
Holiday houses in Dedham
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Top-rated holiday rentals in Dedham
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All New Private Country Setting (2 Level-No Share)
We built this 2 level home 6 years ago and it is located on Washington St in the towns Historic district. The home is set back from street with a long country style driveway. We designed it with large windows in all rooms, welcoming the sunlight and peaceful setting. Access to clean and empty garage for storage (No parking). We have no personal items in the guest level - all closets and dressers are empty and yours for full use! Co Host reside in lower separate entrance suite. Nothing Shared.

World Cup | Elegant 4BR | Yard & Parking | Dedham
Welcome to your elegant Dedham retreat! This fully renovated 4BR/3BA home blends modern design with comfort, featuring an open living and dining area, a fully equipped kitchen, and beautifully styled bedrooms. Enjoy a private fenced yard, four parking spots, and in-home laundry. Just a 10-minute walk to the subway for easy access to downtown Boston, and about 18 minutes to Gillette Stadium depending on traffic. We’d be delighted to host you book now and experience comfort with a touch of luxury!

Charming Townhouse in Historic Town near Boston.
Spacious freshly renovated townhouse, part of an antique two family house. Separate entrance, private parking space. One big bedroom with a very comfortable queen size bed and huge closet. Living room has a queen size sofa sleeper, new smart TV, and two closets. Window a/c in the bedroom, window fan in the living room. Fully equipped eat-in kitchen. Brand new beautiful bathroom with a tub. For stays longer than 3 nights you can use washer and dryer that are located in the basement. (Not shared)

Peaceful Country Home, Dover, Ma: Private Entrance
Graceful country oasis in a renovated 125 year old historic home, 35 minutes driving time from downtown Boston. (Important-stair climbing required to reach bedroom suite.) I welcome quiet, mature guests as this is a very peaceful (non-party)environment. We are located on a scenic road in sophisticated Dover, Ma, a commuter/country setting, with miles of hiking trails and roads ideal for cycling. I have owned and loved this home for 35 years and take great joy in its charm and outdoor spaces.

Two bedrooms, full bathroom, and breakfast room
We offer the entire second floor of our home: two bedrooms, each with a queen-size bed, a full bathroom, and a well-stocked breakfast / snack room. We are located literally seconds off Rt. 128 / I-95, in a quiet, secluded area. Our deck, gardens and grounds (which include a pond, birdfeeders, and, perhaps, wildlife sightings) are available for your enjoyment. You will have complete privacy in your quarters, but we will be close at hand should you need advice or service. Gretje and Bob

Modern Upper-Level Oasis Minutes to Boston Stadium
Perfect for families or friends, this bright and stylish 3-bedroom upper level features a brand-new renovated kitchen with new appliances, a cozy living room with an electric fireplace, dining area, private laundry, a large deck, and 2 driveway parking spaces. Peaceful neighborhood near Boston and Gillette Stadium, quick access to the highway and Commuter Rail station to Boston in a 1/2 hour. The host lives on-site in the lower level of the house and is available for assistance if needed.

Modern Studio Above Detached Garage Near Boston
Modern private studio above a detached garage in a quiet neighborhood near Boston. Features a queen bed, full-size couch, dining table, fast WiFi, and 55” smart TV. Floor mattress. No cooking surfaces, but includes a mini fridge, microwave, toaster, drip coffee maker, Nespresso, and electric kettle. Bathroom with stand-up shower, no bath tub. Towels and linens provided. Private entrance, on-street parking. Close to restaurants, shopping, MBTA Franklin line commuter rail to South Station

Country Cottage in the City
This poolside cottage is a country retreat in the city. We are nestled into a small bit of woods on top of the "hill" as it is called locally. The cottage is a studio apartment that has a microwave and mini-fridge as well as sitting area and table. It has a lovely view of the pool and gardens. Besides the pool, there are two garden ponds where we keep ornamental fish. Outside the garden fence there is often a parade of various types of birds, bunnies and even wild turkeys and deer.

Conveniently Located Private Garden Apartment
Garden-level apartment next to public park, yet convenient to Newton Centre, Chestnut Hill, Boston College, Longwood Medical Area, and public transit. Easy access to Boston area attractions. Sleep late in a comfy bedroom with blackout shades, relax in front of the 55" HDTV, whip up a quick meal in the kitchenette, or enjoy the outdoors sitting on the patio. Come and go as you please with a private entry. Great for quick visits or extended stay. Newton Short Term Rental - STRA-23

the house of id; vintage shop, accessible space
🏡🚨‼️ Now Featured in The Boston Globe ‼️🚨🏡 Stay. Id's design is informed by our firsthand experience of living with a chronic/invisible illness. To us, accessibility means joy at your fingertips; and participation without overexertion. Unmask. Shop. We did the legwork, filling the house with buyable treasures. Live with the pieces you love. Then take them home. Take Part. Some of the house is experiential. Change hardware. Move art. Bake for the community. Get involved.

Cozy, historic 3 bedroom home close to Boston!
Welcome to our cozy home. Our place blends historic charm with modern comfort. Enjoy a large, fenced yard with a grill, fire pit, and deck to relax. Inside, you'll find a well-equipped kitchen and a dining room. We offer three bedrooms with comfortable mattresses and soft bedding. The living room has a big TV with cable and streaming apps, plus high-speed Wi-Fi. Families with dogs are warmly welcomed.

