Vacation rentals in Pittsfield, VT

Best vacation rentals and Airbnb offers in Pittsfield, VT

Cozy Studio at Killington Center: Close to it all with pool, bus and discounted ski rentals. 441

Condo, Pittsfield

Cozy Studio at Killington Center: Close to it all with pool, bus and discounted ski rentals. 441 is a condo in Pittsfield, with pool access and parking. This stay gives travelers a…

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About Cozy Studio at Killington Center: Close to it all with pool, bus and discounted ski rentals. 441

Cozy Studio at Killington Center: Close to it all with pool, bus and discounted ski rentals. 441 is a condo in Pittsfield, with 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, parking, free parking, and ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $687.

From$98/night

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The Suites at Killington Center

Condo, Pittsfield

The Suites at Killington Center is a condo in Pittsfield, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

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About The Suites at Killington Center

The Suites at Killington Center is a condo in Pittsfield, 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: pool, hot tub, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $983.

From$99/night

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Sunrise - Timberline-L5

Apartment, Pittsfield

Sunrise - Timberline-L5 is a apartment in Pittsfield, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with…

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About Sunrise - Timberline-L5

Sunrise - Timberline-L5 is a apartment in Pittsfield, with 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: pool, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,168.

From$104/night

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Skiers Suite Annex: Renovated Studio on the Bus Route. Discounted Ski Rentals.

Apartment, Pittsfield

Skiers Suite Annex: Renovated Studio on the Bus Route. Discounted Ski Rentals. is a apartment in Pittsfield, with pool access and parking. This stay gives travelers a comfortable base for…

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About Skiers Suite Annex: Renovated Studio on the Bus Route. Discounted Ski Rentals.

Skiers Suite Annex: Renovated Studio on the Bus Route. Discounted Ski Rentals. is a apartment in Pittsfield, with 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, free wifi, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $742.

From$106/night

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Vacation rentals with a pool in Pittsfield, VT

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

Swirl Suite Annex: Studio w/ Kitchenette and Workspace. Discounted Ski Rentals.

Condo, Pittsfield

Swirl Suite Annex: Studio w/ Kitchenette and Workspace. Discounted Ski Rentals. is a condo in Pittsfield, with pool access, parking, and kitchen access. This stay gives travelers a…

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About Swirl Suite Annex: Studio w/ Kitchenette and Workspace. Discounted Ski Rentals.

Swirl Suite Annex: Studio w/ Kitchenette and Workspace. Discounted Ski Rentals. is a condo in Pittsfield, with pool access, 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, pool, parking, free parking, and ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $802.

From$115/night

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Killington Studio: Great Location! Comfy. 431

Condo, Pittsfield

Killington Studio: Great Location! Comfy. 431 is a condo in Pittsfield, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area,…

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About Killington Studio: Great Location! Comfy. 431

Killington Studio: Great Location! Comfy. 431 is a condo in Pittsfield, 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 $816.

From$117/night

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The Swell Annex: Studio w/ Kitchenette Close to Mtn 641

Condo, Pittsfield

The Swell Annex: Studio w/ Kitchenette Close to Mtn 641 is a condo in Pittsfield, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring…

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About The Swell Annex: Studio w/ Kitchenette Close to Mtn 641

The Swell Annex: Studio w/ Kitchenette Close to Mtn 641 is a condo in Pittsfield, with pool access, 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, pool, free wifi, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $848.

From$121/night

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Studio with two queen beds renovated on bus route close to all

Condo, Pittsfield

Studio with two queen beds renovated on bus route close to all is a condo in Pittsfield, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Studio with two queen beds renovated on bus route close to all

Studio with two queen beds renovated on bus route close to all is a condo in Pittsfield, with 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: pool, ac, air conditioning, and tv.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $921.

From$132/night

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Vacation rentals with parking in Pittsfield, VT

Find vacation rentals that make arriving by car easier.

Pico C103

Holiday Home, Pittsfield

Pico C103 is a holiday home in Pittsfield, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or…

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About Pico C103

Pico C103 is a holiday home in Pittsfield, 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 wifi, gym, parking, and paid parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,369.

From$129/night

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Pico D305

Holiday Home, Pittsfield

Pico D305 is a holiday home in Pittsfield, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or…

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About Pico D305

Pico D305 is a holiday home in Pittsfield, 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 wifi, gym, parking, and paid parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,363.

From$129/night

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Killington Center 632: a spacious 2RM/2BA condo in the heart of Killington. Discounted ski rentals.

Condo, Pittsfield

Killington Center 632: a spacious 2RM/2BA condo in the heart of Killington. Discounted ski rentals. is a condo in Pittsfield, with pool access, parking, and kitchen access. This stay gives…

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About Killington Center 632: a spacious 2RM/2BA condo in the heart of Killington. Discounted ski rentals.

Killington Center 632: a spacious 2RM/2BA condo in the heart of Killington. Discounted ski rentals. is a condo in Pittsfield, with pool access, 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, pool, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,035.

From$148/night

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Killington Center 531

Apartment, Pittsfield

Killington Center 531 is a apartment in Pittsfield, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Killington Center 531

Killington Center 531 is a apartment in Pittsfield, 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 $1,273.

From$150/night

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Pet-friendly vacation rentals in Pittsfield, VT

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

Killington Studio: Location! Location! 323

Condo, Pittsfield

Killington Studio: Location! Location! 323 is a condo in Pittsfield, with pool access and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Killington Studio: Location! Location! 323

Killington Studio: Location! Location! 323 is a condo in Pittsfield, with 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, free wifi, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $788.

