Vacation rentals in Boston

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, 303 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.

4.95 out of 5 average rating, 152 reviews

The image showcases a collage of four distinct areas within the unit. A cozy living space features a red sofa and coffee table, while a modern kitchen boasts stainless steel appliances and a spacious countertop. A serene sleeping area includes a large bed with a blue-and-white patterned backdrop. Lastly, a vibrant patio is visible through open doors, framed by greenery.

Condo in Gloucester

KeyWest Vibe, PrivatePatio, Close2Salem, WalkDWNTN

Looking for the perfect Gloucester retreat for your group or family? Look no further than this spacious and inviting 2-bedroom unit, ideal for families and groups seeking comfort, style, and ample room to relax. Step inside and be greeted by a bright and spacious living area, perfect for gathering together after a day of exploring all that Gloucester has to offer. With its comfortable furnishings and modern amenities, this unit is designed to provide you with the ultimate vacation experience.

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.

4.87 out of 5 average rating, 111 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, 118 reviews

The exterior of a charming two-story home is showcased, featuring wooden paneling and a welcoming wreath on the front door. A large balcony offers views of the serene harbor, surrounded by low shrubs and a path leading down to the water.

Home in Gloucester

Harbor View Walk to Beach & Town, 6Guests KingBeds

Spectacular Gloucester home on Cape Ann. Walk to Stage Fort Park & local beaches right across the street. Gloucester center is about 1 mile. On the way to town, walk by beaches & the park with waterfront tennis & bocce ball courts, plus a great water view playground and playing fields. Just beyond the park is famous Stacy Boulevard with the Fisherman's Memorial Monument along the waterfront. There are beautiful white sandy beaches (Good Harbor, Wingaersheek, Singing, & Crane's Beach).

4.95 out of 5 average rating, 912 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.

4.96 out of 5 average rating, 100 reviews

A well-maintained outdoor area is highlighted, featuring a grassy lawn leading up to stone steps. The house, adorned with dark siding, is framed by a large tree and offers a welcoming seating arrangement on the porch. Clear skies provide ample natural light.

Condo in Gloucester

Luxurious beach house w/ harbor views & near beach

There isn't a better location on Cape Ann! Rocky Neck is the oldest art colony in the US. This luxurious 1br boasts ocean views & was updated w/ designer & custom features. Not only can you walk to the beach, there are amazing restaurants across the street and a wine & cheese bar featuring local art you can peruse while having a cocktail. Come and enjoy sunsets from the deck and everything else Gloucester has to offer!

4.84 out of 5 average rating, 167 reviews

A private patio area features a stone floor surrounded by lush greenery and wooden fencing. A set of modern chairs sits on the patio, while a flight of stairs leads to the entrance of the apartment. The overall space invites an atmosphere of relaxation.

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.

Vacation rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Apartments

Convenient locations with everyday essentials

Villas

Luxurious estates for the ultimate escape

Popular amenities for Boston vacation rentals

Laptop-friendly workspace

Stay near Boston's top sights

Boston University110 locals recommend

Harvard University574 locals recommend

Fenway Park815 locals recommend

Boston Common567 locals recommend

TD Garden243 locals recommend

New England Aquarium399 locals recommend

Private vacation rentals in Boston

4.95 out of 5 average rating, 252 reviews

A wooden deck overlooks marsh views, featuring tall bar stools and small tables arranged neatly. Guests can be seen enjoying their time at the water's edge as the sun sets, casting a warm glow across the scene.

Cottage in Essex

French Flair "Pied a Terre" Cottage on the Marsh

4.82 out of 5 average rating, 128 reviews

A spacious outdoor deck is furnished with black rattan chairs, providing comfortable seating for gatherings. The ocean view stretches out across the horizon, with boats visible on the water. The inviting atmosphere is complemented by clear skies and distant coastal scenery.

Bungalow in Beachmont

Cape cod style seaside condo Boston, Airport,Train

4.97 out of 5 average rating, 151 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

4.88 out of 5 average rating, 147 reviews

The kitchen features modern appliances, including a stove, microwave, and refrigerator. Light-colored cabinetry complements the clean countertops. Natural light floods the space through a window, creating a bright and inviting atmosphere. The flooring is finished in warm wood tones.

Home in Quincy

284 - New! Tranquil & Cozy Boston Home

4.97 out of 5 average rating, 101 reviews

A staircase with white railings is surrounded by tall trees and lush greenery, leading down toward a pond. The steps are made of stone and arranged with interspersed paved sections, creating a natural pathway down the slope.

Guesthouse in Westford

Detached Waterfront Guest House

4.88 out of 5 average rating, 421 reviews

An open living area features a cozy striped sofa and a bright red pub table. A winding black staircase leads to the upper sleeping area. Natural light enters through a nearby door. A flat-screen TV is mounted on the wall, enhancing the space's functionality.

Barn in Carlisle

✨Private Studio w/ Loft Center Historic Carlisle✨

4.89 out of 5 average rating, 137 reviews

A modern kitchen features white cabinetry with a gray island and two black bar stools. Stainless steel appliances, including an oven and refrigerator, complement the light countertops. Pendant lights hang above the island, illuminating the space, while natural light streams through the window.

