Dedham, MA Rentals by Owner

Dedham Rentals by Owner

House

FIFA World CUP Updated historic home located near Gillette Stadium.

2 Bedrooms 3 Baths 4 Guests

US $709/Night 7 Nights - US $4,966

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Apartment

Comfy & Chic Apartment for 2026 World Cup FREE PARKING

10.0

Exceptional

(1 Review)

3 Bedrooms 1 Bath 6 Guests 1097.92 ft²

US $240/Night 7 Nights - US $1,681

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Apartment

Cozy 2-bedroom apartment in charming Boston with WiFi, AC. Commuter train

10.0

Exceptional

(19 Reviews)

2 Bedrooms 1 Bath 4 Guests

US $275/Night 7 Nights - US $1,923

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Unique & Peaceful Boston Home(Free Parking)

Highly Rated

Apartment

Unique & Peaceful Boston Home(Free Parking)

9.3

Exceptional

(71 Reviews)

2 Bedrooms 1 Bath 5 Guests 947.22 ft²

US $264/Night 7 Nights - US $1,847

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BOSTON-PRIVATE SUITE, WITH PRIVATE BATHROOM- WALK TO TRAIN & BUSES

Price Dropped

Apartment

BOSTON-PRIVATE SUITE, WITH PRIVATE BATHROOM- WALK TO TRAIN & BUSES

10.0

Exceptional

(4 Reviews)

1 Bedroom 1 Bath 1 Guest 700 ft²

US $173/Night 7 Nights - US $1,212

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Cozy Boston Getaway Apartment Perfect for 2026 World Cup Visit, Free Parking

Highly Rated

Apartment

Cozy Boston Getaway Apartment Perfect for 2026 World Cup Visit, Free Parking

9.1

Exceptional

(57 Reviews)

1 Bedroom 1 Bath 3 Guests 118.4 ft²

US $216/Night 7 Nights - US $1,514

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Apartment

Charming Victorian Furnished Home

9.8

Exceptional

(8 Reviews)

2 Bedrooms 2 Baths 7 Guests

US $349/Night 7 Nights - US $2,444

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House

Boston Single Family House - Super Quiet and Private

9.1

Exceptional

(14 Reviews)

5 Bedrooms 4 Baths 12 Guests 2604.87 ft²

US $444/Night 7 Nights - US $3,108

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Apartment

Boston Cozy studio Apt. near Train&Buses ,Parking included

9.8

Exceptional

(6 Reviews)

1 Bedroom 1 Bath 1 Guest

US $218/Night 7 Nights - US $1,523

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Apartment

Modern Beautiful Apartment-5 Beds-Full Kitchen-Parking-Super Clean-Great for Groups

8.2

Excellent

(73 Reviews)

2 Bedrooms 1 Bath 7 Guests 1108.68 ft²

US $70/Night 7 Nights - US $490

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Apartment

Large 5-Bed Modern Family Retreat with Kitchen & Free Parking Near Boston!

9.4

Exceptional

(23 Reviews)

2 Bedrooms 1 Bath 7 Guests 1111 ft²

US $251/Night 7 Nights - US $1,756

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Boston Duplex w/Foosball Table: 11 Mi to Downtown

Apartment

Boston Duplex w/Foosball Table: 11 Mi to Downtown

7.0

Very Good

(3 Reviews)

3 Bedrooms 1 Bath 6 Guests 1420.84 ft²

US $669/Night 7 Nights - US $4,683

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More Top-Rated Rentals by Owner in Dedham Area

Why Choose Rent By Owner for your Dedham vacation rental?

What makes our Rentals by Owner special?

Verified Listings

Book with confidence knowing every property meets our quality and safety standards.

Unbeatable Value

Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.

Diverse Options

From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Popular Areas for Dedham Rentals by Owner

Where are the best neighborhoods to stay in Dedham?

