
Holiday rentals in Dedham
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Top-rated holiday rentals in Dedham
Guests agree: these stays are highly rated for location, cleanliness and more.

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)

Flower Farm Getaway 2BR, 20 Min To Boston
Spacious two-bedroom in-law suite attached to 1700’s farmhouse, situated on our small flower farm and garden co-op just 20 minutes from Boston. Only a mile from the Mass Pike & Rt. 128 (I-95). Centrally located to all Rt. 128 businesses, colleges & hospitals. A 7-min drive to Riverside Green line “D” subway stop into Boston (parking available), or commuter rail stops (Auburndale, Wellesley & Kendal Green Stations). It's a 20-minute drive to Amtrak's "Route 128" station to NYC and points south.

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.

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.

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.

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.

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!

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!

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.

Entire guest suite in Stoneham
Come enjoy this quiet and comfy home in the heart of Stoneham—your perfect getaway just 20 minutes from the airport and the historic city of Boston. Conveniently located near shopping malls, restaurants, coffee shops, grocery stores, and the natural beauty of Middlesex Fells Reservation and Stone Zoo, this peaceful retreat is designed to make your trip relaxing, enjoyable, and stress-free.

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.

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 holiday rentals
Other great holiday rentals in Dedham

Chic and Cozy Family Retreat Close to Boston

Cozy & Bright Guest Unit

The Plant Haus

Your home in Boston

Kailyn Apartment Boston, Massachusetts

94_Elegant 4BR Home w/Yard & Ample Parking, Dedham

Cozy 2-Bedroom Apartment Near Dedham Legacy

Gorgeous 2nd Floor Home with Private Entry
When is the best time to visit Dedham?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ₹8,386 | ₹8,476 | ₹8,386 | ₹9,017 | ₹9,558 | ₹9,558 | ₹9,378 | ₹9,468 | ₹9,378 | ₹9,648 | ₹9,919 | ₹8,927 |
| Avg. temp | -3°C | -2°C | 2°C | 8°C | 14°C | 19°C | 22°C | 22°C | 18°C | 11°C | 6°C | 0°C |
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 320 vacation rentals in Greenlodge, over 290 vacation rentals in East Dedham, 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 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 free parking, over 40 homes with a kitchen, over 50 homes with air conditioning, 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 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 apartment rentals in Dedham?
Four-legged friends are welcome in Dedham. Choose from more than 10 apartment rentals for guests traveling with pets.
Do apartment rentals in Dedham have wifi?
Absolutely! We offer over 30 apartment rentals with wifi in Dedham. Enjoy a tailored experience with all the comforts you desire.
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 ₹3,607 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 & child-friendly amenities

Pet-friendly holiday rentals
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
80 properties have a dedicated workspace

Wifi availability
120 of Dedham holiday 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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- Hampton Beach
- Fenway Park
- TD Garden
- Boston Common
- Harvard University
- Revere Beach
- Brown University
- Lynn Beach
- New England Aquarium
- MIT Museum
- Good Harbor Beach
- Freedom Trail
- Duxbury Beach
- Canobie Lake Park
- Crane Beach
- Museum of Fine Arts, Boston
- Onset Beach
- Quincy Market
- Prudential Center
- Oakland Beach
- White Horse Beach
- Roger Williams Park Zoo
- Salem Willows Park
- Franklin Park Zoo




