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

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

We built this 2 level home 9 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.

4.97 out of 5 average rating, 144 reviews

Top guest favorite

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

Cozy en suite w/ high ceilings

Relax in this peaceful private en-suite with breathtaking backyard views of the tall pine forest. 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. Just 25 min to Boston, 40 min. to Gillette Stadium. Enjoy shopping at the Natick Mall, AMC movies, tons of diverse dining & grocery options. Backyard has firepit for outdoor eves. Very safe walkable neighborhood

4.98 out of 5 average rating, 145 reviews

Top guest favorite

A fully equipped kitchen is shown, featuring stainless steel appliances including a refrigerator, microwave, and dishwasher. Granite countertops provide ample workspace, while natural light filters through the two windows above the sink. A coffee maker sits on the counter, adding to the amenities.

Home in Framingham

1BR Sunlit 2-Story | Boston 25 Min | Free Parking

800ft² 2-Level Apt Private 1BR @ our 3-Rental Property Perfect for Long-Term 1st Floor: —Fully Equipped Granite Kitchen w/Dishwasher + Essentials & Cookware —Living Room w/Queen Sofa Bed + Dining Area 2nd Floor: —Bedroom - Memory Foam Queen Bed —Full Length Mirror —Desk & Chair + Dresser —Bathroom - Shower/Tub 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 Deep Cleaned & Sanitized

4.9 out of 5 average rating, 269 reviews

Top guest favorite

Guest suite in Dover

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.

4.98 out of 5 average rating, 347 reviews

Top guest favorite

The exterior of a spacious guesthouse showcases a blend of siding and stone finishes. A paved driveway leads to a two-car garage. Lush greenery and flower beds enhance the inviting entrance, while multiple windows allow natural light to fill the interior.

Guest suite in Sharon

Cozy Lakeview Guesthouse Near BOS, PVD, Cape Cod

Stunning CLG with private entrance, deck, & parking. •Bedroom #1 ground floor (2 guests only) has a Queen bed & smart TV with deck access. •Bedroom #2 upstairs is ONLY AVAILABLE FOR BOOKINGS OF 3–4 GUESTS and includes a Queen bed, smart TV, mini gym & office. •Living room with lake view & smart TV. •Bathroom with tub and sitting shower bench. •Fully equipped kitchen with stainless steel appliances. •Internet Access, You Tube, and Netflix. •Summer lake access.

4.96 out of 5 average rating, 235 reviews

Top guest favorite

An outdoor swimming pool is surrounded by a spacious patio and lush greenery. Sun loungers are arranged around the pool, with a shaded seating area nearby. The house features a multi-level deck overlooking the pool, creating a relaxing outdoor space for guests.

Home in Hopkinton

Hopkinton Mass 3+ Bedrooms - Great location!

This my home in which I am now an "empty-nester". I have 3 bedrooms available, each with a Queen bed, plus a room over the garage with 4 futons/mattresses. NOTE: I live here and will be home during your stay. You'll have access to a private bathroom and the rest of the house: kitchen, dining room, living room, etc. NO pets allowed My place is close to Boston, Worcester, Providence, state parks, etc. Good for singles, couples, business travelers and families. Great pool and hot tub!

4.95 out of 5 average rating, 180 reviews

Guest favorite

Guest suite in Hopkinton

Studio W/ King Bed, Full Kitchen, & Peaceful Deck

This cozy studio sits above a detached garage on a quiet dead-end street, surrounded by trees and next to a walking trail, with downtown just a short walk away. Centrally located with quick access to I-495, it’s an easy home base for day trips to Boston and other New England destinations. Gillette Stadium and Xfinity Center are about 30 minutes away. Enjoy a king bed, full kitchen, and a really nice deck perched up high. Note: stairs required; may not suit guests with mobility concerns.

4.97 out of 5 average rating, 77 reviews

Top guest favorite

A historic stone farmhouse is set on a spacious green lawn, complemented by a vibrant red barn in the background. Tall trees provide shade, and a carefully arranged stone border outlines the lush garden area, creating a tranquil outdoor setting.

Farm stay in Hopkinton

1790 Stone Manor Farm

This historic New England farm and home is on almost 7 acres of land with mature gardens and places to hike, it is a warm and inviting place to spend lovely summer days by the pool and enjoy warm nights by the fire in the fall and winter. Kitchen and bathrooms all renovated. Located centrally in Ma- 90/495 interchange. Located 45 minutes from Boston, beach, history, mountains, lakes, & NE sports. This home is in historic Hopkinton, where the Boston Marathon starts, center of MA.

4.96 out of 5 average rating, 166 reviews

Guest favorite

Home in Framingham

Retreat Near Boston | AC, BBQ, Deck, Pets OK

Welcome to your perfect home base just outside Boston—ideal for families, groups, and business travelers alike. This bright and spacious 4-bedroom home comfortably accommodates your group with 5 beds and plenty of room to relax. Enjoy a fully fenced in backyard. Enjoy a large, sun-filled living area, a bonus dining space with beautiful vaulted ceilings, Kawaii Piano, and a fully equipped kitchen with modern stainless steel appliances—perfect for gathering and entertaining.

4.92 out of 5 average rating, 12 reviews

Guest favorite

Apartment in Framingham

Comfy Cute lovely 1 BR 1 bed APT w/Private Access.

Cozy and lovely 1 bedroom 1 bed apartment in Framingham with private access and parking. Everything nearby is perfect for solo adventures, couples, and business travelers, with groceries, restaurants, train stations, shopping centers, Natick Mall, and Framingham State University just minutes away. You can get around Boston and Providence with ease! Occupancy: Maximum 2 adults. Property type One-bedroom apartment or guest suite Property type: Entire house/apartment

4.82 out of 5 average rating, 115 reviews

Guest favorite

Home in Wayland

Spacious 4 bedroom home with large yard

Private and clean renovated 4 bedroom house in "Safest Town" in Massachusetts, 25 minutes from Boston. Perfect for families or travelers wanting extra space. Sleeps 8 comfortably in 4 bedrooms. Pets are completely welcome! Lots of walking trails nearby. Connected to another unit and shares the large backyard. Kids will enjoy the swingset. Lake Chochituate is near with canoe, kayak, and swimming. Close to MassPike, Rt.30 & 27, and many colleges and MetroWest office parks.

4.89 out of 5 average rating, 133 reviews

Superhost

The exterior of a historic two-story home is showcased, featuring a light-colored façade and multiple large windows. The entrance is marked by a welcoming door with a bright hue. Nearby, recycling and trash bins are visible, accompanied by landscaped trees in autumn colors.

Guesthouse in Holliston

2BR/2BA in a Duplex | Private Entry | Downtown

Suitable for family stays due to railroad bedroom setting. Beautifully restored 1850s home, 2-bed, 2-bath home. Downtown&Walkable. The home is close to Hopkinton, Framingham, Boston, Providence, and Worcester, with easy day trips to Cape Cod, Salem, North Shore beaches, and several ski areas. Gillette Stadium is about 25 minutes away for concerts and upcoming World Cup events, and you’re just 7 minutes from the starting line of the Boston Marathon in Hopkinton.

4.74 out of 5 average rating, 27 reviews