What are the top family-friendly attractions in Dedham, MA?

Dedham is a great place for families! The Endicott Estate is a popular spot with its beautiful gardens and the Endicott Mansion. There's also the Dedham Public Library, which has a great children's section and hosts fun events for kids.

What are the best Airbnb and vacation rentals in Dedham, MA?

Hidden Gem Near Boston W/ 2 Bedrooms Highspeedwifi , Private Apartment Close The City and The Gatehouse - Cheerful 3 Bedroom 3 Bathroom House are the most popular Airbnb and vacation rentals in Dedham, MA among travelers.

When is the best time to book a vacation rental in Dedham, MA?

The best time to book a vacation rental in Dedham is during the shoulder seasons, like spring or fall. You'll avoid the summer crowds and get better rates. Plus, the weather is still pleasant, so you can enjoy outdoor activities.

What are the most popular Airbnbs in Dedham, MA?

Among the Airbnbs in Dedham, MA, Hidden Gem Near Boston W/ 2 Bedrooms Highspeedwifi , Private Apartment Close The City and Charming Townhouse In Historic Town Near Boston are the most popular ones.

What events or festivals should visitors check out in and around Dedham, MA?

Dedham has a few fun events throughout the year. The Dedham Farmers Market is a great place to find local produce and crafts. In the fall, the Dedham Fall Festival is always a hit with its parade, live music, and family-friendly activities.

What are the best vacation rentals with a pool in Dedham, MA?

The best vacation rental with a pool in Dedham, MA is The Commonwealth Estate .

What are the best budget-friendly activities in Dedham, MA?

Dedham has plenty of budget-friendly activities. You can take a walk or bike ride along the Charles River, visit the free Dedham Public Library, or explore the historic Dedham Square. There are also a few parks with playgrounds and picnic areas where you can relax and enjoy the scenery.

What are the best rentals for families and kids in Dedham, MA?

The best rentals for families and kids in Dedham, MA are Private Apartment Close The City , The Gatehouse - Cheerful 3 Bedroom 3 Bathroom House and Lovely Townhouse Apartment Minutes From Boston .

What are the best restaurants with local dishes in Dedham, MA?

If you're looking for local fare, you can't go wrong with The Blue Rooster. They're known for their New England comfort food, like clam chowder and lobster rolls. Another favorite is The Tavern on the Square, which serves classic American dishes with a modern twist.

What are the best rentals or Airbnbs with a jacuzzi in Dedham, MA?

The best vacation rental or Airbnb with a jacuzzi in Dedham, MA is 5 Room In Law Apartment - Close To Boston .

What are the best walking or cycling routes in Dedham, MA?

Dedham has a great network of walking and biking trails. The Charles River Path is a popular choice, offering scenic views of the river. You can also check out the trails at the Endicott Estate or the Dedham Town Forest.

Are there pet-friendly attractions in Dedham, MA?

Dedham is a pretty dog-friendly town! Many of the parks, like the Endicott Estate and the Dedham Town Forest, welcome leashed pets. There are also a few pet-friendly restaurants and cafes in Dedham Square.

What are the benefits of choosing a vacation rental in Dedham, MA?

Vacation rentals offer more space and privacy than a hotel. You can cook your own meals, which can save money, and you'll have the flexibility to come and go as you please. Plus, many rentals have unique features, like a fireplace or a backyard, that you won't find in a hotel.

Dedham, MA Vacation rentals & Airbnb

10 1 review

Airy 1br Walkable To Everywhere In Boston | W+d

apartment, Boston

This one-bedroom rental is located in Boston's Bay Village, just 500 feet from Boston Common, offering convenient access to major attractions like Fenway Park and Faneuil Hall Marketplace.
This pet-friendly apartment includes utilities, Wi-Fi, a fully stocked kitchen, and air conditioning, with touchless check-in and walk-up access in a building with tall ceilings, accommodating up to two guests.

