Holiday houses in Dedham

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Top-rated holiday rentals in Dedham

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Guest favourite
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, 232 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)

Guesthouse in Dedham
5 out of 5 average rating, 3 reviews

Your home in Boston

Welcome to a relaxing and peaceful stay surrounded by nature — just a 20-minute drive from the amazing city of Boston. 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

Superhost
A spacious living room features a dark sofa adorned with decorative pillows, situated next to a wooden coffee table. Light wood flooring complements the neutral wall color. Nearby, a ceiling fan provides airflow, and artworks adorn the walls, enhancing the relaxed atmosphere.
Apartment in Dedham
4.82 out of 5 average rating, 207 reviews

Lovely townhouse apartment minutes from Boston

Book your stay at this peaceful and centrally-located townhouse-style apartment just minutes from Boston. This newly renovated space features 2 bedrooms (one queen bed and one twin bed), one full bath (second floor), cozy living room with pull out sofa, and eat-in kitchen. Take advantage and relax by the outdoor fire pit (reservations required) or walk to Dedham Square for delicious food and shopping. Dates you need not available? Make sure to check out our other listing just next door!

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
4.97 out of 5 average rating, 316 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!

A spacious living area is highlighted by a wooden entertainment unit housing a television, with a cozy couch positioned nearby. A stone feature wall adds texture to the space, while built-in shelving displays books and decorative items. Soft overhead lighting creates an inviting ambiance.
Apartment in Dedham
4.79 out of 5 average rating, 1,021 reviews

Hidden Gem Near Boston w/ 2 bedrooms HighSpeedWifi

Our place is close to LegacyPlace w/ shopping, restaurant, cinema, bowling, whole foods. Less than 10 minutes to Trillium Brewing. 4-5 minutes walk to Train Station, around 20 min commute to Boston. Separate entrance, living room, big play room, full bath, fully equipped kitchen. Free Washer & Dryer. High speed internet. Off street parking. Our place attracts Boston Marathon runners. Very convenient for runners to get to Boston Common shuttle bus then to the Start line of the Marathon.

Top Guest favourite
A compact kitchenette features a vibrant red refrigerator alongside a small microwave and sink. Modern cabinetry provides storage for dishes and kitchen essentials, while decorative items add a touch of character to the space.
Apartment in West Roxbury
4.97 out of 5 average rating, 31 reviews

Cozy studio near-Train&Bus, safe area in Boston

Small.studio, Newly renovated , with private Parking included,, free WIFI, Smart TV 55” ,Smart lock (keyless) with code. Near VA Hospital and Faulkner Hospital and next to train and buses in Boston, quiet and safe neighborhood, , walking to restaurants, supermarket Market, gyms, CVS , Walgreens, Parks, and less than 15 minutes from Brigham and women Hospital, Beth Israel Hospital, and Harvard Medical school. And is Not allowing smoke and Not pets (dogs, cats , ect. ) in this property

Superhost
A cozy bedroom features a full-size bed adorned with a patterned duvet cover. Two nightstands with brass lamps are positioned on either side of the bed. Natural light filters through a window, enhancing the room's calming atmosphere.
Private room in Dedham
4.84 out of 5 average rating, 130 reviews

#214-D Easy Commute and Mature Trees

Relax and recharge at this peaceful place. Surrounded by mature trees, this conveniently located house has easy access to the I-95 highway, Legacy Place shopping mall w/ restaurant, cinema, bowling, whole foods. 10 minutes walk to the Endicott Train Station, around 25 min commute to Boston. This room has a full-size bed (sleeps 2) and a folding bed (sleeps 1). Need to specify three guests to have the folding bed ready. Public space shared with other guests.

Apartment in Boston
4.67 out of 5 average rating, 3 reviews

Cozy Whole-Apt | Free Parking & Easy Transit

Perfect for short stays, this cozy and peaceful apartment offers a clean, inviting space just a 20-minute drive to downtown Boston. Enjoy a comfy queen bed, modern living area, and a fully equipped kitchen. Natural light, hardwood floors, and thoughtful details creating a relaxed vibe. FREE parking and easy access to public transportation makes getting around simple and stress-free. Ideal for quick getaways, solo travelers, or couples exploring the area.

Superhost
Home in Dedham
4.84 out of 5 average rating, 566 reviews

Private apartment close the city!

New couch! New towels and linens! Fresh paint! New flooring coming soon. I heard the feedback and am refreshing/updating everything! My goal is happy guests and I'll do my best to make that happen. 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.

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, 267 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.

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, 205 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
Guesthouse in Westwood
5 out of 5 average rating, 19 reviews

Cozy & Bright Guest Unit

Welcome to your home away from home! This newly renovated, garden-level 1-bedroom apartment suite offers the perfect mix of comfort and convenience. Whether you’re staying for a short visit or an extended trip, you’ll have everything you need to relax and enjoy the Greater Boston area.

Popular amenities for Dedham holiday rentals

When is the best time to visit Dedham?

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Avg. price$141 AUD$143 AUD$141 AUD$152 AUD$161 AUD$161 AUD$157 AUD$161 AUD$152 AUD$163 AUD$167 AUD$151 AUD
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Quick stats about holiday rentals in Dedham

  • Total holiday rentals

    Explore 120 holiday rentals in Dedham

  • Nightly prices starting at

    Dedham holiday rentals start at $61 AUD per night before taxes and fees

  • Verified guest reviews

    Over 7,750 verified reviews to help you choose

  • Family-friendly holiday rentals

    50 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 30 rentals that welcome pets

  • Rentals with dedicated workspaces

    80 properties have a dedicated workspace

  • Wi-Fi availability

    120 of Dedham holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi 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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