Madison holiday homes

We found 1,385 holiday rentals — enter your dates for availability
Select from 49 homes, 11 cottages and other holiday rentals in Madison to find one that's perfect for your trip. Whether you're going on holiday with family or friends, holiday rentals have the best amenities for spending time at your holiday home, which might include Wi-Fi and a washer and dryer. Whatever you're looking for, you'll be able to choose a property to rent to meet everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts – Madison

Showing deals for:18 Dec - 25 Dec

Interior
Exterior
Kitchen island with live edge countertop
Come Winter in the White's!
Exceptional
(12 reviews)

MODERN CHALET 3-BDRM-FAMILY & DOG friendly- Luxury & Affordability Combined

Madison

8% off
NZ$4,737
for 7 nights, 1 chalet
NZ$677 per night
includes taxes & fees
MODERN CHALET 3-BDRM-FAMILY & DOG friendly- Luxury & Affordability Combined
Dining
Living area
Private kitchen
Exterior detail
Exceptional
(13 reviews)

LUXURY on SACO RIVER with HOT TUB & MOUNTAIN VIEWS

North Conway Village

13% off
NZ$18,166
for 7 nights, 1 home
NZ$2,595 per night
includes taxes & fees
LUXURY on SACO RIVER with HOT TUB & MOUNTAIN VIEWS
Living area
Dining
Exterior
Exterior
Exceptional
(6 reviews)

White Mtn Lux Retreat - Hot Tub, Sauna & Game Room

Bartlett

8% off
NZ$14,423
for 7 nights, 1 room
NZ$2,060 per night
includes taxes & fees
White Mtn Lux Retreat - Hot Tub, Sauna & Game Room
Living room
Sap House Meadery in Ossipee
Kitchen
Indian Mound Golf Club
Exceptional
(44 reviews)

Beautiful property with Mountain View & privacy. Near slopes, trails & eateries!

West Ossipee

8% off
NZ$4,579
for 7 nights, 1 home
NZ$654 per night
includes taxes & fees
Beautiful property with Mountain View & privacy. Near slopes, trails & eateries!
Sunrise from the deck
Beautiful lake views and private dock
No wake cove perfect for swimming, floating and wading
Evening from the deck
Exceptional
(7 reviews)

Lakefront home with private dock on Lake Ossipee in Freedom, NH sleeps up to 10

Freedom

8% off
NZ$6,076
for 7 nights, 1 home
NZ$868 per night
includes taxes & fees
Lakefront home with private dock on Lake Ossipee in Freedom, NH sleeps up to 10
Living area
3 season front porch
Hot Tub view of courtyard
Outdoor dining
Exceptional
(26 reviews)

Troy's Cabin in North Conway with Hot Tub

Conway

9% off
NZ$4,711
for 7 nights, 1 cabin
NZ$673 per night
includes taxes & fees
Troy's Cabin in North Conway with Hot Tub
Dining
Dining
Private kitchen
Interior
Exceptional
(18 reviews)

The Nordic - 3 Bed Mountain Home in Bartlett, NH

Bartlett

8% off
NZ$8,388
for 7 nights, 1 cabin
NZ$1,198 per night
includes taxes & fees
The Nordic - 3 Bed Mountain Home in Bartlett, NH
Kitchen
Living room
Living room
Kitchen/Dinning area
Exceptional
(75 reviews)

Perfect location - very close to Skiing, Hiking, Beach, Storyland - 4BR,3 BA

Bartlett

8% off
NZ$5,546
for 7 nights, 1 home
NZ$792 per night
includes taxes & fees
Perfect location - very close to Skiing, Hiking, Beach, Storyland - 4BR,3 BA
Interior
Private kitchen
Property grounds
Living area
Exceptional
(29 reviews)

Riverfront Getaway in Conway, Saco River Farmhouse

Conway

12% off
NZ$6,686
for 7 nights, 1 home
NZ$955 per night
includes taxes & fees
Riverfront Getaway in Conway, Saco River Farmhouse
Interior
Best views in the area!
Terrace/patio
Games room
Exceptional
(20 reviews)

Gorgeous views await you at the 6 Bed Room 3200 sq ft Hites Peak!

