Vacation rentals in Holliston

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Top-rated vacation rentals in Holliston

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Top guest favorite

The kitchen features modern appliances and a central island with seating for five. Light-colored cabinetry and a mosaic tile backsplash complement the dark granite countertops. Pendant lights illuminate the workspace, while a large window brings in natural light.

Home in Holliston

4.97 out of 5 average rating, 86 reviews

All New Private Country Setting (2 Level-No Share)

We built this 2 level home 6 years ago and it is located on Washington St in the towns Historic district. The home is set back from street with a long country style driveway. We designed it with large windows in all rooms, welcoming the sunlight and peaceful setting. Access to clean and empty garage for storage (No parking). We have no personal items in the guest level - all closets and dressers are empty and yours for full use! Co Host reside in lower separate entrance suite. Nothing Shared.

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Home in Framingham

4.98 out of 5 average rating, 244 reviews

2BR—Lovely 1900s Home—1200sqft—25 Min to Boston

Welcome to our Charming 1900s House! 1200sqft 2nd/Top Floor Private Apartment @ our 3-Rental Property **Children 10+ Welcome** Granite Kitchen w/ Dishwasher - Fully Equipped w/ Essentials & Cookware Tiled Bathroom w/ Bathtub & Shower 2 Queen Bedrooms 2 Desks & Chairs Reclining Sofa & Glider Loveseat Laundry Room (Basement) Patio & Grill Driveway Parking—2 Spaces Private Entrance 25 Min Drive to Boston 15 Min Walk to Train 5 Min Walk to Jack's Abby 3 Min Walk to Park Deep Cleaned & Sanitized

Top guest favorite

The exterior of a historic home is surrounded by tall trees, with a gentle slope of green lawn leading to the entrance. A spacious garage is visible on the right. The sky is painted in soft hues, indicating sunset.

Guest suite in Dover

4.97 out of 5 average rating, 260 reviews

Peaceful Country Home, Dover, Ma: Private Entrance

Graceful country oasis in a renovated 125 year old historic home, 35 minutes driving time from downtown Boston. (Important-stair climbing required to reach bedroom suite.) I welcome quiet, mature guests as this is a very peaceful (non-party)environment. We are located on a scenic road in sophisticated Dover, Ma, a commuter/country setting, with miles of hiking trails and roads ideal for cycling. I have owned and loved this home for 35 years and take great joy in its charm and outdoor spaces.

Top guest favorite

A sign indicating 'The 1780 Suite Guest Parking' is softly illuminated at dusk. The sign is surrounded by a small arrangement of greenery and decorative elements, creating a welcoming entrance point for guests arriving at the property.

Guest suite in Uxbridge

4.97 out of 5 average rating, 191 reviews

The 1780 Suite

Join us for a step back in time at our unique bucolic property. Set on a scenic road, the post and beam farmhouse was built in 1780 and offers a haven of peace and tranquillity after a busy day of exploring New England. Guests have a private entrance and wind their way up the period staircase to the second-floor suite with two bedrooms, a sitting room, a breakfast nook, and a bathroom. Enjoy your morning coffee outside on the Adirondack chairs as you contemplate the charms of country living.

Top guest favorite

An inviting living space features exposed beams and a spacious layout. A comfortable sofa and accent chair provide seating, while a rustic coffee table anchors the area. A large farmhouse dining table with seating for six is positioned nearby, surrounded by artwork and natural light.

Place to stay in Sherborn

4.97 out of 5 average rating, 297 reviews

Entire Historic Carriage House with Fireplace & AC

Escape to our charming Carriage House in the Historic District of Sherborn which offers the feel of a country retreat without being far from civilization. Great for travelers looking for a peaceful getaway, checking out nearby colleges or attending a celebration like a wedding or graduation. You will love the feel of the Carriage House, its spacious living and dining room, well-equipped kitchen, and the beautiful grounds. Check us out on IG @carriagehousema. NEW in 2022: Mini-split AC!

Superhost

A well-organized surface displays a circular mirror and a decorative tissue box featuring purple flowers. Nearby, clear bottles are neatly arranged in a green wicker tray, accompanied by a small metallic container and a stack of paper coasters.

