Vacation rentals in Winchester, MA

112 available vacation rental offers

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Best Vacation rentals and Airbnb offers in Winchester, MA

Queen Bed - Boston - RM 2 - Winchester, MA

Queen Bed - Boston - RM 2

Homestay, Winchester

Queen Bed - Boston - RM 2 is a homestay in Winchester, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with…

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About Queen Bed - Boston - RM 2

Queen Bed - Boston - RM 2 is a homestay in Winchester, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, parking, paid parking, and ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,165.

From$109/night
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Queen Bed - Boston - RM 3 - Winchester, MA

Queen Bed - Boston - RM 3

Homestay, Winchester

Queen Bed - Boston - RM 3 is a homestay in Winchester, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with…

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About Queen Bed - Boston - RM 3

Queen Bed - Boston - RM 3 is a homestay in Winchester, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, parking, paid parking, and ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,166.

From$109/night
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Train to Boston! Cozy Apartment in Winchester - Winchester, MA

Train to Boston! Cozy Apartment in Winchester

Apartment, Winchester

Train to Boston! Cozy Apartment in Winchester is a apartment in Winchester, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Train to Boston! Cozy Apartment in Winchester

Train to Boston! Cozy Apartment in Winchester is a apartment in Winchester, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,020.

From$120/night
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Train to Boston! Cozy Apartment in Winchester - Winchester, MA

Train to Boston! Cozy Apartment in Winchester

Apartment, Winchester

Train to Boston! Cozy Apartment in Winchester is a apartment in Winchester, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Train to Boston! Cozy Apartment in Winchester

Train to Boston! Cozy Apartment in Winchester is a apartment in Winchester, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $904.

From$129/night
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Browse Vacation Rentals with a Pool in Winchester, MA

Add a pool to the search when you want an easy place to cool off between outings.

Global Luxury Suites East Boston - Winchester, MA

Global Luxury Suites East Boston

Apartment, Winchester

Global Luxury Suites East Boston is a apartment in Winchester, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Global Luxury Suites East Boston

Global Luxury Suites East Boston is a apartment in Winchester, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,032.

From$232/night
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Spacious vacation townhome unit with a pool - Winchester, MA

Spacious vacation townhome unit with a pool

Holiday Home, Winchester

Spacious vacation townhome unit with a pool is a holiday home in Winchester, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Spacious vacation townhome unit with a pool

Spacious vacation townhome unit with a pool is a holiday home in Winchester, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,862.

From$409/night
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Luxe Everett 2BR–2BA w/ Pool, Gym & Parking - Winchester, MA

Luxe Everett 2BR–2BA w/ Pool, Gym & Parking

Apartment, Winchester

Luxe Everett 2BR–2BA w/ Pool, Gym & Parking is a apartment in Winchester, with pet-friendly space, pool access, and parking. This stay gives travelers a comfortable base for exploring the…

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About Luxe Everett 2BR–2BA w/ Pool, Gym & Parking

Luxe Everett 2BR–2BA w/ Pool, Gym & Parking is a apartment in Winchester, with pet-friendly space, pool access, and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,940.

From$420/night
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\"1855 Grand Mansion In Historical Charlestown\" 6 bed 4.5 bath Renovated 2021 - Winchester, MA

\"1855 Grand Mansion In Historical Charlestown\" 6 bed 4.5 bath Renovated 2021

Holiday Home, Winchester

\"1855 Grand Mansion In Historical Charlestown\" 6 bed 4.5 bath Renovated 2021 is a holiday home in Winchester, with pet-friendly space and pool access. This stay gives travelers a…

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About \"1855 Grand Mansion In Historical Charlestown\" 6 bed 4.5 bath Renovated 2021

\"1855 Grand Mansion In Historical Charlestown\" 6 bed 4.5 bath Renovated 2021 is a holiday home in Winchester, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, hot tub, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $20,145.

From$2,878/night
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Best Winchester, MA vacation rentals with parking

Find vacation rentals that make arriving by car easier.

