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Holiday houses in Upa

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Top-rated holiday rentals in Upa

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
A charming outdoor scene showcases a wooden cabin on a spacious grassy area, framed by lush trees. Colorful flowers bloom in the foreground, adding vibrancy. A patio with a grill and seating offers a relaxing space, while another cabin is seen in the distance.
Tiny home in Upa

Ärmapesa - private house with sauna, close to town

Ärmapesa is a cosy and private holiday home in Saaremaa. Only 5 km from the city of Kuressaare, but at the same time pleasantly in the countryside in a quiet and green environment. Tall trees, a large courtyard and a quiet location create an ideal place for a holiday for a family or group of friends who value privacy, closeness to nature and a homely atmosphere. The house has air conditioning, which ensures a pleasant indoor climate even on warmer days, and the fireplace with a live fire in the living room adds cosiness. There is a sauna house in the courtyard and you can also have a campfire! We look forward to seeing you!

LocationFamilyAir conditioning

4.96 out of 5 average rating, 55 reviews
Guest favourite
Windmill in Kuusiku

Windmill with sauna

Meela farm accommodation is a wonderful, cosy and quiet place to stay for up to 17 people. Meela's Tuulik Adventure Accommodation is sustainable, nature-friendly, and based on Estonian culture and heritage. It includes a sauna house with sleeping places for 5 people. The windmill has 3 beds on the ground floor and 2 beds on the first floor. The sauna house has a kitchenette with everything you need, a steam room and a shower room. Use of the sauna is included in the price. In front of the house there is a terrace and a large dining table with a roof. The toilet is located in a separate cabin.

LocationFamilyAmenities

4.9 out of 5 average rating, 103 reviews
Guest favourite
A dining area features a wooden table surrounded by four yellow upholstered chairs. Natural light enters through large windows, complemented by soft curtains. Decorative items, including woven placemats and a small bowl, are placed on the table, enhancing the space's inviting ambiance.
Apartment in Kuressaare

Cozy penthouse with large balcony in Old Town

A great place to recharge your batteries, where you can spend time with your loved ones, either in the room in front of the TV or on a cozy 10m2 balcony while enjoying the sun. For those looking for great adventures, the city center, Kuressaare Castle, great taste experiences, park, beach, etc. are a short walk away. There are many different playgrounds in the area for families with small children to have fun. The apartment has a smaller travel bed (if desired, you can also take it to the balcony) and a toy box with exciting contents.

FamilyLocationSleep quality

4.86 out of 5 average rating, 107 reviews
Top Guest favourite
A spacious living area features a wooden dining table surrounded by chairs. A sofa offers comfortable seating, complemented by soft cushions. Natural light filters through the windows, illuminating the decorative wall art and wooden furniture, creating a relaxed and inviting setting.
Apartment in Kuressaare

Artisan studio in Kuressaare old town

Artisan Studio Khiron (1860) is located in the old town of Kuressaare, 2 mins walk from the central square. Welcome to this haven of calm! New kitchen (07/24) in solid oak with induction hob & dishwasher. Renovated and furnished with a special flare - the thick stone walls lend a peaceful ambience. New single bed & new double sofa-bed, sleeping max 3. Perfect for couples, solo adventurers, as well business travellers. Enjoy unlimited WIFI and cable TV. The cosy bathroom has under-floor heating.

LocationValueCheckout

4.93 out of 5 average rating, 105 reviews
Guest favourite
A modern living area features a spacious gray sectional sofa arranged comfortably around a round coffee table. Large windows allow natural light to flood the space, offering views of the lush greenery outside. Wooden accents and a textured rug enhance the welcoming ambiance.
Home in Kuressaare

Green Field Villa

Welcome to a brand-new (2025) stylish villa located in a unique area of Saaremaa. This spacious 150 m² home is designed in a modern style, with a focus on natural materials, light, and comfort. The interior features thoughtful design, plenty of natural light, high-quality furniture, and elegant details. The villa is located in a prestigious area of new private homes, next to the beautifully maintained Saare Golf course with lakes and landscaped surroundings. The sunsets here are truly magical.

