Vacation rentals in Tolland, MA

41 available vacation rental offers

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Best vacation rentals and Airbnb offers in Tolland, MA

East Otis Reservoir Cabin w/ Porch - Walk to Lake! - Tolland, MA

East Otis Reservoir Cabin w/ Porch - Walk to Lake!

Holiday Home, Tolland

East Otis Reservoir Cabin w/ Porch - Walk to Lake! is a holiday home in Tolland, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area,…

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About East Otis Reservoir Cabin w/ Porch - Walk to Lake!

East Otis Reservoir Cabin w/ Porch - Walk to Lake! is a holiday home in Tolland, 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 paid parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,492.

From$153/night
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Relax And Enjoy A Fun Getaway At The Bacchus Cottage! - Tolland, MA

Relax And Enjoy A Fun Getaway At The Bacchus Cottage!

Cottage, Tolland

Relax And Enjoy A Fun Getaway At The Bacchus Cottage! is a cottage in Tolland, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for…

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About Relax And Enjoy A Fun Getaway At The Bacchus Cottage!

Relax And Enjoy A Fun Getaway At The Bacchus Cottage! is a cottage in Tolland, 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, kids friendly, and kids friendly videos or books.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,145.

From$164/night
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Bring Your Pet & Visit Springfield: Westfield Home - Tolland, MA

Bring Your Pet & Visit Springfield: Westfield Home

Holiday Home, Tolland

Bring Your Pet & Visit Springfield: Westfield Home is a holiday home in Tolland, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Bring Your Pet & Visit Springfield: Westfield Home

Bring Your Pet & Visit Springfield: Westfield Home is a holiday home in Tolland, 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 $1,265.

From$181/night
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East Otis Reservoir Cabin w/ Porch - Walk to Lake! - Tolland, MA

East Otis Reservoir Cabin w/ Porch - Walk to Lake!

Cottage, Tolland

East Otis Reservoir Cabin w/ Porch - Walk to Lake! is a cottage in Tolland, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring…

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About East Otis Reservoir Cabin w/ Porch - Walk to Lake!

East Otis Reservoir Cabin w/ Porch - Walk to Lake! is a cottage in Tolland, 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 $1,552.

From$181/night
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Vacation rentals with parking in Tolland, MA

Find vacation rentals that make arriving by car easier.

Historic Huntington Home - Walk to Westfield River - Tolland, MA

Historic Huntington Home - Walk to Westfield River

Holiday Home, Tolland

Historic Huntington Home - Walk to Westfield River is a holiday home in Tolland, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Historic Huntington Home - Walk to Westfield River

Historic Huntington Home - Walk to Westfield River is a holiday home in Tolland, 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 $1,912.

From$273/night
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Berkshires Cabin 2 Mi to Appalachian Trail! - Tolland, MA

Berkshires Cabin 2 Mi to Appalachian Trail!

Cabin, Tolland

Berkshires Cabin 2 Mi to Appalachian Trail! is a cabin in Tolland, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Berkshires Cabin 2 Mi to Appalachian Trail!

Berkshires Cabin 2 Mi to Appalachian Trail! is a cabin in Tolland, 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 $2,157.

From$308/night
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2nd Floor The Inn at Highland Lake - Tolland, MA

2nd Floor The Inn at Highland Lake

Apartment, Tolland

2nd Floor The Inn at Highland Lake is a apartment in Tolland, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

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About 2nd Floor The Inn at Highland Lake

2nd Floor The Inn at Highland Lake is a apartment in Tolland, 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 $2,464.

From$352/night
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Steepletop: Nature Lover’s Paradise w/Rec Room - Tolland, MA

Steepletop: Nature Lover’s Paradise w/Rec Room

Holiday Home, Tolland

Steepletop: Nature Lover’s Paradise w/Rec Room is a holiday home in Tolland, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Steepletop: Nature Lover’s Paradise w/Rec Room

Steepletop: Nature Lover’s Paradise w/Rec Room is a holiday home in Tolland, 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 $2,812.

From$402/night
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Pet-friendly vacation rentals in Tolland, MA

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

Misty Pines Cabin | Wood Stove • Sauna - Tolland, MA

Misty Pines Cabin | Wood Stove • Sauna

Cabin, Tolland

Misty Pines Cabin · Wood Stove · Sauna is a cabin in Tolland, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Misty Pines Cabin | Wood Stove • Sauna

Misty Pines Cabin · Wood Stove · Sauna is a cabin in Tolland, 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 $2,457.

From$351/night
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Beautifully Restored Federal Colonial. New pool,Large Deck, New Hot tub, privacy - Tolland, MA

Beautifully Restored Federal Colonial. New pool,Large Deck, New Hot tub, privacy

Holiday Home, Tolland

Beautifully Restored Federal Colonial. New pool,Large Deck, New Hot tub, privacy is a holiday home in Tolland, with pet-friendly space, pool access, and outdoor space. This stay gives…

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About Beautifully Restored Federal Colonial. New pool,Large Deck, New Hot tub, privacy

Beautifully Restored Federal Colonial. New pool,Large Deck, New Hot tub, privacy is a holiday home in Tolland, with pet-friendly space, pool access, and outdoor 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, pool, hot tub, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,234.

