Vacations Close To Castle Island

Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*

Choose two or more items and save on your trip:

Castle Island Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Sunbird Cape Cod Resort

Sunbird Cape Cod Resort

2.5 out of 5
Price was $876, price is now $708 per person
$708
per person
Aug 24 - Aug 28
found 1 day ago
Roundtrip flight included
Chicago (MDW) to Boston (BOS)
They never said anything about putting a card on your door if you wanted your room cleaned

Reviewed on Jul 7, 2026

Sea Crest Beach Resort

Sea Crest Beach Resort

3.5 out of 5
Save 100% on your flight
Price was $1,572, price is now $1,191 per person
$1,191
per person
Aug 24 - Aug 28
found 1 day ago
Roundtrip flight included
Chicago (MDW) to Boston (BOS)
Great location

Reviewed on Jul 9, 2026

The Cape Club Resort

The Cape Club Resort

2 out of 5
Price was $1,288, price is now $1,014 per person
$1,014
per person
Aug 24 - Aug 28
found 1 day ago
Roundtrip flight included
Chicago (MDW) to Boston (BOS)
Great place

Reviewed on Jul 6, 2026

Centerboard

Centerboard

2 out of 5
Nantucket Town
Save 100% on your flight
Price was $2,138, price is now $1,724 per person
$1,724
per person
Aug 24 - Aug 28
found 1 day ago
Roundtrip flight included
Chicago (MDW) to Boston (BOS)
A+ Room 3 was so quiet & perfect for me for a solo business traveler - would be nice for a couple too - thank you for a lovely stay - see you again soon!

Reviewed on Jul 9, 2026

Green Harbor Resort

Green Harbor Resort

3 out of 5
Price was $1,621, price is now $1,381 per person
$1,381
per person
Aug 24 - Aug 28
found 1 day ago
Roundtrip flight included
Chicago (MDW) to Boston (BOS)
Great spot ! Beautiful beach

Reviewed on Jul 4, 2026

The Coonamessett

The Coonamessett

3.5 out of 5
Price was $1,387, price is now $1,196 per person
$1,196
per person
Aug 24 - Aug 28
found 1 day ago
Roundtrip flight included
Chicago (MDW) to Boston (BOS)

Riviera Beach Resort

Riviera Beach Resort

3 out of 5
Bass River
Price was $1,459, price is now $1,259 per person
$1,259
per person
Aug 24 - Aug 28
found 1 day ago
Roundtrip flight included
Chicago (MDW) to Boston (BOS)
Great view of pool and beach from our 2nd floor room. Highly recommended. We will definitely go back.

Reviewed on Jul 8, 2026

AutoCamp Cape Cod

AutoCamp Cape Cod

4 out of 5
Price was $1,100, price is now $954 per person
$954
per person
Aug 24 - Aug 28
found 1 day ago
Roundtrip flight included
Chicago (MDW) to Boston (BOS)
Great place to stay. Helpful staff

Reviewed on Jul 7, 2026

Don't see what you're looking for?
See all available trips from Columbus to Castle Island
View all trips

Best Lodging Options Near Castle Island

Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane Boston MA
2.42 km from Castle Island
Book a stay at this business-friendly hotel in Boston. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the breakfast and the restaurant ...
Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

5 out of 5
450 Summer Street Boston MA
2.45 km from Castle Island
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, a full-service spa, and 4 restaurants. Our guests praise the breakfast and the pool in our reviews. ...
The Westin Boston Seaport District

The Westin Boston Seaport District

4 out of 5
425 Summer St Boston MA
2.43 km from Castle Island
Book a stay at this business-friendly hotel in Boston. Enjoy 2 bars/lounges, breakfast (surcharge), and room service. Our guests praise the breakfast and the ...
Hyatt Place Boston/Seaport District

Hyatt Place Boston/Seaport District

3 out of 5
295 NORTHERN AVENUE Boston MA
2.03 km from Castle Island
Book a stay at this business-friendly hotel in Boston. Enjoy free breakfast, free WiFi, and a rooftop terrace. Our guests praise the breakfast and the helpful ...
Hampton by Hilton at the Boston Seaport District

Hampton by Hilton at the Boston Seaport District

3 out of 5
670 Summer Street Boston MA
1.95 km from Castle Island
Book a stay at this business-friendly hotel in Boston. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the ...
The Langham, Boston

The Langham, Boston

5 out of 5
250 Franklin St Boston MA
3.78 km from Castle Island
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms ...
Hyatt Regency Boston Harbor

Hyatt Regency Boston Harbor

4 out of 5
101 Harborside Drive Boston MA
2.48 km from Castle Island
Stay at this hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the restaurant and the helpful staff in our ...
Harborside Inn Of Boston

Harborside Inn Of Boston

4 out of 5
185 State St Boston MA
3.84 km from Castle Island
Stay at this hotel in Boston. Enjoy free WiFi, a 24-hour front desk, and a business center. Our guests praise the breakfast and the restaurant in our reviews. ...
Don't see what you're looking for?
See all available properties in Castle Island
View all properties
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.