Discover Your Perfect Historic Dedham Square Vacation Homes

Best Vacation Homes in Historic Dedham Square

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7.8 (1054 Reviews)
Hotel
Hilton Boston/Dedham
  • Air Conditioner
  • Parking
  • Wheelchair Accessible
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Why Choose Rent By Owner for your Historic Dedham Square Vacation Rental Homes?

What makes our Vacation Rentals special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Popular Areas for Historic Dedham Square Vacation Rentals

Where are the best neighborhoods to stay in Historic Dedham Square?

Situated in the charming heart of Dedham, Massachusetts, Historic Dedham Square offers a vibrant neighborhood experience perfect for your stay. Here, you can enjoy easy access to local shops, dining, and community events that showcase the area's rich history and welcoming atmosphere. Booking a vacation rental in this area allows you to immerse yourself in the authentic character of Dedham while enjoying the convenience of nearby amenities. Whether you're exploring the town or seeking a comfortable base, staying in Historic Dedham Square ensures a memorable visit to this quintessential New England locale.

Downtown Boston

In the heart of the city, downtown Boston offers convenient access to historical sites and vibrant urban life, making it an ideal area for exploring the region’s rich heritage.

View 362+ Rentals in Downtown Boston

Back Bay

Known for its elegant architecture and boutique shopping, this neighborhood provides a refined setting that complements your stay near the historic region.

View 276+ Rentals in Back Bay

Seaport District

This waterfront district features modern amenities and scenic views, perfect for experiencing the region’s dynamic development while staying close to cultural attractions.

View 136+ Rentals in Seaport District

Dorchester

Diverse and vibrant, Dorchester offers authentic local experiences and easy access to the area's historical and cultural landmarks.

View 161+ Rentals in Dorchester

North End

Famous for its Italian heritage, the North End provides a charming atmosphere and proximity to key sights worth exploring during your visit.

View 56+ Rentals in North End

Fenway–Kenmore

A lively neighborhood renowned for sports and entertainment, here you’ll find a blend of energetic venues and convenient access to the region’s attractions.

View 200+ Rentals in Fenway–Kenmore

South Boston

With its waterfront views and welcoming community, South Boston is a great base for experiencing both local charm and the region’s maritime history.

View 45+ Rentals in South Boston

Beacon Hill

Characterized by historic brick streets and elegant row houses, this neighborhood embodies classic New England architecture, perfect for immersing yourself in the area's historic ambiance.

View 56+ Rentals in Beacon Hill

Best Times to Visit Historic Dedham Square

When should you plan your Vacation Rentals stay?

Choosing the ideal time to visit here can enhance your experience, as the best seasons for exploring this destination often depend on your preferences for weather and local events in the region.

Peak Season Highlights

summer
Late spring to early summer (May to June)

During this period, the area experiences pleasant weather, making it ideal for exploring historic sites and enjoying outdoor dining in this charming destination.

Average Temperature Daytime: Mid-70s°F - Nighttime: Mid-50s°F
autumn
Early fall (September to October)

The early fall months offer comfortable temperatures and vibrant scenery, perfect for immersing yourself in the local culture and heritage.

Average Temperature Daytime: Low 70s°F - Nighttime: Mid-50s°F

Off-Season Highlights

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Winter (December to February)

During the colder months, fewer visitors choose to explore here, providing a peaceful atmosphere and intimate experience with the area's historic charm.

Average Temperature Daytime: High 30s°F to Low 40s°F - Nighttime: 20s°F to 30s°F
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Late fall (November)

As the region transitions into winter, this time offers a quieter experience, yet still allows you to enjoy the local ambiance and seasonal decorations.

Average Temperature Daytime: High 40s°F - Nighttime: Low 30s°F

Weekly Weather Forecast for Historic Dedham Square

How to Book Your Historic Dedham Square Vacation Rental Home

What's our booking process?

Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Historic Dedham Square

More Top-Rated Vacation Rentals in Historic Dedham Square Area

Common Vacation Rentals Amenities

What amenities can you expect?

Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:

Indoor Features

  • Fully-equipped kitchens with modern appliances
  • Comfortable living areas with flat-screen TVs
  • Free Wi-Fi for staying connected
  • Air conditioning and heating for year-round comfort
  • In-unit washers and dryers for convenience
  • Luxurious bedrooms with premium bedding
  • Spa-like bathrooms with soaking tubs or walk-in showers

Outdoor Amenities

  • Enjoy a private outdoor patio or garden space to relax after exploring the area.
  • Take advantage of on-site barbecue facilities to prepare outdoor meals in the fresh air.
  • Make use of shared or dedicated outdoor seating areas to unwind with friends or family.
  • Benefit from nearby walking trails or parks for outdoor recreation and sightseeing.
  • If available, utilize outdoor pool options for a refreshing dip during your stay.
  • Experience convenient access to outdoor fitness equipment for active pursuits.
  • Capitalize on outdoor dining setups that allow you to enjoy local flavors al fresco.

