Dedham Holiday Rentals

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Dedham holiday rentals

Room

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, (16 reviews)
"Great place for nearby Boston and driving around."
United States
Justin
The price is NZ$451
includes taxes & fees
13 Dec - 14 Dec
Cozy 2-bedroom apartment in charming Dedham - Legacy Mall with WiFi
A gazebo with a stone barbecue grill and a table with chairs.

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, (74 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$395
includes taxes & fees
15 Nov - 16 Nov
Hidden Gem Near Boston w/ 2 bedrooms and huge family and activity room space
A modern kitchen with a built-in washer and dryer, a flat-screen TV, and a dining area with a marble table.

3. Cozy 2 Bedroom/2 Bathroom by Dedham Legacy, Close to Transit & Free Parking

Cozy 2 Bedroom/2 Bathroom by Dedham Legacy, Close to Transit & Free Parking
Dedham
The price is NZ$546
includes taxes & fees
18 Nov - 19 Nov
Cozy 2 Bedroom/2 Bathroom by Dedham Legacy, Close to Transit & Free Parking
A modern kitchen with white cabinets, a central island with bar stools, a stainless steel stove, and a pendant light.

4. 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, (14 reviews)
"A comfortable property in a lovely neighborhood."
United States
Mary Lynn M.
The price is NZ$1,145
includes taxes & fees
13 Dec - 14 Dec
Elegant 4BR/3BR Home w/Yard & 4 Parking in Dedham
A spacious living area with a dining table, black sofa, and a small side table. A kitchen is visible in the background with white cabinets and a window.

5. 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$552
includes taxes & fees
13 Dec - 14 Dec
Renovated 3-bedroom apartment in Dedham - Legacy Mall
A wooden hallway with a patterned floor leading to a door.

6. Maverick Suites at 89 Marion

Maverick Suites at 89 Marion
2.0 star property
Coolidge Corner
8.4 out of 10, Very good, (357 reviews)
"The area was walkable and the room was great!"
United States
Edna
The price is NZ$321
includes taxes & fees
15 Nov - 16 Nov
Maverick Suites at 89 Marion
An outdoor patio with round tables and chairs, surrounded by green umbrellas.

7. Crescent Suites Hotel

Crescent Suites Hotel
3.0 star property
South Side
9.6 out of 10, Exceptional, (1,357 reviews)
"Wehave stayed here several times and each time has been a pleasure."
United States
Kasandra
The price is NZ$248
includes taxes & fees
15 Nov - 16 Nov
Crescent Suites Hotel
A row of brick buildings with storefronts, including a bakery and a liquor store.

8. Maverick Suites at 245 Newbury St

Maverick Suites at 245 Newbury St
2.0 star property
Back Bay
8.4 out of 10, Very good, (219 reviews)
"Great location - plenty to do."
United States
Chloe
The price is NZ$345
includes taxes & fees
6 Dec - 7 Dec
Maverick Suites at 245 Newbury St
A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

9. Modern Boston Stay, Full-Sized Kitchen, Electric Sauna, Added Driveway Parking

Modern Boston Stay, Full-Sized Kitchen, Electric Sauna, Added Driveway Parking
Dorchester
9.6 out of 10, Exceptional, (11 reviews)
"Amazing place and great host!"
United States
Harmoni C.
The price is NZ$369
includes taxes & fees
16 Nov - 17 Nov
Modern Boston Stay, Full-Sized Kitchen, Electric Sauna, Added Driveway Parking
A modern lobby with a wooden panel wall, a beige sofa, a patterned rug, and a large abstract painting.

10. Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston
4.0 star property
Chinatown
8.0 out of 10, Very good, (776 reviews)
"Great room: new and spacious. The kitchenette has everything i needed and more."
United States
Yelitza
The price is NZ$407
includes taxes & fees
13 Dec - 14 Dec
Global Luxury Suites Downtown Boston
A row of brick townhouses with fire escapes, a brick sidewalk, and potted plants.

11. Maverick Suites at 40 Temple St

Maverick Suites at 40 Temple St
2.5 star property
Beacon Hill
8.0 out of 10, Very good, (169 reviews)
"great location near the commons. nice space for single traveler."
United States
Andrea
The price is NZ$312
includes taxes & fees
1 Dec - 2 Dec
Maverick Suites at 40 Temple St
A white table with a vase of white orchids, a white chair, and a view of a cityscape through a window with a black frame.

12. Maverick Suites at 400 Columbus Ave

Maverick Suites at 400 Columbus Ave
2.0 star property
South End
7.4 out of 10, Good, (186 reviews)
"Very well located. Close to two subways and Copeland Square."
Canada
Lorne
The price is NZ$330
includes taxes & fees
15 Nov - 16 Nov
Maverick Suites at 400 Columbus Ave
An outdoor patio area with a covered seating area, a fire pit, and a well-lit ambiance.

