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.

Top guest favorite

Home in Framingham

4.98 out of 5 average rating, 245 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, 261 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.

Guest favorite

Guest suite in Franklin

4.89 out of 5 average rating, 164 reviews

Cozy, Cute & Charming In-Law Apt w/Private Access

Cozy, Cute & Charming In-Law Apt w/ Private Access & Parking in Franklin City Center. Everything is within walking distance. It’s perfect for couples, solo adventures and business travelers. Just minutes walk to Train Station, Shopping Centers, Restaurants, Museum, Theater House, Libraries, Dean College, Trail & Tracking. Few minutes drive to Gillette Stadium, Wrentham Outlets, Xfinity Center, Boston Marathon Starting Point. You can easily visit Boston, Providence, Newport & Worcester, too!

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!

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, 239 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.

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Home in Holliston

4.83 out of 5 average rating, 155 reviews

Spacious, cozy and quiet Cabin style house!

Spacious, cabin style house. Perfect for large families or big groups. Exposed wooden beams and ceiling gives it a warm cozy cabin like feel. Big kitchen with lots of counter space. Stretch dining table that’s great for big dinners. 2 open concept loft style living room spaces. 3 bedrooms and 3 baths. Located in the suburbs right next to Pinecrest Golf Club. Great place to get away from the city. This is not a cabin, its a cabin style home. Mass Certificate Number: C0124661360

Top guest favorite

A sleek kitchen countertop is featured, showcasing a stainless steel sink with a polished faucet. Above, a microwave is positioned, reflecting natural light. The dark granite surface adds elegance to the workspace, complemented by nearby kitchen essentials.

Apartment in Framingham

4.96 out of 5 average rating, 266 reviews

Comfortable apartment in Framingham

Newly renovated basement apartment. Private entrance and living space which includes a kitchen, bedroom, hallway and bathroom. The kitchen has a microwave and refrigerator, but no stove. Very clean and well maintained. Comfortable queen size bed. Driveway space for 1 car and plenty of street parking. Great location. Walking distance to Dunkin' Donuts, Domino's Pizza, and local shops. Less than 2 miles from the Mass Pike. No Pets / No Smoking inside

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.

Top guest favorite

A private wooden deck is accessible via a small set of steps, featuring a railing for safety. The area is bordered by a wooden fence, and lounge chairs are arranged for relaxation. Green grass and shrubs surround the deck, enhancing the natural setting.

Guesthouse in Framingham

4.97 out of 5 average rating, 282 reviews

Private guest house on beautiful country road

Welcome to Grove Street Studio - our detached guest house which sits right behind our home on one of the most beautiful streets in the area. This two-room studio has everything you need for a comfortable stay including your own deck looking out to the woods behind. Perfect for for a hotel alternative for someone working temporarily at nearby businesses.

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Other great vacation rentals in Holliston

Guest favorite

A stairway with dark wooden railings leads up from the lower level. A modern washer/dryer unit is situated beside a vintage radiator, both positioned on polished wooden floors. The wall features an archway, integrating the functional laundry space with the overall design.

Apartment in Framingham

4.93 out of 5 average rating, 15 reviews

Nice, Quiet, down town studio #2A

FainaRating, 5 stars2 months ago

Comfortable place in a great location. Exactly kind of place I was looking for to stay for a week at the great price. Easy parking.

Top guest favorite

A spacious living area is displayed with light gray walls and large windows allowing natural light. A cozy sofa with decorative pillows is centered, complemented by a light area rug. A spiral staircase is visible in the background, leading to the upper level. Seasonal decor is subtly included.

Private room in Natick

4.97 out of 5 average rating, 102 reviews

Chateau Bro H2O Located on Lake Cochituate

KatherineRating, 5 stars3 weeks ago

We had a great stay at Rob and Kristin’s airbnb! Very clean and spacious, beds were comfortable, and we had everything we needed for a few nights stay. It was also conveniently located in a safe neighborhood.

Guest favorite

An open kitchen area is showcased with modern cabinetry and granite countertops. Two stylish bar stools are positioned at the kitchen island. Natural light streams through large sliding glass doors that lead to an outdoor balcony, enhancing the spacious atmosphere.

Private room in Northborough

4.95 out of 5 average rating, 158 reviews

Swan Home with warm vibes - Guest BR & Pvt Bath

PeterRating, 5 stars1 week ago

Very nice place to stay. Quiet and peaceful. Hosts are friendly and responsive to any needs.

Top guest favorite

A charming two-story yellow house is showcased, featuring black shutters and a welcoming front porch. The porch is adorned with hanging plants and flanked by manicured greenery, creating an inviting entrance set against a well-kept yard.

Private room in Westborough

4.98 out of 5 average rating, 749 reviews

Elegant Rooms in My Antique Home

MattRating, 5 stars3 weeks ago

An awesome place for us to stay after moving to Worcester! Cute and comfortable. Philomena was incredibly responsive and accommodating for our late check-in. Extremely comfortable & private accommodations.

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, 178 reviews

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

HannahRating, 5 stars2 weeks 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