Vacation rentals in Monterey, MA

80 available vacation rental offers

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Best vacation rentals and Airbnb offers in Monterey, MA

Cozy 1-bedroom studio in serene Great Barrington with AC - Monterey, MA

Cozy 1-bedroom studio in serene Great Barrington with AC

Apartment, Monterey

Cozy 1-bedroom studio in serene Great Barrington with AC is a apartment in Monterey, with pet-friendly space and room for a group. This stay gives travelers a comfortable base for exploring…

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About Cozy 1-bedroom studio in serene Great Barrington with AC

Cozy 1-bedroom studio in serene Great Barrington with AC is a apartment in Monterey, with pet-friendly space 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, pet friendly, pets friendly, dryer, and ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $846.

From$121/night
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East Otis Reservoir Cabin w/ Porch - Walk to Lake! - Monterey, MA

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

Holiday Home, Monterey

East Otis Reservoir Cabin w/ Porch - Walk to Lake! is a holiday home in Monterey, 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 Monterey, 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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The Berkshire Music Loft at Eastview Studio with Piano, Balcony & Mountain View - Monterey, MA

The Berkshire Music Loft at Eastview Studio with Piano, Balcony & Mountain View

Apartment, Monterey

The Berkshire Music Loft at Eastview Studio with Piano, Balcony & Mountain View is a apartment in Monterey, with outdoor space and parking. This stay gives travelers a comfortable base for…

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About The Berkshire Music Loft at Eastview Studio with Piano, Balcony & Mountain View

The Berkshire Music Loft at Eastview Studio with Piano, Balcony & Mountain View is a apartment in Monterey, with 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, parking, free parking, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,522.

From$217/night
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Berkshires Cabin 2 Mi to Appalachian Trail! - Monterey, MA

Berkshires Cabin 2 Mi to Appalachian Trail!

Holiday Home, Monterey

Berkshires Cabin 2 Mi to Appalachian Trail! is a holiday home in Monterey, with parking. 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 holiday home in Monterey, 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 heating.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,485.

From$250/night
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Vacation rentals with a pool in Monterey, MA

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

Charming 2-bedroom apartment in Lee with fitness room, WiFi - Monterey, MA

Charming 2-bedroom apartment in Lee with fitness room, WiFi

Apartment, Monterey

Charming 2-bedroom apartment in Lee with fitness room, WiFi is a apartment in Monterey, with pool access, kitchen access, and room for a group. This stay gives travelers a comfortable base…

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About Charming 2-bedroom apartment in Lee with fitness room, WiFi

Charming 2-bedroom apartment in Lee with fitness room, WiFi is a apartment in Monterey, with pool 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: pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,040.

From$291/night
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Cozy 2-bedroom apartment with fitness room, WiFi in fabulous Lee - Monterey, MA

Cozy 2-bedroom apartment with fitness room, WiFi in fabulous Lee

Apartment, Monterey

Cozy 2-bedroom apartment with fitness room, WiFi in fabulous Lee is a apartment in Monterey, with pool access, kitchen access, and room for a group. This stay gives travelers a comfortable…

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About Cozy 2-bedroom apartment with fitness room, WiFi in fabulous Lee

Cozy 2-bedroom apartment with fitness room, WiFi in fabulous Lee is a apartment in Monterey, with pool 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: pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,040.

From$291/night
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Cozy 2-bedroom apartment with WiFi, AC in welcoming Lee - Monterey, MA

Cozy 2-bedroom apartment with WiFi, AC in welcoming Lee

Apartment, Monterey

Cozy 2-bedroom apartment with WiFi, AC in welcoming Lee is a apartment in Monterey, with pool access, kitchen access, and room for a group. This stay gives travelers a comfortable base for…

Read more

About Cozy 2-bedroom apartment with WiFi, AC in welcoming Lee

Cozy 2-bedroom apartment with WiFi, AC in welcoming Lee is a apartment in Monterey, with pool 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: pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,040.

