Vacation rentals in Holliston

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Top-rated vacation rentals in Holliston

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favorite

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

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.

Guest favorite

A serene outdoor seating area is surrounded by lush greenery, featuring two dark wooden chairs and a small table. A natural landscape includes a gently flowing brook nearby, with a weathered bench positioned to enjoy the peaceful view.

Home in Plymouth

4.83 out of 5 average rating, 322 reviews

Historic 1 Bed/In Town/Best Location/Hot tub/deck

PLEASE DO NOT BOOK WEEKENDS/HOLIDAYS/SUMMERS in advanced. I only use this 1 bed to fill gaps when the larger listing for this home isn't rented (mostly midweek) Beautifully restored historic home, directly in town, steps away from the Pilgrims 1st settlement, ocean, award winning restaurants, historic attractions, shops, nightlife, entertainment, tours,ferries, etc. Directly on the town brook/gristmill. Deck with view, firepit, hot tub, grill. Comfortable/clean/cozy bed, working wood stove.

Guest favorite

A wooden deck overlooks Johnson's Pond, with a table at the center surrounded by four chairs. Two red cushioned rocking chairs provide a comfortable seating option, and a vibrant red umbrella offers shade. Lush green trees frame the serene water view.

Home in Coventry

4.86 out of 5 average rating, 131 reviews

Awesome 3 bed vacation lake house. Great location!

Three bedroom house right on Johnson’s Pond with private water access right in the back yard. House features queen master with deck overlooking the pond. 2nd bedroom features a full bed with twin bunk bed above along with a stand alone twin bed. 3rd bedroom has a queen bed. Perfect for one or two couples to share. Full kitchen and laundry along with WiFi and streaming services. Use of 2 kayaks and pedal boat. Just two miles from I-95, so everything in southern New England is just minutes away!!

Guest favorite

A sandy beach extends along a calm ocean, where gentle waves lap at the shore. Rocky formations are visible in the water, and a clear blue sky overhead enhances the serene coastal view.

Home in Scituate

4.95 out of 5 average rating, 20 reviews

Button Beach Cottage

Capture the breeze of the coast at Button Beach Cottage! •5 min walk to beach. •Brand new remodel. •Family friendly. •Oceanview balcony. •Luxury bunk room. •Dedicated workspace. •Outdoor dining area on spacious deck directly off kitchen. •Access to lifeguard beach Primary BR: king bed, TV, reading nook, ocean view & balcony. BR #2: queen bed, dedicated work space, ocean view & balcony. Bunk room: 5 twin beds with play space. Full bath on each floor. Tub, standing shower, washer & dryer.

Guest favorite

Cottage in Oakland Beach

4.98 out of 5 average rating, 142 reviews

Renovated cottage w water views and walk to beach

This beautiful cottage has waterviews from most rooms. 1st floor has 4 season porch, Living room opens to white kitchen w quartz countertops, dining area , bedroom and 1/2 bath. 2nd floor has 2 bedrooms & full bath with laundry. Outdoor sitting at Small table in the front garden & Adirondack chairs in the backyard. 1/2 block to the beach, kayak, fishing, boat launch, cafe & 2 restaurants. Home has been renovated w love and caring. No parties. Please be considerate of cleaning person.

Superhost

Cottage in Westford

4.92 out of 5 average rating, 36 reviews

Beach & pond cottage ! Westford MA and Boston!

Summer Village resort is only 20 miles from Boston. Best of both worlds! Your New England style cottage is steps to the beach, Lodge restaurant & bar, heated pools (family & adult), hot-tub, playground, tennis/ basketball/ fire pits pocket parks, golf putt, fishing, 24-hr fitness center. You'll enjoy lake views of Long Sought for Pond from the sun-filled porch, sandy beach, nestled in a beautiful gated seasonal cottage community. CENTRAL A/C !! Queen beds, Bunk bed. Weber outdoor grilling.

