Compare vacation rentals in Dedham, MA from 100+ sites!
106 available vacation rental offers
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating
Best Vacation rentals and Airbnb offers in Dedham, MA
9.6 379 reviews
Dedham, MA
07/28 – 08/01
$268/nighttotal: $1072 (4 )
~*Pet Friendly 30min To Downtown*~ The Bostonian
2 4
house , Boston
This Boston home is located just 7 miles from the Hynes Convention Center and Back Bay, offering easy access to these popular districts while providing a quieter atmosphere. The home has consistently received excellent ratings for its cleanliness, location, and overall user experience. The 2-bedroom, 1-bathroom home spans 1000 square feet and provides comfortable accommodations for families or groups of travelers. Guests can enjoy amenities like a fully equipped kitchen, air conditioning, a private garden, and parking, making it an ideal choice for a relaxing and convenient Boston stay.
9.0 3 reviews
Dedham, MA
06/20 – 06/27
$353/nighttotal: $2471 (7 )
Boston Vacation,longwood Medical,mins To Mbta,pkg
1 2
apartment , Brookline
This Brookline apartment rental is conveniently located near the Longwood Medical Area, minutes from the MBTA, and within a few miles of Fenway Park, the Museum of Fine Arts, and Boston University. This 650-square-foot one-bedroom, one-bathroom unit sleeps seven guests and offers amenities including free Wi-Fi, a fully equipped kitchen with dishwasher, in-unit laundry, air conditioning, and a spa, plus pet-friendly accommodations.
10 19 reviews
Dedham, MA
07/28 – 08/01
$380/nighttotal: $1520 (4 )
Summer Escape In Milton | 2br Near Blue Hills 14/1
1 4
apartment , Milton
This Milton, MA townhouse, located near Blue Hills Reservation and a short drive from Milton Village, offers easy access to Quincy Center and Boston. The 1300-square-foot, two-bedroom, two-bathroom rental accommodates up to nine guests and includes a fully equipped kitchen, in-unit laundry, and self check-in.
9.7 449 reviews
Dedham, MA
09/05 – 09/12
$232/nighttotal: $1624 (7 )
Cozy Jp Studio-great Location!
1 2
apartment , Boston
This Jamaica Plain studio is a 4-minute walk from the Stony Brook Orange Line station, providing easy access to downtown Boston and proximity to Jamaica Pond and the Arnold Arboretum. The unit features a queen-size bed, a kitchenette with a Nespresso machine, free on-street parking, high-definition cable TV, and Wi-Fi, comfortably accommodating two guests.
9.2 60 reviews
Dedham, MA
06/18 – 06/22
$361/nighttotal: $1444 (4 )
Cozy Boston Getaway Apartment Perfect For 2026 World Cup Visit, Free Parking
1 2
apartment , Boston
This one-bedroom apartment is located in a peaceful residential area of Boston, just a short drive from attractions like the Museum of Fine Arts and Fenway Park. Guests consistently rate the apartment excellent for cleanliness and location, making it a comfortable and convenient choice. The 600-square-foot apartment comfortably accommodates two guests and features a fully equipped kitchen, a private entrance, free parking, and a washing machine. Enjoy amenities like free Wi-Fi, air conditioning, and a garden, perfect for relaxing after a day exploring Boston.
8.0 3 reviews
Dedham, MA
06/20 – 06/27
$363/nighttotal: $2541 (7 )
Wonderful Newbury 1 Bedroom
1 2
apartment , Boston
This 1-bedroom apartment is located in Boston's prime Newbury area, offering excellent walkability to the Hynes Convention Center (a 4-minute walk), Prudential Tower (0.4 miles), MIT (1.2 miles), and the Museum of Fine Arts (1 mile). This dog-friendly rental provides 700 square feet of living space with air conditioning, free WiFi, and a kitchen equipped with a fridge, microwave, and oven, accommodating up to 3 guests.
9.4 22 reviews
Dedham, MA
06/20 – 06/27
$506/nighttotal: $3542 (7 )
Cozy Harvard/mit Victorian
2 2
apartment , Cambridge
This remodeled Victorian home is located in Cambridge's Huron Village, offering a quiet, historic atmosphere just a 10-minute walk to Harvard University and Harvard Square, with immediate T access to MIT and Boston. This 820-square-foot rental accommodates up to 6 guests in 2 bedrooms, featuring a fully equipped kitchen, in-unit laundry, air conditioning, a terrace, garden, and rare off-street parking, with optional housekeeping for monthly stays.
