Vacation rentals in Boylston

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Top-rated vacation rentals in Boylston

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favourite

An outdoor lounge area features a circular table surrounded by curved sofas adorned with cushions. Soft curtains frame the space, while potted flowers add vibrant color. Natural light filters through the overhead structure, creating a relaxed atmosphere for gatherings.

Home in Worcester

Gather, Cook & Unwind, 3BR, Fireplace

A private resort — without leaving Worcester. Heated pool, fire table, garden courtyard … your own enclosed escape. ★ "Tania’s place was much more than a place….it was a full on fabulous experience." 🏊Heated Pool (to 81F) 🌿 Courtyard w. lounge + garden 🔥Patio w/ Zen fire table* 🍽️ Natural gas + charcoal grills 💧 Reverse osmosis water filter 66” smart TV projector ❄️ Central air conditioning 🔥Indoor gas fireplace 📶300+ Mbps WiFi For non-smokers. No smoking/vaping inside or outside.

4.97 out of 5 average rating, 130 reviews

Top guest favourite

A spacious bedroom features a large bed with a quilted taupe cover and decorative pillows. Framed artwork hangs on the walls alongside window treatments, while warm table lamps provide gentle lighting on both sides of the bed. Soft textiles create a calming atmosphere.

Condo in Shrewsbury

Luxury Spacious 2BR • King & Queen Beds • 2 Baths

Family-Friendly 2BR Getaway! Spacious stay with a 🛏️ King & Queen bed, ☀️ outdoor patio, 👶 baby crib! 🐶 pet-friendly neighborhood! Great for 🩺 travel nurses & 💼 professionals with ⚡ high-speed WiFi, 📺 Roku TV & 🎬 Netflix. Easy access to UMASS and St Vincent Hospitals 🏥 for work or care for loved ones. Close to 👵 Southgate Shrewsbury—perfect for visiting Grandma & Grandpa! Close to beautiful Dean Park—perfect for walks, playtime, or just soaking up nature. We’d love to host you!

4.82 out of 5 average rating, 118 reviews

Top guest favourite

The charming exterior of a two-story house is showcased, featuring a gray façade with white trim and an inviting front porch. American flags adorn the porch, while well-maintained shrubs and a grassy area complement the space. A brick pathway leads toward the entrance.

Home in Worcester

Charming Large Entire Home Spacious 3 Bed 2.5 Bath

Make some memories at this unique and family-friendly place. A charming home with an eclectic style has tall ceilings, wide open spaces and just that home-sweet-home, comfy feel. Enjoy your morning coffee on the front farmers porch. A jacuzzi bath in the master bathroom. Open the windows and listen to the bird singing in the city. The sunsets are a must and can be seen from the dining room table every night. It’s unreal, really. Centrally located and only 2 minutes away from highways.

5.0 out of 5 average rating, 113 reviews

Guest favourite

Apartment in Shrewsbury

Clean & Cozy 2BR | Great Central Location

Unwind in our 2nd floor apartment across from Lake Quinsigamond with all the essentials for a comfortable stay. Work remotely while facing the lakeview. Super close to UMass Memorial, UMass campus, and just minutes away from Starbucks, Whole Foods, TraderJoe's and many more. Surrounded by many restaurants with great variety of taste. Easy access to the highway. Escape the ordinary and make this homy lakeview apartment your home away from home. Book now for a delightful experience!

4.9 out of 5 average rating, 147 reviews

Superhost

The kitchen showcases a large waterfall granite island with seating for four. A stainless steel refrigerator and dishwasher complement the modern cabinetry. Natural light pours in through the windows, illuminating the space and providing a view of the outdoor deck.

Townhouse in Northborough

Sakura House: Spacious 4BR w/ Gym & Premium Design

Discover this stunning colonial-style retreat, with expansive indoor and outdoor spaces. The beautifully renovated kitchen features a large granite island, opening to a sunlit dining area and cozy living room. Relax on multiple decks with scenic views of the private lot. With a dedicated office, gym, and bonus room, this home offers abundant space for families and groups. Conveniently located near major highways and the Apex Center, it’s the ideal blend of comfort and accessibility.

4.78 out of 5 average rating, 46 reviews

Top guest favourite

Home in Sterling

Stunning Sterling Sanctuary: Unwind on the Water!

