Holiday houses in Southborough

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Top-rated holiday rentals in Southborough

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Guest favourite
The charming exterior of a renovated estate home is showcased, featuring green siding, white trim, and an expansive porch. Lush greenery surrounds the home, highlighting a large red barn adjacent to the property. A clear blue sky enhances the inviting appearance of this spacious residence.
Home in Southborough
4.87 out of 5 average rating, 179 reviews

Luxury Living at its Best in Extra Large 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, 4.5 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.

Guest favourite
The exterior view showcases a spacious two-story building with a gray siding finish. A large patio area is visible, furnished with a table and chairs, surrounded by lush green grass and trees. The large windows invite natural light, enhancing the serene outdoor setting.
Apartment in Framingham
4.91 out of 5 average rating, 296 reviews

Spacious 2 Br with All The Comforts Of Home

This a quaint apartment . Not your typical hotel room. In a country setting but 5-10 minutes from great shopping, restaurants, parks, colleges and major highways. Boston is 22.5 miles away. Fenway Park is 20 miles. Worcester is 17 miles. Private location overlooking conservation land. Walk to great hiking and biking trails but car needed for other activities. Full kitchen, laundry room and living room in addition to 2 br and bath. It has the comfort of a home away from home. Please NO PETS.

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, 115 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
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, 167 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 comfortable seating area is highlighted by two stylish armchairs and a soft sofa. Natural light filters through large windows that overlook the greenery outside. A modern rug is placed on the wooden floor, complementing the decor, while a lamp and coat rack add functional touches.
Home in Framingham
4.97 out of 5 average rating, 103 reviews

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. 30 min. to Foxboro Stadium. Enjoy shopping at the Natick Mall, AMC movies, tons of diverse dining & grocery options. Backyard has firepit for outdoor eves. Safe walkable neighborhood.

Top Guest favourite
Cottage in Stow
4.96 out of 5 average rating, 215 reviews

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.

Top Guest favourite
A spacious living area features a vaulted ceiling, large windows allowing natural light, and a comfortable sofa. A wooden coffee table sits at the center, complemented by patterned armchairs. Adjacent, a farmhouse dining table accommodates six, enhancing the open layout.
Place to stay in Sherborn
4.98 out of 5 average rating, 328 reviews

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. Check us out on IG @carriagehousema. NEW in 2022: Mini-split AC!

Guest favourite
A modern kitchen area is presented with wooden cabinetry and black appliances, including a refrigerator and microwave. A dining table with place settings is visible, alongside a cozy living area featuring a leather sofa and a ceiling fan overhead.
Home in Framingham
4.97 out of 5 average rating, 146 reviews

1BR Loft | 25 Mins to Boston | Quiet Neighborhood

Welcome to The Loft! 100% Private 1-Bedroom Place Queen Bed — Pillowtop Mattress Full Kitchen — Stove, Fridge, Dishwasher, Pots/Pans, Utensils & Cooking 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 Your Own Driveway Quiet & Safe Neighborhood Deep Cleaned & Sanitized 2 Min Walk to Park 25 Mins to Boston Easy Access —Route 9 & 90-Mass Pike

Top Guest favourite
A tranquil kettle pond is depicted, reflecting the surrounding wooded landscape and soft hues of the sky. The calm water creates a mirrored surface, enhancing the serene atmosphere of the natural setting.
Guest suite in Concord
4.98 out of 5 average rating, 142 reviews

Water front cabin-like guest suite on a quiet pond

Our home is located on a wooded lot overlooking a pristine kettle pond. Access to our home requires ascending a long but gradual set of stairs followed by a second set of stairs to the entrance of the guest suite. The two room suite has a bedroom and a kitchenette with a microwave, toaster, electric kettle and mini frig. There is a French press, coffee bean grinder, tea, cups, dishes and flatware in the cupboards. It does not have a full kitchen ( no stove/ no kitchen sink)

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.
Apartment in Framingham
4.96 out of 5 average rating, 307 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.
Apartment in Hudson
4.92 out of 5 average rating, 561 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!

Guest favourite
A well-lit sleeping area features a spacious bed covered with a light-colored blanket. A desk and chair are positioned near a window with blinds. A decorative plant sits in a pot beside a wooden dresser, adding a touch of greenery to the neutral palette.
Guest suite in Marlborough
4.86 out of 5 average rating, 303 reviews

Professional Accommodations!

Across from Lake Williams near 20 and 495, completely separate entrance and parking, all newly renovated, central air, high speed fios internet, 43 inch smart tv, desk, mini fridge, microwave in separate eating area, walk to Dunkin Donuts, Your completely private space! Walk to restaurant with indoor and outdoor seating. For your safety during Covid I keep 72 hours Between guests and have unit professionally cleaned!

Popular amenities for Southborough holiday rentals