Dedham holiday homes

We found 3,097 holiday rentals — enter your dates for availability
Discover a selection of 7 homes and other holiday rentals in Dedham that are perfect for your trip. Holiday homes provide the amenities that you need and want for your family, friends or furry companion, such as a hot tub and a washer and dryer. No matter what you're looking for, you'll be able to choose a property to rent that has what everyone needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts – Dedham

Showing deals for:8 Jan - 15 Jan

Staircase from waterfront to my home
View of Spinnaker Island and water from Master Bedroom Suite
Portion of garden surrounding my home
Twin bed with trundle bed in second room in Master Bedroom Suite
Excellent
(48 reviews)

Master Bedroom Suite in Beautiful 1880's Victorian. Spectacular ocean views.

Hull

8% off
NZ$3,362
for 7 nights, 1 room
NZ$480 per night
includes taxes & fees
Master Bedroom Suite in Beautiful 1880's Victorian. Spectacular ocean views.
Private kitchen
Interior
Interior
Exceptional
(98 reviews)

Historic Brownstone Townhouse, 7 beds/3.5 baths, Fenway Boston

Boston

8% off
NZ$15,935
for 7 nights, 1 home
NZ$2,276 per night
includes taxes & fees
Historic Brownstone Townhouse, 7 beds/3.5 baths, Fenway Boston
Gourmet kitchen with marble countertop, high-end appliances
Living Room, 65" Smart TV, Crate&Barrel Sofas, Bookshelf & Cabinet
Gourmet kitchen with marble countertop, high-end appliances
Gourmet kitchen with marble countertop, high-end appliances
Exceptional
(7 reviews)

Premium Loft 3BR&2BA • Heart of Downtown Boston • City Retreat

Boston

8% off
NZ$8,113
for 7 nights, 1 apartment
NZ$1,159 per night
includes taxes & fees
Premium Loft 3BR&2BA • Heart of Downtown Boston • City Retreat
View of waterfront from Third Floor Suite Living Room
Marina
Gracious staircase access to Third Floor
Patio garden
Exceptional
(99 reviews)

Third Floor Suite in waterfront Victorian on peninsula surrounded by ocean

Hull

8% off
NZ$3,634
for 7 nights, 1 room
NZ$519 per night
includes taxes & fees
Third Floor Suite in waterfront Victorian on peninsula surrounded by ocean
Living area
Private kitchen
Room
Living area
Exceptional
(34 reviews)

Beacon Hill Penthouse, Stately 2-bedroom apartment with AC, WiFi near MGH

Boston

8% off
NZ$8,530
for 7 nights, 1 apartment
NZ$1,219 per night
includes taxes & fees
Beacon Hill Penthouse, Stately 2-bedroom apartment with AC, WiFi near MGH
Private kitchen
Living area
Dining
Room
Exceptional
(38 reviews)

House in Arlington, near Boston, Harvard, MIT, and Tuft University

Arlington

6% off
NZ$4,408
for 7 nights, 1 home
NZ$630 per night
includes taxes & fees
House in Arlington, near Boston, Harvard, MIT, and Tuft University
Outdoor dining
Exterior detail
Interior
Interior
Exceptional
(6 reviews)

Luxury Tuscan style villa just few miles from downtown Boston .Newton Reg #24-17

Newton

9% off
NZ$32,154
for 7 nights, 1 home
NZ$4,593 per night
includes taxes & fees
Luxury Tuscan style villa just few miles from downtown Boston .Newton Reg #24-17
Dining
Living area
Interior
Private kitchen
Wonderful
(19 reviews)

Newly Renovated Modern Retreat l Near T

Boston

5% off
NZ$7,348
for 7 nights, 1 apartment
NZ$1,050 per night
includes taxes & fees
Newly Renovated Modern Retreat l Near T
No.2 Bedroom with a King bed, TV Stand, large screen smart TV and closet
Living room, 65" Smart TV, Genuine leather sectional sofa, Book and toys shelf.
No.2 Bedroom with a King bed, TV Stand, large screen smart TV and closet
No.2 Bedroom with a King bed, TV Stand, large screen smart TV and closet
Exceptional
(69 reviews)

