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Round O Vacation Packages

Build your package with 2 more options

Round O Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Club Wyndham Ocean Ridge

Club Wyndham Ocean Ridge

3.5 out of 5
Price was $1,634, price is now $1,266 per person
$1,266
per person
Dec 27 - Jan 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Charleston (CHS)
Book a stay at this golf hotel in Edisto Island. Enjoy free WiFi, free parking, and 3 outdoor pools. Popular attractions Edisto Beach State Park and Botany Bay Plantation Heritage Preserve and Wildlife Management Area are located nearby.
The room was clean and spacious for 2 people. Loved renting bikes and riding the paths the island has. It's NICE & QUIET. If you're looking for alot of action you need to go somewhere else. It's a layed back family beach. Hope it can stay that way. FYI...... their is a sale pitch for the time share buy in. JUST SAY NO!

Reviewed on May 22, 2026

The Ryder Hotel

The Ryder Hotel

3.5 out of 5
Save 100% on your flight
Price was $2,127, price is now $1,427 per person
$1,427
per person
Dec 27 - Jan 3
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 Waterfront Park are located nearby.

The Charleston Place

The Charleston Place

5 out of 5
Save 100% on your flight
Price was $4,335, price is now $3,207 per person
$3,207
per person
Dec 27 - Jan 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Charleston (CHS)
Book a stay at this luxury hotel in Charleston. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Charleston City Market and Waterfront Park are located nearby.
To have a luxury hotel like this that is privately owned and not a massive corporate feel is awesome. We love the Charleston place and all the changes they have been making over the past few years. Beautiful property great vibe and quiet luxury.

Reviewed on Oct 18, 2026

Emeline

Emeline

4 out of 5
Price was $2,223, price is now $1,666 per person
$1,666
per person
Dec 27 - Jan 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Charleston (CHS)
Book a stay at this luxury hotel in Charleston. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Charleston City Market and Waterfront Park are located nearby.

The Ansonborough

The Ansonborough

4 out of 5
Save 100% on your flight
Price was $2,648, price is now $2,044 per person
$2,044
per person
Dec 27 - Jan 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Charleston (CHS)
Book a stay at this business-friendly hotel in Charleston. Enjoy free breakfast, free WiFi, and a rooftop terrace. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Charleston City Market and Waterfront Park are located nearby.

Andrew Pinckney Inn

Andrew Pinckney Inn

4 out of 5
Price was $2,051, price is now $1,635 per person
$1,635
per person
Dec 27 - Jan 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Charleston (CHS)
Book a stay at this business-friendly hotel in Charleston. Enjoy free breakfast, free WiFi, and valet parking (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Charleston City Market and Waterfront Park are located nearby.

The Restoration

The Restoration

4 out of 5
Price was $2,245, price is now $1,801 per person
$1,801
per person
Dec 27 - Jan 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Charleston (CHS)
Book a stay at this luxury hotel in Charleston. Enjoy free breakfast, free WiFi, and a rooftop terrace. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Charleston City Market and Waterfront Park are located nearby.
The property needs maintenance, staff need help.

Reviewed on Oct 19, 2026

Elliott House Inn

Elliott House Inn

4 out of 5
Price was $1,612, price is now $1,294 per person
$1,294
per person
Dec 26 - Dec 31
found 1 day ago
Roundtrip flight included
Boston (BOS) to Charleston (CHS)
Stay at this guesthouse in Charleston. Enjoy free WiFi, room service, and free bicycles on site. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Charleston City Market and Waterfront Park are located nearby.

Round O Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
The Ryder Hotel

The Ryder Hotel

3.5 out of 5
Charleston Historic District
Save 100% on your flight
Price was $949, price is now $684 per person
$684
per person
Dec 10 - Dec 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Charleston (CHS)
Emeline

Emeline

4 out of 5
Charleston Historic District
Price was $976, price is now $753 per person
$753
per person
Dec 10 - Dec 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Charleston (CHS)
The Charleston Place

The Charleston Place

5 out of 5
Charleston Historic District
Save 100% on your flight
Price was $2,112, price is now $1,643 per person
$1,643
per person
Dec 29 - Jan 1
found 15 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Charleston (CHS)
9 24th Avenue by Avantstay Walk to Beach + Pool + Rooftop Deck

9 24th Avenue by Avantstay Walk to Beach + Pool + Rooftop Deck

3 out of 5
Save 100% on your flight
Price was $3,464, price is now $2,796 per person
$2,796
per person
Dec 3 - Dec 7
found 8 hours ago
Roundtrip non-stop flight included
New York (NYC) to Charleston (CHS)

Round O Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
The Nicholas

The Nicholas

3 out of 5
Downtown Charleston
Save 100% on your flight
Price was $1,440, price is now $1,086 per person
$1,086
per person
Nov 26 - Dec 1
found 9 hours ago
Roundtrip flight included
New York (NYC) to Charleston (CHS)
The Ryder Hotel

The Ryder Hotel

3.5 out of 5
Charleston Historic District
Save 100% on your flight
Price was $2,127, price is now $1,427 per person
$1,427
per person
Dec 27 - Jan 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Charleston (CHS)
The Charleston Place

The Charleston Place

5 out of 5
Charleston Historic District
Save 100% on your flight
Price was $4,335, price is now $3,207 per person
$3,207
per person
Dec 27 - Jan 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Charleston (CHS)
Emeline

Emeline

4 out of 5
Charleston Historic District
Price was $2,223, price is now $1,666 per person
$1,666
per person
Dec 27 - Jan 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Charleston (CHS)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Breeze Airways
Fri, Jan 22 - Mon, Jan 25
BDL
Bradley Intl.
CHS
Charleston Intl.
$92 Roundtrip, found 1 day ago
$92
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Fri, Jan 22 from Bradley Intl. to Charleston Intl., returning Mon, Jan 25, priced at $92 found 1 day ago
Breeze Airways
Fri, Dec 4 - Mon, Dec 7
SWF
Stewart Intl.
CHS
Charleston Intl.
$142 Roundtrip, found 22 hours ago
$142
Roundtrip
found 22 hours ago
Select Breeze Airways flight, departing Fri, Dec 4 from Stewart Intl. to Charleston Intl., returning Mon, Dec 7, priced at $142 found 22 hours ago
United
Wed, Dec 2 - Tue, Dec 15
EWR
Newark Liberty Intl. Airport
CHS
Charleston Intl.
$199 Roundtrip, just found
$199
Roundtrip
just found
Select United flight, departing Wed, Dec 2 from Newark Liberty Intl. Airport to Charleston Intl., returning Tue, Dec 15, priced at $199 just found
Southwest Airlines
Tue, Nov 10 - Tue, Nov 17
LGA
LaGuardia
CHS
Charleston Intl.
$216 Roundtrip, just found
$216
Roundtrip
just found
Select Southwest Airlines flight, departing Tue, Nov 10 from LaGuardia to Charleston Intl., returning Tue, Nov 17, priced at $216 just found