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Holiday rentals in Annaka

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Top-rated holiday rentals in Annaka

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Guest favourite
Cottage in Karuizawa
4.82 out of 5 average rating, 133 reviews

Complete renovation of a single-storey traditional kominka house [Harunire]

* From June 1, 2026, an accommodation tax system will be introduced in Karuizawa Town.Due to this, the accommodation fee has been updated. All of Naka-Karuizawa's main attractions within walking distance! Within walking distance (about 900 metres) of Shinano Railway's Naka-Karuizawa Station, about 15 minutes by car from Karuizawa Station, and a 1-minute walk to a convenience store You can enjoy a carefree stay in Karuizawa. ・A harmonious blend of traditional charm and sophisticated modernity Surrounded by the reassuring charm of vintage and carefully curated interior design, this space offers a gentle, relaxing moment with a touch of nostalgia. ・Popular Karuizawa tourist spots in the Hoshino area, such as Harunire Terrace and Tonbo-no-Yu, are approximately 5–7 minutes' walk away ・Two bedrooms to ensure privacy Main bedroom with a queen-size bed We have provided a Japanese-style room (with two futons) that feels like a tranquil, secluded annexe. ・A hub supporting a wide range of journeys The popular local supermarket Tsuruya and other shops are nearby, making everyday life convenient. There are several different restaurants in the immediate vicinity, so you can enjoy an active stay in Karuizawa even if you don't have a car. * Same price for up to 2 people (There will be an additional charge if there are more than 2 people) *There are two parking spaces on the premises

Guest favourite
A spacious sunlit dining area features a wooden table surrounded by chairs, offering views of the lush garden outside. Large glass doors open to a wooden deck, enhancing the connection to nature. A soft light filters through a translucent ceiling.
Home in Kamikawa
4.97 out of 5 average rating, 139 reviews

Hirake, made from natural materials. Dog run, BBQ, campfire, playing in the river, hot spring, discount for consecutive stays.

This is a spacious, natural-material bungalow where you can enjoy the greenery of the garden from any room. You can have a barbecue or a bonfire in the garden, and there is a fence so your dog can also roam freely. Also, the garden is beautifully lit up at night. Please enjoy cooking in the spacious kitchen. (Full set of cooking utensils, seasonings and plates) There are also two wonderful hot springs that can be reached in 10 minutes by car, and the on-site restaurants are popular! (Towels are provided at the accommodation. Please bring your own toothbrush.) There is also good access to Nagatoro, Chichibu and Ikaho Onsen🚗 In summer, we recommend playing in the beautiful river nearby! We have many recommendations for hidden gems, so please feel free to ask ♪ ※ High-speed Wi-Fi is available. ※ We will send a detailed map to those who have made a reservation ▪️ Kanto's largest antique market, held every Sunday... 3 minutes on foot ▪️ Blueberry picking (June and July) ▪️ Satsuma orange picking (November and December) ▪️ BBQ… Rental 5,000 yen (Includes grill, grill net, charcoal, lighter fluid, fire starter, work gloves, paper plates, paper cups, and disposable chopsticks) ▪️ Supermarket, butcher's shop… 3 minutes by car ▪️ Bonfire stand rental: 4,000 yen (with firewood) ※ A security camera is installed at the entrance

Top guest favourite
Home in Agatsuma-gun
5.0 out of 5 average rating, 14 reviews

ASAMA HIDEAWAY|Hot spring with water flowing directly from the source|Sauna|BBQ|Entire property rental|About 30 minutes by car from Karuizawa Station

