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Dedham Holiday Rentals

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Our top choices for Dedham holiday rentals

1. Cozy 2-bedroom apartment in charming Dedham - Legacy Mall with WiFi

Cozy 2-bedroom apartment in charming Dedham - Legacy Mall with WiFi
Dedham
9.2 out of 10, Wonderful, (13 reviews)
"Good little spot, would reccommend."
Canada
Julien Alfred Joseph
The price is NZ$473
includes taxes & fees
4 Oct - 5 Oct
Cozy 2-bedroom apartment in charming Dedham - Legacy Mall with WiFi

2. Hidden Gem Near Boston w/ 2 bedrooms and huge family and activity room space

Hidden Gem Near Boston w/ 2 bedrooms and huge family and activity room space
Dedham
9.0 out of 10, Wonderful, (70 reviews)
"Our stay was exactly what we needed while vacationing in Boston. Our host was gracious enough to even let us check in early. We had a ton of space and the beds were very comfortable. Would definitely stay again!"
United States
Cortney
The price is NZ$410
includes taxes & fees
30 Sept - 1 Oct
Hidden Gem Near Boston w/ 2 bedrooms and huge family and activity room space

3. Elegant 4BR/3BR Home w/Yard & 4 Parking in Dedham

Elegant 4BR/3BR Home w/Yard & 4 Parking in Dedham
Dedham
10.0 out of 10, Exceptional, (12 reviews)
"Great property! Perfect for getting around Boston area. Jenny Lee was responsive to questions and made sure everything was okay."
United States
Trish G.
The price is NZ$1,114
includes taxes & fees
30 Sept - 1 Oct
Elegant 4BR/3BR Home w/Yard & 4 Parking in Dedham

4. Renovated 3-bedroom apartment in Dedham - Legacy Mall

Renovated 3-bedroom apartment in Dedham - Legacy Mall
Dedham
9.8 out of 10, Exceptional, (12 reviews)
"Half way between Wellesley and Boston, the location was the perfect place to stay for our daughter’s graduation weekend. We communicated with the owner ahead of our trip and he was very accommodating.The apt was clean and spacious, the beds were extremely comfortable and there was ample parking. Would stay here again."
United States
Georgie D.
The price is NZ$562
includes taxes & fees
4 Oct - 5 Oct
Renovated 3-bedroom apartment in Dedham - Legacy Mall

5. Newly Renovated 4BR Boston - Cozy Apt near Franklin Park • Pet-Friendly 601

Newly Renovated 4BR Boston - Cozy Apt near Franklin Park • Pet-Friendly 601
Mattapan
9.6 out of 10, Exceptional, (26 reviews)
"Was such a great spot for the 11 of us!! "
United States
Bryston J.
Newly Renovated 4BR Boston - Cozy Apt near Franklin Park • Pet-Friendly 601

6. 🎖The Boiler Room - Close to Subway & Downtown🎖

🎖The Boiler Room - Close to Subway & Downtown🎖
Dorchester
9.8 out of 10, Exceptional, (92 reviews)
"Honestly, the Boiler Room is even bigger than it looks in the pictures and is so perfectly curated! We LOVED our stay and if I ever get the opportunity to come back to Boaton, I will be staying here!"
United States
Katie C.
The price is NZ$605
includes taxes & fees
5 Oct - 6 Oct
🎖The Boiler Room - Close to Subway & Downtown🎖

7. Crescent Suites Hotel

Crescent Suites Hotel
3.0 star property
South Side
9.6 out of 10, Exceptional, (1,289 reviews)
"Great location, close to restaurants and stores. Beautiful rooms. Close enought to Boston without all the traffic. Close to Mass Pike."
United States
Mark
The price is NZ$312
includes taxes & fees
11 Oct - 12 Oct
Crescent Suites Hotel

8. Modern Boston Townhouse Near Transit • Private Deck • Pet-Friendly - 383

Modern Boston Townhouse Near Transit • Private Deck • Pet-Friendly - 383
Quincy
9.8 out of 10, Exceptional, (52 reviews)
"Very cute property that was very clean, the host was extreme nice with great knowledge of the area and a prefect parking map!"
United States
Alicia R.
The price is NZ$741
includes taxes & fees
4 Oct - 5 Oct
Modern Boston Townhouse Near Transit • Private Deck • Pet-Friendly - 383

9. Newly Built Greater Boston Townhouse Near I-93 • Parking • Pet-Friendly - 39

Newly Built Greater Boston Townhouse Near I-93 • Parking • Pet-Friendly - 39
Quincy
9.6 out of 10, Exceptional, (54 reviews)
"Very clean and stay was enjoyable. "
United States
Sheldon S.
The price is NZ$614
includes taxes & fees
1 Oct - 2 Oct
Newly Built Greater Boston Townhouse Near I-93 • Parking • Pet-Friendly - 39

10. Maverick Suites at 89 Marion

Maverick Suites at 89 Marion
2.0 star property
Coolidge Corner
8.4 out of 10, Very good, (319 reviews)
"Room was clean, neat area."
United States
Keir
The price is NZ$399
includes taxes & fees
29 Sept - 30 Sept
Maverick Suites at 89 Marion