10 1 review
Dedham, MA
06/20 – 06/27
$504/nighttotal: $3528 (7 )
Beautiful 2br In Savin Hill Boston
1 2
apartment , Boston
This 2-bedroom apartment in Boston's Savin Hill neighborhood is located 1.3 miles from Carson Beach and within 3.5 miles of the JFK Presidential Library & Museum, Boston Tea Party Ship & Museum, Boston Convention Exhibitors Center, and Boston South Station. This 1050 square foot rental can accommodate up to 7 guests and features air conditioning, a balcony, free WiFi, a fully equipped kitchen with a dishwasher and microwave, and an in-unit washing machine.
9.6 149 reviews
Dedham, MA
07/28 – 08/01
$342/nighttotal: $1368 (4 )
Maria's Jp Rental - Boston Duplex In Popular Jamaica Plain "Jp" Area
2 4
apartment , Boston
This apartment is located in the heart of Boston, within easy walking distance of Franklin Park Zoo, Northeastern University, and Brigham and Women's Hospital. Guests consistently rate this property as excellent, making it a popular choice for travelers seeking a convenient and comfortable stay. The two-bedroom apartment offers 800 square feet of space, comfortably accommodating up to five guests. Enjoy amenities like a fully equipped kitchen, private yard, and free Wi-Fi, along with access to a garden, tennis court, and parking.
10 1 review
Dedham, MA
06/18 – 06/22
$331/nighttotal: $1324 (4 )
3 Mi To Blue Hills Skiing & Hiking! Couples Apt
1 2
apartment , Milton
This Milton apartment is located in a quiet suburban neighborhood, offering a peaceful retreat 10 miles from downtown Boston with easy access to Blue Hills Reservation (3 miles) and historic sites like Eustis Estate Museum (2 miles). This 1-bedroom, 1-bathroom unit spans 500 square feet, accommodates 2 guests, and features a covered balcony, 2 Smart TVs, free WiFi, and central heating with window A/C units.
9.5 2 reviews
Dedham, MA
06/20 – 06/27
$430/nighttotal: $3010 (7 )
New And Lovely 1br In Fidi District With Keyless Entry
1 2
apartment , Boston
This Boston Financial District apartment rental is ideally located less than a mile from the Freedom Trail and a six-minute walk from King's Chapel and Burying Ground. The 650-square-foot unit features one bedroom, one bathroom, accommodates three guests, and includes a fully equipped kitchen, in-unit laundry, keyless entry, and free Wi-Fi.
9.9 45 reviews
Dedham, MA
06/18 – 06/22
$457/nighttotal: $1828 (4 )
3 Bedroom 1.5 Bath Home Minutes From Boston!! Beautifully Decorated And Cozy.
3 2
apartment , Randolph
This vacation home in Randolph, Massachusetts is located within a 15-kilometer radius of South Shore Plaza, Granite Links Golf Club, and Legacy Place, offering easy access to shopping, dining, and entertainment. The property boasts excellent user, location, and cleanliness ratings, making it a comfortable and enjoyable choice for travelers. The 3-bedroom home spans 1250 square feet, comfortably accommodating up to 6 guests. The property features a fully equipped kitchen, a spacious patio, free Wi-Fi, a spa, and parking, providing everything you need for a relaxing and enjoyable stay.
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.
9.8 398 reviews
Dedham, MA
07/28 – 08/01
$506/nighttotal: $2024 (4 )
383 - 3br Quincy - Chic House Near Adams Park
3 4
apartment , Quincy
This modern townhouse is located in a busy street in Quincy, just a short distance from the Quincy Red Line T Station and the highway. The property has consistently received excellent ratings for cleanliness, location, and user experience. The three-bedroom townhouse is perfect for families or groups of up to 11 guests. The spacious kitchen is fully equipped for preparing meals, and the master bedroom features a luxurious Jacuzzi for relaxation.
