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Vacation rentals in Holliston

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Top-rated vacation rentals in Holliston

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Top guest favourite
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, 117 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 favourite
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, 306 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 favourite
The exterior of a Victorian home is showcased, featuring a light-colored facade with decorative trim. A welcoming porch area is accented by potted plants, and steps lead up to a wooden front door flanked by tall windows. Lush greenery surrounds the property.
Apartment in Newtonville
4.87 out of 5 average rating, 565 reviews

Country Charm minutes from the Hub - 1st Floor Apt

Private, smoke/pet-free 1st floor efficiency apartment with independent access for ONE PERSON ONLY at back of family home. Includes full bathroom, refrigerator, microwave, coffee maker + WiFi. All basic supplies provided. Driveway parking. Mins from MBTA transit including commuter rail. Laundry-room access for rentals of 7 nights ore more. Sorry, no vaping and no smokers - even if you smoke outside - because smoke odor on you or your clothes can be left in your wake in the room. No open flame.

Top guest favourite
A comfortable seating area is highlighted by two stylish armchairs and a soft sofa. Natural light filters through large windows that overlook the greenery outside. A modern rug is placed on the wooden floor, complementing the decor, while a lamp and coat rack add functional touches.
Home in Framingham
4.97 out of 5 average rating, 107 reviews

Cozy en suite w/ high ceilings

 Relax in this peaceful private en suite with breathtaking backyard views of the tall pine forest. Lots of natural light fills the space with room darkening shades to sleep in. Enjoy cozy nights by the fireplace and a well stocked granite kitchen. Great location only minutes to the Mass Pike. 25 min to Boston. 30 min. to Foxboro Stadium. Enjoy shopping at the Natick Mall, AMC movies, tons of diverse dining & grocery options. Backyard has firepit for outdoor eves. Safe walkable neighborhood.

Top guest favourite
A cozy lounge area is presented with a plush gray couch, an armchair in deep green, and a round coffee table. Natural light flows in through two skylights and windows, while a small bar table with stools offers a casual dining or workspace option. A flat-screen TV is mounted on the wall.
Guest suite in Hope
4.99 out of 5 average rating, 311 reviews

Sunny studio on the East Side!

Quiet, sunny 300 sq foot studio, great neighborhood, on National Historic Register! Close to Miriam, Brown & RISD. You have the entire second floor to yourself, w/ driveway parking, private entrance & bath, lounge, work/eating counter, high speed WiFi & Roku Smart TV. There's a small fridge, microwave, Brio hot/cold filtered water dispenser, Keurig. Coffee, tea, milks, homemade muffins, granola bars :). Please note: GUESTS MUST BE ON THE LISTING. VISITORS MUST BE APPROVED PRIOR TO STAY.

Top guest favourite
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
4.98 out of 5 average rating, 333 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!

Top guest favourite
The kitchen area features white cabinetry and a light countertop, equipped with a microwave, dishwasher, and a compact refrigerator. A cozy seating nook by the window includes a modern black chair and a small table, with a patterned rug adding warmth to the space.
Apartment in Downtown Providence
4.98 out of 5 average rating, 101 reviews

Walking Distance to RISD, Brown, & Convention Hall

Historic charm in downtown Providence! Enjoy restaurants and attractions within walking distance! Conveniently located in the heart of DownCity, and less than a half mile from Brown University, you'll enjoy endless dining options in one of America's top 10 foodie cities. Take a quick walk over to the East Side to experience Providence's historic culture while walking the grounds of Brown University. Whether you're staying a week or a month you will have endless options to explore in PVD!

Top guest favourite
A charming historical two-story house features a gray exterior with dark trim, complemented by vibrant flower beds in front. The main entrance showcases a bold red door, flanked by several windows that illuminate the inviting facade.
Guest suite in Uxbridge
4.98 out of 5 average rating, 121 reviews

Privacy & Peacefulness @ Emerson Brook

A 2nd floor separate entrance and self-checkin / checkout make this your perfect getaway in Blackstone Valley (halfway between Worcester and Providence RI). A private deck and 400 sf of space - kitchen, bedroom, dining, living room and great work space - is all yours. The bathroom includes a clawfoot tub/shower. Expect a Keurig (with k-cups), great linens, wifi, cable and smart tv. Sit on your deck, grab a drink, relax and enjoy the sound and views of Emerson Brook Farm...

Guest favourite
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, 310 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 favourite
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
4.93 out of 5 average rating, 134 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 favourite
A well-lit sleeping area features a spacious bed covered with a light-colored blanket. A desk and chair are positioned near a window with blinds. A decorative plant sits in a pot beside a wooden dresser, adding a touch of greenery to the neutral palette.
Guest suite in Marlborough
4.85 out of 5 average rating, 305 reviews

Professional Accommodations!

Across from Lake Williams near 20 and 495, completely separate entrance and parking, all newly renovated, central air, high speed fios internet, 43 inch smart tv, desk, mini fridge, microwave in separate eating area, walk to Dunkin Donuts, Your completely private space! Walk to restaurant with indoor and outdoor seating. For your safety during Covid I keep 72 hours Between guests and have unit professionally cleaned!

Top guest favourite
A leather recliner sofa is positioned in a light-filled living area, complemented by a large painting of a serene landscape. A full-size refrigerator and a TV stand are visible, providing essential amenities. An entryway is seen in the background, leading to additional rooms.
Guesthouse in Framingham
4.98 out of 5 average rating, 320 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.

Popular amenities for Holliston vacation rentals