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Wellesley Holiday Rentals

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48 rentals in Wellesley.
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Heart of Wellesley.prvt ent,sgl and full bed,prvt bath,mcrwave,fridge,air con, holiday rental in Wellesley
Heart of Wellesley.prvt ent,sgl and full bed,prvt bath,mcrwave,fridge,air con, holiday rental in Wellesley
Heart of Wellesley.prvt ent,sgl and full bed,prvt bath,mcrwave,fridge,air con, holiday rental in Wellesley

Heart of Wellesley.prvt ent,sgl and full bed,prvt bath,mcrwave,fridge,air con

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Spacious Private Entrance Master Bedroom/Bath, holiday rental in Wellesley
Spacious Private Entrance Master Bedroom/Bath, holiday rental in Wellesley
Spacious Private Entrance Master Bedroom/Bath, holiday rental in Wellesley

Spacious Private Entrance Master Bedroom/Bath

Private Room
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Charming 3BR Colonial Home in Wellesley, holiday rental in Wellesley
Charming 3BR Colonial Home in Wellesley, holiday rental in Wellesley
Charming 3BR Colonial Home in Wellesley, holiday rental in Wellesley

Charming 3BR Colonial Home in Wellesley

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Cozy 4 Bedroom Apartment near Boston, holiday rental in Wellesley
Cozy 4 Bedroom Apartment near Boston, holiday rental in Wellesley
Cozy 4 Bedroom Apartment near Boston, holiday rental in Wellesley

Cozy 4 Bedroom Apartment near Boston

Condo/Apartment
4 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Gorgeous super clean newly renovated modern colonial, holiday rental in Wellesley
Gorgeous super clean newly renovated modern colonial, holiday rental in Wellesley
Gorgeous super clean newly renovated modern colonial, holiday rental in Wellesley

Gorgeous super clean newly renovated modern colonial

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Furnished Studio + Private Patio + parking in Wellesley Square, holiday rental in Wellesley
Furnished Studio + Private Patio + parking in Wellesley Square, holiday rental in Wellesley
Furnished Studio + Private Patio + parking in Wellesley Square, holiday rental in Wellesley

Furnished Studio + Private Patio + parking in Wellesley Square

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Quiet Home/Office - Best Location - Walk to Train/Colleges/Grocery, holiday rental in Wellesley
Quiet Home/Office - Best Location - Walk to Train/Colleges/Grocery, holiday rental in Wellesley
Quiet Home/Office - Best Location - Walk to Train/Colleges/Grocery, holiday rental in Wellesley

Quiet Home/Office - Best Location - Walk to Train/Colleges/Grocery

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Near All Colleges Quiet home /Office in Central Wellesley, holiday rental in Wellesley
Near All Colleges Quiet home /Office in Central Wellesley, holiday rental in Wellesley
Near All Colleges Quiet home /Office in Central Wellesley, holiday rental in Wellesley

Near All Colleges Quiet home /Office in Central Wellesley

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Extend your rest in the Wellesley Square's best, holiday rental in Wellesley
Extend your rest in the Wellesley Square's best, holiday rental in Wellesley
Extend your rest in the Wellesley Square's best, holiday rental in Wellesley

Extend your rest in the Wellesley Square's best

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Beautiful Carriage House in exclusive Cliff Estates area of Wellesley, MA, holiday rental in Wellesley
Beautiful Carriage House in exclusive Cliff Estates area of Wellesley, MA, holiday rental in Wellesley
Beautiful Carriage House in exclusive Cliff Estates area of Wellesley, MA, holiday rental in Wellesley

Beautiful Carriage House in exclusive Cliff Estates area of Wellesley, MA

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Contemporary Style And Comfort Convenient To Boston And Route 128, holiday rental in Wellesley
Contemporary Style And Comfort Convenient To Boston And Route 128, holiday rental in Wellesley
Contemporary Style And Comfort Convenient To Boston And Route 128, holiday rental in Wellesley