9.4 18 reviews
Dedham, MA
09/05 – 09/12
$258/nighttotal: $1806 (7 )
Boston Area Hub By Train Station, Gillette Stadium
2 2
apartment , Stoughton
This 2-bedroom apartment is located in Stoughton, within walking distance of Stoughton Station and a 3-mile radius of popular attractions. It has an excellent user rating. The 1400-square-foot apartment features a fully equipped kitchen, a comfortable living space, and a family-friendly atmosphere. It can accommodate up to 5 guests and includes amenities such as air conditioning, internet, and parking. Guests can also enjoy proximity to outdoor recreation, historical charm, and easy access to medical care.
9.8 51 reviews
Dedham, MA
09/05 – 09/12
$237/nighttotal: $1659 (7 )
Beautiful Studio In Historic Neighborhood Of Boston. Super Close To Downtown!
1 2
studio , Boston
This Roxbury rental is conveniently located within 3 miles of Boston Medical Center, Northeastern University, Fenway Park, Copley Square, and Boston Common, offering easy access to public transportation via Uphams Corner and Newmarket Stations. The one-bedroom, one-bathroom apartment sleeps four guests and features a kitchenette with refrigerator, oven, stovetop, coffee maker, and electric kettle, free WiFi, air conditioning, a balcony, on-site garden, and parking.
8.2 82 reviews
Dedham, MA
06/18 – 06/22
$514/nighttotal: $2056 (4 )
Harmony Medical Suites Chinatown
1 2
studio , Boston
This Boston apartment in Chinatown is a 6-minute walk from the Freedom Trail and Boston South Station, and an 11-minute walk from the Boston Tea Party Ship & Museum. This pet-friendly residence offers air-conditioned units with free WiFi, some featuring full kitchens, and an on-site fitness center.
Best Dedham, MA vacation rentals with parking
8.7 3 reviews
Dedham, MA
06/18 – 06/22
$542/nighttotal: $2168 (4 )
Upscale 1br Mit Harvard Wifi Gym W D Parking
1 2
apartment , Cambridge
This Cambridge apartment rental is centrally located, a short walk from Central Square and within easy reach of MIT, Harvard University, and Inman Square. The 650-square-foot, one-bedroom unit sleeps seven guests and features a fully equipped kitchen, in-unit laundry, a private garden, on-site fitness center, parking, and free Wi-Fi.
8.8 15 reviews
Dedham, MA
09/05 – 09/12
$331/nighttotal: $2317 (7 )
74r - 2br Quincy - Romantic Stay Near Wollaston Beach
2 2
apartment , Quincy
This Tirrel Street rental in Quincy, MA, offers a convenient location near Wollaston Beach and downtown Quincy, providing easy access to local attractions. This 1,100-square-foot apartment features two bedrooms, one bathroom, and sleeps up to nine guests (with extra fees after four), boasting a fully equipped kitchen, in-unit laundry, central A/C, and one reserved parking space.
9.4 80 reviews
Dedham, MA
06/20 – 06/27
$1133/nighttotal: $7931 (7 )
Beautiful 6000 Sq Ft Home 20 Min To Boston
3 2
apartment , Newton
This 6000 sq ft, 3-bedroom, 4-bathroom residence in Newton offers a secluded 1/2 acre private lot and is conveniently located within a few miles of Encore Boston Harbor and Boston Port, with easy access to Boston Common and Revere Beach. This family-friendly apartment boasts a gourmet chef's kitchen with Miele appliances, a 2-story living room with a fireplace, a luxurious master suite, and a first-floor 3-bedroom suite, accommodating up to 9 guests with amenities including air conditioning, a jacuzzi, tennis court, and parking.
Dedham, MA
06/18 – 06/22
$479/nighttotal: $1916 (4 )
Spacious And Comfortable 1 Bed 25 Km From Gillette
1 2
apartment , Milton
This Milton apartment is located 6.1 miles from the Boston Museum of Fine Arts and approximately 7 miles from Back Bay and Fenway Park. This 500 sq ft, 1-bedroom unit accommodates up to 3 guests and features a full kitchen, air conditioning, private patio, and on-site 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?
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 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?
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?
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?
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.
Destinations nearby
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.
