Holiday houses in Westborough

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.

Family · Value · Layout

2BR Private Suite - Sleeps 6

Welcome to your home away from home! This private, spacious two-bedroom guest suite spans the entire lower level of our home and features a private entrance, walk-out patio, full kitchen, laundry, and open living/dining area. Located just 26 min. from Gillette Stadium/World Cup via an easy highway drive, and in Hopkinton, the start of the Boston Marathon. It’s ideal for event visitors, runners, and families. Please note: we have a (ridiculously friendly) non shedding, labradoodle on property.

Family · Location · Backyard

Large Luxury Private Estate

The talk & admiration of the neighborhood. Airbnb Guests’ Favorite with over 130+ 5 Star Reviews. When you book, we aim to deliver everything that is described in order to earn the same 5 stars all around review from you. This large expansive 8 bedrooms, 5 baths estate home has had a complete renovation adding today’s high end touches, yet preserving old world charm. You will experience modern amenities, a massive kitchen & luxury living in a large open space. SORRY: We do not allow parties.

Location · Family · Access

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!

Location · Family · Access

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!

Location · Family · Comfort

Hopkinton 3B2B Apt with 3 bed 2bath 2 futon

Just minutes away is Hopkinton State Park,large picnic and BBQ areas, fishing spots, scenic trails, and boat rentals. It’s only a short drive to I-495, I-90, Route 9, and Route 135. Boston’s vibrant downtown is just 40 minutes away by car, or you can drive about 15 minutes to the nearby commuter rail (Purple Line) station, with trains to Boston running every 30 minutes from 5:30 AM to midnight. Grocery shopping is a breeze with Stop & Shop just 10 minutes away and Walmart 15 minutes away.

Family · Location · Walkability

Cozy Lake Cottage: Hot Tub, Gym & Waterfront Views

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!

Family · Value · Wi-Fi

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.

Value · Location · Getting around

Luxury Retreat | Theater | Game Room | Garden Spa

More than a luxury home, this is a collection of unforgettable experiences. Wander through your private garden sanctuary, relax in the glass conservatory, curl up in the custom-built library with 1,000+ books, unwind in the spa-inspired primary suite with its private jacuzzi, or gather for movie nights with the 100-inch projector, pool table, and pinball. Designed for families, friends, executive retreats, celebrations, and memorable getaways, every space inspires connection!

Family · Location · Comfort

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!

Location · Family · Accuracy

Garden Paradise Retreat in Marlboro

The Perfect Location Forget about traffic and the stress of finding parking! Our property boasts a prime central location in Marlboro. You will be just a short, pleasant walk from the city's best restaurants, bars, cafes, and boutique shops. Enjoy the local nightlife and dining on foot, and at the end of the night, quickly return to the comfort and quiet of your private haven.

Family · Value · Hospitality

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.

Location · Family · Indoor spaces