Holiday rentals in Upa

4.93 out of 5 average rating, 45 reviews

Cozy Old Town Penthouse with Large Balcony

A great place to recharge your batteries, where it is possible to spend time with your loved ones, either in the room in front of the TV or enjoying the sun on the 10m2 cozy balcony. For lovers of adventure seekers there is the city centre, Kuressaare Castle, great taste experiences, a park, a beach and more within a short walking distance. For families with young children, there are many different playgrounds in the surrounding area for fun. The apartment has a travel crib for the smaller ones (can also be taken to the balcony if you'd like) and a toy box with exciting content.

5 out of 5 average rating, 20 reviews

Tiny home in Upa

Ärmapesa - private house with sauna, close to town

Ärmapesa is a cozy and private vacation home where you can relax comfortably with family or friends. For sauna lovers, there is a wood-burning sauna in the yard, with fresh birch! We are just 5 km from the city of Kuressaare. The nearest beach is just below the Kuressaare side, by the castle park. Kuressaare is a beautiful town, on a green island with a plethora of attractions, good places to eat, cafes, shopping and entertainment establishments. For Saaremaa and the events/opportunities here, see the visitsaaremaa website. Come visit us!

4.95 out of 5 average rating, 102 reviews

Kuressaare Family and Garden apartment 5+1

Well-equipped, family-friendly two-story apartment with great location (30m wildmill, 400m old town, 950m Kuressaare Castle and city beach). It has private entrance, parking on the premises, yard (BBQ, sandbox) and a sun terrace with outdoor furniture. It is suitable for 5 adults and 1 small child (crib 0-3y). It has 2 bedrooms, a livingroom with well-equipped kitchenette, a bathroom with shower and washing machine. Free wifi, towels and sheets are provided. See more www.kuressaareapartments.com

5 out of 5 average rating, 53 reviews

Cozy & modern apartment with bath

The unit is located near the central square of Kuressaare (~15minute walk). Location is good but quiet. The kitchenette has the necessary accessories (stove, oven, kettle, refrigerator, dishes, pot and pan, oil, salt/pepper, tea, coffee etc). There is a 43’ TV, a hairdryer and a fast internet connection (WiFi). AC in the summertime. There is a washing machine and a drying rack in bathroom. Bed linen and towels are provided. Also a travel cot for a child max age 3. Parking is free near the house.

4.87 out of 5 average rating, 68 reviews

Cottage in Muratsi

Kordoni private house in the middle of the sea

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.

4.88 out of 5 average rating, 73 reviews

Guest house in Kuusiku

Brand new private stylish house with 60m2 terrace

We are surrounded an amazing nature and you can relax and have a good vacation. A superb view to Meelase Windmill. We have a lot of lawned grass and very quiet. This is a private house for maximum 6 people, where is a kitchen corner with all of equipment, shower room with toilet. There is all equipment you need in the kitchen. There is sofas in 60m2 terrace and also you can do BBQ. There is huge relaxing area with hammocks and children's slide also in the yard. You are welcome!

4.97 out of 5 average rating, 99 reviews

Brand new stylish old town apartment

Welcome to our home :) It is a brand new Scandinavian style apartment 48 m2 located in the historical building in the heart of Kuressaare. It is elegance, light-filled apartment with high ceilings and blond timber floors. It has private access and free parking. It is open-plan apartment with fully equipped kitchen, bedroom, bathroom and common space. The flat is in peaceful area just 2 minute walk to the centre. Our place is suitable for couples and for families (with 2- 3 children).

4.98 out of 5 average rating, 121 reviews

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.

4.93 out of 5 average rating, 108 reviews

Nice place to stay in Kuressaare

Meie väike armas korter asub mönusalt vaiksel tänaval bussijaama ja taksopeatuse vahetus läheduses. Kesklinnas asuvad kohvikud ja restoranid on umbes 7 minutilise jalutuskäigu kaugusel. Korter on renoveeritud täielikult 2019 aastal, 2024 värskendasime värvi seintel ning lisasime köögikapid koos kraanikausiga et oleks veelgi mugavam. Kööginurgas on veekeetja ja väike induktsioonpliit. Aias on ka kena nurgake kus sumedatel suveõhtutel istuda.

5 out of 5 average rating, 11 reviews

Cottage in Kailuka

Idyllic Island Escape Cottage

Escape to an idyllic island retreat on the beautiful island of Saaremaa with this charming two-story cottage. Immerse yourself in a tranquil countryside setting, surrounded by nature's beauty while still being just a 10-minute drive away from the vibrant town of Kuressaare. Whether you're seeking a peaceful getaway or an adventurous exploration of the island, this property offers the perfect base for your island adventure.

4.98 out of 5 average rating, 46 reviews

Apartment in Kuressaare

Lovely 1 bed room apartment next to Golf course

Nice and lovely apartment with Sauna in the golf residence next to Saare Golf course, unique, peaceful and friendly neighborhood. Wow center and Gym 3 minutes walking distance. Free private parking lot. Possible use bicycle. Apartment have one bedroom, living room with kitchen area, Sauna, bathroom, 2 balconies(living room and bedroom)both balconies have golf course view.

4.97 out of 5 average rating, 36 reviews

Home in Kuressaare

Hygge Stay

This stylish place to stay is perfect for couples. It has private entrance, parking on the premises, yard and a sun terrace with outdoor furniture. It is suitable for 2 adults and 1 small child (crib 0-3y). It has 1 bedroom, a livingroom with well-equipped kitchen, a bathroom with shower . Free wifi, towels and sheets are provided.

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Other great holiday rentals in Upa

Superhost

4.91 out of 5 average rating, 58 reviews

Luxury Loft next to Castle & Park

KaariRating, 5 stars7 months ago

Everything was exactly like described and like in the photos. The host was really friendly and accommodating to our schedule. All essential amenities were available, including well equipped kitchen, washing machine, sauna, ironing board etc. Thanks for a lovely stay!

4.92 out of 5 average rating, 76 reviews

Artisan studio in Kuressaare old town

KathrynRating, 5 stars5 months ago

Very homey and cosy, easy to access. Quiet whilst central location. Could walk anywhere. Katarina an amazingly responsive and helpful host. The studio so thoughtfully planned and decorated. The only slight difference as my first impression - was that the studio was smaller than I had assumed from the photos. This however did not matter. We loved it.

Tiny home in Kuressaare

4.8 out of 5 average rating, 5 reviews

Unique Tiny House at Saaremaa Golf & Country Club

LiisaRating, 5 stars21 months ago

Thanks for a great stay. And easy communication. We appreciate the early check in too.

4.95 out of 5 average rating, 44 reviews

Cabin in Undva

Bird nest

AndreaRating, 5 stars2 weeks ago

Marko’s place is a fairytale’s place, it’s wonderful be in the middle of the nature. You can really relax yourself and take a break from routine life, we suggest everybody to take some days off in this awesome place!!!!

Superhost

Cottage in Suure-Rootsi

4.88 out of 5 average rating, 43 reviews

Aadukivi cottage

MartinRating, 5 stars1 week ago

Jaan has created a beautiful place with his thatched wooden house between junipers and boulders, where we felt very comfortable. The house is very tastefully decorated and well equipped. The large terrace with comfortable loungers, a hammock, and a view of the greenery also create a beautiful atmosphere. We were able to observe some wild animals, such as deer, foxes and hares, on the nearby meadows. We had wonderful, relaxing days here! The location is perfect for exploring the island, shopping is easily accessible by car. In addition, Jaan is a very friendly and accommodating host. Would love to come again.