LocationViewAccuracy

5.0 out of 5 average rating, 6 reviews
Top Guest favourite
Two comfortable armchairs are positioned facing large glass doors that open to scenic forest views. A round table stands between the chairs, topped with a small plant. Natural light fills the space, enhancing the serene atmosphere created by the surrounding trees.
Cabin in Nässuma

Modern tiny house in the forest with sauna option

Our new and spacious tiny house offers ultimate privacy and nature experience. House is located 25 km from Kuressaare. A unique place in beautiful nature for a relaxing getaway from everyday routine and duties. Ideal for couples and families. Every detail of the house is planned with functionality and design in mind. Small kitchen area, comfy double bed and an extra sleeping area upstairs. Modern, fully equipped bathroom, WIFI and big exterior terrace. All-year house with heating and cooling.

LocationValueIndoor spaces

4.96 out of 5 average rating, 85 reviews
Top Guest favourite
Cottage in Laevaranna

Vanatuuliku log house with sauna

Cozy log house at Saaremaa for people who search comfortable getaway to the nature. Perfect place for distance working or learning, romantic holiday or a family getaway with a chance to spend some quality time together. Take a vacation and recharge yourself being surrounded with the beauty of nature and the sea with a beach just a walking distance away. Dogs are welcome! Last but not least - choir of birds singing and unlimited number of stars in the night sky are all included in the price.

FamilyValueWalkability

4.98 out of 5 average rating, 115 reviews
Superhost
Home in Upa

Cozy part of a house 80 m2 with a garden

The house is located in the district of private houses in Upa, 3 km from Kuressaare. The house is divided into two separate apartments. Accommodation is located on the first floor. You have private entrance. You have the opportunity to use the grilling area in the garden next to your entrance. The accommodation has a living room, kitchen, bathroom, 1. bedroom with a double bed and 2. bedroom with two single beds. The kitchen is equipped with dishes, a stove, a fridge and a hot air fryer.

FamilyBikingLayout

5.0 out of 5 average rating, 4 reviews
Guest favourite
A charming house with a thatched roof is positioned on a grassy hillside. The image features a wooden deck with railings, leading to the entrance. Surrounding landscapes include open fields under a clear blue sky, providing a sense of tranquility and privacy.
Cottage in Muratsi

Kordoni private house, Bird Watch, Sea views!

Cozy, spacious and bright house (Kordoni holiday home) is truly private and perfect for nature lovers, around is the sea. It is situated in Muratsi village on Vani peninsula. The place is close to Kuressaare, about 8km from city center. In the house there is everything you may need for carefree vacation (kitchen with all the necessary equipment). Wood-heated sauna with view to sea and large terrace for relaxing on second floor. Fireplace on living room.There are 2 bicycles for you, to use.

LocationValueIndoor spaces

4.89 out of 5 average rating, 98 reviews
Guest favourite
Home in Kirikuküla

Villa Männituka Retreat – Feel at Home

Villa Männituka Retreat is a peaceful escape in Saaremaa, a short drive from Kuressaare. Surrounded by nature and a pine forest, it offers a quiet retreat from everyday life. Mornings start with birdsong and fresh air, evenings bring silence. The natural setting slows time and helps you relax. Designed for comfort and simplicity, it is ideal for a relaxing holiday, small gatherings, and reconnecting with nature. For larger groups, see: https://www.airbnb.com.ee/rooms/30416910

LocationFamilyComfort

4.91 out of 5 average rating, 11 reviews
Top Guest favourite
Home in Muratsi

Peaceful Kivima guesthouse near Kuressaare

We offer a quiet and cozy little house only 3 km away from Kuressaare. It is a good holiday spot for couples, friends, solo travelers as well as families. It is more convenient to reach us by car. The guest house includes a relaxing wood heated sauna (1x15€). It is surrounded by a garden with plenty of grass-space for outdoor games. There is also a bicycle road that leads straight to Kuressaare from just behind the house. It is also possible to rent some bikes (2) from us.

ValueLocationAccuracy

4.97 out of 5 average rating, 145 reviews
Top Guest favourite
Home in Lahetaguse

Charming Seaside Country Cottage

Peaceful seaside cottage by Riksu Nature Protected area. Just a short 200 m walk to shoreside. This two-bedroom holiday home is fully equipped, with a cozy living area and a big dining table — perfect for family meals or relaxed mornings. Surrounded by nature and sea air, it’s an ideal hideaway for couples, families, or bird-watching lovers. Sleep well, breathe deeply, and start each day with coastal calm and forest birdsong.

LocationValueAccuracy

5.0 out of 5 average rating, 14 reviews

Popular amenities for Upa holiday rentals