
Vacation rentals in Dedham
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Top-rated vacation rentals in Dedham
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The Red Door Carriage House
The Red Door Carriage house is a historic 90 year-old structure that was the carriage house for the original farmhouse (our home) on the property. Located in beautiful West Roxbury Mass., the unit is 3 miles from Fenway (Red Sox), Longwood Medical Center (all of the major hospitals) and 2 miles from Boston College. A 5 minute walk to the West Roxbury commuter rail station (10 minutes to South Station) and all bus lines into Boston, this apartment is a spectacular private and tranquil retreat.

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)

~*Pet Friendly 30min to Downtown*~ THE BOSTONIAN
Relax in the Bostonian, a stylish, pet-friendly apartment on the semi-basement level of a charming multi-family house. The apartment is air conditioned & overlooks a beautiful patio and backyard. Located in quiet Hyde Park neighborhood, a 30 minute drive into downtown Boston. Plenty of free streetside parking. Private in unit laundry. Professionally cleaned. Room 1: Queen size bed Room 2: Queen size bed Room 3: Living room couch, TV, electric fireplace Dining room: includes two wall arcades

Flower Farm Getaway 2BR, 20 Min To Boston
Spacious two-bedroom in-law suite attached to 1700’s farmhouse, situated on our small flower farm and garden co-op just 20 minutes from Boston. Only a mile from the Mass Pike & Rt. 128 (I-95). Centrally located to all Rt. 128 businesses, colleges & hospitals. A 7-min drive to Riverside Green line “D” subway stop into Boston (parking available), or commuter rail stops (Auburndale, Wellesley & Kendal Green Stations). It's a 20-minute drive to Amtrak's "Route 128" station to NYC and points south.

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.

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.

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

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!

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

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.

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!

The Plant Haus
A peaceful oasis with easy access to Rt 1, Rt 128, and walking distance from Norwood Center and the Norwood Depot commuter rail stop that goes to South Station. 30 mins from Providence and Boston and less than 20 mins to Gillette Stadium. My place is located in a quiet community. I am just a phone call or text away should you need me!
Popular amenities for Dedham vacation rentals
Other great vacation rentals in Dedham

Charming 3BR Boston Stay Garage + EV + Pool Table

Chic and Cozy Family Retreat Close to Boston

Lakefront Cottage w/Private Beach

Boston Buccaneer Retreat

Hidden Gem near Boston w/ Private lake access

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

Cozy 2-Bedroom Apartment Near Dedham Legacy

Sleek & Stylish Master Suite
When is the best time to visit Dedham?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ353 | ﺩ.ﺇ367 | ﺩ.ﺇ426 | ﺩ.ﺇ367 | ﺩ.ﺇ389 | ﺩ.ﺇ389 | ﺩ.ﺇ382 | ﺩ.ﺇ386 | ﺩ.ﺇ382 | ﺩ.ﺇ400 | ﺩ.ﺇ389 | ﺩ.ﺇ393 |
| 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 vacation rentals in Dedham

Total vacation rentals
Explore 140 vacation rentals in Dedham

Nightly prices starting at
Dedham vacation rentals start at ﺩ.ﺇ110 per night before taxes and fees

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

Family-friendly vacation rentals
60 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 40 rentals that welcome pets

Rentals with dedicated workspaces
100 properties have a dedicated workspace

Wi-Fi availability
140 of Dedham vacation 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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