Vacation rentals in Brookline

4.87 out of 5 average rating, 109 reviews

A serene morning on the lake is depicted, with two individuals paddling a kayak through mist-covered water. The surrounding landscape features dense trees and gentle hills, while soft light reflects off the calm surface, creating a peaceful atmosphere.

Vacation home in Natick

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

4.96 out of 5 average rating, 302 reviews

The spacious bedroom features two queen beds with light green bedding, positioned beside a large window that allows natural light to fill the room. A modern bathroom is visible in the background, with neutral tones and elegant fixtures. Wooden benches provide additional seating.

Apartment in Winthrop

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.

Condo in Lakeside Marblehead

An expansive view of the harbor is captured, showcasing numerous sailboats anchored in the water. Lush green grass and wooden benches frame the scene, with a flagpole standing nearby. A large tree casts shade on the area, contributing to a peaceful atmosphere.

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.

4.98 out of 5 average rating, 377 reviews

A multi-story coastal home is seen from a rocky shoreline, surrounded by lush greenery. Several white Adirondack chairs are positioned on the patio, enhancing outdoor relaxation. The gray exterior of the house features a large balcony with white railings, blending harmoniously with the natural landscape.

Apartment in Salem

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.

4.97 out of 5 average rating, 249 reviews

An open living area showcases a warm ambiance with string lights overhead. A dining table is set for six, and a cozy seating arrangement includes a colorful armchair and a plush sofa. A wall-mounted TV is positioned beside vibrant artwork against the white walls.

Condo in Salem

*Historic1710 2Br|Halloween Downtown+Parking

This stylish 2-bedroom home, designed by the homme team, offers a cozy retreat with Free parking onsite, for those seeking Salem’s spooky history and enchanting charm. The Archer House combines modern comforts with prime access to Salem’s best attractions, dining, and nightlife—perfect for families or friends. Explore the magic with iconic sites just moments away! 🕸 Hocus Pocus House - 5 min walk 🧙🏻‍♀️ Witch Museum - 5 min walk 🎃 Witch House - 10 min walk See below to discover more!

4.87 out of 5 average rating, 109 reviews

An aerial view captures the scenic coastline and sandy beach lined with boats. A variety of residential buildings dot the landscape, interspersed with greenery. The neighborhood showcases the charm of coastal living, with the sea and a pier visible in the background.

Apartment in Swampscott

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.

4.97 out of 5 average rating, 149 reviews

A modern kitchen features a large island with seating for three, situated adjacent to exposed brick walls. Stainless steel appliances are prominently displayed, complemented by white cabinetry and a sleek countertop. Natural light brightens the space, highlighting the warm wooden flooring.

Apartment in East Boston

Nxt to ocean, 5 min dntwn by T

Embark on an urban escape! Immerse yourself in our chic 2BR/1B + office retreat, ideal for up to 4 guests. Enjoy fast WiFi, steps away from an oceanfront park with stunning Boston skyline views. Walk to the Blue Line T station, one stop to downtown or the airport. Dive into our vibrant, safe historic neighborhood with restaurants, bars, yoga, sailing, and galleries. Not suitable for children, no parking/pets/smoking/cannabis/parties. Make this urban oasis your next unforgettable getaway!

4.95 out of 5 average rating, 909 reviews

A wooden dock extends over the water, featuring a metallic ramp with handrails. The serene waters reflect the soft hues of a pastel sky, while residential homes line the shore in the background. Trees are visible, adding a natural element to the view.

Guest suite in Winthrop

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 suite in Lakeside Marblehead

A plush white bathrobe is hung on a hook, providing easy access for guests. Behind the robe, a well-organized shelf showcases an array of personal care products. A clean sink area with modern fixtures is visible below a framed mirror.

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.

4.86 out of 5 average rating, 178 reviews

The entrance to the bungalow features a welcoming wooden door with a decorative glass panel. Soft lighting illuminates the path and entryway, surrounded by well-maintained plants. Stone steps lead up to the door, creating a charming approach to the home.

Home in Beverly

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.

4.84 out of 5 average rating, 167 reviews

A compact kitchen is visible through an open archway, featuring modern appliances and wooden cabinetry. The microwave is installed above the stove, with a stainless steel refrigerator adjacent. The adjoining dining area includes a wooden table and chairs, with warm hardwood flooring extending throughout the space.

Apartment in South End

* 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.

4.97 out of 5 average rating, 168 reviews

A charming outdoor space is showcased with decorative metal cat figures positioned along the garden bed. A bird feeder stands prominently, surrounded by lush green grass and mature trees. Several seating options are visible in the background, creating a welcoming atmosphere for gatherings.

Condo in Salem

The River House Salem North Fields neighborhood

Your family will be close to everything when you stay at this centrally-located place. MBTA 5 min. walk, play ground, tennis court and basketball courts across the street. Public access to rivers high tide for kayaking across the st. Great for families and Friends Salem getaway.. There will be tennis rackets, basketballs for your use.

