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

Holiday home in Natick

4.87 out of 5 average rating, 109 reviews

Private Lakefront with game room/Newly renovated

Ideal private location on crystal clear Lake Cochituate! Peaceful quiet spot w amazing view only 20 min to Boston & 1 or 2 min drive to anything u could need Fun game room &free use of tandem kayak & paddleboard and fishing Sliding barn door separates main king bedroom, bath, & open kitchen & livingroom from the back 2 queen beds, game room & bath Im always available to answer questions + provide tips, but I also respect your privacy & want u to feel comfy & independent 》25 6 person 3 car limit

Guest favourite

Apartment in Winthrop

4.96 out of 5 average rating, 302 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.

Top Guest favourite

Condo in Lakeside Marblehead

4.99 out of 5 average rating, 174 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.

Top Guest favourite

Apartment in Salem

4.98 out of 5 average rating, 377 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.

Superhost

Apartment in Swampscott

4.87 out of 5 average rating, 109 reviews

Ocean views, Large Deck, Grill, Kid/Dog Friendly

The product of a complete gut renovation in 2020. The unit is 300 yards to Fisherman's Beach at the bottom of the street. The apartment is the 1st floor of a two family home (our family lives upstairs). It consists of 2 bedrooms, 2 full baths, pro kitchen, open living/dining area. The driveway can fit 2 cars (tight). There is additional parking at the bottom of the street. Please see house rules settings for holiday minimum bookings. We are pet friendly, but require case by case approval.

Guest favourite

Guest suite in Winthrop

4.95 out of 5 average rating, 909 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.

Top Guest favourite

Apartment in Beverly

5 out of 5 average rating, 32 reviews

#1 Top Flr Waterview|Lux Design|Pvt Balcony

Experience luxury in this top-floor apartment with stunning water views. Enjoy air conditioning, a private balcony, plush linens, and a custom desk with wireless monitor. Free off-street parking included. Centrally located, you're steps from restaurants and a short walk to the train station for easy access to Boston. Perfect for a serene getaway or productive stay, with Salem's historic charm just minutes away. Book now for a blend of comfort, convenience, and coastal beauty!

Superhost

Apartment in Lakeside Marblehead

5 out of 5 average rating, 3 reviews

Captains Qs 2 bed, downtown MHD sleeps 4, parking

‘Captain’s Quarters’ New! In the heart of Historic Old Town Marblehead. Situated close to Maddies, the Landing, shopping and right next to the Driftwood diner, for the best breakfasts and fried dough on the weekends! Steps to the harbor where you can easily access local yacht clubs and a Public launch service is available for Harbour tours. Prime parking, AC, a fresh modern clean space and amenities will provide you with a very relaxing stay in our beautiful seaside town

Guest favourite

Guest suite in Lakeside Marblehead

4.91 out of 5 average rating, 228 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.

Superhost

Home in Beverly

4.86 out of 5 average rating, 178 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.

Superhost

Apartment in South End

4.84 out of 5 average rating, 167 reviews

* NEW Listing * A True GEM in South End , Boston!!

Experience Boston at its Best in this true gem apartment in the heart of desirable South End! Best Location! Best Neighborhood! Best bars and restaurants! A guests favorite in the neighborhood, you will fall in love of this charming 1 bedroom apartment with cozy and relaxing private patio in the heart of historical and trendy South End in Boston.

Guest favourite

Cottage in Stow

4.95 out of 5 average rating, 171 reviews

White Pine Cottage

Cozy 1930s cottage in Stow, MA with modern amenities. Great landing pad if you are visiting the area. Located in quiet neighborhood with very little traffic. Convenient to local farms, orchards, golfing, parks and more. Hudson, Sudbury and Maynard's restaurants and shops 15 minutes away and big city Boston / Cambridge only 40 minutes.

