Holiday houses 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.

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.

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.

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.

White Pine Cottage – Cozy 3BR w/ Fireplace

Welcome to White Pine Cottage - a cozy 1930s cottage in Stow, MA with modern amenities. Great landing pad if you are coming to the area to visit family, work or a weekend getaway. Located in quiet wooded neighborhood with very little traffic. Relax by the fireplace and enjoy a soak in the whirlpool tub. Convenient to local farms, orchards, golfing, wooded trails and more. Hudson, Sudbury and Maynard's restaurants and shops 15 minutes away and big city Boston / Cambridge only 40 minutes.

Handcrafted Timber Frame Cabin Retreat

Escape to the woods and slow things down at this beautifully handcrafted timber frame cabin, tucked away among towering trees and nature’s quiet. Built with exposed beams, natural wood, and timeless craftsmanship, this cabin blends rustic charm with modern comfort—perfect for a romantic getaway, creative retreat, or unplugged weekend escape. Whether you’re looking to reconnect, recharge, or simply enjoy the beauty of the forest, this timber frame cabin offers a warm and memorable escape.

Peaceful Guest House | Hot Tub | 20 Min to Boston

Welcome to our Guest House! 100% Private 1-Bedroom Place We Live In/Rent Main House (Details Below — See ⭐️) Queen Bed—New Memory Foam Mattress Fully Stocked Kitchen—Utensils, Pots/Pans & Essentials Dining Area—Table & Chairs Living Room—Leather Recliner Sofa Bathroom—Plush Towels & Natural Products 43” SmartTV—Netflix+Sling Live TV Private Porch & Private Entrance w/Keypad Hot Tub—On Back Deck Complementary Laundry Service Quiet Neighborhood 20 Mins to Boston Cleaned & Sanitized

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!

Spacious 3BD Ranch With Fenced-In Yard

Enjoy 3 large bedrooms and 2.5 bathrooms in this modern single level ranch in a quiet neighborhood. A large fenced yard enables you to enjoy the wooded setting for a backyard BBQ or relaxing by the firepit. Enjoy a modern eat-in kitchen with a large island, quartz countertops with barstools, under-cabinet lighting. Large living room for your family as well as a semi-separated office space with desk. The primary bedroom has hard wood floors & an en-suite with rainfall shower.

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

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.

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.