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Dedham Holiday Rentals

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48 rentals in Dedham.
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Hidden Gem Near Boston w/ 2 bedrooms and huge family and activity room space, holiday rental in Dedham

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

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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18 bedroom Estate &  Adventure Compound, holiday rental in Dedham

18 bedroom Estate & Adventure Compound

10 bedrooms
12 bathrooms
Sleeps 16
Match: Sleeps
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The Alameda 2 w/AC | 2BR 1BA w/En-Suite HdTV's | Short walk to train, shops and, holiday rental in Dedham

The Alameda 2 w/AC | 2BR 1BA w/En-Suite HdTV's | Short walk to train, shops and

West Roxbury, Brook Farm
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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The Redlands 1 w/AC | 2BR 1BA w/EnSuite HdTv's | Short walk to train and near Br, holiday rental in Dedham

The Redlands 1 w/AC | 2BR 1BA w/EnSuite HdTv's | Short walk to train and near Br

West Roxbury, Brook Farm
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Colonial Home, holiday rental in Dedham

Colonial Home

1 bedroom
1 bathroom
Sleeps 1
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Boston's 2 bedroom vacation rental condo near Stony Brook's Orange line subway, holiday rental in Dedham

Boston's 2 bedroom vacation rental condo near Stony Brook's Orange line subway

Jamaica Plain, Egleston Square
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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~*Pet Friendly 30min to Downtown*~ THE BOSTONIAN, holiday rental in Dedham

~*Pet Friendly 30min to Downtown*~ THE BOSTONIAN

Hyde Park
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Private Nice and Cozy 4BR-Close to Boston, holiday rental in Dedham

Private Nice and Cozy 4BR-Close to Boston

4 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Boston a la Francaise, holiday rental in Dedham

Boston a la Francaise

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Spacious Studio Boston-Longwood, holiday rental in Dedham

Spacious Studio Boston-Longwood

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Jacaranda, holiday rental in Dedham

Jacaranda

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Luxury 2 Bedroom 2 Bath Apartment  Fenway Park Boston, holiday rental in Dedham

Luxury 2 Bedroom 2 Bath Apartment Fenway Park Boston

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Serene space in Milton, holiday rental in Dedham

Serene space in Milton

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Furnished Comfy Tina's private villa, holiday rental in Dedham

Furnished Comfy Tina's private villa

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Beautiful Updated 3 BR Condo in Boston (Entire), holiday rental in Dedham

Beautiful Updated 3 BR Condo in Boston (Entire)

Jamaica Plain, Lower Washington - Mount Hope, Roslindale
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Big Studio near Longwood Medical area, holiday rental in Dedham

Big Studio near Longwood Medical area

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Spacious, Sunny, Steps to MBTA, Fenway Park, Hospitals (Parking avail), holiday rental in Dedham

Spacious, Sunny, Steps to MBTA, Fenway Park, Hospitals (Parking avail)

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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2Private Bedroom Close Copley, Fenway Park & Downtown Boston, holiday rental in Dedham

2Private Bedroom Close Copley, Fenway Park & Downtown Boston

Mission Hill
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
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1 Private Bedroom 5 Guest Close to Fenway Park & Downtown Boston, holiday rental in Dedham

1 Private Bedroom 5 Guest Close to Fenway Park & Downtown Boston

Jamaica Plain
1 bedroom
2 bathrooms
Sleeps 5
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1 Private Bedroom 6 Guest Close to Fenway Park & Downtown Boston, holiday rental in Dedham

1 Private Bedroom 6 Guest Close to Fenway Park & Downtown Boston

Jamaica Plain
1 bedroom
2 bathrooms
Sleeps 6
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1 Private Bedroom 5 Guest Close to Fenway Park & Downtown Boston, holiday rental in Dedham

1 Private Bedroom 5 Guest Close to Fenway Park & Downtown Boston

Jamaica Plain
1 bedroom
2 bathrooms
Sleeps 5
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3Private Bedroom Close Copley, Fenway Park & Downtown Boston, holiday rental in Dedham

3Private Bedroom Close Copley, Fenway Park & Downtown Boston

Mission Hill
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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1 Private Bedroom 4 Guest Close to Fenway Park & Downtown Boston, holiday rental in Dedham

1 Private Bedroom 4 Guest Close to Fenway Park & Downtown Boston

Jamaica Plain
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Cozy 4 Bedroom Apartment near Boston, holiday rental in Dedham

Cozy 4 Bedroom Apartment near Boston

4 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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~*30min to Downtown*~ THE COSMOPOLITAN, holiday rental in Dedham

~*30min to Downtown*~ THE COSMOPOLITAN

Hyde Park
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Stunning 3BD/3BA in Jamaica Plain Near the Trains #2, holiday rental in Dedham

Stunning 3BD/3BA in Jamaica Plain Near the Trains #2

Jamaica Plain
3 bedrooms
5 bathrooms
Sleeps 6
Match: Sleeps
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Stunning 3BD/3BA in Jamaica Plain Near the Trains #1, holiday rental in Dedham