No reviews

Spacious Studio | 1 King Bed | Near Boston Waltham Center

studio, Waltham

This studio apartment is located in downtown Waltham, offering a prime lakeside setting with convenient access to Harvard Square and Newbury Street, situated approximately 6 miles from Boston Common and Boston Harbor.
This pet-friendly studio features air conditioning, a balcony with views, complimentary Wi-Fi, a fully equipped kitchen with a fridge and microwave, and includes daily breakfast and access to an on-site fitness center for up to 2 guests.

9.6 6 reviews

Sleek 3br Boston - World Cup 2026 Escape - Near Franklin Park 60-3

apartment, Boston

This three-bedroom Boston apartment near Wollaston Beach offers a peaceful retreat, conveniently located 6.5 miles from Fenway Park and 7 miles from South Station.
The 1300-square-foot rental boasts two bathrooms, free parking and Wi-Fi, a fully equipped kitchen, and accommodates up to 29 guests, perfect for large groups visiting Boston.

8.3 6 reviews

Stunning 1br Steps To Fenway

apartment, Boston

This Fenway apartment is a short walk from Fenway Park, and within 12 minutes of Boston University and 17 minutes from the Museum of Fine Arts.
This 650-square-foot unit features one bedroom, one bathroom, sleeps three guests, and includes free Wi-Fi, air conditioning, and a fully equipped kitchen.

10 12 reviews

Woodland Retreat

apartment, Canton

This 3-bedroom, 2-bathroom apartment in Canton offers a secluded woodland setting 20 miles from Boston, with Gillette Stadium 14 miles away.
This rental accommodates up to 6 guests and features air conditioning, a fully equipped kitchen with a dishwasher and microwave, high-speed Wi-Fi, and private parking, plus a yard ideal for outdoor relaxation.

No reviews

Rv-with-me: World Cup Foxborough (Stationary Rv)

house, Canton

This stationary Jayco Redhawk RV is located 6 miles from Foxborough Stadium in Canton, offering a unique lodging experience.
This accommodation features internet, a kitchen, air conditioning, one bathroom, and can host up to 4 guests.

8.8 10 reviews

Spacious And Bright Studio

studio, Boston

This Boston studio apartment is conveniently located near Back Bay, a 13-minute walk from the Museum of Fine Arts, and 1.2 miles from Fenway Park.
The 310-square-foot unit features a separate bedroom, a full kitchen with oven and toaster, free Wi-Fi, air conditioning, and accommodates up to three guests.

9.5 4 reviews

West Roxbury Pet Friendly A.c Private Bath

apartment, Boston

This Boston-area guesthouse, registered with the city (STR-513970), offers a private third-floor unit a 25-minute drive from Downtown Boston and 15–30 minutes from area hospitals, conveniently located near the Needham Line Commuter Rail for easy access to South Station.
The 1-bedroom, 1-bathroom unit sleeps 4, includes a full-size bed, dining and sitting areas, a kitchen with fridge, freezer, and microwave, air conditioning, parking, and excellent guest reviews.

9.8 11 reviews

Charming Dedham Retreat !

apartment, Dedham

This Dedham rental unit is situated for prime access to Legacy Place, a shopping and entertainment hub, and is a 20-mile drive from Gillette Stadium.
This pet-friendly, 2-bedroom, 2-bathroom condo accommodates up to 6 guests, offering a full kitchen, air conditioning, and a private backyard, with 24/7 self check-in available.

9.0 2 reviews

Stunning 1br | Steps To Fenway!

apartment, Boston

This one-bedroom condo is located in Boston's Fenway-Kenmore district, offering proximity to Fenway Park, Newbury Street, and Copley Place, with public transportation a short walk away for easy access to Back Bay and Cambridge. This pet-friendly unit accommodates two guests and includes air conditioning, internet, a fully equipped kitchen, and keyless entry, with potential for city noise due to its central location.

No reviews

Plannetsmart

apartment, Boston

This Planet Smart Boston apartment, located approximately 6-8 miles from attractions like the Museum of Fine Arts, Fenway Park, and Back Bay, offers easy access to Boston's major sights via car or public transportation.
This 1190-square-foot rental boasts two bedrooms, one bathroom, and sleeps up to 11 guests, featuring a fully equipped kitchen, in-unit laundry, free Wi-Fi, a private balcony, free parking, and a shared lounge area.