Contemporary Style And Comfort Convenient To Boston And Route 128

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Harvard House  Boutique Conference Center and Guest Quarters, holiday rental in Wellesley
Harvard House  Boutique Conference Center and Guest Quarters, holiday rental in Wellesley
Harvard House  Boutique Conference Center and Guest Quarters, holiday rental in Wellesley

Harvard House Boutique Conference Center and Guest Quarters

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Beautiful 6000 sq ft home 20 min to Boston, holiday rental in Wellesley
Beautiful 6000 sq ft home 20 min to Boston, holiday rental in Wellesley
Beautiful 6000 sq ft home 20 min to Boston, holiday rental in Wellesley

Beautiful 6000 sq ft home 20 min to Boston

Holiday Rental House
6 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
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2 BR, 1 Bath, Sleeps 4+, Furnished and spacious apt. in quiet Boston suburb, holiday rental in Wellesley
2 BR, 1 Bath, Sleeps 4+, Furnished and spacious apt. in quiet Boston suburb, holiday rental in Wellesley
2 BR, 1 Bath, Sleeps 4+, Furnished and spacious apt. in quiet Boston suburb, holiday rental in Wellesley

2 BR, 1 Bath, Sleeps 4+, Furnished and spacious apt. in quiet Boston suburb

Condo/Apartment in West Roxbury, Brook Farm
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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Relaxing Cottage on the Woods!, holiday rental in Wellesley
Relaxing Cottage on the Woods!, holiday rental in Wellesley
Relaxing Cottage on the Woods!, holiday rental in Wellesley

Relaxing Cottage on the Woods!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Grand 6 Bedroom Home Near Boston Sleeps 14+ with free parking, holiday rental in Wellesley
Grand 6 Bedroom Home Near Boston Sleeps 14+ with free parking, holiday rental in Wellesley
Grand 6 Bedroom Home Near Boston Sleeps 14+ with free parking, holiday rental in Wellesley

Grand 6 Bedroom Home Near Boston Sleeps 14+ with free parking

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 14
Match: Sleeps
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Private 4 BR Condo Close to Boston, holiday rental in Wellesley
Private 4 BR Condo Close to Boston, holiday rental in Wellesley
Private 4 BR Condo Close to Boston, holiday rental in Wellesley

Private 4 BR Condo Close to Boston

Condo/Apartment
4 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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1 bedroom/1 private bath in our shared home, holiday rental in Wellesley
1 bedroom/1 private bath in our shared home, holiday rental in Wellesley
1 bedroom/1 private bath in our shared home, holiday rental in Wellesley

1 bedroom/1 private bath in our shared home

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Feel at Home in spacious 3B-2.5Ba -Mall/MBTA/Park, holiday rental in Wellesley
Feel at Home in spacious 3B-2.5Ba -Mall/MBTA/Park, holiday rental in Wellesley
Feel at Home in spacious 3B-2.5Ba -Mall/MBTA/Park, holiday rental in Wellesley

Feel at Home in spacious 3B-2.5Ba -Mall/MBTA/Park

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Huge 10 Bedroom House on Boston City Line. Sleeps 27. Free parking for 4 cars, holiday rental in Wellesley
Huge 10 Bedroom House on Boston City Line. Sleeps 27. Free parking for 4 cars, holiday rental in Wellesley
Huge 10 Bedroom House on Boston City Line. Sleeps 27. Free parking for 4 cars, holiday rental in Wellesley

Huge 10 Bedroom House on Boston City Line. Sleeps 27. Free parking for 4 cars

Holiday Rental House
6 bedrooms
4 bathrooms
Sleeps 24
Match: Sleeps
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Best of Boston Spacious Modern Comfy Porch Jacuzzi Near Buses BC BU Downtown NE, holiday rental in Wellesley
Best of Boston Spacious Modern Comfy Porch Jacuzzi Near Buses BC BU Downtown NE, holiday rental in Wellesley
Best of Boston Spacious Modern Comfy Porch Jacuzzi Near Buses BC BU Downtown NE, holiday rental in Wellesley

Best of Boston Spacious Modern Comfy Porch Jacuzzi Near Buses BC BU Downtown NE

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful Apartment-5 Beds-Parking-Super Clean!