From$291/night
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Cozy 2-bedroom apartment with WiFi, fitness room in enjoyable Lee - Monterey, MA

Cozy 2-bedroom apartment with WiFi, fitness room in enjoyable Lee

Apartment, Monterey

Cozy 2-bedroom apartment with WiFi, fitness room in enjoyable Lee is a apartment in Monterey, with pool access, kitchen access, and room for a group. This stay gives travelers a comfortable…

Read more

About Cozy 2-bedroom apartment with WiFi, fitness room in enjoyable Lee

Cozy 2-bedroom apartment with WiFi, fitness room in enjoyable Lee is a apartment in Monterey, with pool 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: pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,040.

From$291/night
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Vacation rentals with parking in Monterey, MA

Find vacation rentals that make arriving by car easier.

2 bedroom Riverhouse in the Heart of the Berkshires! Summer & winter coziness! - Monterey, MA

2 bedroom Riverhouse in the Heart of the Berkshires! Summer & winter coziness!

Apartment, Monterey

2 bedroom Riverhouse in the Heart of the Berkshires! Summer & winter coziness! is a apartment in Monterey, with parking, kitchen access, and room for a group. This stay gives travelers a…

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About 2 bedroom Riverhouse in the Heart of the Berkshires! Summer & winter coziness!

2 bedroom Riverhouse in the Heart of the Berkshires! Summer & winter coziness! is a apartment in Monterey, 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: kitchen, with kitchen, parking, free parking, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,737.

From$248/night
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Modern secluded home in wooded Setting - Monterey, MA

Modern secluded home in wooded Setting

Holiday Home, Monterey

Modern secluded home in wooded Setting is a holiday home in Monterey, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Modern secluded home in wooded Setting

Modern secluded home in wooded Setting is a holiday home in Monterey, 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, gym, parking, and free parking.

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

From$298/night
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Hilltop Escape with Views & Hot Tub - Monterey, MA

Hilltop Escape with Views & Hot Tub

Holiday Home, Monterey

Hilltop Escape with Views & Hot Tub is a holiday home in Monterey, 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 Monterey, 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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Locust Tree Bed and Breakfast LLC - Monterey, MA

Locust Tree Bed and Breakfast LLC

B & B, Monterey

Locust Tree Bed and Breakfast LLC is a b & b in Monterey, 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 Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC is a b & b in Monterey, 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 breakfast, parking, free parking, and breakfast::free.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $845.

From$105/night
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Pet-friendly vacation rentals in Monterey, MA

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

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

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

Cabin, Monterey

East Otis Reservoir Cabin w/ Porch - Walk to Lake! is a cabin in Monterey, 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 cabin in Monterey, 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 $1,407.

From$201/night
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Log Cabin w/ fire pit, close to Ski Catamount, Butternut Ski, Great Barrington - Monterey, MA

Log Cabin w/ fire pit, close to Ski Catamount, Butternut Ski, Great Barrington

Holiday Home, Monterey

Log Cabin w/ fire pit, close to Ski Catamount, Butternut Ski, Great Barrington is a holiday home in Monterey, with parking and kitchen access. This stay gives travelers a comfortable base…

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About Log Cabin w/ fire pit, close to Ski Catamount, Butternut Ski, Great Barrington

Log Cabin w/ fire pit, close to Ski Catamount, Butternut Ski, Great Barrington is a holiday home in Monterey, 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 $2,782.

From$397/night
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Family vacation home in Great Barrington - Monterey, MA

Family vacation home in Great Barrington

Holiday Home, Monterey

Family vacation home in Great Barrington is a holiday home in Monterey, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a comfortable base for…

Read more

About Family vacation home in Great Barrington

Family vacation home in Great Barrington is a holiday home in Monterey, 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 $3,077.