No reviews

Morden King Room In Boston King (Tropical Vibez#2)

apartment, Boston

This 1-bedroom condo is located in Boston's Roxbury neighborhood, offering proximity to the Museum of Fine Arts, Berklee College of Music, Boston Harbor, and Flynn Cruiseport Boston.
This pet-friendly unit accommodates 2 guests and features air conditioning, internet, an indoor fireplace, a private balcony, and a 3-bathroom layout.

Browse Vacation Rentals in the Historic District of Dedham, MA

Choose a downtown Dedham, MA vacation rental for easy sightseeing. Compare the top centrally located properties and book your city stay with confidence.

10 6 reviews

Great 1bd | Close To Boston & 20 Mins To Gillette

apartment, Norwood

This Norwood apartment offers convenient access to Boston via commuter rail and is less than 20 miles from Foxboro and World Cup event venues.
This one-bedroom, one-bathroom condo accommodates up to four guests and features a fully equipped kitchen with a fridge, freezer, microwave, and dishwasher, along with air conditioning, high-speed WiFi, and off-street parking.

10 1 review

A New 3 Bedroom 4 Beds 2 Bath, Apt 3

apartment, Boston

This 3-bedroom apartment in Boston is situated approximately 7 miles from the Museum of Fine Arts and 7.5 miles from Fenway Park, offering a suburban base with convenient access to key city attractions.
This 1500 square foot residence features 3 bedrooms, 2 bathrooms, and accommodates up to 13 guests with amenities including a full kitchen with a dishwasher and microwave, air conditioning, and complimentary Wi-Fi.

10 12 reviews

Woodland Retreat

apartment, Canton

9.8 11 reviews

Charming Dedham Retreat !

apartment, Dedham

Best Dedham, MA vacation rentals with air conditioning

9.0 2 reviews

Walk Everywhere - Seaport, North End, Beacon Hill. Steps From Mbta Public Transit. Keyless Entry!

apartment, Boston

This professionally designed 1-bedroom apartment is located in Downtown Boston, offering proximity to Boston Harbor, Flynn Cruiseport Boston, Boston Common, and is within 0.5 miles of the New England Aquarium and Museum of Science.
This thoughtfully furnished flat accommodates up to 4 guests with an optional air mattress, features a full kitchen with a fridge, microwave, and dishwasher, and is equipped with air conditioning and internet, with parking available for an additional fee.

10 4 reviews

Quiet, Private 1 Bedroom Garden Apt Near Harvard/mit, Sleeps 4 Adults + 1 Infant

apartment, Cambridge

This Cambridge apartment is located in Riverside, an 8-minute walk from the Red Line metro station at Central Square and within walking distance of Harvard, HBS, and MIT. It has received excellent user ratings and is a great option for travelers looking for a comfortable and convenient stay in Cambridge.
The apartment is a spacious 1-bedroom unit that can accommodate up to 5 guests and features a fully equipped kitchen, a private backyard, free parking, and a washer and dryer. Guests can enjoy amenities such as air conditioning, internet access, and a garden, making it a perfect choice for families or groups of friends.

9.8 6 reviews

8-peaceful & Bright Apt/3br Right To Boston Line

apartment, Milton

This Milton apartment rental is conveniently located near I-93/95, the MBTA Red Line, and Andrews Park, offering easy access to downtown Boston (7 miles away).
The three-bedroom unit sleeps up to 10 guests, features in-unit laundry, one garage parking space plus off-street parking, and is close to restaurants, shops, President Golf Course, and Wollaston Beach.

No reviews

Modern Room In Central Boston Queen Room(wavez#3)

apartment, Boston

This Boston flat is located in Roxbury, offering proximity to Fenway Park and Faneuil Hall Marketplace, with convenient access to public transport.
This one-bedroom, two-bathroom rental accommodates two guests and includes a private balcony, indoor fireplace, air conditioning, and parking.

