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Vacation rentals in Dedham

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Quick stats about vacation rentals in Dedham

  • Total vacation rentals

    Explore 150 vacation rentals in Dedham

  • Nightly prices starting at

    Dedham vacation rentals start at €26 per night before taxes and fees

  • Verified guest reviews

    Over 9,600 verified reviews to help you choose

  • Family-friendly vacation rentals

    60 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 50 rentals that welcome pets

  • Rentals with dedicated workspaces

    100 properties have a dedicated workspace

  • Wi-Fi availability

    150 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!

Top-rated vacation rentals in Dedham

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

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Guest favorite
Home in Dedham

Elegant 4BR Retreat | Yard & Parking | Dedham 94

Welcome to your elegant Dedham retreat! This fully renovated 4BR/3BA home blends modern design with comfort, featuring an open living and dining area, a fully equipped kitchen, and beautifully styled bedrooms. Enjoy a private fenced yard, four parking spots, and in-home laundry. Just a 10-minute walk to the subway for easy access to downtown Boston, and about 18 minutes to Gillette Stadium depending on traffic. We’d be delighted to host you book now and experience comfort with a touch of luxury!

4.97 out of 5 average rating, 29 reviews
Top guest favorite
Guest suite in Dover

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.

4.98 out of 5 average rating, 340 reviews
Top guest favorite
The exterior of a spacious guesthouse showcases a blend of siding and stone finishes. A paved driveway leads to a two-car garage. Lush greenery and flower beds enhance the inviting entrance, while multiple windows allow natural light to fill the interior.
Guest suite in Sharon

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.

4.96 out of 5 average rating, 232 reviews
Top guest favorite
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

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

4.95 out of 5 average rating, 222 reviews
Guest favorite
The living room features a comfortable couch adorned with a soft throw blanket. A large piece of artwork hangs on the wall, showcasing a vibrant floral design. Two stylish glass tables are positioned in front of the couch, accompanied by a decorative rug.
Home in Hyde Park

~*30min to Downtown*~ THE COSMOPOLITAN

Stylish contemporary kid-friendly apartment on the first floor of a multi-family. Bright and roomy bedrooms with a large eat-in kitchen. Central air conditioning. Plenty of free street parking. Access to shared laundry room. Located in Hyde Park neighborhood, 30 minute drive into downtown Boston. Professionally cleaned and disinfected. Room 1: Queen size bed, closet, TV Room 2: Queen size bed, closet Room 3: Living room couch bed, closet, TV Entryway: Includes Mrs. Pac Man wall arcade

4.9 out of 5 average rating, 389 reviews
Top guest favorite
Apartment in Dedham

Modern Studio Above Detached Garage Near Boston

Modern private studio above a detached garage in a quiet neighborhood near Boston. Features a queen bed, full-size couch, dining table, fast WiFi, and 55” smart TV. Floor mattress. No cooking surfaces, but includes a mini fridge, microwave, toaster, drip coffee maker, Nespresso, and electric kettle. Bathroom with stand-up shower, no bath tub. Towels and linens provided. Private entrance, on-street parking. Close to restaurants, shopping, MBTA Franklin line commuter rail to South Station

5.0 out of 5 average rating, 44 reviews
Guest favorite
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

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. The cottage is a studio apartment that has a microwave and mini-fridge as well as sitting area and table. It has a lovely view of the pool and gardens. Besides the pool, there are two garden ponds where we keep ornamental fish. Outside the garden fence there is often a parade of various types of birds, bunnies and even wild turkeys and deer.

4.95 out of 5 average rating, 217 reviews
Guest favorite
A spacious living room features a large flat-screen TV mounted on the wall, complemented by decorative plants on a console. Neutral-colored walls are adorned with two abstract art pieces. A round, golden coffee table sits in the center, surrounded by a comfortable sectional sofa.
Condo in Dedham

Chic and Cozy Family Retreat Close to Boston

Bring the whole family to this great place with lots of room for fun. Welcome to our 5-bedroom modern oasis in Dedham, MA. Spacious bedrooms, well-furnished, comfy bedding. Amenities: AC throughout, fully equipped kitchen, spacious living room, large TV, Wi-Fi, private porch, free parking, washer/dryer. Conveniently located near shops, groceries, and malls. Nearby: Gillette Stadium, Back Bay (25 min). Book now for an unforgettable Dedham experience!

