Holiday houses in Ramona

4.8 out of 5 average rating, 111 reviews

Cabin in Ramona

Wine Country Cabin Near San Diego - Private

Kick back and relax in this private cabin on 9 acre ranch. It’s a true get away. Come enjoy all the amenities including: Queen bed, full kitchen/bath, spa shower, 9 acres of private trails, intentional spaces, majestic views and a huge deck with a soaking tub to cool you in the summer (June - October). New A/C and heating. Enjoy a 5 minute walk to Milagro Winery and return to Littlepage for the amazing sunset. Or venture 15 minutes to the towns of Ramona, Julian or San Ysabel. Book Now!

4.9 out of 5 average rating, 132 reviews

Cabin in Ramona

Modern vineyard cabins in Ramona

Travino, a unique luxury vineyard glamping concept, is located in the beautiful Ramona Valley, just 40 min from San Diego! Named for winemaker’s favorite grapes Malbec and Syrah, our modern tiny cabins allow guests to wake up to beautiful views of the vineyard, offering the perfect escape from the city! Enjoy the opportunity to walk to the on-site vineyard tasting room or take a short drive to many other vineyards, great hiking trails, golfing, local restaurants, boutiques and shopping center.

4.97 out of 5 average rating, 832 reviews

Home in Ramona

The Glass House - A Nature Retreat

Enjoy a unique retreat; 180 degrees of views from inside the home. Nestled at the end of a private road, our place is nearby great hiking and countryside wineries. The Glass House provides a magical space and nature retreat where individuals, couples, families and friends can gather together to re-connect with nature, each other, and themselves. The breathtaking mountain top views, the huge deck, hot tub, fireplace, and the open concept living space is unbeatable for the perfect getaway.

4.99 out of 5 average rating, 135 reviews

Home in Julian

Private Getaway - Breathtaking Views

Discover the Julian Ridgetop Retreat, a private haven with breathtaking panoramic views. 🔸Wake to stunning Salton Sea sunrises from your bed 🔸Unwind in the hot tub under starry skies. 🔸Immerse yourself in nature with nearby trails and adventures 🔸Enjoying year-round comfort with central AC/heat. 🔸Explore historic Julian's charms—apple orchards, wineries, and quaint shops—just minutes away. 🔸Book now and receive our exclusive local guide for an unforgettable mountain escape.

4.83 out of 5 average rating, 183 reviews

Home in Ramona

ENJOY A REAL FARM EXPERIENCE!

EXPERIENCE FARM LIFE! RESTORED OLD 3-BEDROOM 2-BATH FARMHOUSE ON 20 ACRES OF COWS, GOATS, CHICKENS, DUCKS! FEED THEM IF YOU LIKE. COLLECT EGGS FROM THE COOP AND PREPARE THEM IN THE OLD KITCHEN, RING THE TRIANGLE BELL AND DINE IN THE PASTURE! Stocked for breakfast, and since our farm is near town, a short drive for more groceries. Wi-fi. Netflix. Stay for a night or stay a month! Ramona offers antiquing, 3 excellent golf courses, 30 wineries, hiking, horseback riding, birdwatching.

4.96 out of 5 average rating, 113 reviews

Home in Ramona

The little Farm stay

Escape to our charming two-bedroom farmhouse and experience the relaxing life outside the city. Enjoy watching our farm animals including Horses, Sheep, Pigs, Goats and two lovely Great Danes! Enjoy a complementary Farm Basket with your stay. Included in 2 night stays or more is a free farm tour, scheduled at booking. Sweet Heart Farms Sourdough is a popular local treat included in your farm basket, and available in our Farm Stand. This is not a wheel chair accessible property.

5 out of 5 average rating, 132 reviews

Cabin in Ramona

Red Tail Ranch

A custom Log Cabin, perched on top of 15 acres located just outside of Ramona.You have an open-air experience while still having all necessary amenities to feel at home.Step outside and be surrounded by green, rolling hills and tall trees.Interact with animals, and enjoy the outdoors.Evenings you can retreat inside, sit by the cozy fireplace, play a game of pool, or go sit under the stars . Come fall in love with animals like mini highlands, alpaca, emu, mini donkeys, and more .

4.96 out of 5 average rating, 124 reviews

Guesthouse in Ramona

Adorable Hawaiian themed Guest House

Enjoy the quaintness of country living just 35 miles from San Diego. Ramona is the heart of San Diego's wine country; home to many boutique winery’s and vineyards. Our guesthouse will provide the perfect space to unwind and relax after sightseeing, beaching, or visiting the world famous San Diego zoo. Guest home has one bedroom with king bed, separate great room/kitchenette w/hide-a bed and a couch. Fire pit, large grassy play area with zip-line and a pool to cool off in.

4.86 out of 5 average rating, 112 reviews

Campervan/RV in Ramona

Vintage Airstream w/ Farm Experience & Jacuzzi

Join the royal court & stay in our 1975 Airstream Sovereign Land Yacht! Immerse yourself in a budding rescue ranch with pot belly pigs, horse, mini horse, mini donkey, alpacas, sheep, and tortoises, or take a romp on our 5 acres with lots of hidden gems to discover, or explore the many hiking trails nearby. You also have exclusive access to your own jacuzzi & 300sf deck! Our location is also unique because we are fully fenced in & an additional camper for more sleeping space!

