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Madison flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
Saybrook Manor
Price was $668, price is now $527 per person
$527
per person
Dec 3 - Dec 8
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to New Haven (HVN)
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including an off-leash area. A picnic area is also provided.
Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
North End
Save 100% on your flight
Price was $3,710, price is now $1,966 per person
$1,966
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New Haven (HVN)
This vacation home doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a garden, and a communal living room are also on offer.
Las Flores Villa

Las Flores Villa

5 out of 5
Save 100% on your flight
Price was $7,136, price is now $4,414 per person
$4,414
per person
Nov 26 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to New Haven (HVN)
This vacation home features an outdoor pool and a hot tub. Families will appreciate the playground and onsite laundry facilities. Enjoy the sauna and perks like free self parking.
Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 out of 5
Westbrook Center
Save 100% on your flight
Price was $1,198, price is now $888 per person
$888
per person
Dec 3 - Dec 8
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to New Haven (HVN)
This smoke-free resort features a private beach, a full-service spa, and 3 restaurants. Relax with beach cabanas and sun loungers, and cool off with a drink at the beachside bar. Enjoy the 2 outdoor tennis courts and perks like free valet parking and free WiFi.
Head of Pond House

Head of Pond House

3 out of 5
Price was $1,237, price is now $934 per person
$934
per person
Dec 3 - Dec 8
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to New Haven (HVN)
A seasonal outdoor pool is featured at this bed & breakfast, along with free self parking. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A terrace, a garden, and a communal living room are also on offer.

Top Madison hotels deals

Madison Beach Hotel

Madison Beach Hotel

4 out of 5
94 West Wharf Road Madison CT
$450 nightly
The price is $518 total per night
$518 total
Oct 7 - Oct 8
Total with taxes and fees
This smoke-free hotel features a private beach, a full-service spa, and a restaurant. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Enjoy the 24-hour gym and perks like free WiFi.
On private beach
Spa
New Haven Hotel

New Haven Hotel

3.5 out of 5
229 George Street New Haven CT
Free Cancellation
Reserve now, pay when you stay
$139 nightly
The price is $160 total per night
$160 total
Sep 21 - Sep 22
Total with taxes and fees
A gym, self parking, and laundry facilities are featured at this hotel. WiFi in public areas is free. Traveling on business? Take advantage of the 2 conference rooms, along with dry cleaning/laundry services.
Pet friendly
Free WiFi
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48 Greenport NY
$262 nightly
The price is $299 total per night
$299 total
Oct 5 - Oct 6
Total with taxes and fees
A private beach and a restaurant are featured at this smoke-free hotel. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Unwind with a drink at one of the 2 bars/lounges and enjoy free perks like continental breakfast and WiFi in public areas.
On private beach
Pool
Hampton Inn & Suites New Haven - South - West Haven

Hampton Inn & Suites New Haven - South - West Haven

2.5 out of 5
510 Saw Mill Rd West Haven CT
Free Cancellation
Reserve now, pay when you stay
$135 nightly
The price is $155 total per night
$155 total
Sep 20 - Sep 21
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free buffet breakfast and free WiFi. Traveling on business? Take advantage of the express check-in and free internet in public areas. There's a gym on site, and a 24-hour front desk and a fireplace in the lobby are also provided.
Breakfast included
Pet friendly
Best Western Executive Hotel Of New Haven - West Haven

Best Western Executive Hotel Of New Haven - West Haven

2.5 out of 5
490 Saw Mill Rd West Haven CT
Free Cancellation
Reserve now, pay when you stay
$114 nightly
The price is $131 total per night
$131 total
Sep 29 - Sep 30
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like full breakfast and free self parking.
Pool
Breakfast included
Motel 6 New Haven - Branford, CT

Motel 6 New Haven - Branford, CT

2 out of 5
320 E Main St Branford CT
Free Cancellation
$71 nightly
The price is $82 total per night
$82 total
Sep 13 - Sep 14
Total with taxes and fees
A restaurant, free self parking, and a 24-hour front desk are among this motel's amenities. WiFi in public areas is free. A snack bar/deli is also provided.
Pet friendly
Parking included
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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.

Stay near popular Madison attractions

A rural landscape with a large fallen tree in the foreground, fields, and a forest in the background.
Photo by Shannon Willitts
Open Photo by Shannon Willitts

Hammonasset Beach State Park

8.8/10 (137 reviews)
You can take time to visit Hammonasset Beach State Park during your travels to Madison. While you're in the area, stroll along the beautiful beaches.
See properties

Frequently asked questions

How much are vacation packages to Madison?
Travelocity provides flight and hotel vacation packages starting as low as $527. With such amazing bargains, you'll be exploring all of Madison in no time.
How long should my Madison vacation be?
Around 2 nights is the average amount of time travelers vacation in Madison. But how long is right for you all depends on how many magical memories you want to create. Why not stay a couple of extra days and discover some hidden treasures?
Where can I get the best vacation package deals for Madison?
Picking up the perfect package deal to Madison couldn't be easier with Travelocity. With around 400 partner airlines and 1,000,000 properties worldwide, you're flush with choice when it comes to picking your flights and hotels.
Why should I book my Madison vacation bundle via Travelocity?
From our 24/7 customer support to our range of amazing destinations, we're committed to giving you the vacation of a lifetime. All you'll have to do is to click and book — our Price Match Guarantee will make sure you lock in the best price.
Can I save on my Madison car rental if I combine it with my hotel or flight?
With a Madison vacation package, you can bundle your hotel, car and flight bookings and save loads. If you'd love to discover the best of this impressive location, why not make a beeline for Times Square? This renowned attraction is 85 mi from Madison. With a rental car, you'll be there in a flash.
Which airport is best for Madison?
Bradley Intl. Airport (BDL) is one of the top airports for Madison. You'll find it 45 mi north of the buzzing city center. Your other choices are MacArthur Airport (ISP) (45 mi away from central Madison) and Tweed - New Haven Regional Airport (HVN) (17 mi away from central Madison).
What is there to do in Madison?
While veering off the tourist trail is rewarding, you really shouldn't miss the popular attractions that make a place famous. Hammonasset Beach State Park and Hammonasset Beach are just two of them in Madison.
Where should I stay when visiting Madison?
If you're searching for someplace comfortable to base yourself, consider the The Homestead. It's the top pick for many travelers.

Photos of local treasures

Browse Madison vacation photos for more inspiration

A cityscape at dusk with a prominent dome-shaped building, a waterfront, and a circular structure with multiple towers.
A calm lake at sunset with several sailboats anchored near the shore.
A coastal scene with a stone breakwater extending into the sea, a clear sky with wispy clouds, and a calm ocean.
A beach with boats, a sandy shore, and houses in the background.
A house surrounded by autumn-colored trees and a calm lake.

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