Holiday rentals near Montgomery Hill
We found 368 holiday rentals — enter your dates for availability
Discover a selection of holiday rentals near Montgomery Hill that are perfect for your trip. Whether you’re travelling with friends, family or even pets, holiday homes have the amenities that you expect for your stay, which might include Wi-Fi and a pool. No matter what you're looking for, you'll find a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.
Holiday rentals with weekly discounts - Montgomery Hill
Showing deals for:26 Sept - 3 Oct
Image gallery for The Villa at The Ranch Almaden beautiful winery location
9.89.8 out of 10 rating
Exceptional
(6 reviews)
The Villa at The Ranch Almaden beautiful winery location
San Jose, CA
9% off
Price is AU$40,337
AU$40,337
AU$5,762 per night
includes taxes & fees
Image gallery for Evergreen Area - Spacious, Convenient for Family and Business
9.29.2 out of 10 rating
Wonderful
(5 reviews)
Evergreen Area - Spacious, Convenient for Family and Business
San Jose, CA
12% off
Price is AU$4,090
AU$4,090
AU$584 per night
includes taxes & fees
Image gallery for Modern 2Bed/1Bath bungalow style suite in Willow Glen
9.69.6 out of 10 rating
Exceptional
(30 reviews)
Modern 2Bed/1Bath bungalow style suite in Willow Glen
San Jose, CA
6% off
Price is AU$1,823
AU$1,823
AU$260 per night
includes taxes & fees
Image gallery for Wow! Beautiful house at Great Location, Much Bigger and Better than A Hotel!
1010 out of 10 rating
Exceptional
(5 reviews)
Wow! Beautiful house at Great Location, Much Bigger and Better than A Hotel!
San Jose, CA
12% off
Price is AU$6,396
AU$6,396
AU$914 per night
includes taxes & fees
Image gallery for Two Bedroom One Bath Condo ~ "Home Away From Home"
9.69.6 out of 10 rating
Exceptional
(33 reviews)
Two Bedroom One Bath Condo ~ "Home Away From Home"
San Jose, CA
7% off
Price is AU$2,037
AU$2,037
AU$291 per night
includes taxes & fees
Image gallery for Spacious 3bed/3bath w/ Library Served as extra Bedroom Home in Willow Glen!
9.49.4 out of 10 rating
Exceptional
(26 reviews)
Spacious 3bed/3bath w/ Library Served as extra Bedroom Home in Willow Glen!
San Jose, CA
6% off
Price is AU$3,969
AU$3,969
AU$567 per night
includes taxes & fees
Image gallery for Quiet 2B2.5 townhome in San Jose
8.08.0 out of 10 rating
Very good
(7 reviews)
Quiet 2B2.5 townhome in San Jose
San Jose, CA
7% off
Price is AU$2,589
AU$2,589
AU$370 per night
includes taxes & fees
Image gallery for Private Willow Glen Studio Guesthouse
1010 out of 10 rating
Exceptional
(54 reviews)
Private Willow Glen Studio Guesthouse
San Jose, CA
8% off
Price is AU$1,676
AU$1,676
AU$239 per night
includes taxes & fees
Image gallery for @ Marbella Lane -SiliconValley 3BR Gem in SJ
8.68.6 out of 10 rating
Excellent
(10 reviews)
@ Marbella Lane -SiliconValley 3BR Gem in SJ
San Jose, California
14% off
Price is AU$2,685
AU$2,685
AU$384 per night
includes taxes & fees
Image gallery for @ Marbella Lane - NEW! 3BR CozyRetreat in DTWN SJ
8.08.0 out of 10 rating
Very good
(11 reviews)
@ Marbella Lane - NEW! 3BR CozyRetreat in DTWN SJ
San Jose, California
14% off
Price is AU$2,741
AU$2,741
AU$392 per night
includes taxes & fees
Image gallery for Charming House in San Jose Evergreen 5Br/3Bt 8Beds
9.09.0 out of 10 rating
Wonderful
(21 reviews)
Charming House in San Jose Evergreen 5Br/3Bt 8Beds
San Jose, CA
7% off
