harvard, MIT and steps to all public trans & blue bikes! Gorgeous fully furnished (1 month minimum). stays! Great for visiting nurses, Harvard, MIT fellows! In-unit washer/dryer and full eat in kitchen with granite counters, dishwasher/disposal (all cooking utensils, etc.). Light filled living room with custom built in bookshelves, large bay windows, and great picture book collection... All wood floors. AC/WIFI/all utilities included! Pets (yes large dogs too) welcome approval only.

Guest favourite

Condo in Marblehead

4.99 out of 5 average rating, 171 reviews

Harbor Hideaway

A uniquely detailed single-floor unit in a 2 unit house featuring a large kitchen/dining room, living room, and a private cozy veranda. Queen Bedroom & additional sleeping for 2 with a deluxe air mattress. This space is perfect for couples, families with young children, or a single person. Only one dog allowed no cats. This unit is on the lower floor of a two-family house occasionally you can hear steps from the upstairs. PLEASE note parking on site is very tight small cars compact SUVs only.

Guest favourite

Condo in Salem

4.97 out of 5 average rating, 237 reviews

*Historic1710 2Br-Sleeps 7 Halloween|Salem|Parking

Experience spooky fall luxury at The Archer House, Salem’s historic gem! •⁠⁠Elegant 2BR, 2BA apartment with haunted charm •⁠⁠Fast 200mb Wi-Fi, 4K Smart TV for cozy nights •⁠Private workspace for productivity •⁠In-suite washer/dryer for convenience •⁠Fully equipped kitchen with K-cups •⁠Free Level 2 EV charging •⁠10-minute walk to Salem’s fall attractions Your perfect Halloween retreat awaits! ⭐5Star Review This was a perfect location to explore Salem. Super clean, big, and well decorated.

Guest favourite

Rental unit in Salem

4.98 out of 5 average rating, 368 reviews

Winter Island Retreat

Effective 4/1/23, NON Owner occupied listings have a 3% impact fee that is charged on the total expenses associated with the rental. Winter Island Retreat is a OWNER OCCUPIED listing that is the place; For total relaxation. Watch the sunrise and experience the Atlantic Ocean. Enjoy your favorite beverage while rocking in an Adirondack chair on the patio. Inhale the smell of the ocean breeze and fragrant sea roses. Winter Island Retreat is an experience like no other in the Witch City.

Guest favourite

Guest suite in Winthrop

4.95 out of 5 average rating, 889 reviews

Get to The Point, Winthrop

The Boston Skyline sunsets are beautiful during the summer, just a minute down the street from your Airbnb. This cozy one bedroom, private entrance, and bathroom includes FREE off-street parking, high-speed internet access, comfy and cozy queen bed with premium linens, nespresso, fridge, with complimentary munchies and NO cleaning fee. Check out the beaches and restaurants. Relax watching your favorite show on the HD smart television or catch up on work with the spacious desk area.

Guest favourite

Home in Salem

4.97 out of 5 average rating, 104 reviews

Sunny Salem Condo: Quiet, convenient & parking.

Enjoy historic Salem in this bright, lovely condominium on the second and third floors of a fully renovated house. Two bedrooms, two family rooms, hardwood floors, and full kitchen with major appliances, dishwasher, and a sunny table for dining. In unit washer and dryer and two parking spots in a private driveway. Walking distance to Hocus Pocus house, downtown Salem, and a great local grocery store. This location is incredibly comfortable, clean, private and relaxing.

Guest favourite

Guest suite in Marblehead

4.91 out of 5 average rating, 227 reviews

"Sweet 57" - private entrance suite

Suite with private entrance in quiet family home. Includes kitchenette with a microwave, mini fridge, and coffee maker. Washer/dryer available for week+ long stays (subject to host assistance). Includes access to family room with tv. Ample closet space. Beach chairs, towels, & bikes available. Come for a day or a week. You will not run out of things to do and will find your accommodations private, quiet and safe. NO SMOKING permitted in or anywhere near home.

Guest favourite

Condo in Marblehead

4.94 out of 5 average rating, 139 reviews

1742 Marblehead Studio|Minutes to Salem|Parking

*INQUIRE ABOUT WINTER RENTAL PRICING (30+ day stays) KEY FEATURES: ☀️Reserved parking for 1 vehicle ☀️Fully equipped + stocked kitchen ☀️New stainless steel appliances ☀️Light and bright space with four oversized windows ☀️Smart 4K TV ☀️Keurig with complimentary coffee ☀️Family Friendly! We provide pack and play, high chair, bouncer and stroller. No need to overpack with all of that baby gear! ☀️Futon that turns into a full sized bed ☀️Lots of natural lighting

Superhost

Home in Beverly

4.86 out of 5 average rating, 175 reviews

Beverly Beach House- Upper Deck

Half block from the beach in the scenic North Shore. Get away from it all in this beach bungalow. Close to downtown restaurants and shops, Historic Cabot theater and more. Large historic colonial home with 3 bedrooms and 2 bath with ocean views and off street parking. Large deck and full kitchen. 30 min train to Boston. Easy quick access to popular destinations such as Marblehead, Rockport, Newburyport, Gloucester and more.