Vacation rentals in Dedham

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Top-rated vacation rentals in Dedham

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

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Guest favorite
A bright and airy room features a comfortable bed adorned with colorful bedding. Two wooden desks with chairs are positioned thoughtfully, along with various seating options. Natural light filters through a window, accentuating the room's warm wood flooring and blue walls.
Guest suite in Boston
4.89 out of 5 average rating, 166 reviews

Boston arbor oasis - cute one bedroom suite

Upbeat, beautiful one bedroom with attached bathroom. Have the ground floor / lower level of our home to yourself. Your own private entrance, come and go as you like. Located on a quiet, dead end street in a very safe, residential Boston neighborhood, with big beautiful evergreen trees. Convenient to 93. Five minute Uber or short bus ride to Ashmont station, from here take the train downtown Boston. Free off street parking. Easy walk to coffee shops, restaurants, bars, and Neponset River trail!

Top guest favorite
A spacious master bedroom is depicted, featuring a large bed with crisp white linens. Rich, dark curtains frame tall windows, complementing the soft pink walls. A modern television is mounted on the wall, and mirrored doors reflect the inviting decor, enhancing the room's brightness.
Guest suite in Ashmont
4.95 out of 5 average rating, 260 reviews

Upscale 2 Bdrm Suite: Kitchen, Spa Bath, Laundry

The home is a short 7 minute walk to Ashmont T Stop. A unique master bedroom and a cozy 2nd bedroom adjacent to a marble spa bathroom (with heated floor and a large shower & built-in bench). With a clean, glass-tiled kitchen & granite-top counters, you’ll be staying in a nice deluxe suite that is set in a friendly, safe neighborhood. Enjoy the feel of a downtown hotel without the high price. Note: There’s no separate living room, but comfortable seating is available in the 2nd bedroom & kitchen

Guest favorite
A spacious studio features a comfortable bed with a decorative pillow against the warm wood headboard. Soft, natural light fills the room, highlighting the wooden floors and cozy seating area. A kitchenette is visible in the background with cabinets and a small coffee setup.
Guest suite in Jamaica Plain
4.92 out of 5 average rating, 238 reviews

Ann and Esther's Cozy Studio near the Heart of JP

This airy and light private studio is set in a beautiful, secluded backyard/garden. Close to restaurants, shops and acres of green space. Your reservation confirms that you have read "Other Things to Note" in The Space section below and "House Rules" before booking. Guests can only book for themselves. We are 5-7 minutes from the 39 bus and 15 from the Orange line. There is microwave, fridge, counter w/ sink. No stove or cooking. We declined ALL requests for dates >6 mos ahead/not open yet

Guest favorite
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)

Guest favorite
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, 118 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 favorite
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, 299 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.

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 favorite
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!

Guest favorite
A spacious living area features large windows offering views of greenery. A comfortable queen bed is set against one wall, while a pullout sofa sits opposite. Light-colored curtains frame the windows, and a stylish lamp is placed beside a round table.
Guest suite in Roslindale
4.91 out of 5 average rating, 201 reviews

Cozy Renovated Suite w/Free St Parking near Train

Newly renovated in-law suite located in the charming Roslindale neighborhood of Boston. A short walk from West Roxbury Center, Roslindale Village's shops and restaurants, and Bellevue commuter rail stop which gets you to Back Bay in 15 mins (or 20 Min Uber/drive). Features include a private entrance kitchenette, bathroom, large quiet back yard with patio and fire pit (avail Apr-Oct). Perfect for weekend getaways, working/commuting to Boston, or visiting friends and family!

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 favorite
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 favorite
A leather recliner sofa is positioned in a light-filled living area, complemented by a large painting of a serene landscape. A full-size refrigerator and a TV stand are visible, providing essential amenities. An entryway is seen in the background, leading to additional rooms.
Guesthouse in Framingham
4.97 out of 5 average rating, 302 reviews

Private guest house on beautiful country road

Welcome to Grove Street Studio - our detached guest house which sits right behind our home on one of the most beautiful streets in the area. This two-room studio has everything you need for a comfortable stay including your own deck looking out to the woods behind. Perfect for for a hotel alternative for someone working temporarily at nearby businesses.

Popular amenities for Dedham vacation rentals

When is the best time to visit Dedham?

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Avg. priceR1,607 ZARR1,625 ZARR1,607 ZARR1,728 ZARR1,832 ZARR1,832 ZARR1,780 ZARR1,832 ZARR1,728 ZARR1,849 ZARR1,901 ZARR1,711 ZAR
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Frequently Asked Questions

  • 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.

  • Where should I stay in Dedham?

    Make yourself at home in Dedham by choosing from our most frequently booked neighborhoods. We have over 290 vacation rentals in East Dedham, over 320 vacation rentals in Greenlodge, and over 2,070 vacation rentals in Metropolitan Hill - Beach Street.

  • Do house rentals in Dedham have free parking?

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

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

    Yes! Work meets play with ease at over 40 house rentals in Dedham featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there family-friendly house rentals in Dedham?

    Dedham has more than 20 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

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

    Enhance your stay in our Apartment Rentals with the most popular amenities: over 30 homes with air conditioning, over 30 homes with a kitchen, over 30 homes with wifi, over 20 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • 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 air conditioning?

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

  • 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.

  • Do house rentals in Dedham have wifi?

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

Quick stats about vacation rentals in Dedham

  • Total vacation rentals

    Explore 120 vacation rentals in Dedham

  • Nightly prices starting at

    Dedham vacation rentals start at R691 ZAR per night before taxes and fees

  • Verified guest reviews

    Over 7,750 verified reviews to help you choose

  • Family-friendly vacation rentals

    50 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 30 rentals that welcome pets

  • Rentals with dedicated workspaces

    80 properties have a dedicated workspace

  • Wi-Fi availability

    120 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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