Historic Dedham Square Holiday Rentals

      Highly Rated

Apartment

Contemporary Style And Comfort Convenient To Boston And Route 128

• Boston
• ·
• Dedham
• 0.56 mi to center

10.0

Exceptional

(71 Reviews)

1 Bedroom 1 Bath 2 Guests 600 ft²

• 
  Parking
• 
  Kitchen
• 
  Air Conditioner
• 
  Internet

R1,679/Night 7 Nights - R11,754

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New

Apartment

A New 3 bedroom 4 beds 2 Bath, Apt 3

• Boston
• ·
• Hyde Park
• 0.51 mi to center

10.0

Exceptional

(1 Review)

3 Bedrooms 2 Baths 7 Guests 1496.18 ft²

• 
  Internet
• 
  Child Friendly
• 
  Security/Safety

R7,265/Night 7 Nights - R50,861

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Hotel

Residence Inn Boston Dedham

• Boston
• ·
• Dedham
• 1.31 mi to center

8.4

Excellent

(562 Reviews)

1 Bath

• 
  Breakfast
• 
  Parking
• 
  Pool
• 
  Balcony/Terrace

R2,710/Night 7 Nights - R18,979

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Apartment

Cozy Private Garden Suite near Gillette Stadium,Boston/BBQ/Parking/Walk to Train

• Boston
• ·
• Westwood
• 1.64 mi to center

10.0

Exceptional

(2 Reviews)

1 Bedroom 1 Bath 4 Guests

• 
  Parking
• 
  Air Conditioner
• 
  Internet
• 
  Laundry

R3,616/Night 7 Nights - R25,311

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Apartment

Comfy & Chic Apartment for 2026 World Cup FREE PARKING

• Boston
• ·
• West Roxbury
• 0.68 mi to center

10.0

Exceptional

(1 Review)

3 Bedrooms 1 Bath 6 Guests 1097.92 ft²

• 
  Parking
• 
  View
• 
  Air Conditioner
• 
  Internet

R3,829/Night 7 Nights - R26,810

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      Price Dropped

Hotel

Hilton Boston/Dedham

• Boston
• ·
• Dedham
• 1.51 mi to center

7.8

Very Good

(1068 Reviews)

1 Bath

• 
  Breakfast
• 
  Parking
• 
  Balcony/Terrace
• 
  Kitchen

R1,953/Night 7 Nights - R13,668

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Cottage

Charming 2-bedroom Guest House in Dedham on Private Estate

• Boston
• ·
• Dedham
• 2.23 mi to center

10.0

Exceptional

(1 Review)

2 Bedrooms 1 Bath 4 Guests

• 
  Air Conditioner
• 
  Internet
• 
  Pet Friendly
• 
  Child Friendly

R7,961/Night 7 Nights - R55,725

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House

Boston Single Family House - 19' Train to Back Bay

• Boston
• ·
• West Roxbury
• 0.48 mi to center

9.7

Exceptional

(8 Reviews)

5 Bedrooms 4 Baths 12 Guests 2604.87 ft²

• 
  Parking
• 
  Balcony/Terrace
• 
  View
• 
  Air Conditioner

R14,210/Night 7 Nights - R99,472

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      Price Dropped

Hotel

Comfort Inn - Dedham-Boston MetroWest

• Boston
• ·
• Dedham
• 1.26 mi to center

7.4

Very Good

(1007 Reviews)

1 Bath

• 
  Parking
• 
  Balcony/Terrace
• 
  Kitchen
• 
  Air Conditioner

R2,710/Night 7 Nights - R18,979

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Apartment

Perfectly Located & Comfy Suite - Summer Best !

• Boston
• ·
• Westwood
• 1.97 mi to center

9.8

Exceptional

(9 Reviews)

1 Bedroom 1 Bath 4 Guests 900 ft²

• 
  Parking
• 
  Balcony/Terrace
• 
  Kitchen
• 
  Air Conditioner

R3,743/Night 7 Nights - R26,204

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      Highly Rated

Apartment

Unique & Peaceful Boston Home(Free Parking)

• Boston
• ·
• West Roxbury
• 0.68 mi to center

9.3

Exceptional

(71 Reviews)

2 Bedrooms 1 Bath 5 Guests 947.22 ft²

• 
  Parking
• 
  View
• 
  Air Conditioner
• 
  Internet

R4,648/Night 7 Nights - R32,535

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House

Easy access! 1br, 5 min walk to T train, easy access to Highway

• Massachusetts
• ·
• Readville
• 2.24 mi to center

9.2

Exceptional

(16 Reviews)

1 Bedroom 1 Bath 4 Guests 600 ft²

• 
  Parking
• 
  Balcony/Terrace
• 
  Kitchen
• 
  Air Conditioner

R3,588/Night 7 Nights - R25,119

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      Highly Rated

Apartment

Cozy Boston Getaway Apartment Perfect for 2026 World Cup Visit, Free Parking

• Boston
• ·
• West Roxbury
• 0.68 mi to center

9.1

Exceptional

(57 Reviews)