Guest favorite

Home in Fairhaven

4.93 out of 5 average rating, 106 reviews

Cozy Beach House with 270° Spectacular Views

Enjoy your getaway at our elevated beach house, the Fairhaven Seaside Retreat! Named one of Fodor's Top Ten Airbnbs for Socially Distanced Getaways in 2020 for its seclusion, stunning views, and easy access to many of New England's vacation spots, our home is perfect for adventurous vacations, quiet retreats, or remote working. Featuring 270 degree views that include the Atlantic ocean and a protected state marsh, our cozy home is also close to local restaurants, grocery stores, and shops.

Superhost

A tranquil shoreline is depicted, featuring gently sloping grass leading to a calm body of water. Soft ripples reflect the blue sky and fluffy clouds. In the distance, a house is visible, framed by the natural landscape.

Cottage in Fairhaven

4.83 out of 5 average rating, 217 reviews

Cottage by the Bay

Cottage in Fairhaven, perfect for a vacation for a small family, a romantic getaway or a home away from home if you are in the area for business. Enjoy all a vacation has to offer. During warmer weather, walk to the public beach and boat ramp - swim, sun, boat. Spend evenings by the outdoor fireplace. When it is cold out side, enjoy parks, museums, arts and cultural events, with evenings spent enjoying hot chocolate in front of the gas stove as the fire blazes providing a cozy warmth.

Superhost

The image captures a serene beachfront with gentle waves lapping against sandy shores. Rocks line the edge of the beach, while a clear blue sky stretches overhead, merging with the tranquil sea. The distant coastline features various structures, enhancing the scenic view.

Home in Scituate

4.83 out of 5 average rating, 60 reviews

Sand Hills Barker Tavern RiverClub lighthouse -

Walking distance to sand hills beach - super close to BARKER TAVERN! One mile from center of town with restaurants and shops. Nearby basketball court. Grassy backyard . New furnishings new full bath and new mattresses. Freshly painted well maintained by owner bedrooms are upstairs. There is only one full bath upstairs Totally redone 2024. Bungalow beach style home. some guests find stairs to be “ steep” … my 82 year old mom does fine with the stairs and rail!

Top guest favorite

A harbor scene features numerous boats docked alongside wooden piers, with a small fuel dock prominently situated at the center. Lush greenery surrounds the area, and a soft, golden light fills the sky as the sun sets, creating a serene atmosphere.

Home in Scituate

5 out of 5 average rating, 20 reviews

Coastal Retreat

Welcome to our coastal rental, a charming retreat nestled in the heart of a vibrant beach town. With modern amenities and coastal decor, unwind in the light-filled spaces and savor beautiful marsh views from the well manicured backyard. Located about a mile from Main Street, you can walk or bike on the flat sidewalk to restaurants, shops and the harbor. Close by you'll also find a dog park, the beautiful public golf course, Widow's Walk and of course the beach!

Guest favorite

An expansive wooden deck features a large rectangular dining table surrounded by several chairs, suitable for outdoor gatherings. The space is bordered by greenery and offers a clear view of the surrounding landscape, creating an inviting area for relaxation.

Home in Middletown

4.86 out of 5 average rating, 29 reviews

Little Creek Retreat - RIBryan Property

Tranquil location near Pebble Beach, 3rd Beach, and Indian Ave, this 4-bedroom, 3-bath house offers privacy and seclusion on a 9-acre plot. It includes a master suite with an en-suite bathroom. The property is well-suited for families, featuring a hot tub, a fenced-in yard, and extra space available for children under 12. This home combines the comfort of expansive private grounds with the convenience of nearby coastal access, providing a peaceful retreat.

Guest favorite

A tranquil outdoor area is featured with a natural stone fire pit surrounded by stones and mulch. The calm lake is visible in the background, complemented by trees lining the shore, creating a serene outdoor space for relaxation.

Home in Plymouth

4.93 out of 5 average rating, 41 reviews

Serene Lakefront Retreat: Your Perfect Getaway!