Bartlett

8% off
NZ$13,789
for 7 nights, 1 home
NZ$1,970 per night
includes taxes & fees
Gorgeous views await you at the 6 Bed Room 3200 sq ft Hites Peak!
Living area
Terrace/patio
Pool
Exterior
Exceptional
(25 reviews)

Bear Brook Lodge - Large house with pool

Bartlett

13% off
NZ$14,905
for 7 nights, 1 home
NZ$2,129 per night
includes taxes & fees
Bear Brook Lodge - Large house with pool
Work Station with Receptacles and usb plugs
Exterior
Living area
Exterior
Exceptional
(119 reviews)

Spacious 3-level AC. home featuring a game room, two family rooms, a fenced yard

North Conway

8% off
NZ$5,751
for 7 nights, 1 home
NZ$822 per night
includes taxes & fees
Spacious 3-level AC. home featuring a game room, two family rooms, a fenced yard
Fox Run Entrance
Deck - From the Right
Four Story Townhouse with Deck
Fully Equipped Kitchen - Bar Seating for Five
Exceptional
(48 reviews)

4-Level Townhouse Near Story Land, Skiing

Bartlett

28% off
NZ$3,303
for 7 nights, 1 home
NZ$472 per night
includes taxes & fees
4-Level Townhouse Near Story Land, Skiing
Open living room/kitchen/dining space.
Cozy living room with gas fire place open to kitchen and dining space.
The kitchen space is quite large, which allows plenty of room for cooking and entertaining.
The loft is complete with two queen pull-out couches.
Exceptional
(7 reviews)

Leaf Peeping Retreat w/Hot Tub, Pet Friendly

Conway

8% off
NZ$12,225
for 7 nights, 1 home
NZ$1,746 per night
includes taxes & fees
Leaf Peeping Retreat w/Hot Tub, Pet Friendly
Brand new driveway and slip free granite stairs
Living area
New slip free stairs 2025
Key code entry door
Exceptional
(94 reviews)

Private Saco River Beach access, Storyland & Attitash 3 miles away

Bartlett

8% off
NZ$4,852
for 7 nights, 1 home
NZ$693 per night
includes taxes & fees
Private Saco River Beach access, Storyland & Attitash 3 miles away
Private kitchen
Interior
Interior
fire pit and grilling area.
Exceptional
(15 reviews)

Perfect Location in North Conway Village

Conway

8% off
NZ$7,510
for 7 nights, 1 home
NZ$1,073 per night
includes taxes & fees
Perfect Location in North Conway Village
Outdoor dining
Private kitchen
Living area
Interior
Exceptional
(41 reviews)

Madison Cottage, 2 Bedroom,

Madison

17% off
NZ$1,897
for 7 nights, 1 cottage
NZ$271 per night
includes taxes & fees
Madison Cottage, 2 Bedroom,
Interior
Living area
Property grounds
Dining
Exceptional
(10 reviews)

Cozy 4 bd/3.5 br in N. Conway by town & mountains

Conway

5% off
NZ$5,899
for 7 nights, 1 home
NZ$843 per night
includes taxes & fees
Cozy 4 bd/3.5 br in N. Conway by town & mountains
Master Bedroom
Dining area and stairs up to loft and master bedroom
Fireplace in living room
Dining area
Exceptional
(47 reviews)

Mt. Washington Valley Get Away - near Attitash Ski Resort & North Conway

Hart's Location

8% off
NZ$3,561
for 7 nights, 1 home
NZ$509 per night
includes taxes & fees
Mt. Washington Valley Get Away - near Attitash Ski Resort & North Conway
Fully Applianced Kitchen
Stonehurst Manor hotel, be sure to treat yourself to a meal at the Wild Rose
End Unit Townhouse
Back deck with new gas grill
Exceptional
(70 reviews)

North Conway townhouse! 3 Bed Plus loft! Stonehurst Village Condos!Close to town

Conway

12% off
NZ$3,629
for 7 nights, 1 home
NZ$518 per night
includes taxes & fees
North Conway townhouse! 3 Bed Plus loft! Stonehurst Village Condos!Close to town
Living area
Front Foyer
Dining area of the kitchen
Kitchen
Exceptional
(18 reviews)

