Vacation rentals in Holliston

4.83 out of 5 average rating, 322 reviews

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

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

LiviaRating, 5 stars3 weeks ago

I had an amazing stay! The place was clean, well-organized, and had everything we needed. The location is great, just a short walk to lots of restaurants and coffee places, making it easy to explore. All the pictures are accurate. Highly recommend!

4.95 out of 5 average rating, 20 reviews

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

Button Beach Cottage

Kevin Rating, 5 stars1 month ago

Location, location, location! What a wonderful place to stay! A block from the best beach in Massachusetts. Plenty of space to feel right at work. Supermarkets and restaurants are nearby and the host is amazing! You can’t go wrong renting at 18 Buttonwood! Thank you again!

4.98 out of 5 average rating, 144 reviews

Cottage in Oakland Beach

Renovated cottage w water views and walk to beach

Emily DianaRating, 5 starstoday

Angela and her husband Jim were very friendly, sweet helpful and very accommodating. I highly recommend staying at their house in the beautiful quaint beach neighborhood of Warwick. One thing that stood out was the house did not smell like heavy and scents. I am a stage three cancer survivor so I live a nontoxic lifestyle. I liked how the bath towels and the bedding And the furniture did not smell like heavy chemicals/scents for me and my toddlers. The house was clean, beautiful and so cozy. My toddlers had a blast, and it was hard for everyone to leave. 10/10. I’ve traveled the world and I’ve stayed at many Airbnb‘s I loved this house :)

4.92 out of 5 average rating, 36 reviews

Cottage in Westford

Beach & pond cottage ! Westford MA and Boston!

MelanieRating, 5 stars6 months ago

We had an absolute blast on our girls getaway weekend!! The cottage and community were amazing, exactly what we were hoping for and Doug couldn't have been nicer or more helpful. He was always available by text or phone. The cottage was clean, nicely equipped, and a great location!! We will definitely be renting this cottage again on our next trip!!! Thanks for having us... we loved every minute!! 🧙🧙🧙

4.83 out of 5 average rating, 60 reviews

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

Sand Hills Barker Tavern RiverClub lighthouse -

KimberlyRating, 5 stars1 month ago

Stayed here with a few of my friends for a wedding and the place was perfect! Really close to the Barker House wedding venue, walkable to downtown Scituate. Beds were very comfy and the place was very clean. Overall, a great stay!

5 out of 5 average rating, 20 reviews

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

Coastal Retreat

RachelRating, 5 stars2 months ago

Our stay at this lovely Scituate Coastal Retreat was fabulous. The house was immaculately clean and the decor was perfection. The common areas were cozy, but spacious and the kitchen was well stocked with any tools/utensils we needed. Beds were comfortable and our party of 4 adults had plenty of room. The hosts left great suggestions for local dining and the house was only a 2 min drive (15min walk) to downtown Front St restaurants and shopping. Host Andrew was very responsive and wonderfully accommodating, allowing for a later check-out when requested. We were staying in the Winter, so perhsps check out time may not be as flexible in the warmer months. Check-in & check-out was a breeze! We hope to rent this property again. Thank you Andrew & Madeline!

5 out of 5 average rating, 21 reviews

A modern beachfront home is illuminated against a twilight sky, highlighting its multiple gabled roofs and large windows. The structure is elevated with an expansive porch and a staircase leading to the upper level, surrounded by well-maintained greenery.

Home in Fairhaven

Stunning Luxury House with Sunset & Private Beach

SerenaRating, 5 stars1 week ago

We wouldn’t hesitate to stay at Bill’s place again. The private beach was amazing. The views were stunning and the outside well well equipped with furniture. The house itself was beautiful. Updated and spacious. The kitchen had everything you could possible need for a gourmet meal. Sometimes when we rent houses, they are poorly equipped. Not this one. It was such a relief. The neighborhood was great and the next door neighbor was very friendly. The area has a lot of restaurants and stores, so everything is close by. Bill was very communicative and quickly responded to any inquiries. He was a great host. Honestly I have nothing bad to say.