4.9 out of 5 average rating, 59 reviews
Guest favorite
A spacious bedroom features a large bed with a light-colored comforter and decorative pillows. Two lamps provide soft lighting. Mirrored closet doors reflect the room, and artwork hangs on the wall, adding a touch of character. Warm wooden flooring complements the neutral decor.
Home in Canton

Gorgeous 2nd Floor Home with Private Entry

Welcome to your home away from home! This beautiful second-floor 2 BR unit keyless self check in offers a private entrance and private stairs. Features: · Newly Installed AC · Fully Kitchen: Equipped with smart utilities, including an oven, microwave, dishwasher, washer, and dryer. · High-speed internet. · Comfortable Sleeping Arrangements: 2 beds & a sofa bed, perfect for accommodating up to 4 guests.

4.95 out of 5 average rating, 104 reviews
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

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.

4.98 out of 5 average rating, 302 reviews
Guest favorite
Guesthouse in Dedham

Slow Down| Your Boston Getaway

Private entrance, 6+ private parking spaces, and a large green outdoor area perfect for relaxing. Quiet family-friendly neighborhood. Features 2 spacious bedrooms with 3 queen beds, smart bathroom, modern kitchen, and smart self check-in with a unique code for each guest. Enjoy complimentary Colombian coffee plus starter essentials including toilet paper and cleaning supplies for a comfortable stay.

4.89 out of 5 average rating, 28 reviews
Top guest favorite
A spacious living area features a high wood-beamed ceiling and large windows overlooking greenery. A comfortable couch and plush chairs are arranged around a coffee table. A staircase leads to a loft area, and a flat-screen TV is visible in the background.
Apartment in Roxbury

Light-Filled Luxury Apartment with View

Beautiful top floor luxury apartment in stately Victorian home. Extraordinary views of historic park as your front yard! Your own entrance through a private garden. Apartment is a studio-style open living space with full kitchen, living area, and bedroom bay with queen bed. Also includes loft bedroom with 2 twin beds.

4.97 out of 5 average rating, 431 reviews

Popular amenities for Dedham vacation rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Stay near Dedham's top sights

Blue Hills Ski Area

34 locals recommend

Wilson Mountain Reservation

10 locals recommend

George Wright Golf Course

7 locals recommend

Cutler Park Reservation

6 locals recommend

Millennium Park

5 locals recommend

Turtle Pond

4 locals recommend

Other great vacation rentals in Dedham

Guest favorite
Apartment in Dedham

Charming Dedham Retreat !

4.91 out of 5 average rating, 11 reviews
Top guest favorite
Townhouse in West Roxbury

Top of the Hill Townhouse

4.99 out of 5 average rating, 98 reviews
Top guest favorite
Guest suite in Norwood

Modern Upper-Level Oasis in Norwood

4.93 out of 5 average rating, 28 reviews
Top guest favorite
Home in Roslindale

New modern 2bd condo: free parking/near train

4.94 out of 5 average rating, 49 reviews
Guest favorite
A compact kitchenette is displayed, featuring a microwave, small refrigerator, dishware, and a coffee maker arranged on minimalistic shelves. The countertop has a sleek, white surface with decorative plants, providing a practical space for meal preparation.
Place to stay in Dedham

Tiny-home like living

4.88 out of 5 average rating, 85 reviews
Guest favorite
Guesthouse in Westwood

Private Suite•Gillette Stadium/Boston•BBQ•Parking

4.96 out of 5 average rating, 57 reviews
Guest favorite
Apartment in West Roxbury

Comfy & Chic 3 bedroom in Boston w/ FREE Parking

4.85 out of 5 average rating, 52 reviews
Top guest favorite
The exterior of the house is shown at dusk, featuring a two-story design with a mix of gray siding and white trim. Soft lighting highlights the entrance and landscaping along the front, while a large grassy area is visible in front of the home.
Townhouse in Norwood

Family Vacation Modern Home

4.96 out of 5 average rating, 57 reviews

When is the best time to visit Dedham?

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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.

Destinations to explore