Vacation rentals near Guido's Marketplace
We found 951 vacation rentals — enter your dates for availability
Discover a selection of private vacation rentals close to Guido's Marketplace that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, vacation rentals have the best amenities for spending time at your vacation home, which might include parking and a pool. What you'll find is a rental that has what everyone needs, including places that are non-smoking or accessible.
Vacation rentals with weekly discounts - Guido's Marketplace
Showing deals for:Nov 7 - Nov 14
Image gallery for Berkshires Summer Chalet w/ Pool + Private Hiking Trails
1010 out of 10 rating
Exceptional
(7 reviews)
Berkshires Summer Chalet w/ Pool + Private Hiking Trails
Great Barrington, MA
20% off
Price is CA $739
CA $739
CA $6,870 total
CA $6,870 total
includes taxes & fees
Image gallery for Peaceful, Post and Beam Loft, Sleeps 9
1010 out of 10 rating
Exceptional
(19 reviews)
Peaceful, Post and Beam Loft, Sleeps 9
Great Barrington, MA
20% off
Price is CA $227
CA $227
CA $2,436 total
CA $2,436 total
includes taxes & fees
Image gallery for Indoor Pool & Lofted Game Area | Sunroom w/ Sweeping Mountain Views | Wellspring
1010 out of 10 rating
Exceptional
(13 reviews)
Indoor Pool & Lofted Game Area | Sunroom w/ Sweeping Mountain Views | Wellspring
West Stockbridge, MA
23% off
Price is CA $1,063
CA $1,063
CA $10,773 total
CA $10,773 total
includes taxes & fees
Image gallery for Waterfront Cottage 10 Min From Great Barrington
1010 out of 10 rating
Exceptional
(97 reviews)
Waterfront Cottage 10 Min From Great Barrington
Great Barrington, MA
10% off
Price is CA $472
CA $472
CA $4,221 total
CA $4,221 total
includes taxes & fees
Image gallery for Imagine Being Lakeside This Summer! Book Now!
9.69.6 out of 10 rating
Exceptional
(18 reviews)
Imagine Being Lakeside This Summer! Book Now!
Lenox, MA
20% off
Price is CA $513
CA $513
CA $5,239 total
CA $5,239 total
includes taxes & fees
Image gallery for Half Moon by AvantStay | 4BR Cabin w/ Large Deck & Yard
9.89.8 out of 10 rating
Exceptional
(13 reviews)
Half Moon by AvantStay | 4BR Cabin w/ Large Deck & Yard
Great Barrington, MA
8% off
Price is CA $582
CA $582
CA $6,100 total
CA $6,100 total
includes taxes & fees
Image gallery for Taggart River House: Modern Luxury Meets Nature: Stunning river views, sleeps 10
1010 out of 10 rating
Exceptional
(6 reviews)
Taggart River House: Modern Luxury Meets Nature: Stunning river views, sleeps 10
Stockbridge, MA
10% off
Price is CA $1,339
CA $1,339
CA $11,691 total
CA $11,691 total
includes taxes & fees
Image gallery for Modern home with Catskill views, guesthouse and heated pool near Chatham/Hudson
9.49.4 out of 10 rating
Exceptional
(6 reviews)
Modern home with Catskill views, guesthouse and heated pool near Chatham/Hudson
Chatham, NY
10% off
Price is CA $1,549
CA $1,549
CA $13,436 total
CA $13,436 total
includes taxes & fees
Image gallery for Woodland 5-BR Retreat 5-Min to Jiminy Peak
1010 out of 10 rating
Exceptional
(8 reviews)
Woodland 5-BR Retreat 5-Min to Jiminy Peak
Pittsfield, MA
10% off
Price is CA $447
CA $447
CA $4,271 total
CA $4,271 total
includes taxes & fees
Image gallery for Beautiful Home in AMAZING Berkshire Location
1010 out of 10 rating
Exceptional
(17 reviews)
Beautiful Home in AMAZING Berkshire Location
Lee, MA
10% off
Price is CA $682
CA $682
CA $6,118 total
CA $6,118 total
includes taxes & fees
Image gallery for Little Longbow Lakefront Chalet
9.69.6 out of 10 rating
Exceptional
(14 reviews)
Little Longbow Lakefront Chalet
Becket, MA
10% off
Price is CA $558
CA $558
CA $5,009 total
CA $5,009 total
includes taxes & fees
Image gallery for Private Berkshire Cabin on 27acres near Jiminy Peak.
9.69.6 out of 10 rating
Exceptional
(7 reviews)
Private Berkshire Cabin on 27acres near Jiminy Peak.