Spacious home located on Chocorua Dam in the White Mountains of New Hampshire

Tamworth

12% off
NZ$3,486
for 7 nights, 1 home
NZ$498 per night
includes taxes & fees
Spacious home located on Chocorua Dam in the White Mountains of New Hampshire
Exterior
Dining
Private kitchen
Living area
Wonderful
(21 reviews)

Walk to pond / playground in pet friendly chalet while enjoying mountain views

Madison

8% off
NZ$3,334
for 7 nights, 1 home
NZ$476 per night
includes taxes & fees
Walk to pond / playground in pet friendly chalet while enjoying mountain views
Room
Living area
Private kitchen
Interior
Exceptional
(54 reviews)

Good Times to be had at our Luxury new loft condo at the base of Cranmore.

Conway

8% off
NZ$8,356
for 7 nights, 1 apartment
NZ$1,194 per night
includes taxes & fees
Good Times to be had at our Luxury new loft condo at the base of Cranmore.
Property grounds
Private kitchen
Room
Dining
Exceptional
(75 reviews)

2 Woodland Pines Rd.

Bartlett

8% off
NZ$3,276
for 7 nights, 1 home
NZ$468 per night
includes taxes & fees
2 Woodland Pines Rd.

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    Enjoy full kitchens, laundry, pools, gardens and more

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    More space, more privacy, more amenities — more value

The lakeside setting of Madison is ready to explore

The lake and other outdoor surroundings create an inviting atmosphere in Madison. Well known for its shopping, canoeing and skiing, this welcoming city won't disappoint. Many of our holiday rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.

Sightseeing in and around Madison

Do you want to find top things to see and do during your stay? Venture out of your cosy holiday rental and experience everything that makes Madison a fun place to get away to. Here are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • King Pine Ski Area (3.4 mi / 5.5 km)
  • Conway Station (5.5 mi / 8.8 km)
  • Kahuna Laguna (9.9 mi / 15.9 km)
  • North Conway Country Club (10.8 mi / 17.4 km)
  • Cranmore Mountain Resort (11.1 mi / 17.9 km)
  • Cathedral Ledge Lookout (11.4 mi / 18.3 km)

Exploring the natural features in Madison

Whether you're looking for adventure or just want to appreciate the scenery, Madison is a great place to get out in nature. Here are a few of the area's most stunning natural features, all within 30 miles (48.2 km) of the city centre:

  • White Mountain National Forest (21.8 mi / 35.1 km)
  • Chocorua Lake (4.5 mi / 7.2 km)
  • White Lake State Park (5.3 mi / 8.5 km)
  • Saco River (5.9 mi / 9.5 km)
  • Mount Chocorua (7.3 mi / 11.7 km)
  • Ossipee Lake (7.6 mi / 12.3 km)

Transport to and around Madison

The nearest airport is in Fryeburg, ME (FRY-Eastern Slopes Regional), located 11.7 mi (18.8 km) from the city centre. If you can't find a flight that works for your travel itinerary, you can also fly into Laconia, NH (LCI-Laconia Municipal), which is 26.4 mi (42.5 km) away.

