Holiday rentals in Westborough

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Top-rated holiday rentals in Westborough

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

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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, 108 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 pond reflects the white cottage and surrounding trees, creating a tranquil scene. Wildflowers and grasses frame the water's edge, while lush greenery enhances the natural beauty of the area. The peaceful environment is ideal for relaxation and outdoor exploration.
Cottage in Petersham
4.99 out of 5 average rating, 226 reviews

Cider House Cottage

Antique guest cottage on a becountry farm property with acres of fields, ponds, forests and streams, adjoining Quabbin Reservoir domain. Ideal for hikers, bird watchers, and bicyclists, this quiet country retreat offers trails and terrain to explore, only 3 miles away from small historic New England town. Make yourself at home in the comfortably furnished post and beam home with terrace and pond views, adventure in the surroundings, dip in fresh water streams, and relax in the claw foot bathtub

Guest favourite
A spacious, brown leather sofa is positioned in the living area, adorned with two red throw pillows. Bright natural light filters through elegant window treatments featuring floral patterns. A glass coffee table sits in front, complemented by a decorative vase of red roses.
Guest suite in Shrewsbury
4.83 out of 5 average rating, 158 reviews

Beautiful & Lovely 2 BR/2 Beds/ Netflix/Alexa/Roku

Beautiful 2BR 1st floor unit in the heart of Shrewsbury! ☀️ Bright, clean & cozy with full kitchen. 👶 Baby crib available! Walk your pup in a quiet 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. Conveniently close to 👵 Southgate Shrewsbury—perfect for visiting Grandma & Grandpa! Beautiful Dean Park— great for outdoor lovers! We’d love to ho

Superhost
Home in Southborough
New place to stay

Spacious Clean Private Retreat - Luxurious Oasis

Enjoy a sleek spacious 3BR plus Study/4th BR home with 3 ensuite master baths offering a perfect blend of modern comfort and classic New England charm. Ideal for families, business travelers, or groups looking for a peaceful getaway with easy access by car or rail to Boston, Worcester, and MetroWest area. Brand new construction, modern amenities, free WiFi, plenty of parking, and a kitchen equipped to make every stay special. Book your adventure today!​ This home can accomodate up to 12 guests.

Top guest favourite
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
4.95 out of 5 average rating, 165 reviews

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 2 futons and a mattress. 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!

Top guest favourite
A spacious family room is shown, featuring a comfortable brown sofa with decorative pillows and an armchair. A large television is prominently displayed, with a media console below. The walls are a warm tan, and decorative artwork and accents provide visual interest.
Guest suite in Westborough
4.98 out of 5 average rating, 61 reviews

Large, Private Space, Prime Location, Great Price!

PLESE NOTE: Make sure to add all extra guests before booking. Only guests registered in the reservation are allowed to stay in the apartment. Please read additional house rules for details. Perfect location, great value and lots of privacy. Tastefully furnished, clean, organized space, with two bedrooms, a full bathroom, a large family room, and a laundry facility. Very private basement located in the quiet, desirable town of Westborough where you can enjoy a peaceful and relaxing stay.

Superhost
A neatly arranged bedroom features a spacious bed with a patterned beige comforter. Nightstands with lamps flank the bed, and a mirror is positioned above a wooden dresser. Soft beige walls create a warm ambiance, while carpet flooring enhances comfort.
Flat in Hopkinton
4.85 out of 5 average rating, 72 reviews

Cute family getaway near Boston

Have fun with the whole family at this stylish newly built apartment. In the apartment - a bedroom, a TV-room that can be converted to a bedroom (with a convertible Sofa Bed), dining/working space, kitchen. Full bath. The apartment is about a 2 miles from the Hopkinton marathon start line, and has access to a supermarket and restaurants within walking distance. Boston Airport and Boston downtown are about 35 minutes drive (without traffic). If you need, laundry is available on premises.

Top guest favourite
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, 281 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.

Guest favourite
The living area features a light gray sectional sofa adorned with decorative cushions, positioned next to a soft ottoman. A blue area rug covers the hardwood floor, while large windows are draped with sheer curtains, allowing light to fill the space. A desk is visible in the background.
Flat in Shrewsbury
4.93 out of 5 average rating, 110 reviews

Clean & Cozy 2BR Across from Quinsigamond Lake

Unwind in our comfy 2-bedroom apartment 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!

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
4.89 out of 5 average rating, 495 reviews

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 sheep and see the horses and 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.

Top 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.
Flat in Framingham
4.97 out of 5 average rating, 298 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

Superhost
A spacious living area features a dark gray futon adorned with patterned cushions, accompanied by a wooden coffee table. A rustic wooden cabinet houses a television, while natural light is invited through the glass doors leading to an exterior space.
Flat in Hudson
4.92 out of 5 average rating, 557 reviews

Newly Renovated Apartment Near Downtown Hudson

Newly renovated private attic apartment near downtown Hudson with kitchenette, living room and bedroom/office. A warm, cozy space with plenty of natural light! Just upgraded to a new king sized bed! Free parking on site Walking distance to restaurants, cleaners, antique shops, roller skating, shopping center, gym, breweries, golf course... & lots more! Nearby there are lots of historical sites, ski areas, and areas for swimming!

Popular amenities for Westborough holiday rentals

Frequently Asked Questions

  • Are there family-friendly vacation rentals in Westborough?

    Westborough has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Are there pet-friendly vacation rentals in Westborough?

    Four-legged friends are welcome in Westborough. Choose from more than 10 vacation rentals for guests traveling with pets.

  • What are the most popular amenities for House Rentals in Westborough?

    Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with air conditioning, over 10 homes with wifi, over 10 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • How much does it cost to stay in house rentals in Westborough?

    Experience the best of Westborough with our house rentals, starting at about $60 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do house rentals in Westborough have air conditioning?

    Absolutely! We offer over 10 house rentals with air conditioning in Westborough. Enjoy a tailored experience with all the comforts you desire.

  • Are there house rentals with a dedicated workspace in Westborough?

    Yes! Work meets play with ease at over 10 house rentals in Westborough featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do house rentals in Westborough have free parking?

    Absolutely! We offer over 10 house rentals with free parking in Westborough. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Westborough have wifi?

    Absolutely! We offer over 10 house rentals with wifi in Westborough. Enjoy a tailored experience with all the comforts you desire.

Quick stats about holiday rentals in Westborough

  • Total holiday rentals

    Explore 20 holiday rentals in Westborough

  • Nightly prices starting at

    Westborough holiday rentals start at $26 SGD per night before taxes and fees

  • Verified guest reviews

    Over 1,820 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    20 of Westborough holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Westborough rentals

  • 4.7 Average rating

    Westborough stays receive an average rating of 4.7 out of 5 from guests