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

Apartment in Winthrop

4.96 out of 5 average rating, 301 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.

Superhost

Apartment in South Boston

4.8 out of 5 average rating, 5 reviews

Located in the heart of S.Boston

Everything you need and more in private condo. located in the heart of South Boston. Professionally cleaned before every stay. King bed. So much to do in the area in any Season. Updated kitchen (granite, full size appliances including DW), W&D in basement. Less than .5 miles from West Broadway T (Red Line). Walkable to over 20 restaurants. Walkable to the beach. .5 miles from Seaport and Convention Center. Open street parking. Quintessential Boston Condo. Five star reviews on all my rentals

Guest favourite

Holiday home in Natick

4.89 out of 5 average rating, 100 reviews

Private Lakefront with game room/Newly renovated

Entire house is brand new with automated blinds w the front of the house facing 180 degee view of lake. Large game room House screams airbnb set down secluded quiet rd on the lake but a min or 2 to any type of store or restaurant you are looking for w tons to do in area. Sliding barn door separates main living area/main bedroom and kitchen from game room & other 2 bedrooms & extra full bath - returns all texts instantly -Free use of paddle board/kayak -No events -3 car 6 person limit 》25 yr

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

Apartment in Salem

4.98 out of 5 average rating, 373 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

4.89 out of 5 average rating, 102 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

Condo in Salem

4.97 out of 5 average rating, 241 reviews

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

This elegant 2-bedroom apartment, designed by the homme team, is a perfect retreat for those exploring Salem's haunted history and magical charm. The Archer House blends modern comforts with easy access to Salem’s top attractions, restaurants, and bars ideal for family or friend travelers. Immerse yourself in the area's mystique with iconic sites just steps away! 🕸 Hocus Pocus House - 5 min walk 🧙🏻‍♀️ Witch Museum - 5 min walk 🎃 Witch House - 10 min walk See below to discover more!

Guest favourite

Guest suite in Winthrop

4.95 out of 5 average rating, 897 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

Apartment in Beverly

5 out of 5 average rating, 17 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 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 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.

Guest favourite

Home in Hull

4.95 out of 5 average rating, 20 reviews

Every room a water view updated kitchen & bath

Make some memories at this unique and family-friendly place. 5 minute walk to commuter boat/ferry to Boston, Ma/Logan airport. Ferry ride is 15-30 minutes depending if boat is direct to Boston, MA or stops at Logan or Hingham. Please check ferry schedule as it changes to weekday only in the off season. The house is 28 miles south of Boston. Panoramic water views. Beach access across the street. Vacation or work from home with water views from every window.