Frequently asked questions

What is the best area to stay in Madison when booking a holiday rental?
When considering a holiday rental in Madison, New Hampshire, the best area to stay is near the scenic shores of Lake Winnipesaukee. This stunning region is known for its natural beauty and outdoor activities, making it a superb escape for nature lovers. You'll find a variety of properties available here, ranging from charming cabins to modern lakefront homes, which cater to different preferences and budgets.Staying near the lake not only offers breathtaking views but also provides easy access to attractions such as the scenic Mount Chocorua and the picturesque White Mountain National Forest. These areas are ideal for hiking, fishing, and enjoying the tranquil surroundings. Additionally, the quaint village atmosphere of Madison features local shops and eateries, allowing visitors to experience the friendly community vibe.For those who enjoy winter sports, the area is conveniently located near popular skiing and snowboarding destinations.
Where are the best areas for renting a beach house in Madison?
For renting a beach house in Madison, New Hampshire, the area around Lake Winnipesaukee stands out as a prime destination. The shoreline of this picturesque lake features numerous holiday rentals, particularly in the vicinity of the town's public beaches, such as the well-known Jolly Roger Beach. Many properties here offer direct access to the water, with amenities like private docks, spacious decks for outdoor dining, and fire pits for evening gatherings, making them ideal for families or groups seeking a lakeside retreat.Further along the lake, the towns of Alton Bay and Wolfeboro provide additional options, where you can find charming cottages and modern homes, often equipped with features like kayaks, paddleboards, and outdoor grills. These rentals typically include comfortable living spaces, fully equipped kitchens, and multiple bedrooms, suiting larger groups and extended stays.Additionally, the nearby Mount Major State Forest offers hiking opportunities with stunning views of the lake, and many rentals may include easy access to trailheads. Visitors will also find local shops and eateries within a short drive, enhancing the overall experience of staying in this beautiful area.
Where are the best Madison ski resort rentals?
For renting ski accommodations near Madison, New Hampshire, the nearby area around King Pine Ski Area in East Madison is an excellent choice. This family-friendly ski resort offers a variety of slopes suitable for all skill levels, and the proximity to Madison makes it convenient for travellers seeking a winter getaway.In East Madison, visitors can find charming cabins, lodges, and chalets that typically provide amenities such as wood-burning stoves or fireplaces, fully equipped kitchens, and sometimes even hot tubs for relaxation after a day on the slopes. Many properties are located in wooded settings, offering a peaceful retreat with easy access to the ski area and nearby attractions.Additionally, the surrounding area boasts beautiful lakes and mountain views, with opportunities for winter activities like snowshoeing and cross-country skiing. Rentals in the vicinity often feature spacious living areas, ski storage, and outdoor decks, great for enjoying the winter scenery. For those looking to explore, the area also has local dining options and shops, adding convenience to the ski holiday experience.
What is the most popular type of holiday rental accomodation in Madison?
In Madison, holiday houses are the most popular type of holiday rental, with approximately 147 available throughout the area. These properties often feature spacious layouts, multiple bedrooms, fully equipped kitchens, and outdoor spaces for relaxing after a day of exploring. Many are situated near scenic points of interest, such as Lake Ossipee and the surrounding natural beauty, making them ideal for families and larger groups.Chalets are also a top option, with around 33 available, offering a charming and rustic atmosphere. These typically include cozy living areas, kitchen facilities, and often stunning views of the landscape. Additionally, there are about 27 cottages and 21 cabins, which provide a more quaint and intimate setting for those looking for a peaceful getaway.
Are there any family house rentals in Madison?
In Madison, New Hampshire, there is a good selection of family-friendly holiday rentals, with around 64 options available. The area is known for its beautiful landscapes and recreational activities, making it an ideal spot for families. Many of these properties feature spacious living areas, well-equipped kitchens for preparing meals together, and outdoor spaces where children can play and explore.Visitors can enjoy amenities such as Wi-Fi, laundry facilities, and sometimes even access to private docks or yards for summer activities. The proximity to local attractions like the scenic Lake Chocorua and the nearby White Mountain National Forest provides ample opportunities for hiking, fishing, and enjoying the great outdoors.
Can I rent a holiday home with a pool or hot tub in Madison?
In Madison, New Hampshire, there are several holiday homes available for rent that come with pools and hot tubs. This picturesque town, set in the scenic White Mountains region, provides a serene backdrop for a relaxing getaway. Many properties feature private pools, hot tubs, and spacious outdoor areas, great for enjoying warm summer days or unwinding after a day of exploring the nearby lakes and trails. Additionally, these rentals often include fully equipped kitchens, comfortable living spaces, and amenities such as Wi-Fi and air conditioning to ensure a comfortable stay.
Are there pet-friendly house rentals in Madison?