Stunning 3BD/3BA in Jamaica Plain Near the Trains #1

Jamaica Plain
3 bedrooms
5 bathrooms
Sleeps 6
Match: Sleeps
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Perfect location, beautiful settting, holiday rental in Dedham

Perfect location, beautiful settting

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Entire, Lovely 2b. Apt. 35 min to Boston, holiday rental in Dedham

Entire, Lovely 2b. Apt. 35 min to Boston

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Quiet Comfort in Boston - Large 2 Bed Condo, holiday rental in Dedham

Quiet Comfort in Boston - Large 2 Bed Condo

Roslindale, Bellevue
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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The Strathmore 15 w/AC | Queen Bed w/HdTV | One block to Greenline and short wal, holiday rental in Dedham

The Strathmore 15 w/AC | Queen Bed w/HdTV | One block to Greenline and short wal

Cleveland Circle, Brighton
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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The Strathmore 2 w/AC |  Huge 3BR  2BA Bilevel Apt w/En-Suite HdTV's | One block, holiday rental in Dedham

The Strathmore 2 w/AC | Huge 3BR 2BA Bilevel Apt w/En-Suite HdTV's | One block

Cleveland Circle, Brighton
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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The Strathmore 8 w/AC | 1BR 1BA w/HdTV | One block to the Greenline and short wa, holiday rental in Dedham

The Strathmore 8 w/AC | 1BR 1BA w/HdTV | One block to the Greenline and short wa

Cleveland Circle, Brighton
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Fully Furnished Boston Condominium w/ Front Porch, holiday rental in Dedham

Fully Furnished Boston Condominium w/ Front Porch

Cleveland Circle, Brighton
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Sunny, Fully Furnished & Newly Renovated 1Bed, Sleeps 4, Step to Transit, holiday rental in Dedham

Sunny, Fully Furnished & Newly Renovated 1Bed, Sleeps 4, Step to Transit

Cleveland Circle, Brighton
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Bright, Spacious, 1-Bedroom Apartment, Close To MBTA, BU, holiday rental in Dedham

Bright, Spacious, 1-Bedroom Apartment, Close To MBTA, BU

Cleveland Circle, Brighton
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Beautiful B&B Convenient to Boston, holiday rental in Dedham

Beautiful B&B Convenient to Boston

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Top-Floor Furnished Apartment with Natural Light, Centrally Located- Near MBTA, holiday rental in Dedham

Top-Floor Furnished Apartment with Natural Light, Centrally Located- Near MBTA

3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Spacious, Quiet Brookline One Bedroom, Near Transportation Longwood Medical, holiday rental in Dedham

Spacious, Quiet Brookline One Bedroom, Near Transportation Longwood Medical

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Renovated 2 Bed, Sleeps 6, in Boston Victorian Home. Close to BU, BC, Longwood, holiday rental in Dedham

Renovated 2 Bed, Sleeps 6, in Boston Victorian Home. Close to BU, BC, Longwood

Cleveland Circle, Brighton
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Renovated Brookline 1BED, Steps to MBTA, Shops & Restaurants, holiday rental in Dedham

Renovated Brookline 1BED, Steps to MBTA, Shops & Restaurants

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Renovated 3 bed,1.5 bath, close to MIT, Harvard, holiday rental in Dedham

Renovated 3 bed,1.5 bath, close to MIT, Harvard

Cleveland Circle, Brighton
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Brookline, Residential Neighborhood Close to City, Free Parking, Near Longwood M, holiday rental in Dedham

Brookline, Residential Neighborhood Close to City, Free Parking, Near Longwood M

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Spacious, 1-Bedroom Close to Longwood Medical, Jamaica Pond and Boston, holiday rental in Dedham

Spacious, 1-Bedroom Close to Longwood Medical, Jamaica Pond and Boston

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Heart of Brookline Village, 3rd Floor Furnished 2 Bed. Close to Longwood, Shops, holiday rental in Dedham

Heart of Brookline Village, 3rd Floor Furnished 2 Bed. Close to Longwood, Shops

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Sunny, spacious one bedroom, close to Longwood Medical, holiday rental in Dedham

Sunny, spacious one bedroom, close to Longwood Medical

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Sunny, Fully Furnished & Newly Renovated 1 Bed in Victorian Home, Sleeps 4, Step, holiday rental in Dedham

Sunny, Fully Furnished & Newly Renovated 1 Bed in Victorian Home, Sleeps 4, Step

Cleveland Circle, Brighton
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Gut Renovated 1-Bedroom in Brookline Village, Close to Longwood, Shops + MBTA, holiday rental in Dedham

Gut Renovated 1-Bedroom in Brookline Village, Close to Longwood, Shops + MBTA

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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NEW! Boston Apartment - Walk to Downtown Transit!, holiday rental in Dedham

NEW! Boston Apartment - Walk to Downtown Transit!

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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