Monterey Rentals

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15 Houses

NEW! Monterey Home w/Porch by Beach & State Parks!

Monterey house

3 bedrooms / 3 bathrooms / sleeps 7

Responds fast! avg. 2 hours 26 minutes

Match: Skiing – property near ski resort

All filters match

Price per night from

$229

Great rentals within 20 miles that match your search

Tranquil 3BR Stockbridge House w/Private Deck

Stockbridge house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 24 minutes

Match: Skiing – property near ski resort

All filters match

Price per night from

$260

Cozy Stockbridge Home - Walk To Golf Course!

Stockbridge house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 26 minutes

Match: Skiing – property near ski resort

All filters match

Price per night from

$241

3BR Lee House w/ Easy Access to Main Street!

Lee house

3 bedrooms / 2 bathrooms / sleeps 10

Responds fast! avg. 2 hours 26 minutes

Match: Skiing – property near ski resort

All filters match

Price per night from

$275

'The Mill River Cabin’ w/ Fireplace & River View!

New Marlborough cottage

2 bedrooms / 1 bathroom / sleeps 5

Responds fast! avg. 2 hours 26 minutes

Match: Skiing – property near ski resort

All filters match

Price per night from

$201

Waterfront Home in Tolland w/ Deck - Steps to Lake

West Hartland log cabin

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 2 hours 26 minutes

Match: Skiing – property near ski resort

All filters match

Price per night from

$264

Cozy Berkshire Home, 1 Mile to Stockbridge Center!

Stockbridge house

4 bedrooms / 2 bathrooms / sleeps 7

Responds fast! avg. 2 hours 26 minutes

Match: Skiing – property near ski resort

All filters match

Price per night from

$228

Waterfront Cottage - 10 Mins to Great Barrington!

New Marlborough cottage

2 bedrooms / 1 bathroom / sleeps 4

“Clean, attention to detail, everything is updated, fantastic deck, wonderful views.” Loved being so close to Jacob's Pillow and great restaurants (Xochil, Gedney Farm, Dream Away Lodge). Visiting MOCA and the Norman Rockwell were also a wonderful treat. Early dawn and dusk were wonderful at the cottage with daily visits from a bald eagle flying right in front of the deck. Perfect for a restful vacation.

Responds fast! avg. 2 hours 26 minutes

Match: Skiing – property near ski resort

All filters match

Price per night from

$207

NEW! Lakefront Berkshires House w/Deck, Dock +Boat

Housatonic house

4 bedrooms / 2 bathrooms / sleeps 10

Responds fast! avg. 2 hours 26 minutes

Match: Skiing – property near ski resort

All filters match

Price per night from

$212

'Butterfly Hill' West Stockbridge Home on 3 Acres!

West Stockbridge house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 2 hours 26 minutes

Match: Skiing – property near ski resort

All filters match

Price per night from

$189

Luxury Becket Home on 11 Acres W/ Swimming Pond!

Becket house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 2 hours 26 minutes

Match: Skiing – property near ski resort

All filters match

Price per night from

$373

NEW! Charming Berkshires Cottage on Ashmere Lake

Hinsdale cottage

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 26 minutes

Match: Skiing – property near ski resort

All filters match

Price per night from

$224

NEW! Lenox Home Mins to Tanglewood Shakespeare &Co

Lenox house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 2 hours 26 minutes

Match: Skiing – property near ski resort

All filters match

Price per night from

$241

Berkshires Home w/Kayak - Walk to Stockbridge Bowl

Lenox house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 26 minutes

Match: Skiing – property near ski resort

All filters match

Price per night from

$212

Zen Cottage in the Woods

Great Barrington house

3 bedrooms / 1 bathroom / sleeps 6

Match: Skiing – property near ski resort

All filters match

Price per night from

$229

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