Apartment in Franklin

4.91 out of 5 average rating, 201 reviews

Bright Charming Serene Home in City Center

Welcome to the Orange House! We're located at the City Center, close to everything. Just minutes walk to Train Station, Shopping Centers, Restaurants, Museum, Theater House, Libraries, Dean College, Trail & Tracking. Few minutes drive to Gillette Stadium, Wrentham Premium Outlets, Plainridge Casino & Boston Marathon Starting Point. You can easily visit Boston, Providence & Worcester, too! Our place is good for couples, business travelers, small groups & families. Lock on bedroom doors.

Guest favorite

A vintage camper is nestled among lush greenery, surrounded by tall trees that create a serene and secluded environment. The reflective surface of the camper blends harmoniously with the natural backdrop, offering a picturesque camping experience in the woods.

Camper/RV in Millville

4.91 out of 5 average rating, 228 reviews

Vintage Americana style camping - 1950 Spartanette

If you enjoy CAMPING, you will love sleeping in a vintage camper! It's springtime, the birds are singing and the peepers are peeping. Come cozy up at the fire pit to a warm campfire and roast marshmallows. We provide plenty of firewood to build a nice campfire. The camper is safely located on our property and has beautiful views of the woods. Plenty of fresh drinking water is provided. Queen bed. NO SHOWER or Running water. Portable toilet. Heat. Grill. WIFI spotty while in the camper.

Top guest favorite

A serene view from large glass doors reveals a tranquil outdoor area, featuring green grass and trees. A sand garden with small statues occupies the foreground, while a rustic structure and walking path are visible in the background.

Guest suite in Uxbridge

5 out of 5 average rating, 237 reviews

Zen Inspired Retreat with Private Forest Trails

Zig-Zag Trails blends modern comfort with the charm of rural living. Set on 65+ acres of private meadows and forests, our master guest suite is the perfect retreat to relax and recharge. Explore scenic zig-zagging trails, perfect for hiking, mountain and E-biking, and unwinding in nature—a haven for outdoor enthusiasts and homebodies alike. 📍 1 hour from Boston 📍 35 minutes from Providence 📍 25 minutes from Worcester Escape to Zig-Zag Trails—where tranquility meets adventure.

Guest favorite

A heart-shaped hot tub is nestled beside a sparkling swimming pool. The clear water reflects the surrounding greenery. A dog rests comfortably on the edge of the hot tub, observing the tranquil scene. Loungers are positioned nearby for relaxation.

Apartment in Holliston

4.96 out of 5 average rating, 121 reviews

Lake Link

Beautiful fully stocked 2 BR apartment located in Holliston Historic District. Top of the line swimming pool with waterfall and hottub (May 31-Sep 30). Full kitchen, full bath, washer/dryer, central heat and AC, fireplace, wireless internet, Cable TV with almost all premium channels available, private driveway and entrance. Sorry, but no pets allowed. Note: COVID19- We require all eligible guests to be vaccinated or have 72 hr negative test.

Guest favorite

The treehouse is elevated on wooden stilts, surrounded by vibrant autumn foliage. Large windows reflect warm light, showcasing a rustic wooden exterior. A staircase leads up to the entrance, inviting guests to explore this serene retreat among the trees.

Treehouse in Willington

4.91 out of 5 average rating, 444 reviews

Treehouse - Countryside - Farm Animals - Fire Pit

Superhost

Apartment in Milford

4.87 out of 5 average rating, 153 reviews

Milford, spacious and bright first floor

Light and bright first floor unit, 3 bedrooms, I bath, with laundry, large bedrooms and an eat-in kitchen can accommodate six people. Close to everything, has off street parking available and would be great for a holiday stay or a staging location for the Boston Marathon in April!!

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Popular amenities for Holliston vacation rentals

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Other great vacation rentals in Holliston

Top guest favorite

The kitchen features modern white cabinetry and stainless-steel appliances. A large island with seating allows for casual dining. Large windows provide natural light, and a door offers access to the outdoor area. A clock adorns the wall, adding a functional detail.

Guesthouse in Foxborough

4.96 out of 5 average rating, 163 reviews

Bates Boutique ☆ Home Away From Home

NoraRating, 5 stars2 days ago

This is the second time we have stayed at Rodney’s place and have another weekend already scheduled for August. It is a great set up for my family when we are in town visiting other family. Nice quiet neighborhood and easy to get to highway to get places. The house is very clean and he recently added a covered outdoor lounge space that was very comfortable and private to sit and enjoy the outdoors. Rodney was able and willing to be flexible when we realized we needed to extend the trip to include a day before and a day after the original reservation. We will definitely stay there again!