154 Quite & Bright & Spacious Apt in Brighton - Winchester, MA

154 Quite & Bright & Spacious Apt in Brighton

Homestay, Winchester

154 Quite & Bright & Spacious Apt in Brighton is a homestay in Winchester, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About 154 Quite & Bright & Spacious Apt in Brighton

154 Quite & Bright & Spacious Apt in Brighton is a homestay in Winchester, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: parking, free parking, lang::en, can speak english, and non smoking::all.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $765.

From$92/night
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Charming 1BR apt -close to public transit -has parking -30min drive to BOS/Salem - Winchester, MA

Charming 1BR apt -close to public transit -has parking -30min drive to BOS/Salem

Apartment, Winchester

Charming 1BR apt -close to public transit -has parking -30min drive to BOS/Salem is a apartment in Winchester, with parking, kitchen access, and room for a group. This stay gives travelers…

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About Charming 1BR apt -close to public transit -has parking -30min drive to BOS/Salem

Charming 1BR apt -close to public transit -has parking -30min drive to BOS/Salem is a apartment in Winchester, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, gym, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,674.

From$239/night
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5 Mi to TD Garden: Quiet Medford Getaway! - Winchester, MA

5 Mi to TD Garden: Quiet Medford Getaway!

Holiday Home, Winchester

5 Mi to TD Garden: Quiet Medford Getaway! is a holiday home in Winchester, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring…

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About 5 Mi to TD Garden: Quiet Medford Getaway!

5 Mi to TD Garden: Quiet Medford Getaway! is a holiday home in Winchester, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,338.

From$334/night
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Modern Three Bedroom Condo - Near Boston - Winchester, MA

Modern Three Bedroom Condo - Near Boston

Condo, Winchester

Modern Three Bedroom Condo - Near Boston is a condo in Winchester, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area,…

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About Modern Three Bedroom Condo - Near Boston

Modern Three Bedroom Condo - Near Boston is a condo in Winchester, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,507.

From$358/night
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Best Pet-Friendly Vacation Rentals in Winchester, MA

Bring your pet along with stays that welcome four-legged travelers.

Global Luxury Suites East Boston - Winchester, MA

Global Luxury Suites East Boston

Apartment, Winchester

Global Luxury Suites East Boston is a apartment in Winchester, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

Read more

About Global Luxury Suites East Boston

Global Luxury Suites East Boston is a apartment in Winchester, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,032.

From$232/night
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Luxury Apartment with Gym, Steps From Commuter Rail #2009 - Winchester, MA

Luxury Apartment with Gym, Steps From Commuter Rail #2009

Apartment, Winchester

Luxury Apartment with Gym, Steps From Commuter Rail #2009 is a apartment in Winchester, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area,…

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About Luxury Apartment with Gym, Steps From Commuter Rail #2009

Luxury Apartment with Gym, Steps From Commuter Rail #2009 is a apartment in Winchester, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,177.

From$247/night
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Luxury apartment with gym, steps from commuter rail #4011 - Winchester, MA

Luxury apartment with gym, steps from commuter rail #4011

Apartment, Winchester

Luxury apartment with gym, steps from commuter rail #4011 is a apartment in Winchester, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area,…

Read more

About Luxury apartment with gym, steps from commuter rail #4011

Luxury apartment with gym, steps from commuter rail #4011 is a apartment in Winchester, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,269.

From$257/night
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Delightful New England Townhome - Winchester, MA

Delightful New England Townhome

Condo, Winchester

Delightful New England Townhome is a condo in Winchester, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Delightful New England Townhome

Delightful New England Townhome is a condo in Winchester, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,363.

From$338/night
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Best Winchester, MA vacation rentals with a kitchen

Compare stays with kitchen access for longer trips and easier meals.

5BR 2BH Bright & Spacious Apt in Brighton - Winchester, MA

5BR 2BH Bright & Spacious Apt in Brighton

Apartment, Winchester

5BR 2BH Bright & Spacious Apt in Brighton is a apartment in Winchester, with kitchen access and room for a group. This stay gives travelers a comfortable base for exploring the area,…

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About 5BR 2BH Bright & Spacious Apt in Brighton

5BR 2BH Bright & Spacious Apt in Brighton is a apartment in Winchester, with kitchen access and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, kitchen, with kitchen, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,337.