Top Attractions Around Historic Dedham Square

What attractions are nearby?

Within walking distance of your vacation rentals, you'll find a variety of activities in the area that allow you to explore local history, enjoy charming shops, and experience vibrant community events in this historic Massachusetts neighborhood.

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Family Activities

  • Dedham Historical Society Museum: Explore local history through engaging exhibits and artifacts, offering an educational experience for the whole family.
  • Walnut Hill Park: Enjoy a relaxing afternoon outdoors with scenic walking paths, playgrounds, and picnic areas perfect for family outings.
  • Dedham Community Theater: Catch a family-friendly film or live performance in this historic theater nearby, providing entertainment for all ages.
  • Local Farmers Market: Visit the vibrant market to taste fresh produce, artisanal goods, and connect with the community in the heart of the area.
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Adult Activities

  • Historical Walking Tours: Discover the rich history of this destination through guided walking tours that showcase its unique architecture and cultural heritage.
  • Coffee Shop Hopping: Savor locally roasted coffee at charming cafes around the area, perfect for relaxing mornings or casual meetups with friends.
  • Art Galleries and Studios: Explore vibrant art scenes in nearby galleries featuring works from local artists, offering a creative escape in this region.
  • Dining Experiences: Indulge in diverse culinary options at historic eateries and modern restaurants, ideal for savoring regional flavors during your stay.

Historic Dedham Square Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Eateries: Take advantage of the area's charming cafés and restaurants to enjoy authentic regional flavors that enhance your stay in this historic part of Dedham.
  • Visit Community Events: Check out any local festivals or markets happening nearby to immerse yourself in the vibrant culture of the region.
  • Plan Scenic Walks: Discover the quaint streets and scenic parks around your vacation rental to experience the historical charm and natural beauty here.
  • Utilize Public Transportation: Use local transit options or bike rentals to easily navigate the area and make the most of your time exploring Dedham's historic sites.

Transportation Options

  • Dedham Square Trolley Service: This convenient trolley provides easy access around the area, making it simple to explore all that Dedham has to offer without hassle.
  • Massachusetts Bay Transportation Authority (MBTA) Commuter Rail: The nearby MBTA station connects you to Boston and other major cities, offering a reliable transit option for day trips or commuting.
  • Local Taxi and Ride-Sharing Services: Taxis and ride-share apps like Uber and Lyft are readily available here, providing flexible transportation options during your stay.
  • Private Car Rentals: Renting a car gives you the freedom to explore at your own pace and reach destinations beyond this neighborhood with ease.

Local Customs Options

  • Welcome to Dedham's Local Greetings: When visiting here, you'll notice a warm and friendly greeting that reflects the area's welcoming community spirit.
  • Respect for Historical Preservation: It is customary to honor the preservation efforts in this destination by respecting local landmarks and historical sites.
  • Community Celebrations: Participating in seasonal festivals and community events is a common way locals celebrate their heritage and foster a sense of togetherness.
  • Traditional Dining Etiquette: When dining at local establishments, expect a courteous approach to service, with an appreciation for regional culinary traditions.

Frequently Asked Questions About Historic Dedham Square?

1. What are the top vacation rentals in Historic Dedham Square?

There are a lot of options in Historic Dedham Square. If you plan on staying in the Historic Dedham Square area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Historic Dedham Square:

2. How many Rentbyowner vacation rentals are available in Historic Dedham Square?

Currently, the total number of properties listed by Rent By Owner in 2026 is over 79 in the Historic Dedham Square area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Historic Dedham Square. 

3. What is the cancellation policy for bookings in this area?

Cancellation policies can vary depending on the individual property owner. To find out the specific terms and any potential fees, please review the listing details or contact the host directly before confirming your reservation.

4. How do I secure my reservation at a vacation rental here?

Reservations are typically secured through the booking platform by following the outlined steps on the property’s listing page. Make sure to complete all required information and confirm your payment to finalize your booking.

5. Are there any additional fees I should be aware of when booking a vacation rental in this destination?

Additional fees such as cleaning fees, service charges, or local taxes may apply and will be detailed on the listing page. Review these charges carefully before completing your reservation to understand the total cost.

6. What amenities are typically included in rental properties in this part of Massachusetts?

Most vacation rentals in this region offer essential amenities like Wi-Fi, parking, kitchen facilities, and often some special features based on the property. For specific amenities, please check the listing description or contact the owner directly.

7. Is it possible to arrange early check-in or late check-out at a vacation rental in this area?

Early check-in and late check-out options depend on the individual property’s policies and availability. Contact the host in advance to inquire about these arrangements and ensure they can accommodate your travel schedule.

Best Vacation Homes in Historic Dedham Square