Price is AU$3,697
AU$3,697
AU$528 per night
includes taxes & fees
Image gallery for @ Marbella Lane - 2BR LwrLvl | DTWN SJ | Ldry + P
9.89.8 out of 10 rating
Exceptional
(6 reviews)
@ Marbella Lane - 2BR LwrLvl | DTWN SJ | Ldry + P
San Jose, California
14% off
Price is AU$2,150
AU$2,150
AU$307 per night
includes taxes & fees
Image gallery for Best Location - Walk to Downtown Willow Glen - Cozy Covered Balcony
9.69.6 out of 10 rating
Exceptional
(96 reviews)
Best Location - Walk to Downtown Willow Glen - Cozy Covered Balcony
San Jose, CA
8% off
Price is AU$5,343
AU$5,343
AU$763 per night
includes taxes & fees
Image gallery for Willow Glen Hideaway
8.48.4 out of 10 rating
Very good
(8 reviews)
Willow Glen Hideaway
San Jose, CA
10% off
Price is AU$1,580
AU$1,580
AU$226 per night
includes taxes & fees
Image gallery for Cozy Bungalow in Willow Glen
8.48.4 out of 10 rating
Very good
(25 reviews)
Cozy Bungalow in Willow Glen
San Jose, CA
8% off
Price is AU$2,409
AU$2,409
AU$344 per night
includes taxes & fees
Image gallery for Beautiful 2-Bedrooms Guesthouse Nearby Down Town San Jose
8.48.4 out of 10 rating
Very good
(9 reviews)
Beautiful 2-Bedrooms Guesthouse Nearby Down Town San Jose
San Jose, CA
7% off
Price is AU$1,199
AU$1,199
AU$171 per night
includes taxes & fees
Image gallery for @ Marbella Lane - 3BR UpprLvl | DTWN SJ | Ldry + P
9.69.6 out of 10 rating
Exceptional
(21 reviews)
@ Marbella Lane - 3BR UpprLvl | DTWN SJ | Ldry + P
San Jose, California
15% off
Price is AU$3,015
AU$3,015
AU$431 per night
includes taxes & fees
Image gallery for Modern smart home in downtown SJ near Airport
8.88.8 out of 10 rating
Excellent
(10 reviews)
Modern smart home in downtown SJ near Airport
San Jose, CA
8% off
Price is AU$3,665
AU$3,665
AU$524 per night
includes taxes & fees
Image gallery for Serene 2BR Bungalow - Parking + Laundry + Sleep 6
9.69.6 out of 10 rating
Exceptional
(5 reviews)
Serene 2BR Bungalow - Parking + Laundry + Sleep 6
San Jose, CA
8% off
Price is AU$2,339
AU$2,339
AU$334 per night
includes taxes & fees
Image gallery for @ Marbella Lane - 6BR Duplex | DTWN SJ | Laundry + P
9.69.6 out of 10 rating
Exceptional
(5 reviews)
@ Marbella Lane - 6BR Duplex | DTWN SJ | Laundry + P
San Jose, California
15% off
Price is AU$6,009
AU$6,009
AU$858 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Montgomery Hill
Enchanted Redwood Retreat Nature Suite
Sleeps 7 · 3 bedrooms · 2 bathrooms
9.49.4 out of 10
Exceptionalexceptional
Morgan Hill Gem: Spacious 2-BR with stunning view, family and pet friendly.
Sleeps 6 · 2 bedrooms · 1 bathroom
9.09.0 out of 10
Wonderfulwonderful
11 reviews(11 reviews)
Tuscan villa nestled in the vineyard - Villa Riposo
Sleeps 10 · 4 bedrooms · 2 bathrooms
9.69.6 out of 10
Exceptionalexceptional
5 reviews(5 reviews)
Peaceful Place to Relax
Sleeps 8 · 4 bedrooms · 4 bathrooms
9.89.8 out of 10
Exceptionalexceptional
7 reviews(7 reviews)
Luxury Villa: Silicon Valley's 30-Acre Eden of Paradise:Lake Views & Events
Sleeps 10 · 5 bedrooms · 5 bathrooms
1010 out of 10
Exceptionalexceptional
9 reviews(9 reviews)
6 bdrm Farmhouse Estate with pool, bocce, pickle ball, hot tub & more!
Sleeps 15 · 6 bedrooms · 5 bathrooms
9.69.6 out of 10
Exceptionalexceptional
65 reviews(65 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, gardens and more
More for lessMore space, more privacy, more amenities — more value