Holiday rentals in Stoughton

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Top-rated holiday rentals in Stoughton

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
4.98 out of 5 average rating, 125 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.

Guest favourite
An outdoor dining area is set on a spacious deck, featuring a sturdy table surrounded by six comfortable chairs. A large green umbrella provides shade, while a small flower arrangement adds a touch of color amidst a backdrop of lush, green trees.
Home in Foxborough
4.88 out of 5 average rating, 110 reviews

3 bdrm 2 bath home Walk to the Gillette Stadium

Welcome to a perfect getaway just 1 mile from Gillette Stadium! This updated 3-bedroom, 2-bath duplex home is ideal for Patriot games, Concerts, & weekend escapes. Walk to Gillette & avoid parking costs & traffic. Ask about early arrivals, featuring an oversized deck-gas fireplace, grill & firepit. On a quiet wooded acre, this home offers both convenience and relaxation. 1 hr to Beaches/ Mountains. Situated between Boston & Providence Major Events: - World Cup Soccer 2026 - Patriot games

Guest favourite
A living room area is depicted, featuring a green sofa and a wooden TV stand. Skylights allow natural light to fill the room, highlighting the warm wooden floor. In the background, a small kitchen can be seen through an open doorway, with two stools arranged at a counter.
Flat in Bridgewater
4.84 out of 5 average rating, 258 reviews

Charming New England 2brm Apt. South of Boston

Welcome to a bright, comfortable 2-bedroom apartment just a 4-minute walk to BSU. Perfect for visiting families, traveling nurses, professors, and corporate guests. Enjoy private driveway parking, Wi-Fi, a fully equipped kitchen, and quiet residential neighborhood with a spacious backyard. located near Good Samaritan Medical Center and the VA, with easy access 2 Boston, Gillette Stadium, Plymouth, Rhode Island, & Cape Cod. A peaceful, homelike alternative 2 hotels for short or extended stays.

Guest favourite
A welcoming entryway showcases a wooden staircase leading to the upper levels. The space is enhanced by decorative topiary arrangements and features light-colored flooring providing a bright ambiance. Natural light emanates from a nearby doorway, revealing glimpses of the outdoor area.
Home in Stoughton
4.94 out of 5 average rating, 144 reviews

Modern home 22 min Boston, 20 min Gillette Stadium

Experience New England charm in this luxury home, with over 3,500 sq. feet of living space. This home has many unique characteristics that includes a Koi pond, a majestic backyard and an indoor sauna to make your short term or long term stay more comfortable. It's located in a quiet neighborhood that is walking distance to Glen Echo Park, where hiking, and fishing is available. It's 2 min away from shops, major highways, and has a 6-car driveway and abundance on-street parking. Pet friendly!

Top guest favourite
A serene bedroom suite features a spacious bed with a light blue quilt, flanked by two windows allowing natural light. A cozy sitting area includes a comfortable couch with patterned pillows, and decorative rugs are placed on the hardwood floor, enhancing the inviting ambiance.
Guest suite in Dover
4.97 out of 5 average rating, 316 reviews

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.

Guest favourite
Guest suite in Stoughton
4.92 out of 5 average rating, 26 reviews

Peaceful 2BR w/ 2-Car Parking by Gillette & Boston

Relax in this modern, sun-filled 2BR suite, 20 min to Boston or Gillette Stadium and <10 min to Stoughton Commuter Rail (direct to Boston). This spacious retreat features a luxury King-sized master, a second Queen bedroom, and a full kitchen with stainless appliances. Enjoy high-speed WiFi, smart TVs in both the living area and master, and in-unit laundry. Ideal for pros or families, the suite offers a private entrance, 2-car parking, and central air. Strictly smoke-free and quiet property.

Top guest favourite
The exterior of a spacious guesthouse showcases a blend of siding and stone finishes. A paved driveway leads to a two-car garage. Lush greenery and flower beds enhance the inviting entrance, while multiple windows allow natural light to fill the interior.
Guest suite in Sharon
4.95 out of 5 average rating, 216 reviews

Cozy Lakeview Guesthouse Near BOS, PVD, Cape Cod

Stunning CLG with private entrance, deck, & parking. •Bedroom #1 ground floor (2 guests only) has a Queen bed & smart TV with deck access. •Bedroom #2 upstairs is ONLY AVAILABLE FOR BOOKINGS OF 3–4 GUESTS and includes a Queen bed, smart TV, mini gym & office. •Living room with lake view & smart TV. •Bathroom with tub and sitting shower bench. •Fully equipped kitchen with stainless steel appliances. •Internet Access, You Tube, and Netflix. •Summer lake access.

