Cottage vacation rentals in Lakeside

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Top-rated cottage rentals in Lakeside

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

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Top guest favorite
The welcoming entrance of Cedar Cottage is framed by lush greenery and decorative potted plants. A wooden porch, adorned with comfortable seating, leads to glass-paned doors. Elements such as a bubbling fountain and seasonal pumpkins add charm to the rustic facade.
Cottage in El Cajon
4.99 out of 5 average rating, 158 reviews

Cedar Cottage Retreat with Mountain View’s

Welcome to the Cedar Cottage Retreat- a serene countryside escape set on a former horse & cattle ranch, where wide open skies, rolling pastures, and quiet vintage luxury come together. Tucked away in a peaceful valley, this thoughtfully designed cottage invites you to slow down and reconnect-with nature, with loved ones, and with yourself. Once home to horses and grazing cattle, the land still carries that grounding , pastoral beauty. The Cottage sleeps 3. 1 Queen bed, one twin bed. Pets OK

Top guest favorite
The spacious bedroom features a vaulted-beamed ceiling and an inviting California King-size bed, draped with a light blanket. Decorative elements include a wooden headboard, a vintage bench at the foot of the bed, and tasteful wall art. Natural light enters through the frosted window.
Cottage in Normal Heights
4.96 out of 5 average rating, 144 reviews

LOFT: Detached Cottage with Patio

Located in the heart of Normal Heights, where everything is walkable; pubs, markets, cafes. Local’s favorite! The LOFT is a spacious open-space studio loft, in a stand-alone cottage. Whether you fall in love with the vaulted-beamed ceilings, the Loft-style open kitchen, the clawfoot tub, the art & decor, or the lush landscaping, you won’t likely forget this place any time soon. Everywhere you turn is a feast for your eyes. We’ve ensured that comfort is as much of a priority as is beauty.

Guest favorite
Cottage in Lakeside
4.95 out of 5 average rating, 141 reviews

Modern Cottage Getaway!

Welcome to your cozy getaway! This charming 1,000+ sq ft cottage offers an open-concept layout. Perfect for couples, small families, solo travelers, or anyone looking for a peaceful retreat. 🧺 Washer and dryer included for added convenience Located in a very quiet, residential neighborhood—ideal for those seeking rest and relaxation. 🚗 Parking: Guests have 1/2 reserved parking spot in the driveway. No Street Parking 🚭 No smoking 🐾 No pets or service animals due to health concerns

Guest favorite
A bright living area features a comfortable light gray sofa adorned with decorative pillows. A round coffee table sits on a patterned rug, and a wall-mounted television is visible. Natural light filters through a large window beside the front door, which is framed with greenery.
Cottage in Hillcrest
4.96 out of 5 average rating, 254 reviews

Canyon Views w/ Outdoor Seating & Parking

Prime location! Within walking distance to Trader Joe’s, Whole Foods, Ralph’s, cafes, gyms, amazing restaurants, great nightlife, and Sunday's Farmer's Market! This newly restored historic cottage is in the heart of Hillcrest, San Diego. Originally located in Balboa Park, it housed workers for the 1915 Panama–California Exposition. Perched on a canyon, the cottage blends modern amenities with farmhouse charm. Book now for a San Diego stay that fuses the past with modern comforts!

Top guest favorite
A welcoming entrance features a white front door framed by large windows, offering natural light. Two blue chairs are positioned on a small grassy area, ideal for outdoor relaxation. Surrounding plants enhance the calm and inviting setting.
Cottage in La Mesa
4.94 out of 5 average rating, 206 reviews

Private cozy cottage

Set on top of a hill with a wonderful breeze. It is a private, cozy quaint place. Five minutes from the trolley making it easy to go downtown. Close to the 8, 52, 94 & 125 freeways. Downtown San Diego is 20 mins away. If you like to hike we are only 5 minutes from Cowles mountain and other trails. Restaurants and shopping nearby. Beaches are 20 minutes away. We allow house trained pets. Please notify us of pets when booking. Plenty of street parking.