NEW OPENING in July 2026!! ASAMA HIDEAWAY is a luxurious, grown-up hideaway villa nestled at the foot of Mount Asama, designed by architect Keisuke Kojitani. A special location surrounded by a beautiful forest and the babbling of a stream.As you step into the building, which is dominated by a modern, natural black, you are greeted by the overwhelming sense of openness created by the high ceilings and the high-quality interior. The biggest attraction is the completely private spa area located right next to the creek that runs through the property. With a view of dynamic natural rock skin and deep greenery, the "semi open-air bath", and an authentic "sauna and water bath", you can ultimately spend a moment in mind and body. The luxurious outdoor living room is equipped with a BBQ grill and bioethanol fireplace.Enjoy a sophisticated space for adults, where you can enjoy a BBQ amidst the fresh greenery during the day, and be soothed by the flickering flames and the sound of the stream at night. Kita-Karuizawa is easily accessible from Tokyo, yet it offers the richness of nature brought by Mount Asama and an overwhelming silence that is isolated from the hustle and bustle of the city.Please experience a time that can only be found here, where your five senses are sharpened.

Guest favourite
Home in Oazakitakaruizawa
5.0 out of 5 average rating, 8 reviews

The Cabin by Deep Gorge|焚き火と陶器を楽しむ森の一棟貸し

A wood-burning stove, a deck facing the forest, and a bonfire at night. Deep Gorge The Cabin is a private rental accommodation located in the quiet forest of Kita-Karuizawa.Gather around the fire, cook, or enjoy some leisure time.This is a space where you can get away from everyday life and spend some quiet time in the forest. The room has a wood-burning stove, a kitchen and a private bathroom. You can also enjoy a BBQ (additional charge) and an outdoor living room on the deck facing the forest.In the evening, please enjoy a peaceful moment typical of Karuizawa while watching the fire at the bonfire pit in the garden. It is about 10 minutes by car from the Deep Gorge pottery studio.During your stay, you can actually use the utensils made in the workshop.If you would like, you can also take part in a pottery experience at a discounted rate exclusively for guests. It is also convenient for sightseeing and hot spring tours in the direction of Karuizawa and Kusatsu Onsen.A forest cabin that is different from the newly built The Lodge, with a slightly nostalgic and calm atmosphere, where you can enjoy moments in contact with fire, the forest, and nature.

Guest favourite
A spacious living area features a comfortable sofa and colorful chairs around a dining table. Natural light filters in through sheer curtains covering a window. A small coffee table is placed on a textured rug, complementing the warm wooden flooring.
Home in Karuizawa
4.96 out of 5 average rating, 221 reviews

Izumiya house1, a good location for sightseeing access near Izumiya station

IZUMIYA is a newly built, single-family home located about a 7-minute walk from the north exit of Karuizawa Station. The house has 2 units and rents 2 buildings. It is in a good location within walking distance of the popular outlet mall, Kyukaruizawa Ginza, and Unba Pond, and you can also enjoy the beautiful nature unique to Karuizawa. It is very convenient, with a convenience store, supermarket, and delicious restaurants nearby. You can spend a spacious time renting one building, and it is equipped with a kitchen, furniture, and appliances necessary for daily life, so you can stay with your family and friends as if you were living in Karuizawa. Small children are also welcome. We keep the rooms clean and use a professional cleaning service for the towels and linens so that guests can feel at ease. Please let us know if you'd like to be flexible with check-in times, etc.

Superhost
A private villa is nestled among trees, illuminated softly by exterior lighting. Steps lead to a spacious deck with an outdoor hot tub, reflecting the surrounding greenery. Large windows reveal a welcoming interior, seamlessly connecting with nature during the evening twilight.
Villa in Tsumagoi
4.86 out of 5 average rating, 191 reviews

Rock Forest Hokuriku Izawa [BBQ in the fireplace in the forest & hot spring bath fed by a source spring on a rock]

A 1000 square meter private villa with 7 spaces. The entire "Rock Forest" has seven main concepts. We offer each "way of spending time". After procuring fresh ingredients locally, move to the Rock Forest, park your car in the parking lot, and go up the stairs to bring the ingredients to the hearth space. You won't see any other people. It is 60 minutes by Shinkansen from Tokyo to Karuizawa, and 30 minutes by car from Karuizawa Station, so you can work in the morning and take a half-day off in the afternoon, for example. Surrounded by nature, you can relax and enjoy an extraordinary time. < Winter season November-March > The outdoor bath is closed during the winter months.

