Winchester Trip
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Top Winchester Flight + Hotel Deals
Price found within the past 48 hours. Click for updated prices.
Porto Vista Hotel Downtown
Downtown San Diego
Save 100% on your flight
Price was ₹138,026, price is now ₹96,621 per person
₹96,621
per person
14 Jul - 19 Jul
found 10 hours ago
Return direct flight included
Chicago (ORD) to San Diego (SAN)
7.2/10 Good! (1,302 reviews)
The hotel is centrally located in Little Italy and the property is very clean, but the restaurant never seemed open, the curtains don't provide sufficient blocking of the sun, and the hotel is essentially a nicer motel with exterior doors. The beds are clean, though the mattresses are extremely hard and uncomfortable.
Reviewed on 29 May 2026
Margaritaville Hotel San Diego Gaslamp Quarter
Downtown San Diego
Save 100% on your flight
Price was ₹212,320, price is now ₹135,479 per person
₹135,479
per person
14 Jul - 19 Jul
found 10 hours ago
Return direct flight included
Chicago (ORD) to San Diego (SAN)
9/10 Wonderful! (1,377 reviews)
The room was super clean and the decoration was very nice. The location was very convenient to all the places I need to visit. It was a comfortable stay for a business trip.
Reviewed on 4 Jun 2026
Kona Kai San Diego
Point Loma
Save 100% on your flight
Price was ₹158,425, price is now ₹105,251 per person
₹105,251
per person
14 Jul - 19 Jul
found 10 hours ago
Return direct flight included
Chicago (ORD) to San Diego (SAN)
8.2/10 Very Good! (1,003 reviews)
If you are there midweek before June 1, plan for the advertised amenities to be closed. Unfortunately, I was unaware of this and so the adult pool did not have food and beverage service, and similar issues throughout my stay.
Reviewed on 27 May 2026
Urban Boutique Hotel
Downtown San Diego
Save 100% on your flight
Price was ₹148,793, price is now ₹100,532 per person
₹100,532
per person
14 Jul - 19 Jul
found 10 hours ago
Return direct flight included
Chicago (ORD) to San Diego (SAN)
8.6/10 Excellent! (1,283 reviews)
This property was very well maintained very clean very safe. Excellent staff I would stay there again.
Reviewed on 31 May 2026
Surfer Beach Hotel
Pacific Beach
Save 100% on your flight
Price was ₹156,044, price is now ₹109,018 per person
₹109,018
per person
14 Jul - 19 Jul
found 10 hours ago
Return direct flight included
Chicago (ORD) to San Diego (SAN)
8.2/10 Very Good! (1,289 reviews)
Efficiently clean, next to the beach. Pet fees, parking fees in lot area.
Reviewed on 4 Jun 2026
Top hotels in Winchester
Pala Casino Spa And Resort
11154 Highway 76 Valley Center CA
Fully refundableReserve now, pay when you stay
The price is ₹12,415 per night from 8 Jun to 9 Jun
₹12,415
₹15,323 total
8 Jun - 9 Jun
includes taxes & fees
8.8/10 Excellent! (4,647 reviews)
"The check in was smooth, but we found it a little interesting they will charge you $1000 of you smoke or vape in the room but the casino smells like full on cigarettes. But that was big a deal breaker. The overall casino and hotel was great. We enjoyed a few drinks by the pool and ate at the cafe. ..."
Reviewed on 6 Jun 2026
Signature Temecula
28980 Old Town Front St. Temecula CA
Fully refundableReserve now, pay when you stay
The price is ₹8,450 per night from 16 Jun to 17 Jun
₹8,450
₹9,464 total
16 Jun - 17 Jun
includes taxes & fees
8.8/10 Excellent! (1,842 reviews)
"Love it"
Reviewed on 6 Jun 2026
Motel 6 Temecula, CA - Historic Old Town
41900 Moreno Rd Temecula CA
Fully refundableReserve now, pay when you stay
The price is ₹5,411 per night from 22 Jun to 23 Jun
₹5,411
₹6,074 total
22 Jun - 23 Jun
includes taxes & fees
8.2/10 Very Good! (2,109 reviews)
"Walking distance to old town temecula. Great prices for the location. We had a bad experience with neighbors screaming outside our room, making inappropriate comments and felt unsafe."
Reviewed on 5 Jun 2026
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