Condo/Apartment in West Roxbury
2 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Boston Condominium, close to public T, holiday rental in Wellesley
Boston Condominium, close to public T, holiday rental in Wellesley
Boston Condominium, close to public T, holiday rental in Wellesley

Boston Condominium, close to public T

Condo/Apartment in Cleveland Circle, Brighton
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Perfect location, beautiful settting, holiday rental in Wellesley
Perfect location, beautiful settting, holiday rental in Wellesley
Perfect location, beautiful settting, holiday rental in Wellesley

Perfect location, beautiful settting

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Bright, Spacious 1 Bedroom Steps to MBTA, holiday rental in Wellesley
Bright, Spacious 1 Bedroom Steps to MBTA, holiday rental in Wellesley
Bright, Spacious 1 Bedroom Steps to MBTA, holiday rental in Wellesley

Bright, Spacious 1 Bedroom Steps to MBTA

Condo/Apartment in Cleveland Circle, Brighton
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Perfect Getaway in Historic NewtonHighland (CDC Safe), holiday rental in Wellesley
Perfect Getaway in Historic NewtonHighland (CDC Safe), holiday rental in Wellesley
Perfect Getaway in Historic NewtonHighland (CDC Safe), holiday rental in Wellesley

Perfect Getaway in Historic NewtonHighland (CDC Safe)

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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Close to Attractions. Cozy Unit for 4.Free Parking, holiday rental in Wellesley
Close to Attractions. Cozy Unit for 4.Free Parking, holiday rental in Wellesley
Close to Attractions. Cozy Unit for 4.Free Parking, holiday rental in Wellesley

Close to Attractions. Cozy Unit for 4.Free Parking

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Best of Boston Spacious Modern 3br Deck Bathtub BC BU Comfy Bathtub public T Bus, holiday rental in Wellesley
Best of Boston Spacious Modern 3br Deck Bathtub BC BU Comfy Bathtub public T Bus, holiday rental in Wellesley
Best of Boston Spacious Modern 3br Deck Bathtub BC BU Comfy Bathtub public T Bus, holiday rental in Wellesley

Best of Boston Spacious Modern 3br Deck Bathtub BC BU Comfy Bathtub public T Bus

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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★ Backyard ★ Walk & Close Everywhere ★ 1BR ★ Comfy ★ Cozy ★ Entire Apartment, holiday rental in Wellesley
★ Backyard ★ Walk & Close Everywhere ★ 1BR ★ Comfy ★ Cozy ★ Entire Apartment, holiday rental in Wellesley
★ Backyard ★ Walk & Close Everywhere ★ 1BR ★ Comfy ★ Cozy ★ Entire Apartment, holiday rental in Wellesley

★ Backyard ★ Walk & Close Everywhere ★ 1BR ★ Comfy ★ Cozy ★ Entire Apartment

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Unit1 GR8 LOCATION mins to Longwood Medical Area, BC, BU, HarvMedSchool SPACIOUS, holiday rental in Wellesley
Unit1 GR8 LOCATION mins to Longwood Medical Area, BC, BU, HarvMedSchool SPACIOUS, holiday rental in Wellesley
Unit1 GR8 LOCATION mins to Longwood Medical Area, BC, BU, HarvMedSchool SPACIOUS, holiday rental in Wellesley

Unit1 GR8 LOCATION mins to Longwood Medical Area, BC, BU, HarvMedSchool SPACIOUS

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Luxury treat Tuscany style villa just few miles from downtown Boston., holiday rental in Wellesley
Luxury treat Tuscany style villa just few miles from downtown Boston., holiday rental in Wellesley
Luxury treat Tuscany style villa just few miles from downtown Boston., holiday rental in Wellesley

Luxury treat Tuscany style villa just few miles from downtown Boston.