11. Spacious Greater Boston 3BR Townhouse Near I-93 • Parking • Pet-Friendly - 41

Spacious Greater Boston 3BR Townhouse Near I-93 • Parking • Pet-Friendly - 41
Quincy
9.6 out of 10, Exceptional, (33 reviews)
"We enjoyed our stay at this place. Comfortable and plenty of space for us."
United States
Jeff L.
The price is NZ$569
includes taxes & fees
29 Sept - 30 Sept
Spacious Greater Boston 3BR Townhouse Near I-93 • Parking • Pet-Friendly - 41

12. 🎖The Ashmont Apartment - Close to Subway & Downtown Boston🎖

🎖The Ashmont Apartment - Close to Subway & Downtown Boston🎖
Dorchester
9.8 out of 10, Exceptional, (124 reviews)
"Lovely full apartment with a great location. Our host was highly responsive, the property was clean, quiet, and perfectly well appointed. This is a perfect location to catch the T and explore all of Boston from."
United States
Elizabeth F.
The price is NZ$808
includes taxes & fees
30 Sept - 1 Oct
🎖The Ashmont Apartment - Close to Subway & Downtown Boston🎖

13. Bright 2BR by Boston Waterfront

Bright 2BR by Boston Waterfront
East Boston
9.8 out of 10, Exceptional, (44 reviews)
"7 min from the airport, seamless check in and entry and a spotless, welcoming place- with coffee! Great rental- perfect if you’re coming/going from Logan"
United States
Bridget
The price is NZ$643
includes taxes & fees
4 Oct - 5 Oct
Bright 2BR by Boston Waterfront

14. Sleek Studio Apartment in the South End

Sleek Studio Apartment in the South End
Back Bay
9.6 out of 10, Exceptional, (5 reviews)
"A little issue getting in with the door code operation but otherwise great"
United States
Unspecified U.
The price is NZ$442
includes taxes & fees
4 Oct - 5 Oct
Sleek Studio Apartment in the South End

15. The Concord Hotel

The Concord Hotel
2.0 star property
South End
7.6 out of 10, Good, (24 reviews)
"Great room! Cool place to stay. We walked everywhere and stuff was close by. Woud stay here again"
United States
Cotie
The price is NZ$644
includes taxes & fees
30 Sept - 1 Oct
The Concord Hotel

16. NEW Modern Apartment Near Boston & Harvard Square.

NEW Modern Apartment Near Boston & Harvard Square.
Watertown
10.0 out of 10, Exceptional, (53 reviews)
"That was the most comfortable bed I have slept in away from home!"
United States
Kimberly M.
The price is NZ$383
includes taxes & fees
25 Oct - 26 Oct
NEW Modern Apartment Near Boston & Harvard Square.

17. The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.8 out of 10, Excellent, (38 reviews)
"It was in a great neighbourhood and beautiful decorated"
United Kingdom
Shanida
The price is NZ$558
includes taxes & fees
30 Sept - 1 Oct
The Chester Hotel

18. 14a-Cozy and well decorated apartment in awesome Boston

14a-Cozy and well decorated apartment in awesome Boston
Dorchester
10.0 out of 10, Exceptional, (34 reviews)
"The whole place is excellent, location and services just around the corner "
United States
Ramon G.
The price is NZ$1,049
includes taxes & fees
4 Oct - 5 Oct
14a-Cozy and well decorated apartment in awesome Boston

19. 🎖The Ashmont Suite - Close to Subway + Downtown🎖

🎖The Ashmont Suite - Close to Subway + Downtown🎖
Dorchester
10.0 out of 10, Exceptional, (62 reviews)
"Is a great place"
United States
Ramon G.
🎖The Ashmont Suite - Close to Subway + Downtown🎖

20. 284 - Cozy House with free huge parking

284 - Cozy House with free huge parking
Quincy
9.8 out of 10, Exceptional, (80 reviews)
"Nice quiet street perfect for families and close to Boston."
United States
Alisa O.
The price is NZ$874
includes taxes & fees
1 Oct - 2 Oct
284 - Cozy House with free huge parking
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Dedham Hotel Reviews

Find out more about Dedham

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Dedham holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Dedham. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Dedham. Seeing all the best attractions is bound to make you fall in love with Dedham. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Dedham short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a holiday rental in Dedham?

Yes, there are holiday rentals in Dedham close to Blue Hills Reservation, or you can select a more secluded option if you're looking for a relaxing stay. Tourists like the array of shops and top-notch restaurants in Dedham. You can also check out the entertainment venues while you're visiting.

What are some of the best holiday rentals that Dedham has to offer?

Cozy 4BR Home by Tufts w/ Subway Access to Downtown, MIT, Harvard + Free Parking: This holiday home rental outside of Dedham offers a balcony, a selection of games and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals are there in Dedham?

Expedia has 7 holiday rentals for your stay in Dedham.

What can I see and do in Dedham?

Blue Hills Reservation and Kings Bowling are a couple of the family-friendly sights, whereas cultural attractions include Dedham Historical Society and Motherbrook Arts and Community Center. Fenway Park and Gillette Stadium are other popular places to visit in the area.

What are holiday rentals like in Dedham?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Dedham. Holiday rentals offer extras such as WiFi and washers and dryers so you'll have all the conveniences of home. If you're concerned about a clean environment, a holiday rental can offer a sense of safety away from shared hotel lifts and busy concierge desks while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental an attractive option for a small group gathering.