Vacation rentals in Florida, MA

61 available vacation rental offers

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Best vacation rentals and Airbnb offers in Florida, MA

Getaway Near Mass MoCA, Great Hiking, Scenic Views - Florida, MA

Getaway Near Mass MoCA, Great Hiking, Scenic Views

Apartment, Florida

Getaway Near Mass MoCA, Great Hiking, Scenic Views is a apartment in Florida, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Getaway Near Mass MoCA, Great Hiking, Scenic Views

Getaway Near Mass MoCA, Great Hiking, Scenic Views is a apartment in Florida, 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, free wifi, kitchen, with kitchen, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $868.

From$124/night
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Hawley Home w/ Deck: 4 Mi to Berkshire East Resort - Florida, MA

Hawley Home w/ Deck: 4 Mi to Berkshire East Resort

Holiday Home, Florida

Hawley Home w/ Deck: 4 Mi to Berkshire East Resort is a holiday home in Florida, with pet-friendly space, outdoor space, and parking. This stay gives travelers a comfortable base for…

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About Hawley Home w/ Deck: 4 Mi to Berkshire East Resort

Hawley Home w/ Deck: 4 Mi to Berkshire East Resort is a holiday home in Florida, with pet-friendly space, outdoor space, 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, pet friendly, pets friendly, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,236.

From$177/night
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Hawley Home w/ Deck: 4 Mi to Berkshire East Resort - Florida, MA

Hawley Home w/ Deck: 4 Mi to Berkshire East Resort

Cottage, Florida

Hawley Home w/ Deck: 4 Mi to Berkshire East Resort is a cottage in Florida, with pet-friendly space, outdoor space, and kitchen access. This stay gives travelers a comfortable base for…

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About Hawley Home w/ Deck: 4 Mi to Berkshire East Resort

Hawley Home w/ Deck: 4 Mi to Berkshire East Resort is a cottage in Florida, with pet-friendly space, outdoor space, 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, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,491.

From$184/night
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Brookside cottage near the mountains and outdoor recreation - Florida, MA

Brookside cottage near the mountains and outdoor recreation

Cottage, Florida

Brookside cottage near the mountains and outdoor recreation is a cottage in Florida, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Brookside cottage near the mountains and outdoor recreation

Brookside cottage near the mountains and outdoor recreation is a cottage in Florida, with pet-friendly space 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, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,373.

From$196/night
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Vacation rentals with a pool in Florida, MA

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

FARM-TO-TABLE eating, good hot tub soak, S'mores around fire pit, seasonal POOL! - Florida, MA

FARM-TO-TABLE eating, good hot tub soak, S'mores around fire pit, seasonal POOL!

Apartment, Florida

FARM-TO-TABLE eating, good hot tub soak, S'mores around fire pit, seasonal POOL! is a apartment in Florida, with pool access. This stay gives travelers a comfortable base for exploring the…

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About FARM-TO-TABLE eating, good hot tub soak, S'mores around fire pit, seasonal POOL!

FARM-TO-TABLE eating, good hot tub soak, S'mores around fire pit, seasonal POOL! is a apartment in Florida, 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: free cancellation, pool, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,397.

From$200/night
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Mountain Blossom Retreat by Evergreen Home - Florida, MA

Mountain Blossom Retreat by Evergreen Home

Holiday Home, Florida

Mountain Blossom Retreat by Evergreen Home is a holiday home in Florida, with pet-friendly space, pool access, and a quieter setting. This stay gives travelers a comfortable base for…

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About Mountain Blossom Retreat by Evergreen Home

Mountain Blossom Retreat by Evergreen Home is a holiday home in Florida, with pet-friendly space, pool 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, pool, hot tub, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $8,885.

From$1,269/night
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Gracious Williamstown Home with Pool - Florida, MA

Gracious Williamstown Home with Pool

Holiday Home, Florida

Gracious Williamstown Home with Pool is a holiday home in Florida, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Gracious Williamstown Home with Pool

Gracious Williamstown Home with Pool is a holiday home in Florida, 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 $8,998.