9.6 5 reviews
Dedham, MA
07/28 – 08/01
$444/nighttotal: $1776 (4 )
Charming 1br Apt In Boston With Free Parking
1 4
apartment , Boston
This 810 sq ft, 1-bedroom condo in Boston offers convenient access to Cambridge, located approximately 2 miles from John F. Kennedy Park and Brattle Theatre, and about 2.5 miles from Harvard Square and Central Square. This unit features complimentary WiFi, air conditioning, a private balcony, and a fully equipped kitchen with a dishwasher, accommodating up to 7 guests with included parking.
10 1 review
Dedham, MA
09/05 – 09/12
$291/nighttotal: $2037 (7 )
Lorenzo Inn
2 2
apartment , Boston
This 2-bedroom, 2-bathroom apartment in Boston's Dorchester neighborhood is an 8-9 minute drive from the Boston Convention and Exhibition Center and Copley Square. This residence offers on-site parking, a garden, a veranda, and a fully equipped kitchen, accommodating up to 4 guests with Wi-Fi and air conditioning.
9.6 26 reviews
Dedham, MA
07/28 – 08/01
$526/nighttotal: $2104 (4 )
60-3 3br Boston - Sleek Apartment Near Franklin Park
3 4
apartment , Boston
This spacious 1300-square-foot apartment rental in Mattapan, Boston, offers easy access to attractions like Fenway Park and Faneuil Hall Marketplace, though exact distances aren't specified. The three-bedroom, two-bathroom unit sleeps up to 15 guests, features a fully equipped kitchen, in-unit laundry, central air conditioning, free Wi-Fi, reserved parking, and allows pets.
Dedham, MA
06/18 – 06/22
$372/nighttotal: $1488 (4 )
Cozy Studio Suite W/ Full Kitchen Near Minute Man Historical Park
1 2
studio , Waltham
This studio apartment is situated in downtown Waltham on the lakefront, offering convenient access to Fenway Park and Tufts University. This pet-friendly studio features a kitchenette with a fridge and microwave, air conditioning, a balcony with views, and complimentary Wi-Fi, accommodating up to four guests with a 11:00 AM check-out.
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.
Dedham, MA
06/20 – 06/27
$464/nighttotal: $3248 (7 )
King Bed 3 Min > Washington Sq 1 Min >T
1 2
apartment , Brookline
This 1-bedroom apartment in Brookline's Aspinwall Hill neighborhood offers convenient access, located a 1-minute walk from the T Station and a 5-minute walk to Washington Square. This pet-friendly rental accommodates up to 3 guests and includes a kitchen with a fridge, microwave, and dishwasher, with free parking available a 5-minute walk away.
9.8 12 reviews
Dedham, MA
09/05 – 09/12
$360/nighttotal: $2520 (7 )
Modern 2br Near Subway & Parking Available
2 2
apartment , Somerville
This Somerville apartment is located in East Somerville, just a short walk from the Assembly Row shopping center and within a 15-minute walk to both Sullivan and Assembly subway stations. The apartment is close to both the Assembly Row shopping center and the subway, making it easy to explore both Somerville and Boston. The apartment has two bedrooms and one bathroom, comfortably accommodating up to four guests. The apartment offers modern amenities like air conditioning, Wi-Fi, a smart TV, and a fully equipped kitchen, ensuring a comfortable and enjoyable stay.
9.8 36 reviews
Dedham, MA
07/28 – 08/01
$370/nighttotal: $1480 (4 )
New Modern Cozy 3br Condo: Free Parking&near Train
1 4
apartment , Boston
This three-bedroom Boston house rental is located in Roslindale, less than a mile from the Bellevue commuter rail station offering easy access to downtown Boston and the Longwood Medical Area. The renovated unit features a spacious kitchen with modern appliances, in-unit laundry, dedicated parking, two private entrances, and two balconies, comfortably accommodating up to five guests.
9.0 322 reviews
Dedham, MA
09/05 – 09/12
$373/nighttotal: $2611 (7 )
Roslindale Village Condos
1 2
apartment , Boston
This apartment is located in Roslindale, a quiet neighborhood just 5 miles from the Boston Museum of Fine Arts and 5.3 miles from Fenway Park. It has received excellent ratings for cleanliness, user experience, and location. The apartment has a terrace or balcony with garden views, a seating area, and a fully equipped kitchen. Enjoy complimentary internet access, free bikes, air conditioning, satellite TV, and nearby golfing and hiking opportunities.