Feel your worries drift away along the freshwater when you stay at this spacious 3-bedroom, 1.5-bath Sterling vacation rental! Nestled on the serene shores of East Waushacum Pond, this home ensures a fun-filled stay for all. Spend your days exploring the water-by kayak or paddle board-and put your toes in the sand at Sterling Town Beach! When the sun sets, cook a delicious dinner on the gas grill and roast s'mores over the fire for dessert. Adventure is calling -book now!

5.0 out of 5 average rating, 35 reviews

Guest favourite

The stone barn building is framed by vibrant lavender fields in the foreground. Evening light illuminates the windows, while a calm sunset creates a soft gradient in the sky, transitioning from warm hues to deep blues.

Barn in Holden

Farm stay in a Historic Ski Lodge turned Barn

Once a ski lodge, then a horse barn, the hayloft in this unique stone barn has been converted to a comfortable & peaceful getaway. Enjoy a tranquil farm stay on a working Lavender farm. Help feed (if you wish) the horses and ponies and see the chickens. Enjoy the serene views and take in a sunrise or sunset or the stunning evening stars and moon on the back patio, stroll around the farm and hike our 1 mile nature walk. Convenient to local skiing & golfing.

4.9 out of 5 average rating, 541 reviews

Guest favourite

An aerial view captures the farmhouse in a vibrant red hue, surrounded by lush greenery and autumn foliage. The expansive yard includes several parked vehicles, while the mountains rise in the background under a clear blue sky.

Home in Sterling

Quiet country retreat with modern conveniences

Our mountain-view farmhouse sits on a 5 acre knoll, 300' from a quiet country road, surrounded by the sights and sounds of quintessential New England. The location of the property strikes a perfect balance between seclusion and convenience with access to hiking, kayaking, biking, parks, restaurants, grocery, and shopping close by. Restaurant food delivery of local favorites for Japanese (including sushi), Chinese, pizza, sub, salads, etc is available.

4.93 out of 5 average rating, 239 reviews

Superhost

A serene lakeside view is presented, with several docks extending into the water. Leafless trees frame the scene, while a grassy area leads to the water's edge, creating an inviting space for outdoor activities.

Home in Sterling

Charming lakeside cottage.

Charming lakeside cottage is the perfect place to enjoy coffee in the am or a paddle at sunset. This home has 1.5 baths, and 2 bedrooms. The smaller bedroom has a queen bed. The larger bedroom has 2 sets of trundle beds to sleep 4 people. The kitchen is fully stocked with all you need to entertain just bring food. We have some toys for kids if needed. We have a few kayaks and a pedal boat you can use at your own risk or bring your own.

4.89 out of 5 average rating, 57 reviews

Guest favourite

A welcoming living area features a green sofa and a comfortable armchair. A wooden coffee table sits in the center, accompanied by a table lamp. Natural light enters through a window dressed with sheer curtains, while a decorative wall sign adds a friendly touch.

Apartment in Shrewsbury

One Bedroom Apartment with Separate Bunk Bed Area

Located in the Town of Shrewsbury, Massachusetts and less than one mile from UMass Memorial Health- University Campus and UMass Chan Medical School, our tastefully designed fully furnished second floor apartment combines luxury with comfort and has its own private entrance. Our apartment has a bright, airy floor plan, gourmet kitchen, stainless steel appliances, hardwood floors, central A/C, and washer/dryer in-unit.

4.86 out of 5 average rating, 391 reviews

Guest favourite

A spacious bedroom features a large bed adorned with a patterned green and white quilt. Natural light floods the room through multiple windows, highlighting a small desk and ergonomic chair. Soft lighting is provided by sconces on the walls.

Guesthouse in Worcester

Quiet Oasis In The City

Forget your worries in this spacious and serene space. We are right in the city but you'll feel miles away. This two level guest home is surrounded by nature and very relaxing. Two bedrooms and two baths. Two king sized beds. One full bath with oversized tub downstairs. Upstairs bath with standing shower. Full kitchen and coffee and tea. Hot tub is included with BNB. Pool is a separate rental. Message for details.

4.82 out of 5 average rating, 115 reviews

Top guest favourite

Home in Shrewsbury

Historical New England retreat

Relax and recharge at this beautiful antique colonial home. Built in 1749 and steeped in local history, this home offers the perfect blend of classic architectural details and modern comforts. Wake to fresh eggs from our chickens, pick seasonal fruit from espaliered trees, and unwind in thoughtfully designed spaces that feel like home.

4.98 out of 5 average rating, 44 reviews