Williamstown, MA
15% off
Price is CA $380
CA $380
CA $3,247 total
CA $3,247 total
includes taxes & fees
Image gallery for WINTER/SUMMER - ON 5 ACRES, PRIVATE LAKE GARFIELD DOCK, 5 MILES FROM BUTTERNUT
9.69.6 out of 10 rating
Exceptional
(17 reviews)
WINTER/SUMMER - ON 5 ACRES, PRIVATE LAKE GARFIELD DOCK, 5 MILES FROM BUTTERNUT
Monterey, MA
10% off
Price is CA $620
CA $620
CA $5,788 total
CA $5,788 total
includes taxes & fees
Image gallery for Forget-Me-Not by AvantStay | Bold Lakefront Escape
9.29.2 out of 10 rating
Wonderful
(7 reviews)
Forget-Me-Not by AvantStay | Bold Lakefront Escape
Monterey, MA
13% off
Price is CA $935
CA $935
CA $9,193 total
CA $9,193 total
includes taxes & fees
Image gallery for Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
9.09.0 out of 10 rating
Wonderful
(39 reviews)
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
Great Barrington, MA
15% off
Price is CA $191
CA $191
CA $2,018 total
CA $2,018 total
includes taxes & fees
Image gallery for Entire cottage in Berkshire Villiage
9.69.6 out of 10 rating
Exceptional
(5 reviews)
Entire cottage in Berkshire Villiage
Lanesborough, MA
15% off
Price is CA $188
CA $188
CA $1,745 total
CA $1,745 total
includes taxes & fees
Image gallery for Peaceful Retreat Compound 10 Minutes to Great Barrington!
1010 out of 10 rating
Exceptional
(27 reviews)
Peaceful Retreat Compound 10 Minutes to Great Barrington!
Great Barrington, MA
10% off
Price is CA $1,186
CA $1,186
CA $10,808 total
CA $10,808 total
includes taxes & fees
Image gallery for Treetop Hideaway in Tyringham
9.09.0 out of 10 rating
Wonderful
(8 reviews)
Treetop Hideaway in Tyringham
Lee, MA
5% off
Price is CA $460
CA $460
CA $3,848 total
CA $3,848 total
includes taxes & fees
Image gallery for Berkshire Lake at the Pillow, and EV!
9.49.4 out of 10 rating
Exceptional
(15 reviews)
Berkshire Lake at the Pillow, and EV!
Lee, MA
10% off
Price is CA $445
CA $445
CA $4,067 total
CA $4,067 total
includes taxes & fees
Image gallery for BEAUTIFUL ESTATE: POOL, POND, ARCADE, GYM, TRAILS! REDUCED RATE FOR SMALL GROUPS
9.69.6 out of 10 rating
Exceptional
(88 reviews)
BEAUTIFUL ESTATE: POOL, POND, ARCADE, GYM, TRAILS! REDUCED RATE FOR SMALL GROUPS
Old Chatham, NY
10% off
Price is CA $1,859
CA $1,859
CA $15,976 total
CA $15,976 total
includes taxes & fees
Image gallery for Serene Berkshires Home On 5+ Acres, Rustic & Chic
8.88.8 out of 10 rating
Excellent
(6 reviews)
Serene Berkshires Home On 5+ Acres, Rustic & Chic
Otis, MA
20% off
Price is CA $419
CA $419
CA $4,473 total
CA $4,473 total
includes taxes & fees
Image gallery for Stunning Renovated Victorian
1010 out of 10 rating
Exceptional
(53 reviews)
Stunning Renovated Victorian
Great Barrington, MA
20% off
Price is CA $1,102
CA $1,102
CA $10,123 total
CA $10,123 total
includes taxes & fees
Image gallery for 1500 sqft private entrance with beautiful views of the Berkshire Mountains
1010 out of 10 rating
Exceptional
(44 reviews)
1500 sqft private entrance with beautiful views of the Berkshire Mountains
Lee, MA
10% off
Price is CA $372
CA $372
CA $3,426 total
CA $3,426 total
includes taxes & fees
Image gallery for Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
9.69.6 out of 10 rating
Exceptional
(14 reviews)
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
Hinsdale, MA
10% off
Price is CA $211
CA $211
CA $1,868 total
CA $1,868 total
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - Guido's Marketplace
6BR Berkshire Bliss - 38 Acres of nature - minutes from Jiminy Peak Ski Resort
Sleeps 14 · 6 bedrooms · 4+ bathrooms
9.89.8 out of 10
Exceptionalexceptional
28 reviews(28 reviews)
Vacation Village in the Berkshires
Sleeps 4 · 1 bedroom
8.68.6 out of 10
Excellentexcellent
1,933 reviews(1,933 reviews)
Jiminy Peak Mountain Resort
Sleeps 8 · 3 bedrooms
8.28.2 out of 10
Very goodvery good
958 reviews(958 reviews)
Spacious Berkshire Summer Rental, Private Dock on Lake 3 BR/2b
Sleeps 7 · 3 bedrooms · 2 bathrooms
9.69.6 out of 10
Exceptionalexceptional
100 reviews(100 reviews)
Berkshire Village Carriage House - Super Private!!
Sleeps 2 · 1 bedroom · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
254 reviews(254 reviews)
Contemporary Berkshire Home with Views of Taconic Golf Course
Sleeps 10 · 3 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
5 reviews(5 reviews)
Top rated rentals - Guido's Marketplace
Convenient stop
1010 out of 10
Exceptionalexceptional
5 reviews(5 reviews)
Wonderful olace
1010 out of 10
Exceptionalexceptional
235 reviews(235 reviews)
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, yards and more
More for lessMore space, more privacy, more amenities — more value