When selecting a neighborhood to stay in Dedham, Massachusetts, you’ll find a variety of charming options that offer both convenience and comfort. Whether you prefer a quiet residential area close to local amenities or a lively community with easy access to transportation, Dedham’s neighborhoods provide the perfect backdrop for your stay. Exploring rental options by owner through Rent By Owner ensures you can find a reliable and seamless booking experience tailored to your preferences. Each neighborhood in Dedham offers its own unique character, making it easy to enjoy a memorable visit in this welcoming Massachusetts town.

West Roxbury

Located just outside the city, this neighborhood offers a peaceful retreat where you can enjoy a quiet stay while still being close to Boston's vibrant attractions. Choosing a rental here provides easy access to local amenities and scenic surroundings, making it an ideal base for exploring the region.

View 25+ Rentals in West Roxbury

Best Times to Visit Dedham

When should you plan your Rentals by Owner stay?

To make the most of your stay, consider planning your vacation during the optimal times when the climate and local events align perfectly, ensuring a memorable experience while exploring the charming area of Dedham, Massachusetts.

Peak Season Highlights

Summer (June to August)

During the warm summer months, you'll experience ideal weather conditions for exploring the area and enjoying outdoor activities. This is the most popular time to visit, so securing your rental by owner early is recommended.

Average Temperature Daytime: 75-85°F - Nighttime: 60-70°F

Fall (September to November)

Autumn brings vibrant foliage and pleasant temperatures, making it a perfect season for sightseeing and outdoor pursuits in this destination. It's a favorite among travelers seeking a scenic and comfortable stay.

Average Temperature Daytime: 65-75°F - Nighttime: 50-60°F

Off-Season Highlights

Winter (December to February)

The winter months offer a quieter experience with less crowds and cozy ambiance, ideal if you prefer a peaceful retreat. Be prepared for cooler temperatures and possible snow during your stay here.

Average Temperature Daytime: 35-45°F - Nighttime: 20-30°F

Spring (March to May)

As the region begins to thaw, spring offers a fresh atmosphere with blooming landscapes and milder weather. It's an excellent time to enjoy the area's natural beauty without the peak season crowds.

Average Temperature Daytime: 55-65°F - Nighttime: 40-50°F

Weekly Weather Forecast for Dedham

How to Book Your Dedham vacation rental

What's our booking process?

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

Booking Steps

Search Properties

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

Select a Rental

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

Book Online

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

Explore and book the perfect rental in Dedham

More Top-Rated Rentals by Owner in Dedham Area

Common Rentals by Owner Amenities

What amenities can you expect?

Our Rentals by Owner 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 the outdoors with a private patio or deck, perfect for relaxing or dining al fresco.
Take advantage of a spacious backyard, ideal for outdoor activities or barbecues.
Experience the region's natural beauty with access to landscaped gardens or green spaces.
Make use of outdoor dining areas, allowing you to savor meals while soaking in the local scenery.
If available, utilize a lovely porch or veranda to unwind and watch the world go by.
Benefit from outdoor furniture that invites you to lounge comfortably amidst the fresh air.
Some rentals may feature a fire pit for cozy evenings under the stars after exploring here and around.

Top Attractions Around Dedham

What attractions are nearby?

Within this charming area, you can enjoy a variety of outdoor activities, explore local parks, or indulge in cultural experiences nearby, making your stay in Dedham an enriching and memorable experience.

Family Activities

Checking out the Dedham Historical Society Museum: Discover local history and engage your family with interactive exhibits that bring the area's past to life.
Enjoying a day at the Websterville Farm: Experience agricultural fun with hands-on activities and scenic farm views perfect for families seeking outdoor adventures.
Walking along the scenic trails at Blue Hills Reservation: Explore outdoor pathways suitable for all ages, offering fresh air and stunning vistas just minutes from here.
Visiting the Legacy Place shopping and entertainment complex: Spend quality time browsing shops, dining options, and catching family-friendly movies in this vibrant regional destination.