Holiday Rental House
6 bedrooms
8 bathrooms
Sleeps 10
Match: Sleeps
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Great Find! Two Comfy Units, Close to Attractions, holiday rental in Wellesley
Great Find! Two Comfy Units, Close to Attractions, holiday rental in Wellesley
Great Find! Two Comfy Units, Close to Attractions, holiday rental in Wellesley

Great Find! Two Comfy Units, Close to Attractions

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Value Deal Unit, Close to Attractions, Free Parking, holiday rental in Wellesley
Value Deal Unit, Close to Attractions, Free Parking, holiday rental in Wellesley
Value Deal Unit, Close to Attractions, Free Parking, holiday rental in Wellesley

Value Deal Unit, Close to Attractions, Free Parking

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Entire 3br Sunny Beautiful Large w/parking WiFi cable near BC Boston Cambridge ♫, holiday rental in Wellesley
Entire 3br Sunny Beautiful Large w/parking WiFi cable near BC Boston Cambridge ♫, holiday rental in Wellesley
Entire 3br Sunny Beautiful Large w/parking WiFi cable near BC Boston Cambridge ♫, holiday rental in Wellesley

Entire 3br Sunny Beautiful Large w/parking WiFi cable near BC Boston Cambridge ♫

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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5 star accommodation in exclusive estate location, holiday rental in Wellesley
5 star accommodation in exclusive estate location, holiday rental in Wellesley
5 star accommodation in exclusive estate location, holiday rental in Wellesley

5 star accommodation in exclusive estate location

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Apartment in Victorian House, holiday rental in Wellesley
Apartment in Victorian House, holiday rental in Wellesley
Apartment in Victorian House, holiday rental in Wellesley

Apartment in Victorian House

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Sunny Huge Modern 3br w/parking WiFi near BC BU Boston Cambridge MIT fireplace ✈, holiday rental in Wellesley
Sunny Huge Modern 3br w/parking WiFi near BC BU Boston Cambridge MIT fireplace ✈, holiday rental in Wellesley
Sunny Huge Modern 3br w/parking WiFi near BC BU Boston Cambridge MIT fireplace ✈, holiday rental in Wellesley

Sunny Huge Modern 3br w/parking WiFi near BC BU Boston Cambridge MIT fireplace ✈

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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109S15  The Strathmore 15 w/AC | Queen Bed w/HdTV | One block to Greenline and s, holiday rental in Wellesley
109S15  The Strathmore 15 w/AC | Queen Bed w/HdTV | One block to Greenline and s, holiday rental in Wellesley
109S15  The Strathmore 15 w/AC | Queen Bed w/HdTV | One block to Greenline and s, holiday rental in Wellesley

109S15 The Strathmore 15 w/AC | Queen Bed w/HdTV | One block to Greenline and s

Condo/Apartment in Cleveland Circle, Brighton
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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25A2  The Alameda 2 w/AC | 2BR 1BA w/En-Suite HdTV's | Short walk to train, shop, holiday rental in Wellesley
25A2  The Alameda 2 w/AC | 2BR 1BA w/En-Suite HdTV's | Short walk to train, shop, holiday rental in Wellesley
25A2  The Alameda 2 w/AC | 2BR 1BA w/En-Suite HdTV's | Short walk to train, shop, holiday rental in Wellesley

25A2 The Alameda 2 w/AC | 2BR 1BA w/En-Suite HdTV's | Short walk to train, shop

Condo/Apartment in West Roxbury, Brook Farm
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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109S2  The Strathmore 2 w/AC |  Huge 3BR  2BA Bilevel Apt w/En-Suite HdTV's | On, holiday rental in Wellesley
109S2  The Strathmore 2 w/AC |  Huge 3BR  2BA Bilevel Apt w/En-Suite HdTV's | On, holiday rental in Wellesley
109S2  The Strathmore 2 w/AC |  Huge 3BR  2BA Bilevel Apt w/En-Suite HdTV's | On, holiday rental in Wellesley

