Tolentino Vacation Rentals from CA $111: Short-Term Rentals for 2026

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Our top choices for Tolentino vacation rentals

A nighttime outdoor area with a tree, a hot tub, and a grassy platform with seating.

1. Holiday Home "Casa degli Ulivi" with Private Pool and Wi-Fi

tolentino

"Pros: La casa è super attrezzata di tutto quello che può servire, il giardino è molto grande e anche esso ben attrezzato di tutto; il panorama bello è la zona è tranquilla ottima per il relax; Jacuzzi top e in più è stato con noi per tutto il soggiorno il mitico Ugo, un cagnetto simpaticissimo che ha fatto compagnia ai nostri cagnetti. Cons: La piscina dovrebbe essere curata un po' di più."

Anonymous traveller

CA $523 total

includes taxes & fees

Oct 12 - Oct 13

A balcony with a table and chairs, a bed with a white bedspread and rose petals, and a view of the countryside.

2. Holiday Residence Belohorizonte

Macerata

Kelly

CA $132 total

includes taxes & fees

Oct 1 - Oct 2

A view from a balcony overlooking a green landscape with hills and a clear sky.

3. Relais Villa Fornari

Camerino

laura

CA $169 total

includes taxes & fees

Sep 30 - Oct 1

A spacious dining area with a long wooden table set for a meal, a bench along the wall, and a rustic ceiling with exposed beams.

4. Typical Le Marche region house surrounded by lush greenery, perfect for holidays and relaxation!

San Severino Marche

CA $920 total

includes taxes & fees

Oct 5 - Oct 6

A wooden chair with a white cloth draped over it, positioned next to a window with a view of greenery outside.

5. Small cottage near the Sibillini Mountains

Marche

"This is a most delightful place to stay in the heart of a very pretty and friendly town. We were warmly welcomed by the Hosts family who kindly gave us some delicious local olive oil and honey. The place was spotless, equipped with all we needed and has a most beautiful secluded garden with shade and comfortable chairs and table. We stayed an extra night as it was so enjoyable. We would recommend it very highly to anyone wanting a quiet and delightful place to stay at a most reasonable cost."

Annie F.

CA $174 total

includes taxes & fees

Sep 30 - Oct 1

A swimming pool with lounge chairs and umbrellas, surrounded by trees and a clear sky.

6. White Iron Room · Casa del Fattore, Villa Luzi

Treia

CA $343 total

includes taxes & fees

Oct 1 - Oct 2

An arched courtyard with a brick floor, a pergola, and a table with chairs.

7. La Dimora del Borgo

Montecassiano

"What a wonderful, hidden jewel! If you are looking for a true medieval experience with all the modern comforts THIS IS IT! Right off the bus stop, Montecassiano is a beautiful medieval village, with a historic piazza, typical italian bars to grab a breakfast or apperativo. For dinner, I highly recommend La Taverna San Nicola across the hotel with a fantastic wine selection and a unique presentation of popular polenta dish. Well worth the trip!!"

Gabriel

CA $100 total

includes taxes & fees

Oct 23 - Oct 24

A stone building with a wooden deck and a metal railing.

8. A Little House in the Woods

Castelraimondo

CA $145 total

includes taxes & fees

Sep 30 - Oct 1

An outdoor dining area with tables set for two, featuring woven placemats, white plates, and glassware.

9. Villa Elena: Your ideal holiday with an unforgettable view!

San Severino Marche

CA $564 total

includes taxes & fees

Oct 5 - Oct 6

A wooden double door with a decorative glass window above it, set in a brick wall with a potted plant beside it.

10. Palazzo Rossi

Sarnano

CHARLES

CA $169 total

includes taxes & fees

Oct 8 - Oct 9

An outdoor wooden table with benches, surrounded by a stone wall and a wooden fence, with a view of a green landscape in the background.

11. Colle di Pietra - Colle di PIetra

Cessapalombo

"We had a wonderful week in Cessapalombo. Tiziana and Nando were very hospitable, and even laid on a delicious lunch of local specialties for our last day. The accommodation is simple, but has everything you need, and the location of the house is stunning. If you want to get away from it all, we cannot recommend this place highly enough. In the day, butterflies dance and lizards dart around the lovely pool, and by night we were serenaded by crickets and the local peregrine falcons. The Monti...

Kate F.

CA $720 total

includes taxes & fees

Sep 30 - Oct 1

A coastal road with a beach, buildings, and a clear blue sky.

12. Charming Apartment Maison all'arco

Corridonia

CA $162 total

includes taxes & fees

Oct 5 - Oct 6

A stone building with a traditional design, a paved pathway, and surrounding greenery.

13. Villa Teloni, your exclusive place w/private pool

San Severino Marche

Oliver G.

A stone building with a wooden door, shutters, and a tiled roof.