Spacious Sunlit 3BR • Center of Downtown Boston • Family Favorite

Boston

8% off
NZ$6,766
for 7 nights, 1 apartment
NZ$967 per night
includes taxes & fees
Spacious Sunlit 3BR • Center of Downtown Boston • Family Favorite
Living area
Interior
Living area
Property grounds
Exceptional
(20 reviews)

Direct Ocean Front Condo with large wrap around balcony

Hull

8% off
NZ$4,522
for 7 nights, 1 home
NZ$646 per night
includes taxes & fees
Direct Ocean Front Condo with large wrap around balcony
Exterior detail
Exterior detail
Exterior detail
Dining
Exceptional
(53 reviews)

Modern Boston Townhouse Near Transit • Private Deck • Pet-Friendly - 383

Quincy

8% off
NZ$5,025
for 7 nights, 1 home
NZ$718 per night
includes taxes & fees
Modern Boston Townhouse Near Transit • Private Deck • Pet-Friendly - 383
Living area
Living area
Private kitchen
Dining
Exceptional
(81 reviews)

284 - Cozy House with free huge parking

Quincy

8% off
NZ$8,208
for 7 nights, 1 home
NZ$1,173 per night
includes taxes & fees
284 - Cozy House with free huge parking
Living area
Dining
Living area
Room
Exceptional
(97 reviews)

The Inn at Newton Highlands, boutique apartment-hotel

Newton

12% off
NZ$5,239
for 7 nights, 1 room
NZ$748 per night
includes taxes & fees
The Inn at Newton Highlands, boutique apartment-hotel
Private kitchen
Exterior detail
Room
Living area
Exceptional
(30 reviews)

Funky and cozy home ! A little bit of everything for everyone.

Arlington

8% off
NZ$5,708
for 7 nights, 1 home
NZ$815 per night
includes taxes & fees
Funky and cozy home ! A little bit of everything for everyone.
Living area
Interior
Living area
Exterior detail
Exceptional
(34 reviews)

Spacious Greater Boston 3BR Townhouse Near I-93 • Parking • Pet-Friendly - 41

Quincy

8% off
NZ$5,149
for 7 nights, 1 home
NZ$736 per night
includes taxes & fees
Spacious Greater Boston 3BR Townhouse Near I-93 • Parking • Pet-Friendly - 41
Private kitchen
Interior
Dining
Room
Exceptional
(49 reviews)

The Inn at Newton Highlands, Suite 2, Apartment-Hotel

Newton

8% off
NZ$6,487
for 7 nights, 1 apartment
NZ$927 per night
includes taxes & fees
The Inn at Newton Highlands, Suite 2, Apartment-Hotel
Interior
Living area
Room
Dining
Exceptional
(21 reviews)

76/1 - SPRING GETAWAY 10% OFF! Spacious 4-bedroom apartment in charming Boston

Boston

8% off
NZ$6,032
for 7 nights, 1 home
NZ$862 per night
includes taxes & fees
76/1 - SPRING GETAWAY 10% OFF! Spacious 4-bedroom apartment in charming Boston
Interior
Dining
Private kitchen
Living area
Exceptional
(7 reviews)

Pet-Friendly 4BR Single Home • Easy Access I-93 w/ Free Parking 17

Randolph

8% off
NZ$6,548
for 7 nights, 1 home
NZ$935 per night
includes taxes & fees
Pet-Friendly 4BR Single Home • Easy Access I-93 w/ Free Parking 17
Dining
Living area
Interior
Private kitchen
Wonderful
(40 reviews)

