Holiday houses in Glen Ellen

Quiet Wine County Retreat with Bocce and Hot tub!

Central wine country location Close to wineries, tasting rooms, gourmet market, french bakery & restaurants New luxury 3-BR, 2.5 bath Hot tub & bocce ball We can host 5 adults + 2-3 kids Quiet spacious home nestled in the redwoods on 1/2 acre Complimentary pastries from local bakery Linens, towels, spa robes & toiletries provided Complimentary coffee, tea & sugar Huge outdoor decks with 3 seating areas, dining table, fire-pit Corn-hole, giant jenga & board games Kids’ books, games & baby items

Casa de Vincenzi

Beautiful, immaculate private studio, situated in Kenwood village with separate entrance and garden patio offers a quiet retreat in the heart of Sonoma Valley. Walking distance to world class tasting rooms and restaurants. Close to Sonoma, Glen Ellen and fave parks. Enjoy your ensuite bathroom with fluffy towels and toiletries. Indoor or outdoor dining to enjoy wine, tea, conversation, TV or wifi. Sleep in the quiet of your comfy King size bed. TOT (Transient Occupancy Tax) included. TOT #3720N

Sonoma Valley, Glen Ellen Retreat - Wolf Glen

Wolf Glen is on a private road nestled in trees on Sonoma Creek, just a 2 - 3 minute walk to Glen Ellen village restaurants and Sonoma Valley wineries. Wolf Glen offers all the amenities of wine county living at its finest! This newly furnished, elegant 3,000 square foot home, designed for entertaining, offers lavish accommodations for 8 - 10 guests, featuring a gourmet kitchen, fireplace and new Samsung 65' flat screen Smart TV, private outdoor entertaining & eating area and new gas grill.

The Kenwood House, A Place to Stay

The Kenwood House, is a newly renovated turn of the century craftsman cottage, one of the most charming in Kenwood! Walking distance to wineries, vineyards and restaurants! You’ll love our cozy farmhouse style, relax on the front porch with views of the Kenwood Plaza Park. Enjoy the HOT TUB and fire pit under the stars in the magical backyard! Wine country serenity reminiscent of a New England landscape. Tesla Battery protection. $30 per extra guest over 4 per night. Sonoma County TOT #373

The Oak Haven - a relaxing sanctuary w/spa!

Welcome to The Valley Of The Moon! Glen Ellen, a hidden gem in the heart of the rolling hills of wine country, is only 20 minutes from downtown Sonoma and prides itself on offering something amazing for everyone. Many beautiful state parks and famous vineyards are just a few minutes away. Enjoy wilderness and fine wine at your doorstep in a beautiful, private home away from home at The Oak Haven. Relax, take a load off, you deserve it! License Number: LIC24-0319 TOT Certificate No: 1387N

Sonoma Wine Country Cottage

Private cottage on wooded lot in Sonoma Valley wine country with a separate gated entrance. Recently renovated, fully equipped, and very clean. Perfect for couples, weddings, or remote work. We love longer stays, with 30% weekly and 60% monthly discounts. Only 5-10 minutes to top Sonoma wineries, restaurants, hiking and Sonoma Plaza. Open studio design with queen bed, full sofa bed, bathroom/shower, full kitchen with cafe table, private deck with grill, AC, WiFi, Apple TV, EV charger.

Luxury home, heated spa tub, walk to restaurants

Luna Lodge, a 3 bedroom 2 bath Glen Ellen village luxury home in the heart of Sonoma wine country. The home has a beautiful garden with spa pool by a peaceful creek. Everything you need for a great vacation is at your fingertips. Situated on a quiet lane, 5 min walk to wine tasting rooms, top restaurants, food markets. Enjoy a gourmet private chef dinner while at the home. Let us know if you are interested and we will help you arrange a very special dining experience.

Wine Country Harvest Hideaway-Private entry/space

Welcome to our Harvest Hideaway! We’re centrally located in the heart of Sonoma Valley, right in downtown Glen Ellen. We are walking distance to restaurants, tasting rooms, and the great Glen Ellen Village Market. With dozens of wineries nearby, we are a 10 minute drive to Kenwood, and 15 minutes to the Sonoma Square. Within an hour, you can be on the coast in Bodega Bay or on the Golden Gate Bridge entering San Francisco. We are sure you'll have a fantastic stay!

Brand New Farmhouse Cottage in Wine Country

This light filled, modern cottage is perfect for couples and you can't get a better location in Glen Ellen Village than this. Located right next door to the historic Gaige House Bed & Breakfast, you are walking distance to great restaurants, tasting rooms, and the well-stocked village market. Within one mile, there are dozens of wineries and the deck just beckons you to come home after a day of wine tasting and barbecue as the sun goes down.

Glen Ellen Hideaway

One block to downtown Glen Ellen, with dining, shopping, & wine tasting. Hideaway is a charming, private guest house, suite-style behind our home. Spa-like bath, mini kitchen, comfy king bed! There is a large private patio for your enjoyment, great place to relax. Glen Ellen Hideaway is peaceful & private & has a separate entrance for your accommodations. Residents are Constance & Greig, and Franny, the dog, and Charm, the cat!-TOT#2398

Creekside Retreat Cottage – Wine Country Haven

Wake up beside the gentle creek in your own cottage escape! •Queen bed & cozy fireplace •Peaceful waterfront deck •Fully stocked kitchen & coffee bar •Fast Wi-Fi plus workspace •Backyard with creek access Minutes to Sonoma Plaza, wineries and trails, our 800-sq-ft hideaway is perfect for couples or solo travelers seeking nature and convenience. Washer/dryer, board games and parking included. Book your Wine Country Haven today!

The Carriage House Sonoma • Vineyard • Hot Tub

🍷✨ Vineyard Carriage House | Hot Tub + Bocce Ball + Views Escape to your private wine country retreat in the heart of Sonoma Valley! Located on our family’s working vineyard at Hamilton Family Wines, your stay offers the perfect balance of cozy charm and modern comforts — just steps from tasting rooms, shops, and dining in the village of Kenwood.