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What guests are saying

Entire House: Home Away Home

5 out of 5 average rating, 19 reviews3 weeks ago

My two adult children and I stayed here with our two dogs while my wife was having surgery in Boston. The location was great. Car ride to the Longwood medical area was about 25 minutes. The neighborhood consists of single family homes on small lots, not at all fancy but entirely safe as far as we could tell. We were just a few short blocks from a school playing field where leashed dogs were welcome, and other dog-walkers were often on the street in the morning and evening. The house is a bit quirky. There is no seating in the kitchen, but the dining area is very spacious although located down a short hallway from the kitchen. Each of the three bedrooms was more than ample and very quiet at night. We slept well. As we stayed more than a week we were grateful that laundry facilities were present in the basement. Roosevelt was an excellent host and quick to respond to my requests. I would definitely stay in his place again should a similar situation arise.

Home in West Newton

What guests are saying

Enchanted Cottage on 5 Acres

5 out of 5 average rating, 11 reviews5 months ago

The well named enchanted cottage was fabulous. We had a lovely stay, lucky with the weather. Easy reach of Boston on the train. Whole foods just down the road - I cooked in most evenings- as the kitchen had everything we needed. We sat out on the deck chairs and contemplated the Universe over a bottle of wine, watching the birds, squirrels and fall colours. We did a couple of day trips- Concord (loved the antique shops), the Nashoba Winery (get some of the Northern Comfort Apple, Cranberry and Maple Brandy…. Wish I’d bought two, it goes great with Mince Pies). We did the Union Oyster Bar in Boston and Legal Seafood (the oysters were amazing). I would highly recommend The Enchanted Cottage (very comfy beds).

Guesthouse in Framingham

What guests are saying

The Curie-Perfect for Monthly Stays

4.84 out of 5 average rating, 31 reviews1 week ago

This apartment is a great find! The location is perfect, not far from Boston, near every colleges for those who come visiting! This apartment building is indeed very new, built in 2021; but also blended in with history, the leasing office/lobby was converted from an old day chapel, pristine, elegant. Very unique Airbnb experience indeed. The small town is full of vibe with various kinds of cuisines, very good for families, young or old. Melissa, the host is super, giving us very detailed information and instructions from parking to checking in, every tiny details she thoughtfully considered. We couldn’t be happier to stay in this apartment. Highly recommended!

Apartment in Brighton

What guests are saying

Every room a water view updated kitchen & bath

4.95 out of 5 average rating, 21 reviews3 months ago

Excellent experience. Easy check in and the place was perfect, she even had some snacks waiting for us upon arrival. Easy walk to the ferry into Boston, and easy parking. It was winter, but there were plenty of outdoor activities so we'd love to come back during the summer. Older house but so charming and great location. Overall great communication before, during, and after; she even offered to ship a shoe my niece left behind to us. Would love to come back and would absolutely recommend to anyone looking for a great place in Hull.

Home in Hull

What guests are saying

Charming condo steps from beach

4.86 out of 5 average rating, 14 reviews1 month ago

I can’t rave enough about how wonderful our stay was. Casie was absolutely great. She made sure our stay was perfect from the beginning to the end. The location is amazing. There are restaurants and the beach that are walking distance. Winthrop is a true gem! We are looking forward to coming back and staying here again!

Apartment in Winthrop

What guests are saying

Elegant home in historic Marblehead.

4.91 out of 5 average rating, 45 reviews1 week ago

In a sea of Airbnb’s that are soulless money makers for owners, this home is a gem — and a real nod to what the concept of home sharing is about. This is a beautiful home —- appointed perfectly, clean as can be, comfortable, peaceful and clearly loved and cared for by its owner, Eileen. Marblehead is such a stunning place but to have such a fantastic place to call home for a few days made this one of our favorite trips. Very lucky that Eileen makes this home available for guests to enjoy. Thank you again!!!

Home in Lakeside Marblehead

What guests are saying

Luxury Sand Castle Beach House Historic SALEM

4.91 out of 5 average rating, 11 reviews4 months ago

Gary provided an amazing experience during our stay! The home was spotless, beautifully decorated, and equipped with everything we needed for a comfortable visit. The location was perfect, close to main attractions, yet peaceful and relaxing. Gary was incredibly thoughtful and responsive, making us feel right at home. Small touches like a welcoming Thanksgiving card and chocolates really stood out. We couldn’t have asked for a better place to stay and would absolutely recommend this Airbnb to anyone visiting the area. We hope to return soon! Thank you for the exceptional hospitality!

Condo in Salem

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