Spacious Greater Boston Townhouse Near I-93 • Parking • Pet-Friendly | 37

Quincy

8% off
NZ$5,025
for 7 nights, 1 home
NZ$718 per night
includes taxes & fees
Spacious Greater Boston Townhouse Near I-93 • Parking • Pet-Friendly | 37
Room
Living area
Private kitchen
Room
Exceptional
(14 reviews)

Huge Single Family Retreat-Work-Vacation-Near Convention Center & South Station

Boston

20% off
NZ$12,030
for 7 nights, 1 home
NZ$1,719 per night
includes taxes & fees
Huge Single Family Retreat-Work-Vacation-Near Convention Center & South Station
Room
Dining
Living area
Interior
Very good
(5 reviews)

597- SPRING GETAWAY EARLY BIRD 10% OFF! Spacious, cozy 5BR apartment in Medford

Medford

8% off
NZ$6,612
for 7 nights, 1 apartment
NZ$945 per night
includes taxes & fees
597- SPRING GETAWAY EARLY BIRD 10% OFF! Spacious, cozy 5BR apartment in Medford
Interior
Living area
Exterior detail
Exterior detail
Exceptional
(10 reviews)

14/2-SPRING GETAWAY EARLY BIRD 10% Spacious 5-bedroom apartment in Milton

Milton

8% off
NZ$6,186
for 7 nights, 1 apartment
NZ$884 per night
includes taxes & fees
14/2-SPRING GETAWAY EARLY BIRD 10% Spacious 5-bedroom apartment in Milton
The living room is thoughtfully designed, offering a warm & inviting atmosphere.
Room
With stylish touches, cozy seating, and plenty of room to unwind
you’ll find all the basics you need for a comfortable stay.
Exceptional
(5 reviews)

Family-Friendly 3BR Apartment Close to Everything

Boston

8% off
NZ$5,321
for 7 nights, 1 apartment
NZ$760 per night
includes taxes & fees
Family-Friendly 3BR Apartment Close to Everything
Room
Cohasset Harbor is a 3-5 minute walk from the suite.
Private Patio
Living area
Exceptional
(29 reviews)

Coastal Private Guest Suite

Cohasset

8% off
NZ$2,665
for 7 nights, 1 home
NZ$381 per night
includes taxes & fees
Coastal Private Guest Suite

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

The captivating city of Dedham awaits you

The area's churches and entertainment are just some of the reasons to come on holiday to Dedham. Travellers to this welcoming city praise the basketball games, shopping and university setting. Fenway Park and Gillette Stadium are just a couple of the must-see attractions in the area. With a holiday rental, you get a home away from home – many rentals offer full kitchens and outdoor grills for some home cooking.

Activities and attractions in and around Dedham

Are you looking for attractions to visit in the area? Venture out of your cosy holiday rental and check out everything that Dedham has to offer. These are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Encore Boston Harbor (11.6 mi / 18.7 km)
  • The Skating Club of Boston (3.1 mi / 5 km)
  • Blue Hills Ski Area (3.3 mi / 5.3 km)
  • Blue Hills Reservation (4.9 mi / 7.9 km)
  • Franklin Park Zoo (5.9 mi / 9.4 km)
  • Samuel Adams Brewery (5.9 mi / 9.5 km)

Exploring the natural features in Dedham

Whether you're looking for fun outdoor activities or just want to appreciate the scenery, Dedham is a great place to get out in nature. Here are a few of the area's most stunning features, all within 30 miles (48.2 km) of the city centre:

  • Boston Common (9.3 mi / 14.9 km)
  • Copley Square (8.7 mi / 14 km)
  • Arnold Arboretum (4.4 mi / 7.1 km)
  • Chestnut Hill Reservoir (6.3 mi / 10.2 km)
  • The Fens (7.7 mi / 12.3 km)
  • Back Bay Fens (8 mi / 12.8 km)

Transport to and around Dedham

Fly into Norwood, MA (OWD-Norwood Memorial), the closest airport, located 3.9 mi (6.3 km) from the city centre. If you can't find a flight that's convenient for your trip, you could book a flight to Boston, MA (BNH-Boston Harbor Seaplane Base), which is 10.8 mi (17.4 km) away.