1 Bedroom 1 Bath 3 Guests 118.4 ft²

• 
  Parking
• 
  View
• 
  Air Conditioner
• 
  Internet

R3,876/Night 7 Nights - R27,129

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Apartment

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

• Boston
• ·
• Dedham
• 1.08 mi to center

9.2

Exceptional

(11 Reviews)

2 Bedrooms 1 Bath 4 Guests

• 
  Internet
• 
  Pet Friendly
• 
  Laundry
• 
  Bedding/Linens

R4,276/Night 7 Nights - R29,936

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      Highly Rated

Apartment

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

• Massachusetts
• ·
• Readville
• 1.30 mi to center

9.0

Exceptional

(65 Reviews)

2 Bedrooms 1 Bath 6 Guests 1300 ft²

• 
  Parking
• 
  Kitchen
• 
  Air Conditioner
• 
  Internet

R3,830/Night 7 Nights - R26,810

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Apartment

Cozy 1-bedroom apartment in Dedham, a hop skip away from Boston

• Boston
• ·
• Dedham
• 1.00 mi to center

8.0

Excellent

(1 Review)

1 Bedroom 1 Bath 5 Guests 500 ft²

• 
  Air Conditioner
• 
  Internet
• 
  Child Friendly
• 
  Bedding/Linens

R2,966/Night 7 Nights - R20,765

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Apartment

Terrific 2 bedroom apartment in Dedham

• Massachusetts
• ·
• Readville
• 1.30 mi to center

2 Bedrooms 1 Bath 6 Guests

• 
  Internet
• 
  Laundry
• 
  Bedding/Linens
• 
  Wellness Facilities

R5,232/Night 7 Nights - R36,618

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Apartment

Comfortable 2-BR Apt, Eat-In Kitchen & Parking, Quiet Location+Train to Boston

• Boston
• ·
• Dedham
• 0.65 mi to center

2 Bedrooms 1 Bath 4 Guests 900 ft²

• 
  Parking
• 
  Balcony/Terrace
• 
  Kitchen
• 
  Internet

R4,115/Night 7 Nights - R28,803

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Apartment

Cozy 2-bedroom apartment in charming Boston with WiFi, AC. Commuter train

• Boston
• ·
• Hyde Park
• 1.12 mi to center

10.0

Exceptional

(26 Reviews)

2 Bedrooms 1 Bath 4 Guests

• 
  Parking
• 
  Balcony/Terrace
• 
  Kitchen
• 
  Air Conditioner

R5,344/Night 7 Nights - R37,416

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House

Bright & Spacious Boston Retreat

• Boston
• ·
• Brook Farm
• 0.10 mi to center

10.0

Exceptional

(7 Reviews)

2 Bedrooms 1 Bath 6 Guests

• 
  Parking
• 
  Balcony/Terrace
• 
  Kitchen
• 
  Air Conditioner

R5,933/Night 7 Nights - R41,531

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      Price Dropped

Condo

Quiet Comfort in Boston - Large 2 Bed Condo

• Boston
• ·
• Metropolitan Hill - Beech Street
• 0.41 mi to center

10.0

Exceptional

(5 Reviews)

2 Bedrooms 1 Bath 5 Guests 1000 ft²

• 
  Parking
• 
  Balcony/Terrace
• 
  Kitchen
• 
  Air Conditioner

R2,921/Night 7 Nights - R20,446

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Apartment

BOSTON-PRIVATE SUITE, WITH PRIVATE BATHROOM- WALK TO TRAIN & BUSES

• Boston
• ·
• West Roxbury
• 0.06 mi to center

10.0

Exceptional

(4 Reviews)

1 Bedroom 1 Bath 1 Guest 700 ft²

• 
  Oceanfront
• 
  Hot Tub
• 
  Parking
• 
  Ocean View

R2,736/Night 7 Nights - R19,154

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Apartment

Charming Victorian Furnished Home

• Boston
• ·
• Hyde Park
• 0.23 mi to center

9.8

Exceptional

(14 Reviews)

2 Bedrooms 2 Baths 7 Guests

• 
  Parking
• 
  Balcony/Terrace
• 
  Kitchen
• 
  Air Conditioner

R6,206/Night 7 Nights - R43,444

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Apartment

Boston Cozy studio Apt. near Train&Buses ,Parking included

• Boston
• ·
• West Roxbury
• 0.06 mi to center

9.8

Exceptional

(7 Reviews)

1 Bedroom 1 Bath 1 Guest

• 
  Parking
• 
  Balcony/Terrace
• 
  Kitchen
• 
  Air Conditioner

R3,452/Night 7 Nights - R24,162

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