From$113/night

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Bob's Sled Lodge – 2BR Killington Retreat Near Slopes & Trails

Holiday Home, Pittsfield

Bob's Sled Lodge – 2BR Killington Retreat Near Slopes & Trails is a holiday home in Pittsfield, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a…

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About Bob's Sled Lodge – 2BR Killington Retreat Near Slopes & Trails

Bob's Sled Lodge – 2BR Killington Retreat Near Slopes & Trails is a holiday home in Pittsfield, with pet-friendly space, 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, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,656.

From$237/night

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Wonderful One bedroom condo located in Highridge Condominiums J6

Holiday Home, Pittsfield

Wonderful One bedroom condo located in Highridge Condominiums J6 is a holiday home in Pittsfield, with pool access and room for a group. This stay gives travelers a comfortable base for…

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About Wonderful One bedroom condo located in Highridge Condominiums J6

Wonderful One bedroom condo located in Highridge Condominiums J6 is a holiday home in Pittsfield, with pool 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: pool, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,229.

From$238/night

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Wonderful condo located near the pool and hot tub Highridge J6

Condo, Pittsfield

Wonderful condo located near the pool and hot tub Highridge J6 is a condo in Pittsfield, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Wonderful condo located near the pool and hot tub Highridge J6

Wonderful condo located near the pool and hot tub Highridge J6 is a condo in Pittsfield, with 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: pool, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,028.

From$290/night

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Vacation rentals with a kitchen in Pittsfield, VT

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

Charming Killington Center Studio Condo on the Bus Route. Discounted Ski Rentals. Pool.

Condo, Pittsfield

Charming Killington Center Studio Condo on the Bus Route. Discounted Ski Rentals. Pool. is a condo in Pittsfield, with pool access and kitchen access. This stay gives travelers a…

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About Charming Killington Center Studio Condo on the Bus Route. Discounted Ski Rentals. Pool.

Charming Killington Center Studio Condo on the Bus Route. Discounted Ski Rentals. Pool. is a condo in Pittsfield, 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 $937.

From$134/night

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Jack S`Bearo- AC, Pool, Mountain Views, Hiking, Gym

Apartment, Pittsfield

Jack S`Bearo- AC, Pool, Mountain Views, Hiking, Gym is a apartment in Pittsfield, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Jack S`Bearo- AC, Pool, Mountain Views, Hiking, Gym

Jack S`Bearo- AC, Pool, Mountain Views, Hiking, Gym is a apartment in Pittsfield, 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: pool, kitchen, with kitchen, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $942.

From$135/night

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Sweet Suite! Modern, Pool, 2RM, 2BA, Ski Resort 532

Condo, Pittsfield

Sweet Suite! Modern, Pool, 2RM, 2BA, Ski Resort 532 is a condo in Pittsfield, with pet-friendly space, pool access, and kitchen access. This stay gives travelers a comfortable base for…

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About Sweet Suite! Modern, Pool, 2RM, 2BA, Ski Resort 532

Sweet Suite! Modern, Pool, 2RM, 2BA, Ski Resort 532 is a condo in Pittsfield, with pet-friendly space, 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, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $987.

From$141/night

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Hotel Style Condo Promising a Comfortable and Convenient Retreat Right in the Heart of Vermont ski Country

Apartment, Pittsfield

Hotel Style Condo Promising a Comfortable and Convenient Retreat Right in the Heart of Vermont ski Country is a apartment in Pittsfield, with kitchen access and a quieter setting. This stay…

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About Hotel Style Condo Promising a Comfortable and Convenient Retreat Right in the Heart of Vermont ski Country

Hotel Style Condo Promising a Comfortable and Convenient Retreat Right in the Heart of Vermont ski Country is a apartment in Pittsfield, with 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 dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,222.

From$144/night

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Family-friendly vacation rentals in Pittsfield, VT

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

Pico D305 condo ski on/off The best family mountain with access to the Pico Fitness Center

Condo, Pittsfield

Pico D305 condo ski on/off The best family mountain with access to the Pico Fitness Center is a condo in Pittsfield, with pool access, parking, and kitchen access. This stay gives travelers…

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About Pico D305 condo ski on/off The best family mountain with access to the Pico Fitness Center

Pico D305 condo ski on/off The best family mountain with access to the Pico Fitness Center is a condo in Pittsfield, with pool access, 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, pool, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,152.

From$165/night

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Killington condo 5 min to killington resort

Condo, Pittsfield

Killington condo 5 min to killington resort is a condo in Pittsfield, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Killington condo 5 min to killington resort

Killington condo 5 min to killington resort is a condo in Pittsfield, with 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, kids friendly, and kids friendly videos or books.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,281.

From$183/night

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Cozy Killington Mountain View Condo

Condo, Pittsfield

Cozy Killington Mountain View Condo is a condo in Pittsfield, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

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About Cozy Killington Mountain View Condo

Cozy Killington Mountain View Condo is a condo in Pittsfield, 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, kids friendly, and kids friendly videos or books.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,731.

From$247/night

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\"The Crooked House\" with A/C and sauna on private wooded lot near Killington

Holiday Home, Pittsfield

\"The Crooked House\" with A/C and sauna on private wooded lot near Killington is a holiday home in Pittsfield, with kitchen access. This stay gives travelers a comfortable base for…

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About \"The Crooked House\" with A/C and sauna on private wooded lot near Killington

\"The Crooked House\" with A/C and sauna on private wooded lot near Killington is a holiday home in Pittsfield, with 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 wifi, kitchen, with kitchen, kids friendly, and kids friendly videos or books.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,079.

From$297/night

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