Search Deals onLadys Island Vacation Packages
Ladys Island Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Royal Dunes Resort
Save 100% on your flight
Price was $986, price is now $670 per person
$670
per person
Sep 11 - Sep 15
found 15 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Savannah (SAV)
Book a stay at this family-friendly condo in Hilton Head Island. Enjoy free WiFi, 2 outdoor pools, and a fitness center. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Shelter Cove Harbour and Palmetto Dunes Club are located nearby.
Beautiful property. It is immaculately cleaned. The gym is great. Pools are fun and in excellent condition. Beach is less than a 10 min walk away.
Reviewed on Jul 18, 2026
The Cooper
Save 100% on your flight
Price was $1,961, price is now $1,261 per person
$1,261
per person
Sep 2 - Sep 5
found 1 day ago
Roundtrip flight included
Boston (BOS) to Charleston (CHS)
Book a stay at this luxury hotel in Charleston. Enjoy free WiFi, a full-service spa, and 3 restaurants. Popular attractions Waterfront Park and Port of Charleston are located nearby.
From the moment we arrived until the day we departed, we had the most exceptional service! Every need was met, every whim catered to, and extras we weren't expecting!
It has been a very long time since I have had service like this!
Especially loved how welcoming, accommodating, and loving the staff was with my daughter's Golden Retriever, Josie! I think she may have been pampered more than we were.
Reviewed on Jul 16, 2026
The Ryder Hotel
Save 100% on your flight
Price was $1,267, price is now $848 per person
$848
per person
Sep 6 - Sep 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Charleston (CHS)
Stay at this hotel in Charleston. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Charleston City Market and Port of Charleston are located nearby.
Lighthouse by Avantstay Beachfront View Home w/ Pool Table & Ping Pong
Save 100% on your flight
Price was $7,486, price is now $5,287 per person
$5,287
per person
Aug 29 - Sep 3
just found
Roundtrip flight included
Boston (BOS) to Charleston (CHS)
Book a stay at this beach cottage in Folly Beach. Enjoy free parking, a beach locale, and concierge services. Popular attractions Folly Island Beaches and Folly River Park are located nearby.
Ocean View at Island Club
Save 100% on your flight
Price was $1,451, price is now $1,033 per person
$1,033
per person
Aug 23 - Aug 29
found 21 hours ago
Roundtrip flight included
Boston (BOS) to Savannah (SAV)
Book a stay at this beach condo in Hilton Head Island. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Shelter Cove Harbour and Palmetto Dunes Club are located nearby.
Front desk customer service was awful. The worst
Reviewed on May 12, 2026
The Pinch Hotel
Save 100% on your flight
Price was $2,196, price is now $1,599 per person
$1,599
per person
Sep 21 - Sep 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to Charleston (CHS)
Book a stay at this spa hotel in Charleston. Enjoy free breakfast, free WiFi, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions Charleston City Market and Port of Charleston are located nearby.
So well pointed. So professional. Great location. Highest recommendation I can get.
Reviewed on Jul 8, 2026
Sparrow Haus by Avantstay Luxe Isle of Palms Retreat Pool + Firepit + Outdoor Lounge
Save 100% on your flight
Price was $5,860, price is now $4,286 per person
$4,286
per person
Sep 21 - Sep 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to Charleston (CHS)
Stay at this cottage in Isle of Palms. Enjoy free parking, patios, and in-room washers/dryers. Popular attractions Isle of Palms Beach and Front Beach are located nearby.
JW Marriott Savannah Plant Riverside District
Save 100% on your flight
Price was $1,398, price is now $1,026 per person
$1,026
per person
Oct 1 - Oct 5
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Savannah (SAV)
Book a stay at this luxury hotel in Savannah. Enjoy free WiFi, a full-service spa, and 12 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions River Street and City Market are located nearby.
Staff and property were very nice. Only complaint was the unbelievably loud music being played by cars on Saturday night 11 pm-1:30 am.
Reviewed on Jul 20, 2026
Ladys Island Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Ladys Island Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Fri, Sep 11 - Fri, Sep 11
BDL
Bradley Intl.
CHS
Charleston Intl.
$104 Roundtrip, found 1 day ago
$104
Roundtrip
found 1 day ago
Thu, Oct 1 - Sun, Oct 4
TTN
Mercer
CHS
Charleston Intl.
$132 Roundtrip, found 2 days ago
$132
Roundtrip
found 2 days ago
Wed, Sep 9 - Sat, Sep 12
BDL
Bradley Intl.
SAV
Savannah - Hilton Head Intl.
$168 Roundtrip, found 3 days ago
$168
Roundtrip
found 3 days ago
Tue, Sep 8 - Sat, Sep 12
DCA
Ronald Reagan Washington National
CHS
Charleston Intl.
$200 Roundtrip, found 19 hours ago
$200
Roundtrip
found 19 hours ago
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