Slow Down| Your Boston Getaway
Private entrance, 6+ private parking spaces, and a large green outdoor area perfect for relaxing. Quiet family-friendly neighborhood. Features 2 spacious bedrooms with 3 queen beds, smart bathroom, modern kitchen, and smart self check-in with a unique code for each guest. Enjoy complimentary Colombian coffee plus starter essentials including toilet paper and cleaning supplies for a comfortable stay.
Popular amenities for Dedham holiday rentals
Other great holiday rentals in Dedham

Boston Studio Apt. With Parking next to Train&Bus

Conveniently Located & Comfy Suite- FIFA World Cup

Private Suite•Gillette Stadium/Boston•BBQ•Parking

5 min walk to T train, 20 min to Downtown Boston

Quiet 1BR • Wi-Fi • Parking Included • In Randolph

Comfy Chic Boston 3BR w/ FREE Parking - World Cup!

Westwood Airbnb

Serenity
When is the best time to visit Dedham?
| Month | Jan | Feb | Mar | Apr | May | June | July | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $137 AUD | $143 AUD | $165 AUD | $143 AUD | $151 AUD | $151 AUD | $148 AUD | $150 AUD | $148 AUD | $156 AUD | $151 AUD | $153 AUD |
| Avg. temp | -3°C | -2°C | 2°C | 8°C | 14°C | 19°C | 22°C | 22°C | 18°C | 11°C | 6°C | 0°C |
Frequently Asked Questions
What are the best places to stay in Dedham?
Dedham has neighborhoods with historic homes, parks, and convenient access to local cafes or shops. Many travelers look for stays in quiet residential areas or scenic parts of town near landmarks. Choosing a location central to amenities makes it easy to explore.
What are the best things to do in Dedham with kids?
Families in Dedham often explore playgrounds, local parks, and interactive museums. Seasonal events, nature walks, and hands-on learning spaces are frequently suggested for younger visitors.
What are some of the best things to do in Dedham?
Explore Dedham’s historic sites, visit local shops and cafes around town, or wander walking trails in nearby parks. The area also has art galleries and community events throughout the year. Many travelers enjoy the mix of history, arts, and outdoors.
How is the weather in Dedham?
Dedham experiences cold winters, averaging 19–35°F (-7–2°C) in January, and warm summers near 63–82°F (17–28°C) in July. Rain and occasional snow are common, so layered clothing and a raincoat can be helpful year-round.
When is the best time to visit Dedham?
Late spring and early fall are often recommended for milder temperatures, colorful foliage, and outdoor activities. Summer is popular for festivals and a more lively atmosphere around town.
What are the best places to visit in Dedham?
The Fairbanks House, known as one of the oldest timber-frame homes in North America, is frequently suggested for its historic significance. The Mother Brook arts district has creative studios and galleries to explore. Many visitors enjoy green spaces and local shops throughout town.
What are some hiking trails in Dedham?
Explore riverfront paths and wooded trails in local conservation areas, or walk the tree-lined trails around Wilson Mountain Reservation. Many travelers enjoy nature walks that highlight native plants and wildlife.
What are some family activities we can do in Dedham?
Families often visit playgrounds, join community art workshops, or enjoy hands-on exhibits at local museums. Seasonal festivals, sports fields, and picnic spots around town create opportunities for kids and adults.
What are some of the best day trip ideas from Dedham?
Travelers frequently suggest exploring Boston’s historic neighborhoods, visiting coastal towns with scenic waterfronts, or enjoying nature reserves around the region. Art museums and local food markets are also popular for day adventures.
Are there any pet friendly accommodations available in Dedham?
Many stays in Dedham welcome pets, especially in residential neighborhoods with access to open spaces and parks. Be sure to check each property’s guidelines for details on bringing your pet.
What are some local tips for visiting Dedham?
Dedham has historic homes, local parks, and neighborhood cafes worth exploring. Comfortable walking shoes are helpful for visiting sites with scenic paths and preserved architecture. Checking community calendars for pop-up art exhibits or performances can add to your experience.
What is Dedham known for?
Dedham is known for its well-preserved colonial history, traditional architecture, and connection to the early American story. The town also has a creative community centered around the arts and seasonal community events.
What are the best hidden gems to explore in Dedham?
Dedham has quieter walks along Mother Brook and locally owned bookstores tucked off the main street. Art studios and historic cemeteries around town reveal lesser-known aspects of its character.
What are the best foods to try in Dedham?
Dedham has classic New England dishes such as clam chowder and lobster rolls, along with locally made pastries and ice cream. Independent cafes and bakeries around town showcase regional flavors and seasonal specialties.
What should I bring for a trip to Dedham?
Pack comfortable walking shoes for exploring town, a waterproof jacket for changeable weather, and layers for adapting to both cool mornings and warm afternoons. A camera is handy for capturing historic buildings and scenic park views.
What is the nightlife in Dedham like?
Dedham’s nightlife features casual pubs, restaurants with evening hours, and occasional live music in local venues. The atmosphere is laid-back, with many spaces hosting community events and gatherings.
What are the most popular events or festivals in Dedham?
Dedham hosts seasonal festivals, summer concerts on the common, and holiday parades throughout the year. Art fairs and farmers markets are also frequently suggested by locals for a festive community vibe.
Are there family friendly vacation rentals in Dedham?
Dedham has vacation rentals well-suited for families, often located in quiet areas near playgrounds, parks, and community centers. Many hosts provide amenities that make traveling with children convenient and comfortable.
Quick stats about holiday rentals in Dedham

Total holiday rentals
Explore 140 holiday rentals in Dedham

Nightly prices starting at
Dedham holiday rentals start at $43 AUD per night before taxes and fees

Verified guest reviews
Over 9,210 verified reviews to help you choose

Family-friendly holiday rentals
60 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 40 rentals that welcome pets

Rentals with dedicated workspaces
100 properties have a dedicated workspace

Wi-Fi availability
140 of Dedham holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Dedham rentals

4.9 Average rating
Dedham stays are highly rated by guests—averaging 4.9 out of 5!
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