From$1,285/night
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Vacation rentals with parking in Florida, MA

Find vacation rentals that make arriving by car easier.

Log Cabin Escape - Florida, MA

Log Cabin Escape

Holiday Home, Florida

Log Cabin Escape is a holiday home in Florida, 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 Log Cabin Escape

Log Cabin Escape is a holiday home in Florida, 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, parking, paid parking, and heating.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,477.

From$140/night
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Harbour House Inn - Florida, MA

Harbour House Inn

B & B, Florida

Harbour House Inn is a b & b in Florida, 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 Harbour House Inn

Harbour House Inn is a b & b in Florida, 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 breakfast, free wifi, parking, free parking, and ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,905.

From$257/night
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Beauty in the Berkshires - Just up the hill from Mass MoCA and Downtown - Florida, MA

Beauty in the Berkshires - Just up the hill from Mass MoCA and Downtown

Holiday Home, Florida

Beauty in the Berkshires - Just up the hill from Mass MoCA and Downtown is a holiday home in Florida, with parking and kitchen access. This stay gives travelers a comfortable base for…

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About Beauty in the Berkshires - Just up the hill from Mass MoCA and Downtown

Beauty in the Berkshires - Just up the hill from Mass MoCA and Downtown is a holiday home in Florida, 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 $1,948.

From$278/night
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The Trail in Adams - Berkshires’ Art Hotel - Florida, MA

The Trail in Adams - Berkshires’ Art Hotel

B & B, Florida

The Trail in Adams - Berkshires’ Art Hotel is a b & b in Florida, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending…

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About The Trail in Adams - Berkshires’ Art Hotel

The Trail in Adams - Berkshires’ Art Hotel is a b & b in Florida, 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, free parking, and ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,287.

From$293/night
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Pet-friendly vacation rentals in Florida, MA

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

Two Brooks Lodge - Florida, MA

Two Brooks Lodge

Holiday Home, Florida

Two Brooks Lodge is a holiday home in Florida, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Two Brooks Lodge

Two Brooks Lodge is a holiday home in Florida, with pet-friendly space 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, pet friendly, pets friendly, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,594.

From$175/night
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Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort - Florida, MA

Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort

Holiday Home, Florida

Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort is a holiday home in Florida, with pet-friendly space, parking, and kitchen access. This stay gives…

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About Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort

Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort is a holiday home in Florida, 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 $1,663.

From$238/night
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Cozy Home In The Berkshires, Pet Friendly with fenced in yard! - Florida, MA

Cozy Home In The Berkshires, Pet Friendly with fenced in yard!

Holiday Home, Florida

Cozy Home In The Berkshires, Pet Friendly with fenced in yard! is a holiday home in Florida, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for…

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About Cozy Home In The Berkshires, Pet Friendly with fenced in yard!

Cozy Home In The Berkshires, Pet Friendly with fenced in yard! is a holiday home in Florida, with pet-friendly space 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, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,085.

From$298/night
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Charming Retreat by Mass MoCA - Florida, MA

Charming Retreat by Mass MoCA

Holiday Home, Florida

Charming Retreat by Mass MoCA is a holiday home in Florida, with pet-friendly space, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the…

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About Charming Retreat by Mass MoCA

Charming Retreat by Mass MoCA is a holiday home in Florida, with pet-friendly space, 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: pet friendly, pets friendly, kitchen, with kitchen, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,464.

From$352/night
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Vacation rentals with a kitchen in Florida, MA

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

Lake Whitingham & Mount Snow Area Village Apartment - Florida, MA

Lake Whitingham & Mount Snow Area Village Apartment

Apartment, Florida

Lake Whitingham & Mount Snow Area Village Apartment is a apartment in Florida, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Lake Whitingham & Mount Snow Area Village Apartment

Lake Whitingham & Mount Snow Area Village Apartment is a apartment in Florida, 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 wifi, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,155.