From$118/night
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5BR 2BH Bright & Spacious Apt in Brighton - Winchester, MA

5BR 2BH Bright & Spacious Apt in Brighton

Apartment, Winchester

5BR 2BH Bright & Spacious Apt in Brighton is a apartment in Winchester, with kitchen access and room for a group. This stay gives travelers a comfortable base for exploring the area,…

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About 5BR 2BH Bright & Spacious Apt in Brighton

5BR 2BH Bright & Spacious Apt in Brighton is a apartment in Winchester, with kitchen access and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, kitchen, with kitchen, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,337.

From$118/night
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Cozy Up in 5BR Apt Near Charming Oak Square - Winchester, MA

Cozy Up in 5BR Apt Near Charming Oak Square

Apartment, Winchester

Cozy Up in 5BR Apt Near Charming Oak Square is a apartment in Winchester, with kitchen access and room for a group. This stay gives travelers a comfortable base for exploring the area,…

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About Cozy Up in 5BR Apt Near Charming Oak Square

Cozy Up in 5BR Apt Near Charming Oak Square is a apartment in Winchester, with kitchen access and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, kitchen, with kitchen, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,406.

From$125/night
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Enjoyable 2-bedroom apartment near airport with washer and dryer - Winchester, MA

Enjoyable 2-bedroom apartment near airport with washer and dryer

Apartment, Winchester

Enjoyable 2-bedroom apartment near airport with washer and dryer is a apartment in Winchester, with kitchen access and room for a group. This stay gives travelers a comfortable base for…

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About Enjoyable 2-bedroom apartment near airport with washer and dryer

Enjoyable 2-bedroom apartment near airport with washer and dryer is a apartment in Winchester, with kitchen access and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,708.

From$244/night
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Our Favorite Family-Friendly Vacation Rentals in Winchester, MA

Plan a trip with stays that give families more room to spread out.

1000ft² 2BR with Free Parking, King Bed, WFH Setup, Near Harvard, MIT, & Tufts - Winchester, MA

1000ft² 2BR with Free Parking, King Bed, WFH Setup, Near Harvard, MIT, & Tufts

Holiday Home, Winchester

1000ft² 2BR with Free Parking, King Bed, WFH Setup, Near Harvard, MIT, & Tufts is a holiday home in Winchester, with parking, kitchen access, and room for a group. This stay gives travelers…

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About 1000ft² 2BR with Free Parking, King Bed, WFH Setup, Near Harvard, MIT, & Tufts

1000ft² 2BR with Free Parking, King Bed, WFH Setup, Near Harvard, MIT, & Tufts is a holiday home in Winchester, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, kids friendly, and kids friendly videos or books.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,088.

From$298/night
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5 Mi to TD Garden: Quiet Medford Getaway! - Winchester, MA

5 Mi to TD Garden: Quiet Medford Getaway!

Cottage, Winchester

5 Mi to TD Garden: Quiet Medford Getaway! is a cottage in Winchester, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the…

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About 5 Mi to TD Garden: Quiet Medford Getaway!

5 Mi to TD Garden: Quiet Medford Getaway! is a cottage in Winchester, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,574.

From$303/night
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Bright 2BR by Boston Waterfront - Winchester, MA

Bright 2BR by Boston Waterfront

Apartment, Winchester

Bright 2BR by Boston Waterfront is a apartment in Winchester, with easy beach access, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the…

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About Bright 2BR by Boston Waterfront

Bright 2BR by Boston Waterfront is a apartment in Winchester, with easy beach access, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, kids friendly, and kids friendly videos or books.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,176.

From$311/night
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The Niche: A cozy perfection! Newly Renovated Family Friendly! Near Boston - Winchester, MA

The Niche: A cozy perfection! Newly Renovated Family Friendly! Near Boston

Holiday Home, Winchester

The Niche: A cozy perfection! Newly Renovated Family Friendly! Near Boston is a holiday home in Winchester, with kitchen access and room for a group. This stay gives travelers a comfortable…

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About The Niche: A cozy perfection! Newly Renovated Family Friendly! Near Boston

The Niche: A cozy perfection! Newly Renovated Family Friendly! Near Boston is a holiday home in Winchester, with kitchen access and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, kitchen, with kitchen, kids friendly, and kids friendly videos or books.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,827.

From$404/night
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