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

4.97 out of 5 average rating, 262 reviews

The charming entrance of the cottage is framed by vibrant greenery and colorful flowers. Two wooden chairs are positioned in front of the entrance, welcoming guests. A decorative flag flutters above the door, completing the inviting scene.

Guesthouse in Annisquam

Annisquam Village Bunny Cottage

This beautiful Annisquam Village cottage was renovated to the highest level of quality by two artist's. Located just 5 minutes from Lighthouse Beach, Cambridge Beach and Talise Restaurant. Bunny Cottage has beautiful gardens, is surrounded by water on 3 sides, and has peek-a-boo views of Wingaersheek Beach from the bedroom window. The house is charming, with top notch amenities, like, heated floors, air conditioning (indoor/outdoor living). Mass Dept. of Revenue Certificate Number: #C0022781070

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.

Guest suite in Gloucester

A charming beach house is nestled among tall grasses, with a welcoming deck visible on its front. Soft evening light illuminates the exterior, highlighting the inviting atmosphere of the home. A sandy path leads from the beach to the house, suggesting easy access to the shore.

4.98 out of 5 average rating, 424 reviews

SplashLanding Private Beach Getaway in Gloucester

Jan-March 2025 monthly rentals. Must Book Summer 2025 via Airbnb website not the APP! *Can't find an opening in SplashLanding? Our 2nd unit SquishInn has openings June-Oct 2024 airbnb.com/h/squishinn-gloucester-ma Long walks on a private beach. Get sun-kissed; toes in the sand. Romantic dinners on the deck. Cozy in Winter (Energy Star home and Radiant heat throughout). TRAVELING WITH ANOTHER COUPLE? Book Private Beach Getaway SquishInn. Our 2nd unit for adult couples 2 friends can join you!

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, 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, 117 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).

4.98 out of 5 average rating, 182 reviews

A bright interior is showcased with large glass doors opening to scenic harbor views. A cozy seating area includes a gray sofa and armchair, while a circular table with turquoise chairs invites dining or leisure. Soft light hangs from a stylish ceiling fixture.

Condo in Rockport

Bearskin Neck Rockport ★ Amazing Views ★ Parking

From the deck of this New England vacation retreat enjoy amazing views of Rockport Harbor and the iconic Motif #1. Steps from delightful shops, restaurants, and ice cream/coffee, this recently updated 1-bedroom, 1-bathroom condo with rare, on-site parking is located in the heart of Rockport on Bearskin Neck. Enjoy beautiful ocean breezes with coffee or cocktails on the deck of this sweet beach retreat nestled on the N.E. coast. Come fall in love with charming Rockport!

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!

4.95 out of 5 average rating, 171 reviews

The living area features a stone fireplace and a flat-screen television mounted above. The space includes a mix of comfortable seating, such as a blue sofa and patterned armchairs. Exposed wooden beams and a spiral staircase add architectural interest to the cozy environment.

Cottage in Stow

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.

4.98 out of 5 average rating, 140 reviews

Guest suite in Scituate

Beach Garden Studio

Beautiful studio in Scituate Harbor for one or two. All the conveniences in one small space. Private entrance and bath with views from your private deck and patio. Walk to EVERYTHING. Many great restaurants and shops. Queen size bed. (Some of the older reviews may mention the sleeper, which we replaced with a queen bed.)

Vacation rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Houses

A space thats all yours, with room for everyone

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

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Private vacation rentals in Boston

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

4.94 out of 5 average rating, 152 reviews

Home in North Andover

Nana-tucket Inn

4.95 out of 5 average rating, 21 reviews

A spacious deck offers panoramic ocean views with comfortable seating arrangements. A dining table is set with place settings, inviting guests to enjoy meals outdoors. The calm waters and distant shoreline create a serene coastal atmosphere, enhancing the outdoor experience.

Home in Annisquam

Beach House on a Private Beach!

4.97 out of 5 average rating, 125 reviews

A lighthouse is visible standing on a rocky shoreline, surrounded by calm waters. The structure features a white tower topped with a green lantern. In the background, a house is nestled among trees with a clear view of the lighthouse.

Cottage in Gloucester

Sunny & private cottage in Lanesville Village

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

4.84 out of 5 average rating, 31 reviews

Apartment in Brighton

The Curie-Perfect for Monthly Stays

4.98 out of 5 average rating, 45 reviews

Cottage in Scituate

"Shore Bet" Humarock Beach Cottage - Scituate

4.97 out of 5 average rating, 100 reviews

A private outdoor deck is set against a serene pond, surrounded by lush greenery and trees. A pathway of stepping stones leads from the deck to the water's edge, inviting guests to enjoy the peaceful natural surroundings.

Guesthouse in Westford

Detached Waterfront Guest House

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Boston waterfront vacation rentals

4.93 out of 5 average rating, 133 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

4.95 out of 5 average rating, 133 reviews

A small wooden deck offers a view overlooking Lobster Cove, featuring a bottle of wine with two glasses set on the railing. Surrounding greenery and nearby houses complement the serene water view, with a clear sky enhancing the scene.

Home in Annisquam

Views over Lobster Cove! July 4 week still open!

4.98 out of 5 average rating, 176 reviews

The full kitchen features modern appliances, including a stove, oven, and refrigerator. A dining table and window seat provide water views, while a cozy sitting area with a loveseat and a swivel chair invites relaxation. Natural light floods from large windows.

Apartment in Rockport

Waterfront Escape! In-town with onsite parking

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.

4.99 out of 5 average rating, 121 reviews

A spacious family room features large windows offering panoramic ocean views. A modern kitchen island with a marble countertop is complemented by four beige chairs. Natural light illuminates the room, highlighting the comfortable seating area and subtle decorative elements.

Apartment in Rockport

4 Bed 2.5 Bath Water view Downtown with 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.

4.89 out of 5 average rating, 183 reviews

Apartment in Rockport

The Waterline – A Private Harborfront Retreat

4.93 out of 5 average rating, 153 reviews

A two-story white house rests on rocky terrain near the water’s edge. Large windows and a four-season porch are visible, allowing for scenic views. The structure is elevated on stilts, with greenery framing the property and a calm harbor in the background.

Home in Gloucester

Wonderful Rocky Neck home on Gloucester harbor

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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!

4.97 out of 5 average rating, 188 reviews

The exterior of a spacious guesthouse showcases a blend of siding and stone finishes. A paved driveway leads to a two-car garage. Lush greenery and flower beds enhance the inviting entrance, while multiple windows allow natural light to fill the interior.

Guest suite in Sharon

Cozy Lakeview Guesthouse

4.84 out of 5 average rating, 577 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, 255 reviews

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

5 out of 5 average rating, 9 reviews

A private dock extends over gentle waters, complemented by two kayaks in a vibrant blue hue. The sun sets in the background, casting warm light across the scene, while a floating raft drifts nearby amidst lush greenery lining the shore.

Home in Gloucester

Waterfront 4 bed/2 bath-Stunning Annisquam Sunsets

4.81 out of 5 average rating, 157 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