Holiday houses in Dedham

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Top-rated holiday rentals in Dedham

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
Home in Roslindale
5 out of 5 average rating, 29 reviews

New modern 2bd condo: free parking/near train

This newly renovated, modern unit on the 1st floor of a charming two-family house is situated on a quiet side street in Roslindale. Just under a mile from the commuter rail, only a quick 15-20min ride to downtown Boston. conEasy access to restaurants, shops, and some of Boston’s most stunning parks. The unit boasts a spacious kitchen, two cozy bedrooms, an open living, dining area, and two private entries. It’s the perfect retreat for both urban explorers and those seeking a peaceful getaway.

Superhost
A view of a historic church with a tall steeple is framed by nearby houses, showcasing trees without leaves indicating the season. Power lines and street signs are visible, with blue skies overhead.
Townhouse in Dedham
4.77 out of 5 average rating, 235 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, 119 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, 308 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.

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, 212 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 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, 389 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 Oakdale
4.98 out of 5 average rating, 279 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.

Guest favourite
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, 169 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!

Top Guest favourite
Condo in Norwood
4.82 out of 5 average rating, 118 reviews

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!

Top Guest favourite
A bright bedroom features a spacious bed with a white coverlet and colorful pillows. Natural light filters through multiple windows, enhancing the wooden accents of the walls and furniture. A television is mounted on the wall above a wooden dresser, creating a comfortable and inviting space.
Guesthouse in West Roxbury
4.95 out of 5 average rating, 206 reviews

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. Besides the pool, there are two garden ponds where we keep decorative fish, and a regular parade of various types of birds and even wild turkeys and deer.

Guest favourite
Home in Dedham
4.84 out of 5 average rating, 577 reviews

Private apartment close the city!

New couch! New towels and linens! Fresh paint! New flooring coming soon. This private apartment is part of my home but has a separate entrance, full bath, living room and private bedroom. We're in a family neighborhood close to the city, and very convenient for those visiting with a car.

Guest favourite
The exterior of a charming, two-car garage is showcased, featuring natural stone and a shingle roof. Wooden double doors with decorative hardware are visible, along with a basketball hoop attached to the side. The surrounding landscape includes lush green grass and trees.
Home in Westwood
4.85 out of 5 average rating, 104 reviews

sweet little house

Unique 1000 square feet getaway. Minutes to Route 128, Route 1, commuter rail, University Station's shops, dining, and Dedham's Legacy Place Easy access to I-95 -25 min to downtown Boston. -15 min to Gillette Stadium . Private entrance with keyless entry door lock.

Popular amenities for Dedham holiday rentals

When is the best time to visit Dedham?

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Frequently Asked Questions

  • Are there family-friendly apartment rentals in Dedham?

    Dedham has more than 10 family-friendly apartment rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in apartment rentals in Dedham?

    Experience the best of Dedham with our apartment rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there pet-friendly house rentals in Dedham?

    Four-legged friends are welcome in Dedham. Choose from more than 10 house rentals for guests traveling with pets.

  • Are there apartment rentals with a dedicated workspace in Dedham?

    Yes! Work meets play with ease at over 20 apartment rentals in Dedham featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Where should I stay in Dedham?

    Make yourself at home in Dedham by choosing from our most frequently booked neighborhoods. We have over 340 vacation rentals in Greenlodge, over 310 vacation rentals in Readville, and over 310 vacation rentals in East Dedham.

  • Do house rentals in Dedham have air conditioning?

    Absolutely! We offer over 50 house rentals with air conditioning in Dedham. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Dedham have a kitchen?

    Absolutely! We offer over 30 apartment rentals with a kitchen in Dedham. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Dedham have wifi?

    Absolutely! We offer over 40 apartment rentals with wifi in Dedham. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Dedham have free parking?

    Absolutely! We offer over 60 house rentals with free parking in Dedham. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for House Rentals in Dedham?

    Enhance your stay in our House Rentals with the most popular amenities: over 50 homes with air conditioning, over 50 homes with a kitchen, over 60 homes with free parking, over 60 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about holiday rentals in Dedham

  • Total holiday rentals

    Explore 130 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 9,390 verified reviews to help you choose

  • Family-friendly holiday rentals

    50 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 40 rentals that welcome pets

  • Rentals with dedicated workspaces

    90 properties have a dedicated workspace

  • Wi-Fi availability

    130 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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