Vacation rentals in Holliston

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Top-rated vacation rentals in Holliston

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Guest favourite

Home in Framingham

4.89 out of 5 average rating, 246 reviews

1BR—Bright & Cozy 2-Level Home — 25 Min to Boston

750sqft One-Bedroom, 2-Level Apartment @ our 3-Rental Property 1st Floor: —Fully Stocked Granite Kitchen w/Dishwasher + Essentials & Cookware —Living Room w/Queen Sofa Bed & Dining Table 2nd Floor: —Bedroom - Queen Memory Foam Bed + Full Length Mirror —Bathroom - Shower/Tub —Desk & Chair + Wardrobe Backyard Patio Laundry Room (Basement) Driveway Parking 25 min to Boston 15 min walk to Train 5 min walk to Jack’s Abby Brewery 3 min walk to Park/Playground Cleaned & Sanitized/COVID Conscious Host

May 1 – 8

$249 CAD per night

Guest favourite

Apartment in Framingham

4.92 out of 5 average rating, 259 reviews

Spacious 2 Br with All The Comforts Of Home

This a quaint apartment . Not your typical hotel room. In a country setting but 5-10 minutes from great shopping, restaurants, parks, colleges and major highways. Boston is 22.5 miles away. Fenway Park is 20 miles. Worcester is 17 miles. Private location overlooking conservation land. Walk to great hiking and biking trails but car needed for other activities. Full kitchen, laundry room and living room in addition to 2 br and bath. It has the comfort of a home away from home. Please NO PETS.

Dec. 14 – 21

$271 CAD per night

Guest favourite

Guesthouse in Uxbridge

5.0 out of 5 average rating, 122 reviews

Zen Inspired Private Suite with 2-mile Trail Loop

Zig-Zag Trails unique offering is a harmonious blend of modern comfort and the timeless allure of rural living. A newly built 1000 sq ft guest suite situated on over 65 acres of private meadows and forests with zig-zagging trails throughout, providing the ultimate getaway to relax and recharge. This property is a haven for nature lovers and homebodies alike. We are conveniently located in the heart of the Blackstone Valley, 1hr from Boston, 35min from Providence, and 25min from Worcester.

Aug. 29 – Sep. 5

$235 CAD per night

Guest favourite

Guest suite in Franklin

4.88 out of 5 average rating, 145 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!

Jul. 6 – 13

$152 CAD per night

Guest favourite

Guest suite in Sherborn

4.97 out of 5 average rating, 239 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!

Jun. 10 – 17

$293 CAD per night

Guest favourite

Guest suite in Dover

4.98 out of 5 average rating, 181 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-stairs climbing required to reach bedroom suite.) I welcome quiet, mature guests. 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, and surprisingly close to downtown Boston. I have owned and loved this home for 33 years and take great joy in its charm and outdoor spaces.

Mar. 26 – Apr. 2

$227 CAD per night

Guest favourite

Guest suite in Uxbridge

4.99 out of 5 average rating, 134 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 has been restored and updated by two generations of architects in the family. 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.

Feb. 20 – 27

$159 CAD per night

Superhost

Home in Holliston

4.81 out of 5 average rating, 136 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

Sep. 12 – 19

$827 CAD per night

Guest favourite

Apartment in Framingham

4.95 out of 5 average rating, 181 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

Jun. 29 – Jul. 6

$158 CAD per night

Guest favourite

Apartment in Holliston

4.95 out of 5 average rating, 110 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.

Nov. 22 – 29

$239 CAD per night

Guest favourite

Apartment in Hudson

4.85 out of 5 average rating, 292 reviews

Private Mother-In-Law apartment on the lake!

Waterfront on the Lake with a private beach and dock. Relax on your deck and Patio with Wonderful Views. This is a mother-in-law private downstairs apartment complete with kitchen and separate entrance. Enjoy the lake with a fire pit and use of paddle boat and kayaks (life jackets provided). Enjoy the wonderful eclectic restaurants in downtown Hudson including a Micro Brewery, Pub, Martini Bar, Micro Creamery and even a SpeakEasy.

Oct. 21 – 28

$145 CAD per night

Guest favourite

Guesthouse in Framingham

4.97 out of 5 average rating, 197 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.

Jan. 16 – 23

$179 CAD per night