From$165/night
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Secluded large country home for big groups with giant open yard for outdoor fun. - Florida, MA

Secluded large country home for big groups with giant open yard for outdoor fun.

Holiday Home, Florida

Secluded large country home for big groups with giant open yard for outdoor fun. is a holiday home in Florida, with parking and kitchen access. This stay gives travelers a comfortable base…

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About Secluded large country home for big groups with giant open yard for outdoor fun.

Secluded large country home for big groups with giant open yard for outdoor fun. is a holiday home in Florida, 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 $2,353.

From$336/night
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Come stay with us at the Parsonage and enjoy our mountains and rivers. - Florida, MA

Come stay with us at the Parsonage and enjoy our mountains and rivers.

Country House, Florida

Come stay with us at the Parsonage and enjoy our mountains and rivers. is a country house in Florida, with parking and kitchen access. This stay gives travelers a comfortable base for…

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About Come stay with us at the Parsonage and enjoy our mountains and rivers.

Come stay with us at the Parsonage and enjoy our mountains and rivers. is a country house in Florida, 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 $2,492.

From$356/night
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Cozy Condo Near MASS MoCA - Florida, MA

Cozy Condo Near MASS MoCA

Holiday Home, Florida

Cozy Condo Near MASS MoCA is a holiday home in Florida, 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 Cozy Condo Near MASS MoCA

Cozy Condo Near MASS MoCA is a holiday home in Florida, 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: kitchen, with kitchen, parking, free parking, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,513.

From$359/night
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Family-friendly vacation rentals in Florida, MA

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

Berkshire Gorge House, 15 minutes to Williamstown, 15 minutes to Jiminy Peak. - Florida, MA

Berkshire Gorge House, 15 minutes to Williamstown, 15 minutes to Jiminy Peak.

Holiday Home, Florida

Berkshire Gorge House, 15 minutes to Williamstown, 15 minutes to Jiminy Peak. is a holiday home in Florida, with parking and kitchen access. This stay gives travelers a comfortable base for…

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About Berkshire Gorge House, 15 minutes to Williamstown, 15 minutes to Jiminy Peak.

Berkshire Gorge House, 15 minutes to Williamstown, 15 minutes to Jiminy Peak. is a holiday home in Florida, 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 $1,744.

From$249/night
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Charming 1-bedroom cottage on the border of Plainfield, Savoy, on Windsor Pond! - Florida, MA

Charming 1-bedroom cottage on the border of Plainfield, Savoy, on Windsor Pond!

Cottage, Florida

Charming 1-bedroom cottage on the border of Plainfield, Savoy, on Windsor Pond! is a cottage in Florida, with parking and room for a group. This stay gives travelers a comfortable base for…

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About Charming 1-bedroom cottage on the border of Plainfield, Savoy, on Windsor Pond!

Charming 1-bedroom cottage on the border of Plainfield, Savoy, on Windsor Pond! is a cottage in Florida, with parking 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, parking, free parking, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,974.

From$282/night
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Near Berkshire East | River Farmhouse on 10 Acres - Florida, MA

Near Berkshire East | River Farmhouse on 10 Acres

Holiday Home, Florida

Near Berkshire East · River Farmhouse on 10 Acres is a holiday home in Florida, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Near Berkshire East | River Farmhouse on 10 Acres

Near Berkshire East · River Farmhouse on 10 Acres is a holiday home in Florida, with pet-friendly space 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 $2,823.

From$403/night
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Berkshire's Family Gathering & Mountain Escape! - Florida, MA

Berkshire's Family Gathering & Mountain Escape!

Holiday Home, Florida

Berkshire's Family Gathering & Mountain Escape! is a holiday home in Florida, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring…

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About Berkshire's Family Gathering & Mountain Escape!

Berkshire's Family Gathering & Mountain Escape! is a holiday home in Florida, 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 $4,106.

From$587/night
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