Guest favourite
A wooden deck extends from the house, furnished with a dining table and chairs. Lush greenery frames the view, with trees and a body of water visible in the background under a clear blue sky.
Home in Karuizawa
4.95 out of 5 average rating, 113 reviews

[Riverside House] A riverside villa in Karuizawa with a sauna and fireplace

We have renovated a villa along the river in the forest of Karuizawa. Great location is about 2,500 ㎡! Feel the extraordinary feeling of the garden and outdoor dining where you can run around, the living room has a large sofa and fireplace. The bathroom can also be enjoyed in the JAXSON jetted tub, a large sauna for 4 people in the metos, and a rain shower in the water bath. A renovated former holiday home in a nature-rich setting.Please be aware in advance that insects may appear in your room during your stay when making your booking.If you have excessive allergies to insects, etc., please avoid booking.

Guest favourite
Home in Hokuto
4.9 out of 5 average rating, 124 reviews

Yatsugatake Minami Alps View, Relaxing Space, Semi-Open-air Bath Sauna Convenience Store Within Walking Distance

A small house will meet you.Wake up with the birds chirping and listen to the wind whispering through the trees in the morning.The large windows offer beautiful views of the Southern Alps.There are also atmospheric cafes and restaurants within walking distance, as well as the famous risonale hotel.There is also a ranch nearby where you can experience horseback riding, so you can enjoy interacting with nature. If you are looking for tranquility, this is the perfect place.Start with a cup of coffee in the morning, enjoy horseback riding or hiking during the day, and dinner in the candle lights at night.

Guest favourite
The room features a low table surrounded by tatami mats, providing a comfortable and traditional setting. Bright yellow curtains frame the windows, allowing natural light to fill the space. A television set is positioned nearby, creating a cozy atmosphere for relaxation.
Flat in Annaka
4.9 out of 5 average rating, 364 reviews

40 minutes to Karuizawa, next to a hot♨ spring, with a golf course and ski resort close by, 2DK room

◆ Overview 3-minute walk from the nearest station 2DK room with tatami mats and kotatsu for relaxing There is a day-use hot spring with good water quality next door♨ ・ It is a quiet and calm environment with lots of nature Bicycles We have one available, so please feel free to use it☀ However, you are responsible for any accidents, etc. (no insurance) ◆ Neighborhood information ・ Karuizawa: About 40 minutes by car ・ Ikaho Onsen: About 60 minutes by car ・ Kusatsu Onsen: About 90 minutes by car ・ Tomioka Silk Mill: About 20 minutes by car

Top guest favourite
The Capsule House is nestled among autumn foliage, with vibrant orange and yellow leaves surrounding the unique architectural structure. The building features distinct circular windows and a wooden facade, offering a harmonious blend with the natural landscape.
Holiday home in Miyota
5.0 out of 5 average rating, 25 reviews

Capsule House-K, a monumental capsule house in nature designed by Kisho Kurokawa

CAPUSULE HOUSE-K is a private house designed by Kisho Kurokawa. It was created based on the concepts of Metabolism and Homo Mobius. This building is composed of the same capsules as the Chugin Capsule Tower Building, which is also a metabolism building, and was completed in 1973, the year after the building was completed. Until now, it has been open only to a few people and was a little-known building, but in 2019, the restoration was started by Kisho Kurokawa's son, and now it is open to the public with the interior of that time.

Guest favourite
A modern A-frame living area showcases large glass doors that connect the indoor space with a wooden deck. Natural wood walls and flooring create a warm environment. A cozy sitting area includes a three-seater sofa and a coffee table, complemented by a pellet stove.
Home in Shimonita
4.96 out of 5 average rating, 54 reviews

NEW! A-Frame House in Minami Karuizawa

“A-FRAME HOUSE” is a newly built & highly unique triangle shaped house located in beautiful Minami Karuizawa. Gaze for hours at the surrounding trees and mountains through the eight meter tall South facing triangular window. Step outside onto the 20 square meter wood deck and fully immerse yourself in nature. The modern Western style interior will make you feel like you’re in Europe or North America. Come and unwind in a one-of-a-kind home and enjoy the tranquil beauty of Minami Karuizawa.