Adult Activities

Visit the Dedham Historical Society & Museum: Delve into the area's rich history and explore engaging exhibits that showcase the region's past.
Explore the Legacy Place Shopping Center: Enjoy a premium retail experience with a variety of shops, dining options, and entertainment venues within easy reach.
Play at the Blue Hills Reservation: Take advantage of scenic hiking trails and outdoor activities in this expansive natural area close to here.
Dine at local restaurants: Savor diverse culinary experiences at eateries that reflect the region’s vibrant food scene, perfect for relaxing evenings.

Other Places to Stay in Dedham, MA

The Fairbanks House

Explore 90 Properties

Dedham Historical Society

Explore 84 Properties

Fiddlehead Theatre

Explore 82 Properties

Historic Dedham Square

Explore 77 Properties

Harvard Vanguard - Dedham

Explore 62 Properties

Kings Bowling

Explore 56 Properties

Legacy Place

Explore 52 Properties

More Places to Stay Near Dedham

Dedham Travel Tips

How Can You Make the Most of Your Stay?

Plan Your Visit During Off-Peak Seasons: Visiting during less busy times allows for a more relaxed experience and better access to rental options in the area.
Explore Local Dining and Shopping: Take advantage of nearby eateries and shops to enjoy authentic regional flavors and unique souvenirs without the hassle of long travel distances.
Prioritize Convenience in Your Accommodation Search: Look for rentals close to key attractions or transportation hubs to maximize your time and reduce commuting stress here.
Engage with Your Host for Personalized Tips: Reach out to your rental owner for insider recommendations on hidden gems and must-see spots in this destination's surroundings.

Transportation Options

Bay Transportation: Offers convenient bus services within the region, making it easy for you to explore Dedham and its surroundings without hassle.
Dedham Parkway Commuter Rail Station: Provides quick access to Boston and other nearby cities, ideal for travelers planning day trips or commuting from their rental in the area.
Rental Car Services: Numerous local providers in this destination ensure you can easily rent a vehicle to discover the broader region at your own pace.
Taxis and Rideshare Options: Widely available around here, offering flexible transportation solutions for short trips within Dedham and nearby destinations.

Local Customs Options

Respect for Local History: You’ll find that honoring Dedham’s historical sites and stories is a valued custom here, enriching your experience of this destination’s rich past.
Community Engagement: Participating in neighborhood events and supporting local businesses is a common way to connect with the region’s welcoming residents.
Dining Etiquette: When enjoying local cuisine, it’s appreciated to observe customary manners, particularly during traditional gatherings and family-style meals.
Environmental Awareness: The area encourages eco-friendly practices, so you’re encouraged to reduce waste and respect natural surroundings during your stay.

Dedham Rentals by Owner Frequently Asked Questions

1. What are the top Vacation Rentals in Dedham?

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

2. How many Vacation Rentals are available in Dedham?

Currently, the total number of properties listed by RBO in 2026 is over 75 in the Dedham area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Vacation Rentals in Dedham. 

3. What is the cancellation policy for a rental by owner in Dedham, Massachusetts?

The cancellation policy varies by listing. To understand the specific terms, please review the details provided on the property listing or contact the owner directly before booking.

4. How do I communicate with the property owner during my stay in Dedham?

You can typically message the owner through the booking platform used for your reservation. For any urgent questions or special requests, reaching out directly via the contact information provided in the listing is recommended.

5. Are there any additional fees beyond the nightly rate for rentals in Dedham, Massachusetts?

Additional fees such as cleaning, service charges, or local taxes may apply. These will be outlined clearly in the listing details, so be sure to review them before confirming your reservation.

6. What amenities are usually included in rentals by owner here?

Most rentals by owner in this area offer essential amenities like Wi-Fi, parking, and kitchen facilities. Specific amenities vary by property, so check the listing description for detailed information.

7. Is there a minimum stay requirement for renting in Dedham, Massachusetts?

Minimum stay requirements depend on the individual property owner’s policies. Details about stay durations are generally specified in the listing, or you can inquire directly with the owner for clarification.