Escape to our serene lake house with breathtaking views & endless opportunities for outdoor adventure. With a dedicated workspace, stay connected while enjoying tranquility. Take a paddle on the lake with kayaks & pedal boat, or relax on the patio with outdoor fire pit. Fully furnished & decorated, feel at home cooking in the fully equipped kitchen or curling up in the cozy living room. Book your stay today and experience the magic of nature firsthand!

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What guests are saying

Brand new! Whole apartment, huge tub, full kitchen

4.99 out of 5 average rating, 94 reviews4 days ago

Jennifer's home is perfect! From the lovely entrance to the interior of the home, everything is exactly as described in the listing. The bed is super comfortable and you will definitely get a good night's sleep there. The kitchen has everything you need to cook a meal and there is a lovely area outside to eat if you wish. The bathroom is beautiful and the shower has amazing water pressure. Basically a nice home away from home. I would recommend this place to anyone. We will definitely book again when in the area.

Apartment in Mattapoisett

What guests are saying

Lovely Day Oceanside

4.93 out of 5 average rating, 28 reviews3 months ago

"Lovely Day" was the perfect getaway we were hoping for. The place looked exactly like the photos showed: beautiful sun-filled front-room, nice spacious kitchen with an open concept, and the easiest access to a private beach. The place had two bedrooms (one with a queen-sized bed and one with a bed bunk) and a bathroom (with washer and dryer), so it's perfect for a family or a small group of friends. Maybe because it was winter but we were the only ones around, which made our time at the beach even that more enjoyable. Fairhaven is about 10mins away with enough services and restaurants, although we brought everything with us so that we wouldn't have to rely on those. Do note that the exterior and interior walls are a little thin, in case you're sensitive to noise. Overall, a wonderful and peaceful retreat.

Home in Fairhaven

What guests are saying

Village Colonial with Cohasset Harbor Views

4.91 out of 5 average rating, 32 reviews3 weeks ago

This is a beautiful and spacious home with New England charm and in a great location. The house looks exactly as pictured and was spotless. The rooms were well appointed with lots of space to sit and relax. It’s perfect for visiting this beautiful area of MA. Michael is a responsive and helpful host and very considerate of his guests. We would absolutely stay again and can highly recommend this home for your stay. Five star all the way.

Home in Cohasset

What guests are saying

Cottage @ Partridge Pond

5 out of 5 average rating, 59 reviews2 months ago

Todd was so great to work with. Extremely responsive and helpful! His place was so cute, very clean and very well appointed. It has everything you could ever need and very organized. We rented it to ski at Wachusetts and it was great location( only 15 mins away). We would rent again. Thank you!

Cottage in Westminster

What guests are saying

Lakefront Home With a Great Views for Every Season

5 out of 5 average rating, 14 reviews4 months ago

We traveled up from Florida to visit family in RI & MA for Thanksgiving and stayed in the lake house. After a very long drive, it was so lovely checking in to a bright, clean, peaceful house. Everything is brand new and well appointed. Jolene was so responsive on the week leading up, flexible with our arrival time and had great local recommendations. After we arrived she stopped by with flowers to welcome us. We lived in Rhode Island for 40 years and I had never been to that area of the state before! While it feels like a peaceful retreat, the little village center is about 2 miles away and has grocery, cvs, Dunkins, and a brewery among other things. We also drove a few minutes further to one of the oldest country stores in America. The fire pit was fun for the kids to make s’mores and we enjoyed playing all of the games every night. It was a great Airbnb stay and we will definitely be back again to enjoy it in the warmer weather!

Home in Burrillville

What guests are saying

#1 Top Flr Waterview|Lux Design|Pvt Balcony

5 out of 5 average rating, 32 reviews1 week ago

Darryl’s place is in a perfect location to easily walk around Beverly and with a car access Salem and the surrounding area. There’s also a train within walking distance and quick access to Boston. Darryl‘s place itself is definitely a home away from home with everything you need to be comfortable. Darryl himself is immediately responsive and has great local tips. Looking forward to staying again!

Apartment in Beverly

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