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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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
The dining area features a wooden table with six chairs, complemented by a striped table runner. A stylish vase with dried stems is placed at the center. A cozy couch, adorned in rich upholstery, is located beside the table, with a cityscape wall art piece above a dark cabinet.
Home in Hyde Park
4.86 out of 5 average rating, 331 reviews

~*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

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, 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 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, 306 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 Victorian home is showcased, featuring a light-colored facade with decorative trim. A welcoming porch area is accented by potted plants, and steps lead up to a wooden front door flanked by tall windows. Lush greenery surrounds the property.
Apartment in Newtonville
4.87 out of 5 average rating, 560 reviews

Country Charm minutes from the Hub - 1st Floor Apt

Private, smoke/pet-free 1st floor efficiency apartment with independent access for ONE PERSON ONLY at back of family home. Includes full bathroom, refrigerator, microwave, coffee maker + WiFi. All basic supplies provided. Driveway parking. Mins from MBTA transit including commuter rail. Laundry-room access for rentals of 7 nights ore more. Sorry, no vaping and no smokers - even if you smoke outside - because smoke odor on you or your clothes can be left in your wake in the room. No open flame.

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 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, 331 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 favourite
A spacious studio room is highlighted by a plush bed adorned with crisp white linens. A television is positioned on a wooden dresser across from a wooden desk and chair. Natural light filters through a window, complementing the clean tile flooring.
Guest suite in Brighton
4.75 out of 5 average rating, 363 reviews

Sleek Private Suite near BC & Harvard | Parking

Discover a modern escape in this high-end garden suite. Perfectly curated for privacy, the space features elegant Spanish tile and a top-tier gel memory foam mattress with crisp linens. It’s a quiet, tech-friendly retreat featuring a large Smart TV and fast WiFi for your downtime. Just a 5-minute walk to Boston Landing, you have the city’s best—from Fenway to Copley—right at your fingertips. Enjoy a polished, professional stay that prioritizes tranquility and effortless city access.

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
4.92 out of 5 average rating, 384 reviews

Conveniently Located Private Garden Apartment

Garden-level apartment next to a public park yet convenient to Newton Centre, Chestnut Hill, Boston College, Longwood Medical Area, and public transit. Easy to take in all the 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.

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, 276 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 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, 318 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.

Guest favourite
A historic brick brownstone is shown from the street, featuring a classic architectural style with bay windows. The building is framed by vibrant green trees and neatly trimmed bushes, contributing to the residential charm of the neighborhood.
Condo in Jamaica Plain
4.89 out of 5 average rating, 578 reviews

Historic JP Brownstone with Parking. Pets Welcome!

Located in one of Boston's best neighborhoods, this 1200 square foot bright sun filled corner unit in a 120 year old historic Brownstone is the perfect retreat. Its excellent location is just steps from the T and a short walk to Centre Street shops and restaurants. Good for couples, solo adventurers, business travelers, and furry friends (pets).

Popular amenities for Dedham vacation rentals

When is the best time to visit Dedham?

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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 $40 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 310 vacation rentals in Readville, over 340 vacation rentals in Greenlodge, and over 310 vacation rentals in East Dedham.

  • 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 vacation rentals with a dedicated workspace in Dedham?

    Yes! Work meets play with ease at over 80 vacation rentals in Dedham featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there family-friendly vacation rentals in Dedham?

    Dedham has more than 50 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

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

    Enhance your stay in our House Rentals with the most popular amenities: over 60 homes with wifi, over 50 homes with air conditioning, over 40 homes with a kitchen, over 50 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Do house rentals in Dedham have a kitchen?

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

  • 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.

  • Are there pet-friendly vacation rentals in Dedham?

    Four-legged friends are welcome in Dedham. Choose from more than 30 vacation 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 130 vacation rentals in Dedham

  • Nightly prices starting at

    Dedham vacation rentals start at $41 CAD per night before taxes and fees

  • Verified guest reviews

    Over 9,390 verified reviews to help you choose

  • Family-friendly vacation rentals

    50 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 40 rentals that welcome pets

  • Rentals with dedicated workspaces

    90 properties have a dedicated workspace

  • Wifi availability

    130 of Dedham vacation rentals include wifi 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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