Holiday houses in Dedham

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Top-rated holiday rentals in Dedham

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Top Guest favourite
The kitchen features modern appliances and a central island with seating for five. Light-colored cabinetry and a mosaic tile backsplash complement the dark granite countertops. Pendant lights illuminate the workspace, while a large window brings in natural light.
Home in Holliston
4.98 out of 5 average rating, 125 reviews

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.

Superhost
Townhouse in Dedham
4.77 out of 5 average rating, 241 reviews

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)

Top Guest favourite
A stone fireplace is framed by a slate hearth and topped with a white shelf displaying framed photographs. Adjacent, a small black table stands with a decorative plant. Light wood flooring extends into the background, leading to a room with a radiator and a sideboard.
Home in Dedham
4.93 out of 5 average rating, 121 reviews

Cozy house close to Boston

My home is very comfortable with a casual feel. I have three bedrooms with 1.5 bathrooms. I have two queen size beds and one twin size bed. My kitchen and bathrooms are updated. I have a cozy den with a Smart TV and a living room that is a comfortable place to relax. The outdoor area has a deck leading onto a patio with a fire pit. I have an outdoor gas grill. It's a great place to unwind and relax. It is fenced in with privacy. I also have a driveway and on street parking is available.

Top Guest favourite
A serene bedroom suite features a spacious bed with a light blue quilt, flanked by two windows allowing natural light. A cozy sitting area includes a comfortable couch with patterned pillows, and decorative rugs are placed on the hardwood floor, enhancing the inviting ambiance.
Guest suite in Dover
4.97 out of 5 average rating, 316 reviews

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.

Guest favourite
The exterior of a spacious guesthouse showcases a blend of siding and stone finishes. A paved driveway leads to a two-car garage. Lush greenery and flower beds enhance the inviting entrance, while multiple windows allow natural light to fill the interior.
Guest suite in Sharon
4.95 out of 5 average rating, 216 reviews

Cozy Lakeview Guesthouse Near BOS, PVD, Cape Cod

Stunning CLG with private entrance, deck, & parking. •Bedroom #1 ground floor (2 guests only) has a Queen bed & smart TV with deck access. •Bedroom #2 upstairs is ONLY AVAILABLE FOR BOOKINGS OF 3–4 GUESTS and includes a Queen bed, smart TV, mini gym & office. •Living room with lake view & smart TV. •Bathroom with tub and sitting shower bench. •Fully equipped kitchen with stainless steel appliances. •Internet Access, You Tube, and Netflix. •Summer lake access.

Top Guest favourite
The exterior of a red house is framed by a well-maintained garden comprising various flowers and greenery. The house features a welcoming entryway, a chimney, and a grassy area. Sunlight illuminates the scene, highlighting the vibrant colors of the surrounding landscape.
Apartment in Dedham
4.94 out of 5 average rating, 213 reviews

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

Top Guest favourite
A spacious living area features a vaulted ceiling, large windows allowing natural light, and a comfortable sofa. A wooden coffee table sits at the center, complemented by patterned armchairs. Adjacent, a farmhouse dining table accommodates six, enhancing the open layout.
Place to stay in Sherborn
4.98 out of 5 average rating, 343 reviews

Entire Historic Carriage House with Fireplace & AC

Escape to our charming Carriage House in the Historic District of Sherborn which offers the feel of a country retreat without being far from civilization. Great for travelers looking for a peaceful getaway, checking out nearby colleges or attending a celebration like a wedding or graduation. You will love the feel of the Carriage House, its spacious living and dining room, well-equipped kitchen, and the beautiful grounds. Check us out on IG @carriagehousema. NEW in 2022: Mini-split AC!

Top Guest favourite
Apartment in Dedham
5 out of 5 average rating, 19 reviews

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. No cooking surfaces, but includes a mini fridge, microwave, drip coffee maker, Nespresso, and electric kettle. Bathroom with stand-up shower, no bath tub. Towels and linens provided. Private entrance, shared patio access, on-street parking. Close to restaurants, shopping, MBTA Franklin line commuter rail to South Station

Top Guest favourite
A cozy living area is presented with a comfortable gray sofa and a dark wooden coffee table. A small dining table with two chairs is positioned near the patio doors, which are flanked by light curtains. A patterned area rug adds warmth to the hardwood floor.
Apartment in Newton
4.93 out of 5 average rating, 393 reviews

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

Top Guest favourite
A two-story white house features a welcoming front porch and black shutters. Lush greenery surrounds the property, with a well-kept lawn and flower beds. A pathway leads from the road to the entrance, and a driveway is visible beside the house.
Home in Dedham
4.98 out of 5 average rating, 285 reviews

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.

Superhost
An airy living space features high ceilings with slanted angles and large windows allowing natural light to filter in. Wooden floors are complemented by simple furnishings, including a dining table with chairs and a bright arrangement of flowers. Nearby, cabinets provide ample storage.
Home in Jamaica Plain
4.91 out of 5 average rating, 170 reviews

Now availJamaica Plain & Arboretum 20min toBoston

Bright and sunny 2-bedroom retreat with a fully equipped kitchen, spacious bath with rain shower and tub, and TVs in each room. Enjoy fresh coffee daily with espresso maker, milk steamer, and grinder provided. Including a blender..A selection of teas .WiFi and off-street parking included. Private, peaceful, and filled with natural light—perfect for relaxing mornings and cozy evenings!

Guest favourite
Guesthouse in Dedham
4.92 out of 5 average rating, 13 reviews

Slow Down| Your Boston Getaway

You’ll have your own private entrance and a large green outdoor space perfect for unwinding. Enjoy the charm of a quiet neighborhood, ideal for families or travelers seeking comfort. This apartment features: 2 spacious bedrooms with 3 queen beds for maximum comfort A modern bathroom and kitchen with smart features A calm, cozy atmosphere designed to make you feel at home

Popular amenities for Dedham holiday rentals

When is the best time to visit Dedham?

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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 $42 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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