Top guest favorite
The living room features a comfortable sofa and inviting chairs arranged around a low coffee table. A large TV is positioned against a white wall, complementing the artistic decor. Natural light enters through the windows, creating a welcoming ambiance in the cozy space.
Cottage in San Diego
4.94 out of 5 average rating, 441 reviews

Fabulous Cottage at the Beach

Newly remodeled 1940's cottage just 50 steps to the sand with fabulous beach and ocean views. Enjoy the ocean breeze from your front porch and watch people walk by. Go sunbathing and swimming, take a bike ride or a stroll on the beach, have a glass of wine and witness the most beautiful sunsets. We are located in a quiet residential neighborhood of Ocean Beach. This bright and cozy cottage has everything you'll need to feel at home.

Top guest favorite
Cottage in Normal Heights
4.81 out of 5 average rating, 419 reviews

Kensington Cottage Escape- Sleeps 2!

Live and enjoy life like a local in this Chic Cozy Cottage in an upscale Kensington neighborhood! Enjoy the tranquil outdoor dining area along with comfortable queen bed with 1800 thread count sheets. There is ample free street parking. You are only 7-10 minutes to downtown, airport, zoo, Sea World & beaches! Walking distance to tons of restaurants, bars, shops, coffee shops & restaurants! This cottage has AC and heat throughout!

Guest favorite
Cottage in San Diego
4.88 out of 5 average rating, 403 reviews

Green Door Cottage | Charming Coastal Getaway

Just 3 blocks from the beach, Green Door Cottage is a cozy, colorful, dog-friendly escape in the heart of Ocean Beach. Enjoy a private yard, full kitchen, A/C, stylish vintage touches, and free parking for one car. Walk to top restaurants, local shops, tasting rooms, yoga studios, and Dog Beach just a few blocks away. Warm, welcoming, and full of coastal charm, it’s the perfect San Diego getaway.

Guest favorite
Cottage in Hillcrest
4.86 out of 5 average rating, 529 reviews

Dragonfly Cottage - In the Heart of San Diego

Cozy cottage located in HIllcrest, the heart of San Diego. Private entrance with a full kitchen and shared patio/BBQ area and Hot Tub. Super close to Balboa Park, The San Diego Zoo, Beaches and Downtown. Walking distance to an amazing array of restaurants and bars. A great place to relax and enjoy all that San Diego has to offer.

Top guest favorite
Cottage in Sherman Heights
4.96 out of 5 average rating, 268 reviews

Historic Charmer Steps to Downtown

Charming, fully renovated cottage located in an Historic District on the edge of Downtown San Diego. This is a safe, QUIET historic neighborhood. Not a tourist area. Most guests drive or ride share. There is one off-street parking spot for you. There no coffee shops or restaurants in the immediate few blocks.

Guest favorite
A charming outdoor area is surrounded by lush greenery, featuring a small wooden path leading to a light-hued cottage. A pair of red chairs and a round table are positioned on the earthy ground, complemented by various potted plants and a hanging swing nearby.
Cottage in Escondido
4.89 out of 5 average rating, 280 reviews

Mari’s Sunshine Cottage

Sweet little private cottage with a beautiful view. Walk to hiking & biking trails. Peaceful and beautiful surroundings. Please note: must be able to climb stairs to get to the cottage... There is a garden and a chicken coop and a lovely outdoor area for you to enjoy. We are a 100% non-smoking property.

Top guest favorite
A panoramic view of rolling green hills meets a shimmering bay, dotted with residential areas. Lush trees frame the foreground, while the coastline stretches into the distance under a clear blue sky.
Cottage in Pacific Beach
4.94 out of 5 average rating, 355 reviews

Family and Pet Friendly Beach Bungalow

Our newly renovated beach bungalow has 2 bedrooms, a large comfy couch and a full bath. It is located 1 mile from the beach, 0.2 miles to Vons, Starbucks, Trader Joe's, restaurants and bars. Bikes, beach chairs and a beach umbrella are available for use. Private gated parking. Pets welcome.

Popular amenities for Lakeside cottage rentals

Quick stats about cottage rentals in Lakeside

  • Nightly prices starting at

    Lakeside vacation rentals start at € 103 per night before taxes and fees

  • Verified guest reviews

    Over 130 verified reviews to help you choose

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Lakeside rentals

  • 5 Average rating

    Lakeside stays are highly rated by guests—averaging 5 out of 5!