If you prefer train travel, make your way to Dedham Endicott Station or Route 128/University Park Station and explore the city from there. You might consider catching a ride on the metro at Dedham Corporate Center Station to easily navigate the city.

Frequently asked questions

What is the best area to stay in Dedham when booking a holiday rental?
When considering the best area to stay in Dedham, Massachusetts for a holiday rental, the neighbourhood of Dedham Square stands out as a charming option. This area offers a delightful blend of historic architecture and modern amenities, making it a lovely place to explore. You'll find a variety of properties available, from cosy apartments to spacious homes, suiting different preferences and group sizes.In Dedham Square, visitors can enjoy the vibrant local scene, including quaint shops, cafés, and restaurants. One of the top attractions nearby is the Dedham Historical Society and Museum, where you can delve into the rich history of the area. Additionally, the picturesque Riverdale Park offers a lovely setting for a leisurely stroll or a picnic, superb for families or those looking to relax outdoors.Another appealing neighbourhood is Endicott Estate, known for its beautiful grounds and elegant mansion. Staying here provides a tranquil atmosphere, along with easy access to the estate's gardens, which are superb for enjoying a peaceful afternoon.
What is the most popular type of holiday rental accomodation in Dedham?
In Dedham, apartments are the most popular type of holiday rental, with around 24 available throughout the area. These apartments are typically located in convenient neighbourhoods, providing easy access to local amenities and attractions. Most units come with fully equipped kitchens, comfortable living spaces, and some may even feature private balconies for enjoying the fresh air.Additionally, there are about 15 holiday houses scattered across Dedham, which cater to families or groups seeking more space. These houses often include multiple bedrooms, spacious living areas, and outdoor spaces such as gardens or patios, making them ideal for larger gatherings. Furthermore, several charming cottages are also available, offering a quaint and homely atmosphere.
Are there any family house rentals in Dedham?
In Dedham, Massachusetts, there are several family-friendly house rentals available, making it an excellent choice for those travelling with children. This charming town offers a variety of properties with spacious living areas, full kitchens for family meals, and outdoor spaces where kids can enjoy playtime. Many homes also come equipped with conveniences such as Wi-Fi and air conditioning, ensuring a comfortable stay.The neighbourhood features lovely parks, including the scenic Endicott Estate, which is great for picnics and outdoor activities. Additionally, visitors can explore the nearby Dedham Square, known for its shops and restaurants, providing a taste of local culture and cuisine.
Can I rent a holiday home with a pool or hot tub in Dedham?
In Dedham, Massachusetts, there are several holiday homes available for rent that feature pools and hot tubs. This charming suburb, located just a short drive from Boston, offers a peaceful retreat while still providing easy access to urban amenities and attractions. Many of the properties come with inviting outdoor spaces, including private pools superb for summer relaxation, as well as hot tubs for soothing evenings after a busy day of exploring.Travellers can expect amenities such as spacious living areas, fully equipped kitchens for home-cooked meals, and comfortable outdoor seating, making these rentals ideal for families or groups looking to unwind.
Are there pet-friendly house rentals in Dedham?
In Dedham, Massachusetts, there are several pet-friendly house rentals available, making it a great choice for travellers with furry companions. Many of these holiday homes come equipped with modern amenities such as fully fitted kitchens, spacious living areas, and outdoor spaces where pets can enjoy the fresh air.The town's proximity to parks like the Dedham Community House and the nearby Wilson Mountain Reservation provides ample opportunities for pet owners to take their dogs for walks or enjoy a leisurely afternoon in nature. Additionally, the area boasts a friendly community atmosphere, with local shops and cafes that often welcome pets, further ideal for visitors travelling with their pets.
Are there any remote work holiday rentals in Dedham?