4.92 out of 5 average rating, 190 reviews

Tent in Ramona

Star Gazer Tent at Own Rooted Glamping

Own Rooted Glamping is located in the stunning Ballena Valley on the east side of Ramona. The glamp site overlooks Edwards Vineyard and is surrounded by the most stunning mountain views all around. Own Rooted Glamping is on 64 acres, which is private family owned, Please be respectful. The site is completely off-grid and 100% green natural energy. We are located near many attractions such as: Julian Historical Town: 17 min. Julian Pie Company: 10min Ramona: 15min

4.84 out of 5 average rating, 122 reviews

Hotel room in Ramona

One Bedroom Condo in San Diego Country Estates

San Diego Country Estates is nestled against the foothills near the quaint and historic towns of Ramona and Julian. Resort guests enjoy “The Good Life,” a perfect blend of active play and total relaxation with a variety of indoor and outdoor activities. A resort fee of $27.00/night is included in the total price shown on Airbnb. This fee covers parking, Wi-Fi, and access to on-site amenities. Please read through full House Rules prior to booking.

4.96 out of 5 average rating, 143 reviews

Farm stay in Ramona

Casa de Piedra (Stone House) - Winery Guest House

This unique and upscale straw bale-constructed guest house on winery grounds is filled with delightful surprises, from the stone-carved walls to the beautiful artwork and furnishings. The fantastic view from the deck includes our vineyards and a view of Iron Mountain. Located in the heart of wine country, there are many wineries, including our own, that you can visit in Ramona. *Children under 18, pets, and parties not allowed*

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Other great holiday rentals in Ramona

4.99 out of 5 average rating, 262 reviews

Cabin in Julian

MelodiaRating, 5 stars3 days ago

Absolutely loved our stay at this charming A-frame cabin! Spotlessly clean, beautifully designed, and felt brand new. The AC was on when we arrived—such a thoughtful touch on a hot day. Communication with the host was excellent, and the welcome guide made everything super easy. The location is peaceful and private, perfect for bird watching by day and stargazing at night. The beds were comfy, the jacuzzi tub was sparkling clean, and the high-tech toilet (seat warmer + bidet!) was a fun surprise. We loved the collection of vintage records and board games—so cozy and nostalgic. Ideal for a romantic getaway but spacious enough for more guests. We’re already dreaming of our return!

4.96 out of 5 average rating, 112 reviews

Dome in Valley Center

Glamping Sphere/Sunsets Geodesic Dome

IvyRating, 5 stars2 weeks ago

I was with my child (toddler) and husband and we booked this place last min for our first glamping experience! Their thorough directions made it easy to find, the bed was comfy, and the patio was magical. Would definitely love to return to the dome! P.S. while the outdoor compost toilet was a first for us, it was better than expected and it didn’t smell at all!

Cabin in Palomar Mountain

5 out of 5 average rating, 159 reviews

The Wood Pile Inn getaway

SkyRating, 5 stars1 week ago

Such a beautiful and peaceful little cabin in the woods. Everything was absolutely perfect. Sandra was so kind and answered all of our questions and gave such easy instructions to get to the house. It made for the most perfect weekend getaway we could ask for. If we're ever in the area again we know exactly where we're staying!

5 out of 5 average rating, 31 reviews

Tiny home in Ramona

Cozy Country Home

kris Rating, 5 stars1 week ago

Only met Elaine she was great. The house had all needed items and was a cute little place. We had a wonderful time.

4.87 out of 5 average rating, 126 reviews

Campervan/RV in Ramona

Harley Davidson Glampling / Kids Play Area/Hot Tub

EstherRating, 5 stars1 month ago

This was my first experience staying in an RV. I was very satisfied with the amenities and the roominess inside. I would definitely do this again. The location was very peaceful. Close to town for groceries, fast food and restaurants.

5 out of 5 average rating, 102 reviews

Farm stay in Escondido

Peaceful new Tiny Home on farm, steps to wineries!

EricRating, 5 stars2 weeks ago

We had a wonderful time relaxing on the property. It was cozy, clean, and quiet. One of the best parts about the place was that it didn’t have a TV — we wound down with a drink and a book on the deck as the evening cooled off and the stars slowly lit up. It’s a great location if you want to visit wineries, but make sure you check their hours of operation as some are only open on the weekends.

Tiny home in Palomar Mountain

4.93 out of 5 average rating, 138 reviews

Cranberry Cabin

ThuyRating, 5 stars3 weeks ago

Love this little cabin in the mountains. It was a perfect base for our weekend getaway for some fresh mountain air, hiking, and exploring. The large deck is the best feature of the cabin. We had morning coffees and ate all our meals there. Lana was super helpful with suggestions, and even provided cooking oil when we forgot to bring some.