Holiday houses in Annapolis

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Top-rated holiday rentals in Annapolis

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Top Guest favourite
A welcoming living room features a gray sectional sofa and two green armchairs, arranged around a round coffee table. A wood-burning stove is positioned on a raised platform, surrounded by stacked firewood. Large windows provide views of the forest and allow natural light to fill the space.
Home in Sea Ranch
4.96 out of 5 average rating, 376 reviews

Award-Winning Forest Getaway: @thesearanchhouse

**Recently refreshed/re-furnished!** This house was named 'The Ranch House' by its architect Don Jacobs, this updated 70s cabin is a forest getaway with modern sensibility. The house is surrounded by redwoods & has 2 large decks, 1 w/ propane firepit w/ ample seating, the other w/ hot tub. Living room has picture windows w/ forest views & Morso wood-burning stove. Guests are encouraged to enjoy the hiking trails, pools, and outdoor amenities. House comfortably sleeps 4, plus fiber-optic internet

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Top Guest favourite
An aerial view of the Mendocino Tree House reveals its unique octagonal structure nestled among towering redwood trees. The wrap-around deck offers ample outdoor seating, while the landscaped garden features meandering pathways and various plants, creating a serene natural environment.
Home in Mendocino
5 out of 5 average rating, 145 reviews

Private Mendocino Home with Luxury Outdoor Spa

Escape to the privacy of the Mendocino Tree House, an octagon retreat built around an 80 year old redwood tree with a full luxury outdoor spa. The 2 bed/2 bath home blends modern style with natural splendor. Relax on the expansive wrap-around deck, or unwind by the fire pit amidst the redwoods. Indulge under the stars in the outdoor spa oasis, boasting a hot tub, wood-fired sauna, clawfoot tub, and shower. Immerse yourself in comfort, where every detail invites you to embrace peace and serenity.

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Guest favourite
Home in Lower Lake
4.94 out of 5 average rating, 108 reviews

Cozy Lakefront Retreat - Private Trails & Beach

A bright historic farmhouse overlooking Clear Lake, with a private lakefront cove and access to a second shared beach & dock. Scenic views, private trails, and generous indoor and outdoor gathering areas are ideal for unwinding together. Enjoy meals on the covered veranda, cook in the well-stocked kitchen, bathe in the outdoor spa, play in the game room, or gather by the fire pit after sunset. Wineries, farm stands, shops, and hiking nearby make great outings for couples, families, and friends.

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Top Guest favourite
A serene seating area features sleek lounge chairs positioned to face expansive glass windows, showcasing panoramic views of the Pacific Ocean. Natural light floods the space, highlighting the minimalist design and wooden flooring. A private outdoor deck is accessible through the glass door.
Home in Sea Ranch
5 out of 5 average rating, 133 reviews

Design & Style with White Water View

A truly one-of-a-kind, stylish retreat with unobstructed, cliffside Pacific views and all the comforts of a boutique hotel. Located in historic Condo Unit 2 and designed by the original architects, Moore Lyndon Turnbull Whitaker. The home sits adjacent to The Sea Ranch Lodge, with direct access to 10 miles of coastal trails & all The Sea Ranch amenities . It has been thoroughly updated with today's convenience and comfort in mind. Unwind, unplug, relax in this unique paradise on the coast.

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Top Guest favourite
The living room features a circular design with large windows showcasing views of the surrounding forest. A comfortable sofa and armchair are positioned on a textured area rug, complemented by a stone fireplace. The high ceiling enhances the spacious feel of the room.
Home in Sea Ranch
4.99 out of 5 average rating, 168 reviews

Private and spacious redwoods retreat at Sea Ranch

Tucked away in the redwoods, this newly furnished home is a serene retreat at Sea Ranch. It enjoys near-total privacy on three acres of forest, plus the sound, smell and sight of the ocean through a gap in the trees on a clear day. The main room and the master bedroom are spacious, with views of the forest from every angle. The house has fiber-optic internet and has sufficient space for two people to work remotely very comfortably. More pictures on IG: @theseaforesthouse. TOT 3398N.

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Guest favourite
An A-frame cabin stands amid towering redwoods, featuring large glass windows that allow natural light to fill the space. A small seating area is positioned on a wooden deck, surrounded by lush greenery and peaceful forest views.
Cabin in Gualala
4.95 out of 5 average rating, 260 reviews

Cozy A-frame | Hot Tub under Redwoods | Trails

Our A-Frame is as connected as you like 🛜 , but as remote as you need 🌲RELAX and work remote if you choose. *=>PET FRIENDLY<=* Soak in the private hot tub under redwoods and stars on the coastal ridge, (listen for the waves at night), propane fire pit, and outdoor dining High speed internet, kitchen, first floor bedroom with a double/twin bunk-bed, and loft with a queen-bed. Perfect remote retreat or work cabin 4 acres of walking trails are shared with other cabins on the property