Frequently Asked Questions about vacation rentals in Dedham, MA

What are the top family-friendly attractions in Dedham, MA?
Dedham is a great place for families! The Endicott Estate is a popular spot with its beautiful gardens and the Endicott Mansion. There's also the Dedham Public Library, which has a great children's section and hosts fun events for kids.
What are the best Airbnb and vacation rentals in Dedham, MA?
Hidden Gem Near Boston W/ 2 Bedrooms Highspeedwifi, Private Apartment Close The City and The Gatehouse - Cheerful 3 Bedroom 3 Bathroom House are the most popular Airbnb and vacation rentals in Dedham, MA among travelers.
When is the best time to book a vacation rental in Dedham, MA?
The best time to book a vacation rental in Dedham is during the shoulder seasons, like spring or fall. You'll avoid the summer crowds and get better rates. Plus, the weather is still pleasant, so you can enjoy outdoor activities.
What are the most popular Airbnbs in Dedham, MA?
Among the Airbnbs in Dedham, MA, Hidden Gem Near Boston W/ 2 Bedrooms Highspeedwifi, Private Apartment Close The City and Charming Townhouse In Historic Town Near Boston are the most popular ones.
What events or festivals should visitors check out in and around Dedham, MA?
Dedham has a few fun events throughout the year. The Dedham Farmers Market is a great place to find local produce and crafts. In the fall, the Dedham Fall Festival is always a hit with its parade, live music, and family-friendly activities.
What are the best vacation rentals with a pool in Dedham, MA?
The best vacation rental with a pool in Dedham, MA is The Commonwealth Estate.
What are the best budget-friendly activities in Dedham, MA?
Dedham has plenty of budget-friendly activities. You can take a walk or bike ride along the Charles River, visit the free Dedham Public Library, or explore the historic Dedham Square. There are also a few parks with playgrounds and picnic areas where you can relax and enjoy the scenery.
What are the best rentals for families and kids in Dedham, MA?
The best rentals for families and kids in Dedham, MA are Private Apartment Close The City, The Gatehouse - Cheerful 3 Bedroom 3 Bathroom House and Lovely Townhouse Apartment Minutes From Boston.
What are the best restaurants with local dishes in Dedham, MA?
If you're looking for local fare, you can't go wrong with The Blue Rooster. They're known for their New England comfort food, like clam chowder and lobster rolls. Another favorite is The Tavern on the Square, which serves classic American dishes with a modern twist.
What are the best rentals or Airbnbs with a jacuzzi in Dedham, MA?
The best vacation rental or Airbnb with a jacuzzi in Dedham, MA is 5 Room In Law Apartment - Close To Boston.
What are the best walking or cycling routes in Dedham, MA?
Dedham has a great network of walking and biking trails. The Charles River Path is a popular choice, offering scenic views of the river. You can also check out the trails at the Endicott Estate or the Dedham Town Forest.
Are there pet-friendly attractions in Dedham, MA?
Dedham is a pretty dog-friendly town! Many of the parks, like the Endicott Estate and the Dedham Town Forest, welcome leashed pets. There are also a few pet-friendly restaurants and cafes in Dedham Square.
What are the benefits of choosing a vacation rental in Dedham, MA?
Vacation rentals offer more space and privacy than a hotel. You can cook your own meals, which can save money, and you'll have the flexibility to come and go as you please. Plus, many rentals have unique features, like a fireplace or a backyard, that you won't find in a hotel.

Popular destinations

Top Vacation Rentals with Balconies in Dedham, MA

Enjoy a Dedham, MA vacation rental with a balcony and stunning city skyline views for a truly memorable stay.

8.3 3 reviews

Cozy & Private 4br Randolph Home - Near I-93 & Route - Pet-friendly 17

apartment, Randolph

This Randolph rental is conveniently located 12 miles from the John F. Kennedy Presidential Library and Museum and 13 miles from the Museum of Fine Arts, Boston.
This 1500-square-foot, four-bedroom home sleeps 39 guests and features three bathrooms, a fully equipped kitchen, free Wi-Fi, private parking, a terrace, a garden, and concierge service.