14. Affittacamere Castelmanardo

Amandola

CA $90 total

includes taxes & fees

Oct 20 - Oct 21

A window view of a rural landscape with fields, trees, and a distant town.

15. Maceratese Horizons

Macerata

CA $240 total

includes taxes & fees

Oct 3 - Oct 4

A snow-covered landscape with a small cabin structure.

16. In Country Luxury Lodges

Sentino

CA $172 total

includes taxes & fees

Oct 5 - Oct 6

A gated entrance with stone walls and a metal gate, surrounded by trees and a mountainous backdrop.

17. Monti Sibillini House: A Stone House in the Monti Sibillini National Park

Marche

CA $478 total

includes taxes & fees

Sep 30 - Oct 1

A hotel room with two single beds, a small round table, a lamp, a radiator, and a window with curtains.

18. Giaginti House

San Clemente

CA $263 total

includes taxes & fees

Oct 2 - Oct 3

A narrow stone staircase flanked by stone walls, ascending to a building entrance.

19. The Sibillini Chalet

Sossasso

Joanna C.

CA $158 total

includes taxes & fees

Oct 2 - Oct 3

A person in a hot tub with a glass of wine, surrounded by a wooden deck and lush greenery in the background.

20. House in the medieval village Castelletta 700 mt height in the park Gola della Rossa

Castelletta

CA $208 total

includes taxes & fees

Sep 30 - Oct 1

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Top Tolentino Hotel Reviews

La Valle Del Poeta

8/10 Good

"Just I sleep from 0 pm to 6 sm next"

Natural Village Resort

10/10 Excellent

"We had a great time at Natural Village. The entertainment at the theater was a big hit with my older son. The private beach was convenient, and the seaside restaurant was delicious. Make a reservation ahead of time to guarantee a seat, even for lunch! My only complaint is some of the games for the children were broken."

Find out more about Tolentino

Everything you need to know about Tolentino vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Tolentino vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Tolentino vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Tolentino vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Tolentino. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Tolentino vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Tolentino vacation rentals we have selected for you start as low as CA $111 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Tolentino rentals

At Expedia, we put the best Tolentino vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Tolentino rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Tolentino vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Tolentino. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find a vacation rental in Tolentino?

Yes, we offer vacation rentals close to popular local attractions in Tolentino, or you can select a more remote option if you're looking for relaxation. Tolentino is known for its monuments.

What are some of the best vacation home rentals in Tolentino?

Exclusive Use Private 2 BR Villa - Swimming Pool, Large Garden & Great Views: This vacation home rental outside of Tolentino is located in a rural location and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. It offers a balcony, a terrace, and a garden so you can immerse yourself in your vacation.

How many vacation rentals are there in Tolentino?

With 9 Expedia vacation rentals, you're sure to find just the right place for your Tolentino stay.

What’s there to see and do in Tolentino?

Explore the area and family-friendly sights such as Infernaccio Gorge, or get out into nature at a spot like Fiastra Abbey Nature Reserve. While here, Basilica di San Nicola and Castello della Rancia are other places worth a visit.

What’s a vacation rental in Tolentino like?

Vacation rentals are privately owned properties you can stay in for several days or longer in Tolentino. Vacation rentals offer amenities such as hot tubs, fire pits, and patios so you'll have everything you want. If you're concerned about a sanitized environment, vacation rentals can provide a sense of safety away from shared hotel elevators and bustling concierge desks while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a hotel, which makes a vacation rental an attractive choice for small groups.

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Check prices for these dates

Our top choices for Tolentino vacation rentals

1. Holiday Home "Casa degli Ulivi" with Private Pool and Wi-Fi

2. Holiday Residence Belohorizonte

3. Relais Villa Fornari

4. Typical Le Marche region house surrounded by lush greenery, perfect for holidays and relaxation!

5. Small cottage near the Sibillini Mountains

6. White Iron Room · Casa del Fattore, Villa Luzi

7. La Dimora del Borgo

8. A Little House in the Woods

9. Villa Elena: Your ideal holiday with an unforgettable view!

10. Palazzo Rossi

11. Colle di Pietra - Colle di PIetra

12. Charming Apartment Maison all'arco

13. Villa Teloni, your exclusive place w/private pool

14. Affittacamere Castelmanardo

15. Maceratese Horizons

16. In Country Luxury Lodges

17. Monti Sibillini House: A Stone House in the Monti Sibillini National Park

18. Giaginti House

19. The Sibillini Chalet

20. House in the medieval village Castelletta 700 mt height in the park Gola della Rossa

Find vacation rentals that suit your style

Top Tolentino Hotel Reviews

La Valle Del Poeta

Hotel Dimorae Rooms and Suites - Apartments

Natural Village Resort

San Francesco Hotel

Best Western Hotel I Colli

Hotel Belvedere

B&B HOTEL Fabriano Janus

Hotel Horizon

Palace Hotel

Find out more about Tolentino

Frequently asked questions

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