Vacation rentals in Holliston

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Top-rated vacation rentals in Holliston

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Top guest favorite

The exterior of a two-level home is depicted, surrounded by lush green lawns and mature trees. A pathway leads to the welcoming entrance, flanked by garden beds featuring various plants. The house features a traditional design with large windows allowing for ample natural light.

Home in Holliston

4.97 out of 5 average rating, 97 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

The exterior of a charming wooden structure features light brown shingle siding and a welcoming entrance. Two windows flank a set of double black doors, accentuated by decorative lanterns. A stone pathway leads to the entrance, bordered by manicured greenery.

Guest suite in Uxbridge

4.99 out of 5 average rating, 363 reviews

Beautiful, Unique, & Cozy Cedar Flat

Come enjoy this new and beautifully designed space in historic Uxbridge, MA. Set up like a tiny house, it is the most cozy and clean place you will visit. A ship’s ladder will take you to the queen loft bed or use a new PotteryBarn sleeper sofa. The Frame TV will act as a beautiful painting if you prefer to "unplug." Climate control and a hammock chair are a perfect combo! Located on a quiet street, it is an easy 25 min. drive to Providence or Worcester, and only 50 min. to downtown Boston.

Top guest favorite

The kitchen features a modern layout with white cabinets and granite countertops. Stainless steel appliances, including a French door refrigerator, are complemented by a tiled backsplash. Natural light enters through multiple windows, illuminating the spacious area. Two area rugs add warmth to the tiled floor.

Home in Framingham

4.98 out of 5 average rating, 250 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

A serene bedroom suite features a spacious bed with a light blue quilt, flanked by two windows allowing natural light. A cozy sitting area includes a comfortable couch with patterned pillows, and decorative rugs are placed on the hardwood floor, enhancing the inviting ambiance.

Guest suite in Dover

4.97 out of 5 average rating, 281 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.

Guest favorite

The exterior of the building features a unique blend of brick and siding, with a striking orange bottom section. Windows are placed symmetrically, allowing for natural light. A garage door is visible, along with a set of steps leading to the entrance, framed by a well-kept area.

Guest suite in Franklin

4.89 out of 5 average rating, 171 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

A spacious living area features a vaulted ceiling, large windows allowing natural light, and a comfortable sofa. A wooden coffee table sits at the center, complemented by patterned armchairs. Adjacent, a farmhouse dining table accommodates six, enhancing the open layout.

Place to stay in Sherborn

4.97 out of 5 average rating, 309 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 serene lake view is captured at twilight, with soft clouds reflecting in calm waters. Soft lights from nearby docks and boats twinkle in the distance, creating a peaceful ambiance. A yellow inflatable is anchored nearby, and the scene is framed by the gentle curve of the hot tub.

Cottage in Mendon

4.94 out of 5 average rating, 103 reviews

Lake Front with Hot Tub and New Fitness Studio

Welcome to our charming 3-bedroom lake cottage in Mendon, MA, where every sunrise paints the sky with breathtaking hues over tranquil waters. Accommodates 6 guests, making it ideal for families or couples seeking serenity. Enjoy lakeside coffee, fishing, kayaking, and evenings by the fire pit. We are pet-friendly, so feel free to bring your dogs along — if you have more than 1 dog, please let us know. Conveniently located near restaurants and attractions. Book now for a magical getaway!

Top guest favorite

A spacious living area showcases large windows that invite natural light and views of the surrounding landscape. Comfortable seating includes a couch and armchair, complemented by a decorative fish tank. A dining table is visible in the background, enhancing the open and airy atmosphere.

Guest suite in Uxbridge

5 out of 5 average rating, 256 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.

Superhost

A spacious living area is characterized by exposed wooden beams and polished hardwood floors. Two cozy couches are placed around a low coffee table, accompanied by a decorative rug. Natural light streams in through large windows, and a tasteful staircase leads to the upper level.

Home in Holliston

4.82 out of 5 average rating, 160 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

Superhost

A small seating area is presented with a pink loveseat adorned with patterned pillows, positioned beside a bedside table. A soft lamp is placed atop the table, and a tissue box is situated nearby. Light wood flooring complements the neutral color scheme.

Guest suite in Framingham

4.83 out of 5 average rating, 82 reviews

Exquisite 1 Bedroom Suite-Charming,W/Private Entry

An exquisite and convenient I BR Modern suite nestled between Boston and Worcester is available for you. Bright and charm w/ a . Beautiful kitchen, remodeled bathroom and a bedroom. Private entrance w/ it’s lovely courtyard to sit outdoor, a free parking spot/ WiFi. The apartment is conveniently located to Babson and Wellesley College, both within 7 miles , FSU is 1 mile train station 2 miles , easy drive to Cape Cod. For all travelers & enjoy your stay her !

Top guest favorite

A stylish wooden bed frame with a floral-patterned comforter and two pillows is featured in the sleeping area. A bedside table with a lamp stands next to the bed, and a wooden dresser is positioned nearby against the wall.

Apartment in Framingham

4.96 out of 5 average rating, 283 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, 123 reviews

Loch 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.