10 1 review

Walk To Gillette Stadium - Sleeps 6 - Parking

apartment, Walpole

This 2-bedroom, 1.5-bathroom apartment in Walpole is located just a 4-minute drive from Patriot Place and Gillette Stadium, and 5 minutes from Nature Trail and Cranberry Bog.
This dwelling offers complimentary Wi-Fi, air conditioning, a private patio, and on-site laundry facilities, with a guest capacity of four.

10 2 reviews

Modern City & Water View 1-bedroom Apartment With Ac. 4 Blocks From T/ Beach

apartment, Boston

This East Boston residence offers unobstructed views of the Boston skyline and harbor, with Revere Beach just a short drive away and downtown attractions like TD Garden easily accessible.
This 1000-square-foot apartment accommodates up to 4 guests, featuring a king-size Sleep Number bed, a fully equipped kitchen, air conditioning, internet, and a private deck with city and water vistas.

10 1 review

Bostonian 2br2bth / 8 Minutes To Boston

apartment, Somerville

This apartment in East Somerville is a 7-minute walk to the nearest grocery store and within a 10-15 minute walk of Gilman Square, East Somerville, and Union Square T-stations, offering convenient access to Boston.
This 1300 square foot rental accommodates up to 6 guests with 2 bedrooms and 2 bathrooms, featuring central air conditioning, a private balcony, a garden, a spa, and complimentary parking for up to 4 vehicles.

Discover Family-Friendly Vacation Rentals in Dedham, MA

Ideal for family vacations, these Dedham, MA rentals or Airbnbs offer spacious layouts near top city attractions.

No reviews

W.r. Duplex Apt Flrs 2 And 3 Sleeps 10 Boston

apartment, Boston

This Boston apartment rental (STR-513970), sleeps nine guests in two bedrooms and two bathrooms, and includes a kitchen and air conditioning.
Further details regarding the unit's precise location, square footage, interior design, and nearby attractions are needed to provide a complete description.

No reviews

Studio Flat ∙ 1 Bedroom ∙ 2 Guests

studio, Quincy

This upscale studio apartment in Quincy is located directly across from North Quincy Station, providing direct subway access to Boston and placing you within 0.5 miles of Adams National Historic Park and the U.S. Naval Museum.
This family-friendly studio accommodates up to two guests and features a full kitchen with a fridge, microwave, and dishwasher, air conditioning, a fitness center, and complimentary breakfast.

No reviews

Luxe 3bd Allston

apartment, Boston

This 3-bedroom, 2-bathroom rental unit is located in Boston's Allston neighborhood, 1.6 miles from John F. Kennedy Park and 2 miles from Harvard Square.
This 1490 square foot residence accommodates up to 14 guests and features air conditioning, free WiFi, a fully equipped kitchen with a dishwasher, and complimentary private parking.

No reviews

Cozy 2br Cape Bungalow Near Boston

apartment, Milton

This family-friendly 2-bedroom, 1-bathroom apartment in Milton offers easy access to major highways and is located approximately 1 mile from the Blue Hills Reservation, ideal for outdoor activities like hiking and skiing.
This cape-style bungalow provides a comfortable stay for up to 4 guests with amenities including air conditioning, internet, a full kitchen with a dishwasher, and a security system, situated in a desirable suburban neighborhood.

Best Dedham, MA vacation rentals with parking

No reviews

World Cup Boston: Walk To Train + Free Parking

apartment, Norwood

No reviews

Prestigious Milton Designer Home

apartment, Milton

No reviews

World Cup! Norwood House 3 Bed 2 Bath

apartment, Norwood

9.6 28 reviews

Family-friendly 3br Apt - Easy Downtown Boston Accesss - Near Franklin Park 603

apartment, Boston

Best 5-Star Vacation Rentals in Dedham, MA

Stay in a luxury city-center vacation rental in Dedham, MA for a sophisticated urban escape with premium 5-star amenities.