In Dedham, Massachusetts, there are numerous remote work holiday rentals available—around 42 to choose from. This suburban area is well-suited for those looking to blend work and leisure, offering a variety of properties equipped with essential amenities for remote work. Many rentals feature high-speed Wi-Fi, dedicated workspaces with desk chairs, and sometimes even additional tech like computer monitors, ensuring a productive environment for guests.Dedham is conveniently located near the picturesque Legacy Place shopping centre, which offers a range of dining and retail options, making it easy to take breaks and enjoy local amenities. The area is also home to beautiful parks and recreational spaces, providing opportunities for outdoor activities after work. To help narrow your search, insert your dates and apply the "WiFi" filter on Bookabach.
What are popular rental amenities in Dedham?
In Dedham, popular rental amenities include fully equipped kitchens, making it easy for guests to prepare their own meals. Many properties are pet-friendly, allowing travellers to bring their furry companions along. Onsite parking is commonly available, providing convenience for those travelling by car. Additionally, rentals often feature coffee and tea makers, ensuring guests can enjoy a warm beverage at their leisure.
When is the best time to visit Dedham for a holiday rental?
The peak season for holiday rentals in Dedham is during the summer months, specifically from July to September. This vibrant period attracts families and leisure seekers who are eager to enjoy the warm weather, local festivities, and the beautiful surroundings of this charming Massachusetts town.July stands out as the most popular month, when visitors can take part in outdoor activities, from exploring nearby parks to enjoying leisurely strolls along the Neponset River. With average temperatures ranging from 20 to 30 degrees Celsius, the climate is great for enjoying the many attractions Dedham has to offer, including the scenic Legacy Place shopping area and the historic Dedham Village.If you're looking for a more budget-friendly time to visit, consider December. While this month falls outside the peak season, it offers a unique charm, with festive decorations and a quieter atmosphere. December can be a lovely time to experience local holiday events and enjoy cosy dining options without the summer crowds.Ultimately, the best time to book a holiday rental in Dedham depends on your preferences—whether you want to bask in the lively summer atmosphere or enjoy a more relaxed winter experience.
What are the top attractions in Dedham?
In Dedham, Massachusetts, visitors can enjoy a variety of attractions that highlight the area's rich history and natural beauty. The Dedham Historical Society and Museum offers insights into the town's past, showcasing artifacts and exhibits that reflect its historic heritage. Nearby, the beautiful Dedham Square features charming shops, cafes, and restaurants, creating a vibrant community atmosphere.For outdoor enthusiasts, the picturesque Borderland State Park is a must-visit, offering scenic trails for hiking and biking, as well as beautiful gardens and historic structures to explore. The park's expansive grounds provide a ideal setting for picnics and leisurely walks.Another point of interest is the Dedham Heritage Rail Trail, which allows visitors to enjoy a leisurely stroll or bike ride while taking in the natural surroundings. The trail connects various parts of the town, making it a lovely way to experience Dedham's charm.
Are all fees included in the Dedham holiday homes prices shown on Bookabach?
Bookabach provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Dedham holiday homes with parking?
Bookabach offers a wide selection of holiday homes in Dedham with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Dedham holiday homes?
You can find great discounts on holiday homes in Dedham on Bookabach, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Dedham holiday home booking on Bookabach?
To find Dedham holiday rentals with free cancellation, just use Bookabach's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Bookabach makes it easy to book with confidence.
Can I find long-stay holiday homes in Dedham?
A long-stay holiday home in Dedham is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Bookabach?
Bookabach's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Dedham holiday home?
Book your Dedham holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Bookabach booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Dedham?
Prices for holiday homes in Dedham vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Bookabach offers something for every taste and budget, from affordable homes in Dedham to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Bookabach as a host?
Joining Bookabach as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Bookabach makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.