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San Gregorio Vacation Rentals

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Nov 17 - Nov 18
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Nov 21 - Nov 23
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Nov 28 - Nov 30

Vacation Rentals in San Gregorio

Exterior
Mid Century Garden View Home Parking

Mid Century Garden View Home Parking

2.0 star property
East San Mateo
8.8 out of 10, Excellent, (3)
"This is a very clean comfortable property! "
United States
Serena
$254 nightly
The price is $291
Nov 20 - Nov 21
Total with taxes and fees
Mid Century Garden View Home Parking
1 bedroom, desk, iron/ironing board, free WiFi
"Queens Palace" Studio Apt Business Ready - San Jose

"Queens Palace" Studio Apt Business Ready - San Jose

San Tomas
10.0 out of 10, Exceptional, (5)
"Good clean property and check in was easy"
United States
Brij P.
$153 nightly
The price is $153
Nov 19 - Nov 20
Total with taxes and fees
"Queens Palace" Studio Apt Business Ready - San Jose
Yurt On Top - Swim, Hike, Glamp | 1 bedroom, free WiFi
Mays Luxury Farm Stays

Mays Luxury Farm Stays

2.0 star property
Los Gatos
10.0 out of 10, Exceptional, (2)
"What an amazing experience, the host was helpful and attentive to us, whatever we needed was provided promptly. Can't wait to return"
United States
Joie
$210 nightly
The price is $235
Nov 19 - Nov 20
Total with taxes and fees
Mays Luxury Farm Stays
Beach
Nantucket Penthouse - walk to restaurants, beaches, activies & so much more

Nantucket Penthouse - walk to restaurants, beaches, activies & so much more

Half Moon Bay
9.4 out of 10, Exceptional, (35)
"The stay was great, would recommend for quick getaway. "
United States
Kiera E.
$642 nightly
The price is $685
Nov 22 - Nov 23
Total with taxes and fees
Nantucket Penthouse - walk to restaurants, beaches, activies & so much more
Outdoor dining
Either Way Hideaway

Either Way Hideaway

2.0 star property
Boulder Creek
10.0 out of 10, Exceptional, (11)
"Beautiful location, perfect for a peaceful get away.Great hosts!"
United States
Cristina W.
$307 nightly
The price is $327
Nov 25 - Nov 26
Total with taxes and fees
Either Way Hideaway
Exterior
Small Home with Ocean View walk to Restaurants, Brewery, Shops, Beach

Small Home with Ocean View walk to Restaurants, Brewery, Shops, Beach

Pedro Point
9.4 out of 10, Exceptional, (3)
"This place had a great location beautiful view of the ocean it was very cozy "
United States
tammy k.
$276 nightly
The price is $288
Nov 20 - Nov 21
Total with taxes and fees
Small Home with Ocean View walk to Restaurants, Brewery, Shops, Beach
1 bedroom, in-room safe, desk, iron/ironing board
Palo Alto Cottage: Privacy, Comfort & Convenience

Palo Alto Cottage: Privacy, Comfort & Convenience

Midtown
9.6 out of 10, Exceptional, (5)
"Beautiful and great! Friendly hosts"
United States
C D.
$214 nightly
The price is $214
Dec 1 - Dec 2
Total with taxes and fees
Palo Alto Cottage: Privacy, Comfort & Convenience
Dining
Luxury stay near Santana Row for vacation/business

Luxury stay near Santana Row for vacation/business

West San Jose
9.2 out of 10, Wonderful, (50)
"Host was great and very communicative during our stay! Home was clean and felt very cozy! "
United States
Gisselle
$232 nightly
The price is $253
Nov 19 - Nov 20
Total with taxes and fees
Luxury stay near Santana Row for vacation/business
Outdoor dining
Cozy Home - in the redwoods with hot tub!

Cozy Home - in the redwoods with hot tub!

Boulder Creek
9.8 out of 10, Exceptional, (122)
"Very clean home. Beautifully furnished. Nice stay!"
United States
Tran
$497 nightly
The price is $555
Nov 19 - Nov 20
Total with taxes and fees
Cozy Home - in the redwoods with hot tub!
Terrace/patio
Brand New Private One Bedroom Cottage with a Wet Bar/Kitchenette

Brand New Private One Bedroom Cottage with a Wet Bar/Kitchenette

Cupertino
9.6 out of 10, Exceptional, (4)
"This property is located in a residential and quiet neighborhood with a nice park within walking distance! Great place for someone who is traveling by themselves!"
United States
Kevin
$298 nightly
The price is $330
Nov 19 - Nov 20
Total with taxes and fees
Brand New Private One Bedroom Cottage with a Wet Bar/Kitchenette
Private kitchen
Affordable Ground Floor Unit In The Heart Of HMB Downtown: Former Mayor's House

Affordable Ground Floor Unit In The Heart Of HMB Downtown: Former Mayor's House

Half Moon Bay
9.0 out of 10, Wonderful, (4)
"Location, clean rooms,"
United States
Sheridan D.
$170 nightly
The price is $170
Nov 23 - Nov 24
Total with taxes and fees
Affordable Ground Floor Unit In The Heart Of HMB Downtown: Former Mayor's House
Private kitchen
Spacious estate near charming downtown Saratoga and the Montalvo Arts Center.

Spacious estate near charming downtown Saratoga and the Montalvo Arts Center.