109S2 The Strathmore 2 w/AC | Huge 3BR 2BA Bilevel Apt w/En-Suite HdTV's | On

Condo/Apartment in Cleveland Circle, Brighton
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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109S8  The Strathmore 8 w/AC | 1BR 1BA w/HdTV | One block to the Greenline and s, holiday rental in Wellesley
109S8  The Strathmore 8 w/AC | 1BR 1BA w/HdTV | One block to the Greenline and s, holiday rental in Wellesley
109S8  The Strathmore 8 w/AC | 1BR 1BA w/HdTV | One block to the Greenline and s, holiday rental in Wellesley

109S8 The Strathmore 8 w/AC | 1BR 1BA w/HdTV | One block to the Greenline and s

Condo/Apartment in Cleveland Circle, Brighton
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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18 bedroom Estate &  Adventure Compound, holiday rental in Wellesley
18 bedroom Estate &  Adventure Compound, holiday rental in Wellesley
18 bedroom Estate &  Adventure Compound, holiday rental in Wellesley

18 bedroom Estate & Adventure Compound

Holiday Rental House
12 bedrooms
11 bathrooms
Sleeps 25
Match: Sleeps
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Renovated, Chic 3 Bed,1.5 Bath-Harvard, Kendal, MIT, Harvard, holiday rental in Wellesley
Renovated, Chic 3 Bed,1.5 Bath-Harvard, Kendal, MIT, Harvard, holiday rental in Wellesley
Renovated, Chic 3 Bed,1.5 Bath-Harvard, Kendal, MIT, Harvard, holiday rental in Wellesley

Renovated, Chic 3 Bed,1.5 Bath-Harvard, Kendal, MIT, Harvard

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Charming Modern Spacious 3 bedroom House Romantic Getaway near BC Airport Boston, holiday rental in Wellesley
Charming Modern Spacious 3 bedroom House Romantic Getaway near BC Airport Boston, holiday rental in Wellesley
Charming Modern Spacious 3 bedroom House Romantic Getaway near BC Airport Boston, holiday rental in Wellesley

Charming Modern Spacious 3 bedroom House Romantic Getaway near BC Airport Boston

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Framingham condo unit 2, holiday rental in Wellesley
Framingham condo unit 2, holiday rental in Wellesley
Framingham condo unit 2, holiday rental in Wellesley

Framingham condo unit 2

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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109S14  The Strathmore 14 w/AC | Queen Bed w/HdTV | One block to Greenline and w, holiday rental in Wellesley
109S14  The Strathmore 14 w/AC | Queen Bed w/HdTV | One block to Greenline and w, holiday rental in Wellesley
109S14  The Strathmore 14 w/AC | Queen Bed w/HdTV | One block to Greenline and w, holiday rental in Wellesley

109S14 The Strathmore 14 w/AC | Queen Bed w/HdTV | One block to Greenline and w

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Newly remodeled luxury family home for your extended stay., holiday rental in Wellesley
Newly remodeled luxury family home for your extended stay., holiday rental in Wellesley
Newly remodeled luxury family home for your extended stay., holiday rental in Wellesley

Newly remodeled luxury family home for your extended stay.

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 7
Match: Sleeps
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One mile from US OPEN Country Club, holiday rental in Wellesley
One mile from US OPEN Country Club, holiday rental in Wellesley
One mile from US OPEN Country Club, holiday rental in Wellesley

One mile from US OPEN Country Club

Holiday Rental House
0 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Colonial Home , holiday rental in Wellesley
Colonial Home , holiday rental in Wellesley
Colonial Home , holiday rental in Wellesley

Colonial Home

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 1
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Quiet Apt. Ground Flr. Great place, holiday rental in Wellesley
Quiet Apt. Ground Flr. Great place, holiday rental in Wellesley
Quiet Apt. Ground Flr. Great place, holiday rental in Wellesley

Quiet Apt. Ground Flr. Great place

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 1
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