
Madison Vacations from $419
Book a Hotel + Flight or Car together to unlock savings
Your Madison Vacation
From its highlights to its hidden delights, this city is best experienced with a Madison vacation package. Find somewhere to stay in Chocorua, which is great for nature, families and views. Make your trip to Madison even more fulfilling by including some sightseeing. King Pine Ski Area, Saco River and Chocorua Lake are some of the big attractions worth exploring. Expedia can help you escape the everyday. Tailor your vacation to Madison to suit your style of travel, whatever that may be.
The Latest Madison vacation packages
Price found within the past 48 hours. Click for updated prices.

Portland Harbor Hotel
Downtown Portland
Save 100% on your flight
Price was $722, price is now $419 per person
$419
per person
Jan 7 - Jan 13
found 13 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
9.2/10 Wonderful! (1,621 reviews)
Staff was sub par for a 4 star hotel. Bartender and wait staff were more concerned about discussing issues with customers than actually serving people right in front of them. Front desk staff were very curt on the phone.
Reviewed on Oct 23, 2025

The McKernan Inn
Save 100% on your flight
Price was $888, price is now $542 per person
$542
per person
Jan 7 - Jan 13
found 13 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
9.2/10 Wonderful! (69 reviews)
Picturesque and quiet location!
Laundry facilities!
Staff was more than accommodating and a lovely ocean view with a delicious breakfast made for a memorable stay!
Reviewed on Oct 21, 2025

Cliff House Maine
Save 100% on your flight
Price was $1,753, price is now $1,151 per person
$1,151
per person
Jan 15 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Portland (PWM)
9.4/10 Exceptional! (1,016 reviews)
Absoltely incredible views- the cliffs were the perfect place to catch the sunrise. The restaurant was wonderful and the staff were super friendly and helpful. Extremely comfortable room and the hot tub and indoor pool were fantastic.
Reviewed on Oct 20, 2025

Holiday Inn Club Vacations Mount Ascutney Resort by IHG
Save 100% on your flight
Price was $1,236, price is now $848 per person
$848
per person
Dec 28 - Jan 2
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Lebanon (LEB)
9/10 Wonderful! (759 reviews)
The staff was very helpful, the place was comfortable with home amenities, view and property was breathtaking.
Reviewed on Oct 7, 2025

The Docent's Collection
Downtown Portland
Save 100% on your flight
Price was $920, price is now $647 per person
$647
per person
Jan 7 - Jan 13
found 13 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
9.6/10 Exceptional! (239 reviews)
Beautiful space. We will be back.
Reviewed on Oct 21, 2025
Madison Hotel Deals

Purity Spring Resort
1251 Eaton Rd, Madison, NH
Fully refundableReserve now, pay when you stay
$99 nightly
The price is $107 total per night from Nov 9 to Nov 10
$107 total
Nov 9 - Nov 10
Total with taxes and fees
8.6/10 Excellent! (187 reviews)
Very quiet and comfortable stay. Only disappointment was that the resort charges additional rental for on site canoes. I would expect that to be included for a facility of this level.
Reviewed on Oct 9, 2025

North Conway Grand Hotel
72 Common Court, North Conway, NH
Fully refundableReserve now, pay when you stay
$140 nightly
The price is $152 total per night from Nov 23 to Nov 24
$152 total
Nov 23 - Nov 24
Total with taxes and fees
8.2/10 Very Good! (1,030 reviews)
Did not ask for handicap room, but our stay was great. Enjoyed the upgraded outdoor area, convenience to shops. A beautiful spot, stayed here several times now. Only thought is, why the handicap room when we didn't request it? Will definitely return.
Reviewed on Oct 20, 2025

North Conway Mountain Inn
2114 White Mountain Highway, North Conway, NH
$99 nightly
The price is $107 total per night from Oct 31 to Nov 1
$107 total
Oct 31 - Nov 1
Total with taxes and fees
8.6/10 Excellent! (1,159 reviews)
This Inn in very quaint. Perfec!
Reviewed on Oct 19, 2025
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.
Find the Best Madison Vacation Packages
Madison Essential Information
Language | English |
---|---|
Currency | U.S dollars |
Population | 2,100 |
Max Temp Winter | 30ºF |
Max Temp Summer | 75ºF |
Top Sights | Cranmore Mountain Resort, Kahuna Laguna and Echo Lake State Park |
More vacations you might like
Frequently asked questions
Explore a world of travel with Expedia
- Hotels near Silver Lake Railroad
- Cabin Rentals in Silver Lake
- Silver Lake Hotels
- Cottages in Silver Lake
- Vacation Homes in Silver Lake
- B&B in Silver Lake
- Historic Hotels in Silver Lake
- Hotels on the Lake in Silver Lake
- Pet-friendly Hotels in Silver Lake
- 3 Star Hotels in Silver Lake
- Hotels with Free Parking in Silver Lake
- Romantic Hotels in Silver Lake
- Ski Hotels in Silver Lake
- Resorts & Hotels with Spas in Silver Lake
- Motels in Silver Lake
- Hotels with a Gym in Silver Lake
- Hotels with Restaurants in Silver Lake
- Hotels with an Indoor Pool in Silver Lake
- Hotels near Madison Boulder
- Hotels near Eidelweiss Village
- 3 Star Hotels in Eaton Center
- B&B in Eaton Center
- Eaton Center Hotels
- Hotel Wedding Venues Hotels in Eaton Center
- Cabin Rentals in Eaton Center
- Hotels with Free Parking in Eaton Center
- Hotels near King Pine Ski Area
- East Madison Hotels
- Apartments in East Madison
- Ski Hotels in East Madison
- Resorts & Hotels with Spas in East Madison
- Chocorua Hotels
- Condo Rentals in Chocorua
- Motels in Chocorua
- Cabin Rentals in Chocorua
- Resorts in Chocorua
- B&B in Chocorua
- 5 Star Hotels in Chocorua
- 3 Star Hotels in Chocorua
- Hotels near Chocorua Ski and Beach
- Hotels near Monkey Trunk Chocorua
- Hotels near Chocorua Lake
- Albany Hotels
- Cabin Rentals in Albany
- Cottages in Albany
- Resorts & Hotels with Spas in Albany
- Lodges in Albany
- Farmstay in Albany
- Resorts in Albany
- Condo Rentals in Albany
- Hotels & Resorts for Couples in Albany
- Quiet Resorts & in Albany
- Ski Hotels in Albany
- Chalets in Albany
- Guest Houses in Albany
- B&B in Snowville
- Snowville Hotels
- Resorts in Snowville
- Pet-friendly Hotels in Snowville
- Ski Hotels in Snowville
- Romantic Hotels in Snowville
- Cabin Rentals in Snowville
- Hotels near White Lake State Park
- Hotels near Tuckerman Brewery
- Silver Lake Railroad
- Silver Lake Vacations
- Visit Silver Lake
- Madison Boulder
- King Pine Ski Area
- Eaton Center Vacations
- East Madison Vacations
- Visit Eaton Center
- Monkey Trunk Chocorua
- Visit East Madison
- Visit Chocorua
- Chocorua Lake
- Visit Albany
- White Lake State Park
- Tuckerman Brewery
- Conway Station
- L. L. Bean Factory Store
- Visit Snowville
- Handcrafters Barn
- Conway Vacations
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.