Guest favourite
The exterior of the home is showcased under a twilight sky, illuminated by warm lights that highlight the structure's traditional Japanese architecture. Surrounded by lush greenery, the property features a spacious yard and access to natural landscapes.
Villa in Ueda
4.98 out of 5 average rating, 224 reviews

Modern Luxury, Classic Style, Onsen Nearby

Nestled in the mountains of Nagano at an elevation of 860 meters (2,821 feet), this is a luxury home exclusively for those who want to escape tourist traps, experience a side of Japan rarely seen by outsiders, and do it in style. Our 3-bedroom home is 200 sq. meters (2153 sq. feet) large and is a marriage between traditional Japanese architecture and modern technology and comfort. The home is accessible from Tokyo and other major cities via the Shinkansen bullet train or Joshin-etsu Expressway.

Popular amenities for Annaka holiday rentals

Other great holiday rentals in Annaka

Guest favourite
A spacious onsen bathing area is surrounded by wooden walls and large windows, allowing natural light to illuminate the space. Stone flooring complements the wooden features, while two benches and two wash stations with mirrors are positioned near the edges. A deep, stone-lined onsen bath is centrally located.
Villa in Tsumagoi
5.0 out of 5 average rating, 57 reviews

AsamaMori : a private onsen villa in Kitakaruizawa

Superhost
Cabin in Oazakitakaruizawa
New place to stay

【Noël Kitakaruizawa Notch】Pets, Sauna & Jacuzzi

Guest favourite
A traditional-style room features natural wood accents and a low wooden table surrounded by cushions. A television is mounted on the wall, and a dining area is visible in the background. Light is gently diffused through the window, illuminating the space.
Home in Annaka
4.96 out of 5 average rating, 25 reviews

[Kanauya] Kyu-Usui Pass Promenade, Tetsudo Bunka Mura 3 minutes by car, Karuizawa 25 minutes, whole house rental, 2 nights or more

Guest favourite
A spacious living area features a large, dark-colored sofa and a dining table for gatherings. Light enters through multiple windows with shoji screens, illuminating the harmonious blend of traditional design and modern comfort.
Home in Tomioka
5.0 out of 5 average rating, 76 reviews

Jugoya Villa: A soothing house that blends tradition and modernity. Maximum 13 guests. Roofed BBQ. Families welcome

Superhost
Home in Takasaki
4.8 out of 5 average rating, 30 reviews

6 minutes by car from Takasaki Station | P3 parking spaces and 4 bedrooms | A house in a retro-modern building | A hot spring leisure trip to Ikaho, Minakami and Kusatsu

Guest favourite
A spacious living area is depicted, featuring large windows that invite natural light and offer views of the surrounding greenery. A modern sectional sofa and a circular coffee table are located on light hardwood flooring. The room's open design enhances the sense of openness.
Home in Karuizawa
4.98 out of 5 average rating, 83 reviews

[Great call for applications for the best season of autumn leaves in October!] View of Mount Asama! Enjoy the birdsong, tranquillity, convenience and stunning views!

Top guest favourite
Home in Takasaki
4.98 out of 5 average rating, 61 reviews

Entire 3BR House|Free Parking|Family & Group Stay

Superhost
The cottage is nestled in a tranquil forest setting, surrounded by lush greenery and gentle slopes. Its exterior features a simple design with a wooden entrance and expansive windows that blend with the natural landscape, enhancing its peaceful ambiance.
Cottage in Karuizawa
4.89 out of 5 average rating, 57 reviews

R-villa OHK [D-9]: A single-storey villa where you can enjoy the scenery throughout the four seasons