In Madison, New Hampshire, there are a variety of pet-friendly house rentals available, with approximately 30 options to choose from. Many of these properties offer amenities such as fully equipped kitchens, spacious living areas, and outdoor spaces where pets can enjoy the fresh air.The area is known for its beautiful surroundings, with nearby attractions like the scenic Lake Winnipesaukee, which provides opportunities for swimming, boating, and hiking. The local landscape is ideal for outdoor activities, making it a superb destination for travellers looking to explore nature with their pets. Additionally, there are pet-friendly trails and parks in the vicinity, ensuring that both you and your furry companions can enjoy the great outdoors together.
Are there any remote work holiday rentals in Madison?
In Madison, New Hampshire, there are plenty of remote work holiday rentals available, with around 219 options to choose from. This picturesque town, located near the stunning White Mountains, offers a peaceful environment great for working remotely. Many properties feature high-speed Wi-Fi, dedicated workspaces with desks and chairs, and comfortable living areas that allow for a productive work-life balance.Travellers can expect amenities such as fully equipped kitchens for convenient meal preparation, outdoor spaces to enjoy the fresh air, and often access to nearby natural attractions like the beautiful Silver Lake and hiking trails. To help narrow your search, insert your dates and apply the "WiFi" filter on Bookabach.
What are popular rental amenities in Madison?
In Madison, popular rental amenities include well-equipped kitchens, allowing guests to prepare meals at their convenience. Many properties feature outdoor spaces such as decks or patios, superb for enjoying the fresh air and scenic views. Additionally, visitors can expect amenities like coffee and tea makers for that morning brew, and onsite parking to make travelling easier.
When is the best time to visit Madison for a holiday rental?
February is a delightful time to visit Madison, New Hampshire, as it marks the beginning of the peak winter season. During this month, adventure seekers can revel in a winter wonderland, with opportunities for skiing, snowboarding, and snowshoeing at nearby resorts. The crisp air and stunning snow-covered landscapes create an enchanting atmosphere that draws both families and outdoor enthusiasts alike.As you explore Madison in February, you can expect average temperatures ranging from -10 to -5 degrees Celsius, superb for enjoying a variety of outdoor activities. The proximity to pristine lakes allows for ice fishing, while the surrounding White Mountains offer breathtaking views and exhilarating trails for winter sports. The charming local community also hosts winter festivals that showcase the region's culture and warmth.If you're looking for a more budget-friendly option, consider visiting in November. This month presents a serene experience, where you can appreciate the tranquil beauty of Madison in the autumnal transition. The fall foliage, coupled with fewer crowds, allows for peaceful hikes and scenic drives, providing a superb backdrop for relaxation and reflection.Ultimately, your ideal time to visit Madison may depend on whether you prefer the exhilarating winter adventures of February or the quieter, picturesque charm of November.
What are the top attractions in Madison?
In Madison, New Hampshire, visitors can enjoy a range of charming attractions that showcase the area's natural beauty and local culture. The stunning Silver Lake is a popular spot for swimming, kayaking, and relaxing by the water, with several nearby parks offering picnic areas and scenic views. In the summer, the lake is great for outdoor activities, while in the autumn, the surrounding foliage provides a beautiful backdrop for hiking and exploring the trails.The nearby Mount Washington Valley is another key attraction, offering year-round recreational opportunities, including hiking, skiing, and snowmobiling. In winter, the valley transforms into a winter sports hub, with access to ski resorts and snowshoeing trails.Additionally, the quaint village of Madison features local shops and eateries that reflect the area's charm. Visitors can also explore the historical aspects of the region at sites like the Madison Historical Society Museum, which showcases the town's rich heritage.
Are all fees included in the Madison holiday homes prices shown on Bookabach?
Bookabach provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Madison holiday homes with parking?
Bookabach offers a wide selection of holiday homes in Madison with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Madison holiday homes?
You can find great discounts on holiday homes in Madison on Bookabach, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Madison holiday home booking on Bookabach?
To find Madison holiday rentals with free cancellation, just use Bookabach's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Bookabach makes it easy to book with confidence.
Can I find long-stay holiday homes in Madison?
A long-stay holiday home in Madison is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Bookabach?
Bookabach's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Madison holiday home?
Book your Madison holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Bookabach booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Madison?
Prices for holiday homes in Madison vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Bookabach offers something for every taste and budget, from affordable homes in Madison to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Bookabach as a host?
Joining Bookabach as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Bookabach makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.