A well-lit hallway leads to a bedroom featuring a dresser and natural light from the windows. A full-length mirror is positioned along the wall, and a bathroom entrance is visible, showcasing a clean and functional design.

Guesthouse in Holliston

4.5 out of 5 average rating, 10 reviews

Charming 1850s Renovated Home Downtown Holliston

AnnaRating, 5 stars4 months ago

Alex’s house in Holliston was perfect for me and my family on our long weekend stay! The hours has an excellent location, with a short walk to coffee shops, the walking trail, and Main Street. The house itself was a generous size for us - two adults, an almost 3 year old, an infant, and our dog. Having two floors and a bathroom on each floor, our toddler could sleep soundly regardless of activity downstairs. Comfy couch and beds. Host was easily reached as needed and very helpful. Highly recommend!!

Guest favorite

An aerial view captures a serene landscape featuring a calm lake surrounded by vibrant autumn foliage. A building is visible against the backdrop of trees in warm, fall colors, reflecting beautifully on the water's surface.

Guest suite in Marlborough

4.87 out of 5 average rating, 285 reviews

Professional Accommodations!

JohnRating, 5 stars1 week ago

Great host. This was my first time at an abnb and he did everything to make me feel at home. 10plus stars

Top guest favorite

The exterior of the cottage showcases a spacious patio area with outdoor seating, including several white chairs and a table. Lush greenery surrounds the property, with a clear view of the lake in the background. Natural light illuminates the space, enhancing the relaxing atmosphere.

Cottage in Norton

5 out of 5 average rating, 18 reviews

Lakeside Cottage

JacquelineRating, 5 stars1 week ago

This place was incredibly beautiful and peaceful no matter what time of day it was. The space felt spacious, private and clean, making it extremely easy to relax and settle in. It is also very close to the Xfinity center while being far removed from the chaos that comes with it. I cannot recommend that you stay here enough!

Top guest favorite

An outdoor patio area features a covered dining space with a wooden pergola, surrounded by comfortable seating. A sleek grill is positioned nearby, and potted plants add greenery to the stone tiles. The space is well-lit by natural sunlight filtering through surrounding trees.

Private room in Northbridge

4.98 out of 5 average rating, 177 reviews

Japanese-themed B/R In A Quiet & Cozy Country Home

HannahRating, 5 stars1 week ago

Stayed here for over a month for work. I had a nice peaceful stay. Chelle and David were excellent hosts! It was always clean and they gave me some good recommendations of things to do in the area. If I'm ever back in that direction I would gladly book again.

Guest favorite

A scenic view of Dudley Pond is framed by lush greenery and tall trees. The calm water reflects the surrounding landscape under a clear blue sky, offering a peaceful retreat. A wooden deck is partially visible, providing a space to enjoy the natural surroundings.

Apartment in Wayland

5 out of 5 average rating, 14 reviews

Cozy lakeside retreat

NatashaRating, 5 stars1 week ago

Carrie and Craig were awesome hosts and the pictures of the Airbnb don’t do justice to how beautiful Dudley Pond is! My husband and I were in town for 2 nights for a wedding and we really enjoyed staying here! The well stocked fridge with welcome drinks and bars was an added bonus and we loved kayaking on the water (they also have a paddle board that we didn’t get a chance to use). Such a fantastic retreat and would love to visit again soon :)

Top guest favorite

Guest suite in Uxbridge

4.99 out of 5 average rating, 350 reviews

Beautiful, Unique, & Cozy Cedar Flat

TammiRating, 5 stars4 days ago

Love staying at this property. Always have everything we need and more!! Great hosts!!! Our home away from home!!

Guest favorite

A functional laundry room is presented with two washing machines and a dryer, positioned against the far wall. Shelves above hold various laundry supplies. A door leads outside, and a bright overhead light illuminates the space. The room features light-colored walls and a neutral floor.

Private room in Hopkinton

4.88 out of 5 average rating, 164 reviews

Bedroom with Private Full Bath in Quiet Town

TakatsuguRating, 5 stars1 week ago

Chhitiz and his family are very friendly and welcoming folks. I felt at home when I arrived this place. Clean, quiet and cozy place. I highly recommend!

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Vacation rentals in Holliston

Top-rated vacation rentals in Holliston

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Popular amenities for Holliston vacation rentals

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