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Guest favourite
A wooden bridge connects the ground to a treehouse elevated among tall trees. The treehouse features large windows and a circular design, surrounded by lush greenery. A sturdy netting lines the sides of the walkway, ensuring safety while traversing to this unique retreat.
Treehouse in Bodega Bay
4.95 out of 5 average rating, 212 reviews

Eagle's Nest Treehouse Farm Stay

Eagle's Nest Treehouse Farm Stay is a tranquil, secluded, luxurious, romantic wilderness experience in a private forest on a 400 acre working ranch. Thirty feet above the forest floor you are nestled in a gorgeous, well-appointed suite of 1,000 year old polished redwood, with bathroom and amazing copper/glass forest-view shower. Explore hiking trails through the forest and learn about ranch operations (Highland cattle, goats and ducks). See guest comments in the space description.

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Top Guest favourite
A wooden walkway leads towards the entrance of a cabin nestled among towering redwoods. The pathway is flanked by moss-covered stumps, while the warm exterior of the cabin blends harmoniously with the natural surroundings.
Cabin in Sea Ranch
5 out of 5 average rating, 100 reviews

The Tree House, serene Sea Ranch location

Tucked away in a quiet corner of Sea Ranch in Northern Sonoma County, the cabin is surrounded by a half acre of beautiful, towering redwoods. Get away from it all & reconnect with nature. The cabin is truly a special place where you can unplug, relax, & recenter yourself. Winner of a 1986 Sea Ranch Community Enhancement Award, the cabin represents the best of Sea Ranch architecture, designed by architect Don Jacobs & built by Matt Sylvia, builder of the world-renowned Condominium One.

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Guest favourite
A bright dining area is highlighted by a large wooden table surrounded by six rustic chairs. Windows provide natural light and views of the surrounding greenery. A decorative light fixture hangs centrally above the table, adding a touch of charm to the space.
Home in Jenner
4.9 out of 5 average rating, 388 reviews

Serene Coastal Retreat Clark's Cove

Escape to the tranquil beauty of Clark's Cove, a private coastal home with breathtaking Pacific Ocean views. Unwind on expansive decks merging indoor and outdoor spaces. Find serenity in the comfortable main living area and master bedroom. Rejuvenate in the luxurious bathtub. Explore nearby beaches, hiking trails, and wineries for a perfect coastal getaway. Take a short drive to discover beaches, hiking trails, and more! Book now for an unforgettable escape. License #327175

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Top Guest favourite
The interior features warm wooden walls and large windows offering views of the outdoors. Comfortable seating areas with green cushions flank a cozy wood stove. A decorative woven basket and a colorful, striped pouf enhance the inviting atmosphere.
Home in Sea Ranch
5 out of 5 average rating, 125 reviews

ROSEA Ranch: cozy, oceanfront, walk to beach

Located steps from premier sand beach, Walk on Beach. Entering the gates, you'll be greeted by a tranquil, mature garden blocked from the wind, a deck, and a hot tub. Inside this solar powered 1970s modern vernacular contemporary home, you'll find a cozy raised living room positioned for maximum views. Bedrooms are on the ground floor, along with bathrooms, living, dining, fully-equipped kitchen, and laundry. A study is upstairs. 1% of proceeds go to airbnb.org

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Top Guest favourite
A contemporary structure is nestled among tall trees, with a wooden deck extending in front. Warm light spills from multiple windows, creating a welcoming ambiance. The surrounding greenery adds a natural touch to the tranquil hillside setting.
Home in Sea Ranch
4.97 out of 5 average rating, 225 reviews

Gray Fox Dacha: The Sea Ranch Retreat

The Gray Fox Dacha, a concept design retreat in Sea Ranch, outfitted with elemental, organic materials. With spectacular ocean views and perched on a hillside amongst fragrant shore pines, towering redwoods, and rugged, windswept cypress, this sunlit, eclectically designed smart home is ethereal and airy. The Gray Fox Dacha offers a constellation of lovingly curated spaces with globally-sourced artifacts from the host’s personal collection.

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Top Guest favourite
The exterior of a mid-century home is set among towering redwoods, showcasing a rustic wooden facade. Large windows offer views into the cozy interior. A private hot tub is located nearby on a gravel path, surrounded by the natural landscape.
Cabin in Sea Ranch
4.93 out of 5 average rating, 213 reviews

Mini-Mod #3 at The Sea Ranch.

Hidden among the redwoods of California’s Sonoma Coast, roughly three hours north of San Francisco, Mini-Mod #3 is one of only two individual residences at The Sea Ranch listed on the National Register of Historic Places. Designed in 1967 by Joseph Esherick and George Homsey, the small modernist retreat is one of the defining homes from Sea Ranch’s formative years, pairing Northern California modernism with understated contemporary comforts.

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Popular amenities for Annapolis holiday rentals

  1. Airbnb
  2. United States
  3. California
  4. Sonoma County
  5. Annapolis