Saratoga
$9,057 nightly
The price is $9,057
Nov 19 - Nov 20
Total with taxes and fees
Spacious estate near charming downtown Saratoga and the Montalvo Arts Center.
1 bedroom, iron/ironing board, WiFi, bed sheets
Small Beach Cottage near the Coastal Trail and The Ritz

Small Beach Cottage near the Coastal Trail and The Ritz

Half Moon Bay
9.8 out of 10, Exceptional, (113)
"We loved it!"
United States
Mimi H.
$301 nightly
The price is $342
Nov 30 - Dec 1
Total with taxes and fees
Small Beach Cottage near the Coastal Trail and The Ritz
Terrace/patio
Oceanview Penthouse, Stylish & Walking to Beach

Oceanview Penthouse, Stylish & Walking to Beach

El Granada
10.0 out of 10, Exceptional, (35)
"This place is amazing.. great place to stay and enjoy your anniversary "
United States
anthony
$320 nightly
The price is $320
Nov 19 - Nov 20
Total with taxes and fees
Oceanview Penthouse, Stylish & Walking to Beach
Terrace/patio
2 Bedroom Treehouse Cottage

2 Bedroom Treehouse Cottage

Belmont
9.0 out of 10, Wonderful, (2)
"The house is very comfortable and very clean. It contains everything a traveler needs. We arrived at night and had difficulty to locate the place, as there are other residences on the same lot. The Tree House is at the very top, so requires walking up four flights of stairs (65 steps in all), which we did not realize when we first arrived. But it is unique and a fun place to stay, in a nice area. We saw deer around the property three times during our short stay. Still, stores, restaurants...
United States
Jay S.
$286 nightly
The price is $295
Nov 22 - Nov 23
Total with taxes and fees
2 Bedroom Treehouse Cottage
Beach nearby
Stunning Oceanview Coastal Home – Beach, Trails, Family Activities

Stunning Oceanview Coastal Home – Beach, Trails, Family Activities

Montara
9.2 out of 10, Wonderful, (78)
"Nice area to be with beaches and hiking. 20-30 minutes to San Francisco. Quiet area for a restful sleep 2 of us. Room for kids also."
United States
Bob And Polly G.
$285 nightly
The price is $296
Dec 2 - Dec 3
Total with taxes and fees
Stunning Oceanview Coastal Home – Beach, Trails, Family Activities
Terrace/patio
Cozy guest suite in Los Gatos - Beach in 30 min!

Cozy guest suite in Los Gatos - Beach in 30 min!

Los Gatos
8.2 out of 10, Very Good, (11)
"We enjoyed our brief stay here and loved the beautiful view. Host was helpful in providing directions to get to the property."
United States
Kristina L.
$203 nightly
The price is $216
Nov 19 - Nov 20
Total with taxes and fees
Cozy guest suite in Los Gatos - Beach in 30 min!
Fridge, microwave, oven, stovetop
Posh place near Santana Row for vacation/business

Posh place near Santana Row for vacation/business

West San Jose
9.6 out of 10, Exceptional, (22)
"Nice place and close to Santana Row. Also nice to be close to freeway exit"
United States
Hee Sung K.
$236 nightly
The price is $257
Nov 19 - Nov 20
Total with taxes and fees
Posh place near Santana Row for vacation/business
Beach
Modern Coastal Retreat, Walk to Downtown HMB & Beach

Modern Coastal Retreat, Walk to Downtown HMB & Beach

2.0 star property
Half Moon Bay
10.0 out of 10, Exceptional, (6)
"Beach nearby. Very clean and nice vacation rental. The hosts really care about their guests and it shows. "
United States
Angela
$324 nightly
The price is $347
Nov 23 - Nov 24
Total with taxes and fees
Modern Coastal Retreat, Walk to Downtown HMB & Beach
Outdoor dining
Mavericks Penthouse – Downtown Luxury on Main Street, Half Moon Bay

Mavericks Penthouse – Downtown Luxury on Main Street, Half Moon Bay

Half Moon Bay
9.8 out of 10, Exceptional, (7)
"Great place "
United States
Marie S.
$245 nightly
The price is $252
Nov 25 - Nov 26
Total with taxes and fees
Mavericks Penthouse – Downtown Luxury on Main Street, Half Moon Bay
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top San Gregorio Hotel Reviews

Maple Tree Inn

Maple Tree Inn

10/10 Excellent
"Staff was very polite and courteous. Room is wonderful."
Kathi 1-night trip
Posted 23 hours ago
Maple Tree Inn

Find out more about San Gregorio

Everything you need to know about San Gregorio vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the San Gregorio vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect San Gregorio vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

San Gregorio vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in San Gregorio. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit San Gregorio in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $214 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on San Gregorio rentals

At Expedia, we put the best San Gregorio vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top San Gregorio rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream San Gregorio vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around San Gregorio. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Are there vacation rentals in San Gregorio?

Yes, we have vacation rentals close to the most popular points of interest in San Gregorio, or you can select a more secluded option if you're looking for relaxation. San Gregorio is known for its beaches and restaurants.

What are some of the best vacation home rentals in San Gregorio?

Distinguished Oceanfront Point Estate with Iconic Beach + Mountain Vistas: Visitors like this San Gregorio vacation home rental. It is located on the beach and has a fireplace, a balcony, and air-conditioning to put you at ease in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a hot tub.

What’s there to see and do in San Gregorio?

San Gregorio State Beach and Pomponio State Beach are a couple of lovely local spots to get outside and enjoy nature. Pescadero State Beach and Bean Hollow State Beach are a couple of places you'll find in the larger area.

What’s a vacation rental in San Gregorio like?

Vacation rentals are private properties where you can stay for a couple of days or more in San Gregorio. Vacation rentals feature extras such as patios, hot tubs, and fire pits so you'll have all the conveniences of home. If you're concerned about cleanliness, vacation rentals can offer a sense of security away from public hotel elevators and busy reception areas while still allowing you to travel. You'll also have more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive option for a family trip.