From$462/night
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Lakefront Bungalow - Tolland, MA

Lakefront Bungalow

Holiday Home, Tolland

Lakefront Bungalow is a holiday home in Tolland, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

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About Lakefront Bungalow

Lakefront Bungalow is a holiday home in Tolland, 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 wifi, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,768.

From$681/night
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LAKE GARFIELD WATERFRONT HOME AND BOATHOUSE - Tolland, MA

LAKE GARFIELD WATERFRONT HOME AND BOATHOUSE

Cottage, Tolland

LAKE GARFIELD WATERFRONT HOME AND BOATHOUSE is a cottage in Tolland, with pet-friendly space and easy beach access. This stay gives travelers a comfortable base for exploring the area,…

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About LAKE GARFIELD WATERFRONT HOME AND BOATHOUSE

LAKE GARFIELD WATERFRONT HOME AND BOATHOUSE is a cottage in Tolland, with pet-friendly space and easy beach 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, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $5,082.

From$726/night
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Vacation rentals with a kitchen in Tolland, MA

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

Berkshires Cabin 2 Mi to Appalachian Trail! - Tolland, MA

Berkshires Cabin 2 Mi to Appalachian Trail!

Cottage, Tolland

Berkshires Cabin 2 Mi to Appalachian Trail! is a cottage in Tolland, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Berkshires Cabin 2 Mi to Appalachian Trail!

Berkshires Cabin 2 Mi to Appalachian Trail! is a cottage in Tolland, 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, hot tub, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,581.

From$288/night
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Lakes & Leisure! Spacious Berkshire Getaway - Tolland, MA

Lakes & Leisure! Spacious Berkshire Getaway

Holiday Home, Tolland

Lakes & Leisure! Spacious Berkshire Getaway is a holiday home in Tolland, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Lakes & Leisure! Spacious Berkshire Getaway

Lakes & Leisure! Spacious Berkshire Getaway is a holiday home in Tolland, 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 $3,096.

From$442/night
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Hilltop Escape with Views & Hot Tub - Tolland, MA

Hilltop Escape with Views & Hot Tub

Holiday Home, Tolland

Hilltop Escape with Views & Hot Tub is a holiday home in Tolland, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Hilltop Escape with Views & Hot Tub

Hilltop Escape with Views & Hot Tub is a holiday home in Tolland, 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: hot tub, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,132.

From$447/night
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Beautiful four season lakeside log home close to all Berkshires attractions. - Tolland, MA

Beautiful four season lakeside log home close to all Berkshires attractions.

Holiday Home, Tolland

Beautiful four season lakeside log home close to all Berkshires attractions. is a holiday home in Tolland, with parking and kitchen access. This stay gives travelers a comfortable base for…

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About Beautiful four season lakeside log home close to all Berkshires attractions.

Beautiful four season lakeside log home close to all Berkshires attractions. is a holiday home in Tolland, 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 $3,216.

From$459/night
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Family-friendly vacation rentals in Tolland, MA

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

Historic Huntington Home - Walk to Westfield River - Tolland, MA

Historic Huntington Home - Walk to Westfield River

Cottage, Tolland

Historic Huntington Home - Walk to Westfield River is a cottage in Tolland, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

Read more

About Historic Huntington Home - Walk to Westfield River

Historic Huntington Home - Walk to Westfield River is a cottage in Tolland, 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 fireplace.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,206.

From$272/night
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Peaceful, Newly Renovated Lakeside Cottage On Lake Garfield In Berkshires - Tolland, MA

Peaceful, Newly Renovated Lakeside Cottage On Lake Garfield In Berkshires

Cottage, Tolland

Peaceful, Newly Renovated Lakeside Cottage On Lake Garfield In Berkshires is a cottage in Tolland, with pet-friendly space, parking, and kitchen access. This stay gives travelers a…

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About Peaceful, Newly Renovated Lakeside Cottage On Lake Garfield In Berkshires

Peaceful, Newly Renovated Lakeside Cottage On Lake Garfield In Berkshires is a cottage in Tolland, 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 $1,994.

From$285/night
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Cottage is currently rented for the year, and not available until further notice - Tolland, MA

Cottage is currently rented for the year, and not available until further notice

Cottage, Tolland

Cottage is currently rented for the year, and not available until further notice is a cottage in Tolland, with pet-friendly space. This stay gives travelers a comfortable base for exploring…

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About Cottage is currently rented for the year, and not available until further notice

Cottage is currently rented for the year, and not available until further notice is a cottage in Tolland, 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, heating, and internet.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,995.

From$285/night
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Scribe`s Stable | A/C • Screened in Porch • Sleeps 6 - Tolland, MA

Scribe`s Stable | A/C • Screened in Porch • Sleeps 6

Country House, Tolland

Scribe`s Stable · A/C · Screened in Porch · Sleeps 6 is a country house in Tolland, with parking and room for a group. This stay gives travelers a comfortable base for exploring the area,…

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About Scribe`s Stable | A/C • Screened in Porch • Sleeps 6

Scribe`s Stable · A/C · Screened in Porch · Sleeps 6 is a country house in Tolland, 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, free wifi, parking, free parking, and ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,006.

From$287/night
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