Exclusive Windsor Beach Vacation Deals

Windsor Beach vacation package deals

Price found within the past 48 hours. Click for updated prices.
Cambridge Beaches Resort & Spa

Cambridge Beaches Resort & Spa

4 out of 5
Save 100% on your flight
Price was $1,860, price is now $1,294 per person
$1,294
per person
Mar 19 - Mar 23
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to St. George's (BDA)
This smoke-free resort features a private beach, a full-service spa, and a marina. Traveling on business? Take advantage of the laundry service, conference space, and airport shuttle. Enjoy the 3 outdoor tennis courts and get free self parking.
The Reefs Resort & Club

The Reefs Resort & Club

4 out of 5
Save 100% on your flight
Price was $1,970, price is now $1,336 per person
$1,336
per person
Feb 11 - Feb 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to St. George's (BDA)
A full-service spa, 3 restaurants, and 2 outdoor tennis courts are all featured at this hotel. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Enjoy the outdoor pool and perks like free self parking and free WiFi.
Azura Bermuda

Azura Bermuda

4 out of 5
Save 100% on your flight
Price was $2,521, price is now $1,727 per person
$1,727
per person
Feb 11 - Feb 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to St. George's (BDA)
This smoke-free hotel features 4 outdoor pools, a gym, and a restaurant. Business travelers can take advantage of the free WiFi in public areas. Enjoy the a rooftop terrace and perks like free self parking.
Hamilton Princess & Beach Club - a Fairmont Managed Hotel

Hamilton Princess & Beach Club - a Fairmont Managed Hotel

4.5 out of 5
Save 100% on your flight
Price was $2,499, price is now $1,747 per person
$1,747
per person
Feb 11 - Feb 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to St. George's (BDA)
This smoke-free resort features a full-service spa, a marina, and 5 restaurants. Enjoy beachfront dining and relax with beach cabanas and sun loungers. There's fun for all ages with a children's club and a playground, and babysitting is an added bonus.
Hamilton Princess - Fairmont Gold Experience

Hamilton Princess - Fairmont Gold Experience

5 out of 5
Save 100% on your flight
Price was $3,427, price is now $2,453 per person
$2,453
per person
Feb 11 - Feb 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to St. George's (BDA)
A full-service spa, 3 restaurants, and 2 outdoor pools are all featured at this luxury hotel. Unwind with a drink at one of the 5 bars/lounges and enjoy free perks like free self parking and a beach shuttle. Enjoy the hot tub and unwind at the beach bar and poolside bar.
Newstead Belmont Hills Golf Resort & Spa

Newstead Belmont Hills Golf Resort & Spa

4 out of 5
Save 100% on your flight
Price was $2,319, price is now $1,671 per person
$1,671
per person
Feb 11 - Feb 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to St. George's (BDA)
This smoke-free hotel features a golf course, a full-service spa, and 2 restaurants. Traveling on business? Take advantage of the free WiFi in public areas and free internet in public areas. Enjoy the 2 outdoor tennis courts and get free self parking.

Frequently asked questions

How much are vacation packages to Windsor Beach?
Save on your visit to Windsor Beach by combining your flights and hotel into a $1,294 package. With all that extra money in your pocket, why not stay longer and explore even more?
Where can I get the best vacation package deals for Windsor Beach?
Travelocity is the only place you need to go to score a terrific Windsor Beach package deal. Select from as many as 400 air carriers and 1,000,000 properties worldwide and craft a vacation package that's suited to you. With so many options at hand, you'll have plenty of inspiration for your next big adventure.
Why should I book my Windsor Beach vacation package via Travelocity?
Because life is one amazing journey, and we have all you need to help get you on your way. With our superb service and Price Match Guarantee, you can organize your trip with confidence. What's more, you can rest easy while you're on the road knowing we've got you covered with our 24/7 customer support.

Top Windsor Beach hotel deals

Grotto Bay Beach Resort

Grotto Bay Beach Resort

4 out of 5
11 Blue Hole Hill Hamilton Parish
$305 nightly
The price is $345 total per night
$345 total
Jan 10 - Jan 11, 2026
Total with taxes and fees
This resort features a private beach, free water park access, and 3 restaurants. Relax with sun loungers and beach umbrellas, and cool off with a drink at the beachside bar. Relax with a drink at one of the 2 bars/lounges and enjoy free perks like free self parking and WiFi in public areas.
On private beach
Pool
Rosewood Bermuda

Rosewood Bermuda

5 out of 5
60 Tucker's Point Drive Hamilton Parish
$689 nightly
The price is $761 total per night
$761 total
Jan 11 - Jan 12, 2026
Total with taxes and fees
A full-service spa, 3 restaurants, and 2 outdoor pools are all featured at this luxury resort. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Enjoy the 4 outdoor tennis courts and perks like free valet parking and a free beach shuttle.
Pool
Spa
The Loren at Pink Beach

The Loren at Pink Beach

5 out of 5
116 South Shore Rd Smith's Parish
$539 nightly
The price is $598 total per night
$598 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
This luxury hotel features a private beach, a full-service spa, and 2 restaurants. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Bring the family and enjoy the free kid's club, children's pool, and kid-friendly dining.
On private beach
Pool
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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.