Cottage vacation rentals in Lakeside

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Top-rated cottage rentals in Lakeside

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Top guest favorite

Cottage in San Diego

4.95 out of 5 average rating, 132 reviews

Dog friendly California Cottage near SDSU

Whether you're staying in town for business at the college or the local hospitals; or just vacationing for the week or the weekend, this house is centrally located near SDSU, the village of La Mesa & Lake Murray. Relax and enjoy the private setting of your own 1 bed room cottage. We refer to the premises as The Olive Tree Cottages. Our olive trees are original (1935) to the property which host in addition to the tiny house-two cottages; each with their own private yards and private entrances.

Top guest favorite

Cottage in Greater North Park

4.97 out of 5 average rating, 140 reviews

Peaceful North Park Cottage Near Morley Field

Welcome home to the spacious one-bedroom Wightman St cottage. A fully-equipped kitchen supports a romantic dinner for two. Make yourself at home as you'll have plenty of space to stretch out, stow luggage, hang clothes and make the most of your home-away-from-home. Enjoy free Wifi, cable and digital amenities to help you plug-in and chill-out. Washer/dryer are provided to make it feel like you could stay forever. Free beach gear (chairs,umbrella,towels) is included for that fun beach day!

Guest favorite

Cottage in Lakeside

4.95 out of 5 average rating, 132 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

Top guest favorite

Cottage in El Cajon

4.99 out of 5 average rating, 143 reviews

Cedar Cottage Retreat with Mountain View’s

Welcome to the Cedar Cottage nestled in the foothills of San Diego county. Where Vintage/Rustic charm meets modern sophistication. The Cottage sleeps 3 in 1 Queen bed and 1 comfortable Twin bed, 1 bathroom. Pet friendly. Just 2 miles from Sycuan resort, casino & golf . Get back to nature at this delightful cabin hideaway in the hills just 3.5 miles from the quaint town of Alpine. This very special private estate has natural beauty when looking out from the cottage in any direction.

Guest favorite

Cottage in Adams North

4.96 out of 5 average rating, 117 reviews

LOFT: Detached Cottage with Patio

The LOFT is in the heart of Normal Heights; which is by far the best spot in the best part of town you could possibly stay. Everything is walkable, so it’s a local’s favorite! 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.

Superhost

Cottage in Pacific Beach

4.92 out of 5 average rating, 519 reviews

Resort Style - Cottage Getaway

Perfect for staycations, remote work, romantic getaways, or extended stays (weekly & monthly). No parties, please. Charming 1 bed, 1 bath cottage offers resort-style comfort for two guests. Plush queen-sized bed, a luxurious bathroom and fully equipped kitchen. Step outside to your private courtyard and backyard—complete with a firepit, BBQ and outdoor shower. Includes free street parking, bikes, a Pack ’n Play, boogie boards, beach toys, cooler, and more!

Guest favorite

Cottage in Julian

4.98 out of 5 average rating, 733 reviews

Cottage on the Rock | Hot Tub · King Bed · Bikes

Couples, Families, & Mountain Peace Seekers only, please. Perched on top of a granite boulder outcropping sits this idyllic cottage for your magical retreat in Julian. Originally constructed as a tourmaline miner's cabin in 1930, the Cottage on the Rock was completely rebuilt from top-to-bottom nearly a century later for the modern Californian. Brilliantly designed by SoCalSTR® | IG: @socalstr "Top 1%" local market performer according to AirDNA

Guest favorite

Cottage in North Ocean Beach

4.93 out of 5 average rating, 385 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 La Mesa

4.97 out of 5 average rating, 324 reviews

La Mesa House On a Hill With Mountain Views!

SUNRISE PERCH - A standalone guest house, perfect spot for your San Diego stay! Enjoy inspiring sunrise views from the deck or relax indoors with super fast WiFi and a 43" TV. Enjoy a full kitchen! The king bed is super comfy and the bathroom is stocked. The space is only for those looking for quiet. No partying/loud socializing. Families welcome! Located 20 min from downtown San Diego and 25 min from the nearest beach (Ocean Beach).

Top guest favorite

Cottage in La Mesa

4.93 out of 5 average rating, 198 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.

Top guest favorite

Cottage in Julian

5 out of 5 average rating, 251 reviews

Briar Patch Cottage | Hot Tub · Downtown Julian!

Enjoy modern comfort with a twist of vintage charm at Briar Patch Cottage. This 950 square foot cottage has been curated for the ultimate guest experience- with a fully stocked kitchen, efficient (new!) ac/heating, wood burning stove, private patio with hot tub, laundry, alley access, terraced deck and front flower garden- all a block and a half from Main Street in Julian!

Superhost

Cottage in Ocean Beach

4.87 out of 5 average rating, 261 reviews

Ocean Beach ~ Your dream vacation!

Welcome to our charming Beach Bungalow, a coastal haven just steps away from the sand and sea. This idyllic retreat offers a cozy living space with panoramic ocean views, a well-equipped kitchen, and comfortable bedrooms for peaceful nights. Enjoy private patio moments, beach walks, and the soothing sound of the waves. Your ultimate beach bum experience begins here.