8.0 3 reviews

Luxury Studio King Bed Gym Near Mit Harvard

studio, Cambridge

Find the Best Dog-Friendly Vacation Rentals in Dedham, MA

Traveling with pets? These dog-friendly vacation rentals and Airbnbs in Dedham, MA are steps away from dog parks and city walks.

9.7 3 reviews

Luxury At 2br 2ba 200mbps Internet

apartment, Boston

No reviews

Sleeps 4 Queen+futon 15 Min From Gillette Stadium.

apartment, Canton

8.0 1 review

Perfect Traveling Nurse Housing In Theatre District

apartment, Boston

No reviews

Spacious And Bright Studio

studio, Boston

Search Vacation Rentals with Swimming Pool in Dedham, MA

Choose a Dedham, MA rental with a pool for a refreshing swim right in the heart of the city.

No reviews

Family Suite In Boston With Pool Gym & Balcony - Perfect Stay

apartment, Boston

No reviews

What A Gem City Views And A Rooftop Pool Await

apartment, Boston

Top-Rated Vacation Rentals with a Hot Tub in Dedham, MA

Coming home to a private hot tub after a day of urban exploration completely transforms your Dedham, MA experience.

9.6 6 reviews

Sleek 3br Boston - World Cup 2026 Escape - Near Franklin Park 60-3

apartment, Boston

Compare vacation rentals in Dedham, MA from 100+ sites!

Best Vacation rentals and Airbnb offers in Dedham, MA

Airy 1br Walkable To Everywhere In Boston | W+d

Spacious Studio | 1 King Bed | Near Boston Waltham Center

Sleek 3br Boston - World Cup 2026 Escape - Near Franklin Park 60-3

Stunning 1br Steps To Fenway

Woodland Retreat

Rv-with-me: World Cup Foxborough (Stationary Rv)

Spacious And Bright Studio

West Roxbury Pet Friendly A.c Private Bath

Charming Dedham Retreat !

Stunning 1br | Steps To Fenway!

Plannetsmart

Morden King Room In Boston King (Tropical Vibez#2)

Great 1bd | Close To Boston & 20 Mins To Gillette

A New 3 Bedroom 4 Beds 2 Bath, Apt 3

Woodland Retreat

Charming Dedham Retreat !

Walk Everywhere - Seaport, North End, Beacon Hill. Steps From Mbta Public Transit. Keyless Entry!

Quiet, Private 1 Bedroom Garden Apt Near Harvard/mit, Sleeps 4 Adults + 1 Infant

8-peaceful & Bright Apt/3br Right To Boston Line

Modern Room In Central Boston Queen Room(wavez#3)

Cozy & Private 4br Randolph Home - Near I-93 & Route - Pet-friendly 17

Walk To Gillette Stadium - Sleeps 6 - Parking

Modern City & Water View 1-bedroom Apartment With Ac. 4 Blocks From T/ Beach

Bostonian 2br2bth / 8 Minutes To Boston

W.r. Duplex Apt Flrs 2 And 3 Sleeps 10 Boston

Studio Flat ∙ 1 Bedroom ∙ 2 Guests

Luxe 3bd Allston

Cozy 2br Cape Bungalow Near Boston

World Cup Boston: Walk To Train + Free Parking

Prestigious Milton Designer Home

World Cup! Norwood House 3 Bed 2 Bath

Family-friendly 3br Apt - Easy Downtown Boston Accesss - Near Franklin Park 603

Luxury Studio King Bed Gym Near Mit Harvard

Luxury At 2br 2ba 200mbps Internet

Sleeps 4 Queen+futon 15 Min From Gillette Stadium.

Perfect Traveling Nurse Housing In Theatre District

Spacious And Bright Studio

Family Suite In Boston With Pool Gym & Balcony - Perfect Stay

What A Gem City Views And A Rooftop Pool Await

Sleek 3br Boston - World Cup 2026 Escape - Near Franklin Park 60-3