Top guest favourite
An open-concept studio is displayed, featuring a spacious bed with a light gray blanket. A cozy seating area includes a sofa and a chair, while a dining table is positioned in the background. Large windows allow natural light to illuminate the checkered floor.
Guest house in Rumford
4.96 out of 5 average rating, 101 reviews

Beautiful Studio - < 15 mins 2 downtown & Brown

Relax, work, and unwind in “The Treehouse,” our serene, light-filled studio apartment nestled among the trees. Perfectly located in historic Rumford, RI, it’s just 3 miles from Brown, RISD, and Johnson & Wales, and 5 miles from Providence College. Enjoy quick access to the East Side of Providence, Newport, and Little Compton beaches. Conveniently close to Amtrak, bus lines, and the airport, it’s an ideal spot for exploring New England or visiting area colleges.

Top guest favourite
A handcrafted tree house is set among lush greenery, elevated on wooden stilts. Large windows provide ample natural light, showcasing a cozy porch with outdoor seating. The rustic exterior is complemented by cedar shingles and a distinctive peaked roof, blending seamlessly with the surrounding trees.
Treehouse in Wareham
4.97 out of 5 average rating, 223 reviews

Mink Cove Treehouse

A unique adult adventure awaits in this cozy hand crafted tree house! Nestled 12 feet off the ground amongst the chirping birds, red oaks & breathtaking views of Mink Cove in Buzzards Bay. The tree house is accessible by a suspension bridge that leads you to a partially covered porch where you can enjoy a cup of coffee or sit back & take in the sunset with a glass of wine. Step inside to the living space & snuggle up on the couch for an intimate evening.

Top guest favourite
A spacious living room is displayed, featuring a large sectional sofa with accent pillows. A coffee table sits atop a textured area rug. A modern fireplace is framed by brick, and a wall-mounted TV offers entertainment options. Natural light is provided through large windows.
Guest house in Foxborough
4.96 out of 5 average rating, 196 reviews

Bates Boutique ☆ Home Away From Home

Stay at a recently renovated Bates Boutique specifically for your enjoyment. Highlights: - Fully redesigned kitchen & dining area - Relax in the living room with a 65" Smart TV (live channels, Netflix, Disney+, Hulu, Apple+, HBO Max, and others included) - Cozy bedrooms with heavenly bedding - 3 workspaces to ensure you can get work and play done - Outdoor patio & grill for fun inside & out

Guest favourite
Home in Randolph
4.95 out of 5 average rating, 21 reviews

Quiet 1BR • Wi-Fi • Parking Included • In Randolph

Private 1BR basement near Randolph Center. Close to restaurants, fast-foods, cafés and a luxury cinema. Independent entrance with stairs, living room with TV, dining area, equipped kitchen, queen bedroom and renovated bathroom with walk-in shower. Wi-Fi included and parking for 2 cars. Great for short or long stays, ideal for couples, professionals and travelers seeking comfort and value.

Guest favourite
The exterior of a two-story house is illuminated at night, highlighting a welcoming front entrance. A paved pathway leads to the door, surrounded by landscaped grass and light fixtures that create a charming ambiance. The house is set against a darkening sky.
Home in Weymouth
4.91 out of 5 average rating, 143 reviews

Entire House Near South Shore Hospital/Whole Foods

Located in desirable South Weymouth by Columbian Sq. This convenient area offers guests a dense urban feel while still providing a quaint and cozy neighborhood experience. Our fenced-in backyard is dog-friendly. The location is near major roads and highways. About a 23-minute drive to downtown Boston without traffic.

Popular amenities for Stoughton holiday rentals

Frequently Asked Questions

  • Are there family-friendly vacation rentals in Stoughton?

    Stoughton has more than 20 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

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

    Experience the best of Stoughton with our house rentals, starting at about $50 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there pet-friendly vacation rentals in Stoughton?

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

  • Are there vacation rentals with a dedicated workspace in Stoughton?

    Yes! Work meets play with ease at over 20 vacation rentals in Stoughton featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Where should I stay in Stoughton?

    Make yourself at home in Stoughton by choosing from our most frequently booked neighborhoods. We have over 40 vacation rentals in Winters Corner, and over 40 vacation rentals in Brockton Heights.

  • Do apartment rentals in Stoughton have air conditioning?

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

  • Do house rentals in Stoughton have a kitchen?

    Absolutely! We offer over 20 house rentals with a kitchen in Stoughton. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Stoughton have wifi?

    Absolutely! We offer over 20 house rentals with wifi in Stoughton. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Stoughton have free parking?

    Absolutely! We offer over 20 house rentals with free parking in Stoughton. Enjoy a tailored experience with all the comforts you desire.

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

    Enhance your stay in our House Rentals with the most popular amenities: over 20 homes with a kitchen, over 20 homes with wifi, over 20 homes with air conditioning, over 20 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about holiday rentals in Stoughton

  • Total holiday rentals

    Explore 40 holiday rentals in Stoughton

  • Nightly prices starting at

    Stoughton holiday rentals start at $63 SGD per night before taxes and fees

  • Verified guest reviews

    Over 740 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 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

    40 of Stoughton holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Stoughton rentals

  • 4.8 Average rating

    Stoughton stays are highly rated by guests – averaging 4.8 out of 5!