Vacation rentals for every style

Get the amount of space that is right for you

Hotels

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Homes

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Popular amenities for Holliston vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Holliston's top sights

Ashland State Park8 locals recommend

Heritage of Sherborn7 locals recommend

Target6 locals recommend

Coffee Haven5 locals recommend

Fiske's General Store4 locals recommend

Muffin House Cafe4 locals recommend

Other great vacation rentals in Holliston

4.81 out of 5 average rating, 108 reviews

A functional kitchen features light gray cabinetry, a white countertop, and essential appliances, including a refrigerator and stove. A window allows natural light to brighten the space. Two stools are positioned at a bar counter, providing additional seating in the open layout.

Apartment in Revere

Home away from home Beach,Logan,Encore, DownTown

LucasRating, 5 stars3 months ago

I felt at home, the host was very kind, respectful and responsive. Great neighborhood, near to the Logan Airport, shopping centers and restaurants. The house is very clean and well arranged. It’s also very peaceful. We had so much fun staying there.

4.94 out of 5 average rating, 127 reviews

A rustic wooden structure is set against a vibrant blue sky, reflected in the calm waters below. The building features large windows, a clock façade, and a wraparound porch lined with potted plants, surrounded by trees showcasing autumn colors.

Home in Westminster

Wachusett Mountain Get-Away

DaeshaRating, 5 stars3 months ago

It was a pleasure staying here ! Everything is clean and the house is such a nice size !

4.86 out of 5 average rating, 7 reviews

Home in Mattapoisett

5 Blocks to Beach+Town, Stocked Kitchen, Cozy Beds

DavidRating, 5 stars2 months ago

Caitlin was a wonderful hostess, and the house was very nice. I would definitely recommend if you were going to be in the area.

5 out of 5 average rating, 7 reviews

A two-story, light blue house is shown, featuring a well-maintained landscape with shrubs and small trees. A stone wall borders the property, and a concrete walkway with steps leads to a wooden deck at the entryway.

Apartment in North End

Beautiful and spacious lovely home

ChrisRating, 5 stars3 weeks ago

Place worked out perfect

4.95 out of 5 average rating, 21 reviews

A bright bedroom features a spacious bed dressed in crisp white linens. Three windows offer panoramic views of the water, allowing natural light to fill the space. A white shelving unit stands to the side, enhancing the room's functionality.

Home in Hull

Every room a water view updated kitchen & bath

JohnRating, 5 stars3 months ago

Excellent experience. Easy check in and the place was perfect, she even had some snacks waiting for us upon arrival. Easy walk to the ferry into Boston, and easy parking. It was winter, but there were plenty of outdoor activities so we'd love to come back during the summer. Older house but so charming and great location. Overall great communication before, during, and after; she even offered to ship a shoe my niece left behind to us. Would love to come back and would absolutely recommend to anyone looking for a great place in Hull.

4.84 out of 5 average rating, 31 reviews

Apartment in Brighton

The Curie-Perfect for Monthly Stays

XuemeiRating, 5 stars1 week ago

This apartment is a great find! The location is perfect, not far from Boston, near every colleges for those who come visiting! This apartment building is indeed very new, built in 2021; but also blended in with history, the leasing office/lobby was converted from an old day chapel, pristine, elegant. Very unique Airbnb experience indeed. The small town is full of vibe with various kinds of cuisines, very good for families, young or old. Melissa, the host is super, giving us very detailed information and instructions from parking to checking in, every tiny details she thoughtfully considered. We couldn’t be happier to stay in this apartment. Highly recommended!

4.93 out of 5 average rating, 14 reviews

Three turquoise Adirondack chairs are positioned on a grassy area, offering a view of a natural pathway lined with trees. The scene is brightened by natural light filtering through the leaves, creating a serene outdoor environment.

Home in Wareham

Private home, secluded 6 acre lot with water view

JaredRating, 5 stars7 months ago

Rebecca’s house in Wareham was a blessing! She is an attentive and responsive host, any concerns I had she was able to resolve immediately. We found ourselves wishing we had booked a longer stay to enjoy everything there was to offer!! Thank you Rebecca!