Holiday rentals in Southborough

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.

2BR Private Suite Close to World Cup 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.

1BR Loft | 25 Mins to City | Early Check In Option

⏰ Check In 7/2 Anytime After 11am! 100% Private 1-Bedroom Place Queen Bed — Pillowtop Full Kitchen — Stove, Fridge, Dishwasher, Pots/Pans, Utensils & Essentials Dining Area — Table & Chairs Living Room — Leather Sofa 49" SmartTV — Netflix + Sling Live TV Bathroom — Shower, Plush Towels & Natural Bath Products Private 2nd Floor Entrance Heated Outdoor Stairs Your Own Driveway Quiet & Safe Neighborhood Deep Cleaned & Sanitized 2 Min Walk to Park 25 Mins to Boston Easy Access —Route 9 & 90-Mass

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, 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. Safe walkable neighborhood.

39km from World Cup! 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.

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.

Luxury Boston Ranch –Sleeps 8|Pet+|Private pool

A gleaming, beautiful pool – a rare find in the Boston area – awaits you at this must-visit retreat! This Boston getaway has 4 spacious bedrooms & a fully equipped kitchen that blends luxury and comfort. Relax in the cozy living area, challenge your group in the lively game room, or start your mornings with a specialty brew from the charming coffee bar. Spend your afternoons by the private pool in the serene, pet-friendly yard – the ideal escape for creating unforgettable memories together.

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.

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. NEW in 2022: Mini-split AC!

Spacious 3BR Home | Fast Wi-Fi | Parking.

Welcome to your home away from home in Marlborough, Massachusetts! This warm and inviting 3-bedroom, 2-bathroom house is perfect for families, couples, or friends, comfortably accommodating up to 6 guests. Designed for comfort and convenience, the home features a welcoming living space ideal for relaxing after a day of exploring, working, or visiting family nearby.

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.

Heart of Marlborough

Completely separate entrance and parking. There is stairs and a ramp to get to the apartment. All newly renovated, high speed fios internet. 40" smart TV, small living, small kitchen aérea, is fully furnished. The house is located in the downtown Marlborough within walking distance to restaurants, shopping school and nightlife.