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Popular amenities for Brookline vacation rentals

Laptop-friendly workspace

Stay near Brookline's top sights

Boston University110 locals recommend

Fenway Park815 locals recommend

Whole Foods Market1,155 locals recommend

Star Market595 locals recommend

Isabella Stewart Gardner Museum500 locals recommend

Trader Joe's409 locals recommend

Apartment rentals in Brookline

4.91 out of 5 average rating, 107 reviews

A cozy living room is illuminated by a warm ceiling light. A light-colored sofa sits alongside a woven storage ottoman. Large windows allow natural light to fill the space, complemented by soft curtains. Decorative cushions add a touch of comfort to the seating area.

Apartment in Danvers

Historical period home with modern amenities..

4.85 out of 5 average rating, 140 reviews

A charming two-story house is viewed from the front, showcasing a gray exterior with white window frames. A driveway is visible, accommodating a small red car. Lush greenery and vibrant flowers enhance the surrounding landscape, contributing to the inviting atmosphere of the property.

Apartment in West Newton

Entire Apartment in Newton, Close to Boston!

4.89 out of 5 average rating, 105 reviews

A spacious kitchen is defined by rich wooden cabinetry and countertops, featuring a stainless steel refrigerator and microwave. A wooden dining table with multiple chairs is arranged nearby. Soft lighting highlights the tiled floor and decorative backsplash, creating a functional cooking space.

Apartment in Dorchester

Rare 3.5 bed apt, super location Boston, +parking

4.8 out of 5 average rating, 667 reviews

A seating area is presented with two modern chairs facing a small table. A patterned area rug covers the floor, and a window is adorned with a decorative curtain. A blue sofa adds comfort to the space, complemented by soft pillows.

Apartment in Cambridge

MIT/Harvard/Inman- 2 Bedroom Apt.

4.89 out of 5 average rating, 128 reviews

A comfortable sleeping area features a spacious bed dressed in warm tones with decorative pillows. Nightstands with modern lamps frame the bed, and artwork adorns the wall above. Natural light filters in through a window, enhancing the inviting ambiance.

Apartment in Peabody

Private Hotel Residence 206

4.86 out of 5 average rating, 424 reviews

A light-filled living area features a sectional sofa in grey fabric, complemented by a side chair and a wooden coffee table. Large bay windows frame the room, allowing natural light to illuminate the hardwood floor. An artwork depicting a serene landscape is displayed on the wall.

Apartment in Allston

3 Bedroom Apartment with Parking

5 out of 5 average rating, 106 reviews

A spacious living area features a curved sectional sofa adorned with contrasting cushions. A circular table sits on a vibrant red rug in front of the sofa. Wall art and greenery provide visual interest, while a television is positioned nearby for entertainment.

Apartment in Allston

Brookline - Mod Apartment in Classic Neighborhood

4.97 out of 5 average rating, 200 reviews

The living room is furnished with a beige leather sofa and a dark brown armchair, complemented by warm wood flooring. A ceiling fan is mounted above, and natural light filters through two windows adorned with sheer curtains. A flat-screen TV and a coffee table are also visible.

Apartment in East Boston

Apartment w/Parking, minutes to airport / Downtown

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Other great vacation rentals in Brookline

4.95 out of 5 average rating, 74 reviews

A back deck offers unobstructed views of the calm bay and distant shoreline. A wooden railing frames the scene, complementing the expansive sky. The area is embraced by gravel and a paved pathway, suggesting a serene outdoor space perfect for relaxation.

Bungalow in Hull

The Sunset Bay Retreat - Cozy Beach Bungalow

Home in Lakeside Marblehead

A serene view showcases the antique house reflecting in the calm waters of Redd's Pond. Lush greenery and trees frame the scene, creating a peaceful ambiance with clear blue skies above.

4.75 out of 5 average rating, 166 reviews

Walk to Everything Great about Marblehead!

4.92 out of 5 average rating, 12 reviews

Home in Wakefield

60 Jordan-New Construction Townhome

4.96 out of 5 average rating, 27 reviews

The open living space features a large kitchen island with seating and a spacious dining area overlooking the living room. Natural light floods the space through large windows, highlighting the modern decor and elegant light fixtures. Stairs lead to the upper level, inviting exploration.

Home in Swampscott

Master Suite with magnificent views of the ocean

4.5 out of 5 average rating, 4 reviews

A modern kitchen and dining area feature white cabinetry and stainless-steel appliances. A clean white table is surrounded by four chairs, while light hardwood floors create an open and airy feel. Windows allow natural light to illuminate the space.

Apartment in Revere

Charming 3B2B Condo II Near Beach

4.75 out of 5 average rating, 297 reviews

The exterior of the yellow house features a welcoming red door with decorative lighting on either side. A railing surrounds the front porch, adorned with green plants and flowers. Utility meters are positioned along the side of the building, attached to the wall.

Apartment in Beverly

Salem/Beverly- Explore Boston's North Shore!

4.99 out of 5 average rating, 79 reviews

The kitchen features modern white cabinetry and a marble countertop. A stainless steel gas range and exhaust hood are prominently displayed. Natural light from a window illuminates a nearby sink, which is accompanied by a potted orchid and overlooks a serene view of the meadow.

Apartment in Brighton

New 3 bedroom, 2 bath unit, meadow view!