From$440/night
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LAKE GARFIELD WATERFRONT HOME AND BOATHOUSE - Monterey, MA

LAKE GARFIELD WATERFRONT HOME AND BOATHOUSE

Cottage, Monterey

LAKE GARFIELD WATERFRONT HOME AND BOATHOUSE is a cottage in Monterey, 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 Monterey, 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 Monterey, MA

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

Downtown Gateway to the Berkshires. Walk to Everything. - Monterey, MA

Downtown Gateway to the Berkshires. Walk to Everything.

Apartment, Monterey

Downtown Gateway to the Berkshires. Walk to Everything. is a apartment in Monterey, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Downtown Gateway to the Berkshires. Walk to Everything.

Downtown Gateway to the Berkshires. Walk to Everything. is a apartment in Monterey, 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, ac, and air conditioning.

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

From$213/night
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Cozy 2-bedroom apartment with AC, fitness room and WiFi in welcoming Lee - Monterey, MA

Cozy 2-bedroom apartment with AC, fitness room and WiFi in welcoming Lee

Apartment, Monterey

Cozy 2-bedroom apartment with AC, fitness room and WiFi in welcoming Lee is a apartment in Monterey, with pool access, kitchen access, and room for a group. This stay gives travelers a…

Read more

About Cozy 2-bedroom apartment with AC, fitness room and WiFi in welcoming Lee

Cozy 2-bedroom apartment with AC, fitness room and WiFi in welcoming Lee is a apartment in Monterey, with pool 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: pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,040.

From$291/night
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Spacious Villa with Access to Various Amenities! - Monterey, MA

Spacious Villa with Access to Various Amenities!

Villa, Monterey

Spacious Villa with Access to Various Amenities! is a villa in Monterey, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Spacious Villa with Access to Various Amenities!

Spacious Villa with Access to Various Amenities! is a villa in Monterey, 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, hot tub, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,411.

From$344/night
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Private Berkshires Getaway Minutes to Ski Butternut - Monterey, MA

Private Berkshires Getaway Minutes to Ski Butternut

Holiday Home, Monterey

Private Berkshires Getaway Minutes to Ski Butternut is a holiday home in Monterey, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Private Berkshires Getaway Minutes to Ski Butternut

Private Berkshires Getaway Minutes to Ski Butternut is a holiday home in Monterey, 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 $3,253.

From$465/night
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Family-friendly vacation rentals in Monterey, MA

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

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

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

Cottage, Monterey

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

Read more

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

East Otis Reservoir Cabin w/ Porch - Walk to Lake! is a cottage in Monterey, 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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Cozy Becket Cottage Escape w/ Lake Access! - Monterey, MA

Cozy Becket Cottage Escape w/ Lake Access!

Cottage, Monterey

Cozy Becket Cottage Escape w/ Lake Access! is a cottage in Monterey, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Cozy Becket Cottage Escape w/ Lake Access!

Cozy Becket Cottage Escape w/ Lake Access! is a cottage in Monterey, 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 $1,392.

From$199/night
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Lovely Lakefront Cottage, Peaceful Setting, Hiking And More - Monterey, MA

Lovely Lakefront Cottage, Peaceful Setting, Hiking And More

Holiday Home, Monterey

Lovely Lakefront Cottage, Peaceful Setting, Hiking And More is a holiday home in Monterey, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for…

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About Lovely Lakefront Cottage, Peaceful Setting, Hiking And More

Lovely Lakefront Cottage, Peaceful Setting, Hiking And More is a holiday home in Monterey, 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 $2,163.

From$309/night
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Private Woodland Getaway minutes from Ski Butternut - Monterey, MA

Private Woodland Getaway minutes from Ski Butternut

Holiday Home, Monterey

Private Woodland Getaway minutes from Ski Butternut is a holiday home in Monterey, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Private Woodland Getaway minutes from Ski Butternut

Private Woodland Getaway minutes from Ski Butternut is a holiday home in Monterey, 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, kids friendly, kids friendly videos or books, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,753.

From$536/night
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