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

🎖The Ashmont Apartment - Close to Subway & Downtown Boston🎖
Dorchester
9.8 out of 10, Exceptional, (126 reviews)
"What a gorgeous historical property! We found this to be perfect for our group of four. Loved that it had two restrooms."
United States
grwilly00
The price is NZ$687
includes taxes & fees
19 Nov - 20 Nov
🎖The Ashmont Apartment - Close to Subway & Downtown Boston🎖
A row of brick townhouses with ornate architectural details, large windows, and a central staircase.

14. Stunning Back Bay Studio Apartment

Stunning Back Bay Studio Apartment
Back Bay
9.0 out of 10, Wonderful, (25 reviews)
"Great location."
United States
Chloe
The price is NZ$352
includes taxes & fees
8 Dec - 9 Dec
Stunning Back Bay Studio Apartment
A row of multi-story brick buildings with a central entrance, a flag, and parked cars on the street.

15. Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (479 reviews)
"Great location and the room was nicely decorated and clean!"
United States
Judy
The price is NZ$389
includes taxes & fees
6 Dec - 7 Dec
Maverick Suites at 28 Fenway
A modern kitchen with white cabinetry, stainless steel appliances, a large island with bar stools, pendant lighting, and a view of the outdoors through a window.

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

🎖The Ashmont Suite - Close to Subway + Downtown🎖
Dorchester
10.0 out of 10, Exceptional, (62 reviews)
"We had a great visit and the house gave us everything we needed for a comfortable stay. The rooms were nicely furnished and the bedrooms were spacious. The location was convenient for accessing the bus and the subway. The host was very friendly and responsive. We hope to visit again!"
United States
Christina B.
The price is NZ$982
includes taxes & fees
23 Nov - 24 Nov
🎖The Ashmont Suite - Close to Subway + Downtown🎖
A modern living room with a blue wall, a large window, a sofa, a coffee table, and a TV.

17. The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.8 out of 10, Excellent, (45 reviews)
"I had a great stay at The Chester Hotel. Super cute vibe, easy check-in, and good location for where I needed to be for work. Bed is super comfy, the room aesthetic is great and the restaurant MIDA next door was really good!"
United States
Tracy
The price is NZ$485
includes taxes & fees
23 Nov - 24 Nov
The Chester Hotel
A modern kitchen with a large island, white cabinets, and pendant lighting.

18. 60/3 - SPRING GETAWAY 10% OFF !Newly built & cozy apartment in Boston

60/3 - SPRING GETAWAY 10% OFF !Newly built & cozy apartment in Boston
Mattapan
9.6 out of 10, Exceptional, (30 reviews)
"Enjoyed our stay"
United States
Sybal C.
The price is NZ$1,100
includes taxes & fees
27 Nov - 28 Nov
60/3 - SPRING GETAWAY 10% OFF !Newly built & cozy apartment in Boston
A bedroom with a bed, a round table with chairs, a TV, and a large mirror.

19. The Concord Hotel

The Concord Hotel
2.0 star property
South End
8.2 out of 10, Very good, (41 reviews)
"Super nice place to stay plus it was super close to shopping and all the sights"
Canada
Rupintal
The price is NZ$512
includes taxes & fees
24 Nov - 25 Nov
The Concord Hotel
A modern living room with a black leather sofa, grey armchairs, a coffee table, and a large window offering a city view.

20. Kasa Boston at Fenway

Kasa Boston at Fenway
4.0 star property
Fenway–Kenmore
9.0 out of 10, Wonderful, (352 reviews)
"Great location, very comfortable apartment, great facilities, everyone was friendly and helpful!!!"
United States
antonio
The price is NZ$536
includes taxes & fees
23 Nov - 24 Nov
Kasa Boston at Fenway
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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Find holiday rentals that suit your style

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Top Dedham Hotel Reviews

A modern bar area with a long counter, multiple seating options, and large windows providing views of the outside.
Cambria Hotel Boston Somerville

Cambria Hotel Boston Somerville

Cambria Hotel Boston Somerville
Spring Hill

10/10 Excellent

Beautiful hotel, wonderful staff and amenities. Would highly recommend if you need somewhere to stay in the Somerville area. Close to public transport links. Great value!
Australia
Rosemary
Reviewed June 3, 2026
Cambria Hotel Boston Somerville

Find out more about Dedham

Everything you need to know about Dedham holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Dedham holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Dedham holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Dedham holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Dedham. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Dedham holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Dedham holiday rentals we have selected for you start as low as NZ$243 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Dedham rentals

At Expedia, we put the best Dedham holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Dedham rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Dedham holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Dedham. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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.