Condo in East Boston

Luxury Condo in Boston w/ backyard & parking

4.95 out of 5 average rating, 94 reviews

Two white Adirondack chairs are positioned on a stone pathway leading to the entrance of the home. Flower boxes filled with colorful plants enhance the entrance, while a small conifer is visible nearby. The exterior features wooden shingles and a large window, allowing natural light.

Home in Scituate

Minot Beach Home

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Boston waterfront vacation rentals

5 out of 5 average rating, 114 reviews

A cozy living room features large windows that invite natural light, accented by a ceiling fan. Comfortable brown leather seating surrounds a dark coffee table, which holds magazines. A light-colored area rug complements the space, while a wall-mounted shelf displays decorative items.

Apartment in Salem

2-Bedroom Ocean View Walk to Beach and Downtown

4.93 out of 5 average rating, 134 reviews

A scenic view captures a charming two-story white house overlooking the ocean, framed by a vibrant blue sky with scattered clouds. The foreground features a street with pedestrians, while vehicles are parked nearby. Greenery line the roadside, enhancing the coastal setting.

Apartment in Winthrop

Newly Renovated Ocean View 2 Bdrm Apt

4.92 out of 5 average rating, 102 reviews

Two large windows frame a view of the ocean, allowing natural light to fill the space. Bare trees are visible outside, adding a seasonal touch to the serene landscape. Soft window coverings enhance the calm atmosphere of the room.

Apartment in Beverly

Enjoy Stunning Sunrises&Sunsets Ocean Views 33

Guest suite in Lakeside Marblehead

A wooden walkway stretches over the water, leading to a private pier. The railing provides support, while gentle waves lap against the shore. In the distance, a calm blue sky meets the horizon, and small boats can be seen bobbing on the water.

4.91 out of 5 average rating, 271 reviews

Ocean Park Retreat

4.94 out of 5 average rating, 124 reviews

Apartment in Nahant

Ocean view studio with hot tub & access to Boston

4.96 out of 5 average rating, 236 reviews

The outdoor area features a serene saltwater pool surrounded by lounge chairs, all set against a backdrop of panoramic ocean views. A pergola provides partial shade, and vibrant flowers add a touch of color to the landscaped surroundings.

Apartment in Winthrop

Oceanfront Pool. Close to Boston. Free Parking.

4.9 out of 5 average rating, 194 reviews

A welcoming sign for the Rocky Neck Art Colony is displayed prominently. The sign features blue and white colors with decorative elements, including an image of a bird. Text indicates the area is one of America's oldest working art colonies, situated in historic Gloucester.

Loft in Gloucester

Rocky Neck Studio/Loft, Gloucester, Mass.

4.85 out of 5 average rating, 172 reviews

The exterior of a blue cottage is framed by vibrant green foliage and a small red maple tree. A welcoming front door is highlighted by a decorative sign. The upper balcony features black and white railings, with coordinating chairs and a playful rug at the entrance.

Cottage in Gloucester

SeaHaven Cottage at Stage Fort Park

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Boston fishing vacation rentals

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!

4.84 out of 5 average rating, 578 reviews

An outdoor screened deck is furnished with a large glass table surrounded by striped cushioned chairs. Lush greenery and flowers are seen in window boxes, with a scenic view of the Charles River in the background, showcasing the natural beauty of the surroundings.

Home in Newton

WATERFRONT-15 min to BOS/3BdRm/2BA

4.98 out of 5 average rating, 126 reviews

A wooden dock extends over calm waters, surrounded by lush greenery. Two red umbrellas provide shade over metal chairs. A blue inflatable float and a seating area enhance the inviting lakeside atmosphere. Steps lead down into the water from the dock for easy access.

Guest suite in Concord

Water front cabin-like guest suite on a quiet pond

Condo in Jamaica Central - South Sumner

A fully equipped kitchen features a spacious granite countertop with seating for four on elegant black bar stools. Natural light streams in from the nearby window, illuminating the fresh purple flowers arranged as a centerpiece.

4.9 out of 5 average rating, 257 reviews

Fully-Equipped 2nd Floor 1-Bed 1-Bath Apt

5 out of 5 average rating, 9 reviews

An aerial view captures several charming homes nestled along a lush green waterfront. A private dock extends into the water, surrounded by rocks and greenery. The scene conveys a serene landscape, blending nature and cozy residences complemented by gentle water reflections.

Home in Gloucester

Waterfront 4 bed/2 bath-Stunning Annisquam Sunsets

4.96 out of 5 average rating, 99 reviews

The exterior of the cottage is visible, showcasing natural wood siding and a brick patio leading to the entrance. Lush greenery surrounds the property, while a glimpse of Chebacco Lake is seen in the background, contributing to a calm and inviting environment.

Cottage in Essex

Lakefront cottage for a fun, relaxing getaway.

4.81 out of 5 average rating, 158 reviews

A wooden pathway extends over the serene Warner's Pond, framed by dense greenery and blooming flowers on either side. The tranquil water reflects the soft hues of sunset, creating a peaceful ambiance. Natural foliage provides a shaded area, inviting exploration and relaxation.

Townhouse in Concord

Dreamy Waterfront Oasis | 5★ Location, ♛Queen Beds