
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.

The Red Door Carriage House
The Red Door Carriage house is a historic 90 year-old structure that was the carriage house for the original farmhouse (our home) on the property. Located in beautiful West Roxbury Mass., the unit is 3 miles from Fenway (Red Sox), Longwood Medical Center (all of the major hospitals) and 2 miles from Boston College. A 5 minute walk to the West Roxbury commuter rail station (10 minutes to South Station) and all bus lines into Boston, this apartment is a spectacular private and tranquil retreat.

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 unlimited on-street parking. Pet friendly!

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.

The Raven!
Looking for the quintessential Salem stay? Look no further! The main bedroom is designed to get you in the Salem spirit, with its dark gothic decor. Take a reading break in the adjacent room, outfitted to look like a Victorian British library. A spacious living room, dining room, kitchen, and full bath complete this lovely property. Enjoy parking in a driveway in the typically-packed city. We are just a quick and enjoyable 12-minute walk to Essex street and all that downtown has to offer!

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!

101 Steps to Beach/Island/Bike Path
Experience the Seaside Town of Mattapoisett. Location! Relax in this cozy cottage that is 101 steps from the front door to the Beach/Island/Bike Path. Enjoy this popular, sought after scenic Path for walking, biking, or a day at the Beach. The path is known for its picturesque coastal views. Walking distance to the Quaint Town, Shipyard Park, and many restaurants. Ned's Point Lighthouse- 5min. Ferry- 14 min away. Season Open ! Early Bird Specials-3, 4 days-10% off. 5 days -15%. 20%-wk.

Inn at Newton Highlands, Suite 2, Apartment-Hotel
This gorgeous 1,800 sq. ft. 3 bedroom, 2 1/2 bathroom suite at The Inn at Newton Highlands is impeccably designed and decorated. It occupies the second and third floors of the building and immerses you in luxury and style. Its private 800 sq. ft. deck offers stunning views of the village. The space comes with a bonus room. This suite is one of several luxury suites in a small boutique Inn located in the heart of Newton Highlands in a beautiful , fully remodeled historic building.

Luxury Cottage on the Potowomut River 2bd/2b
The Cottage at The Grange is located on the peaceful Potowomut River. It is a beautiful and newly renovated 2 bedroom (king, 2 twin beds) / 2 full bath home with all the modern amenities and conveniences expected from a luxury short-term rental while maintaining the historic charm of this colonial estate. Cook a gourmet meal in the stocked kitchen or BBQ on the deck. Situated on 11 pristine acres enjoy private tennis/pickleball courts, kayak access to Greenwich Bay and much more!

Modern 1BR apt in Boston’s Roslindale Village
This place is on the 3rd floor of our newly renovated home in Boston's Roslindale, which is about 6 miles away from downtown (please look up the neighborhood to have a clear idea where it is). Our place is close to restaurants & bars in Rozzy Village and West Roxbury. There is a connection via bus at the corner to the subway at the Forest Hills Orange Line T-stop that will get you to downtown in about 30 min, and there is commuter rail in Roslindale Village.

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.

Cozy, historic 3 bedroom home close to Boston!
Welcome to our cozy home. Our place blends historic charm with modern comfort. Enjoy a large, fenced yard with a grill, fire pit, and deck to relax. Inside, you'll find a well-equipped kitchen and a dining room. We offer three bedrooms with comfortable mattresses and soft bedding. The living room has a big TV with cable and streaming apps, plus high-speed Wi-Fi. Families with dogs are warmly welcomed.

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
Popular amenities for Stoughton holiday rentals
Stay near Stoughton's top sights
Other great holiday rentals in Stoughton

Peaceful Country Home, Dover, Ma: Private Entrance

Cozy Carriage House Studio

Cottage With Fantastic Beach on Pristine Long Pond

Private 2BR w/parking near Boston & Gillette

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

Charming New England 2brm Apt. South of Boston

Spacious, Comfy Colonial min. to Boston

Gorgeous 2nd Floor Home with Private Entry
When is the best time to visit Stoughton?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $156 SGD | $145 SGD | $121 SGD | $96 SGD | $153 SGD | $156 SGD | $191 SGD | $223 SGD | $191 SGD | $157 SGD | $158 SGD | $259 SGD |
| Avg. temp | -3°C | -2°C | 2°C | 8°C | 14°C | 19°C | 22°C | 22°C | 18°C | 11°C | 6°C | 0°C |
Frequently Asked Questions
Are there family-friendly vacation rentals in Stoughton?
Stoughton has more than 10 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 house rentals in Stoughton have air conditioning?
Absolutely! We offer over 20 house 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 wifi, over 20 homes with a kitchen, 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 $64 SGD per night before taxes and fees

Verified guest reviews
Over 1,220 verified reviews to help you choose

Family-friendly holiday rentals
10 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!
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- Fenway Park
- TD Garden
- Harvard University
- Boston Common
- Brown University
- Revere Beach
- Boston Seaport
- Boston University
- Freedom Trail
- East Sandwich Beach
- New England Aquarium
- MIT Museum
- Boston Convention and Exhibition Center
- Canobie Lake Park
- Gillette Stadium
- Crane Beach
- Duxbury Beach
- Quincy Market
- Easton Beach
- Museum of Fine Arts
- Onset Beach
- Roxbury Crossing Station
- Prudential Center
- Roger Williams Park Zoo




