Oakland vacation rentals

4.91 out of 5 average rating, 85 reviews

Cottage in Windham

Tranquil waterfront cottage

A private clean tranquil cottage, dock, parking, deck, grill, hammock, kitchen & all amenities, bathroom, 2 bedrooms, sleeps 5, futon, WIFI, cable, bidet, washer & dryer, granite outdoor table, kayaks, paddle boards, floats, fire pit and fireplace. Minutes from great restaurants, bars, hiking trails, and shopping. The most amazing sunsets. 30 minutes from Portland. Winter rentals as well. 40 min. from Shawnee Peek, 1 mile from Seacoast tubing. This place is privately yours. Smoke free please!

Condo in Carrabassett Valley

A welcoming entryway features warm wooden paneling and a spacious boot and helmet storage unit. Hooks are available for equipment, while a bench offers a resting spot. Bright red rugs line the area, creating contrast against the neutral carpet and walls.

4.97 out of 5 average rating, 67 reviews

2BR, 2BA Sugarloaf Mountain Ski-in Ski-out condo

Second-level Sugarloaf Mountain condo getaway! Master bedroom w/ queen bed; upper level open loft bedroom sleeps up to 4 in 1 twin-sized bunk beds + 2 twins; 2 full baths; gas-fireplace; laundry; granite kitchen countertops; & private balcony. Extremely convenient 1-min walk to Snubber chairlift, 30-sec walk to shuttle stop, & easy trail access to Sugarloaf Outdoor Center. Year-round activities: alpine skiing, x-country skiing, snow shoeing, fat biking, mountain biking, golf, hiking, & more!

4.81 out of 5 average rating, 103 reviews

A tranquil wooden dock stretches over calm lake waters, leading towards a vibrant sunset reflected on the surface. Silhouettes of two individuals can be seen near the end of the dock, with rocks lining the shore and gentle waves lapping against the edges.

Cottage in Embden

Gorgeous lakefront, sunsets, kayaks, fire pit

Enjoy breathtaking sunset views from this cozy, quiet waterfront home. Relax and play at our serene lake house, 40 feet from the water. Embden is the 3rd cleanest lake in Maine and our lot is wooded for nice privacy. Fire pit, lounge chairs and hammock at the water's edge. Kayak, paddleboard, swim, yard games, fish or relax! Great golf close by! In the winter warm up by the fire after playing outside (sugarloaf 35 mins) ski, snowmobile, ice fish for salmon! Our driveway accommodates trailers.

Home in Carrabassett Valley

5 out of 5 average rating, 16 reviews

Mountainside - Ski In/Out Condo

You'll be close to everything in this modern condo. Top of Mountainside Road - walk 1 min to the trail & ski down to Whiffletree lift. Easy to stop for lunch or quick warm up. Après - stroll down to the Village for food & fun! 3 bedrooms (2 queen beds & 4 bunks) Open Kitchen, living & dining room w/ fireplace. Large mudroom for all your gear. Deck overlooking Bigelow Range. Last 6+ years 4.9 star reviews & managed by rental agent. Now Book direct with owner, a Sugarloafer since 1977!

4.94 out of 5 average rating, 126 reviews

Home in Windham

Waterfront Gem walkable to Restaurants!

Waterfront Oasis on Pettingill Pond. You couldn't get any closer to the water, it's steps away. There are 3 Kayaks, and a paddleboat, firepit and dock for guest use! This a great spot for swimming and watersports! This home has been newly renovated, the effect results in a simple, stylish, comfortable space for guests to enjoy. Walk to Franco's Bistro for from Scratch Italian food, or Bob's Seafood for a fish taco! This is a piece of paradise on sweet Pettingill Pond in the heart of Windham.

Home in Carrabassett Valley

4.92 out of 5 average rating, 37 reviews

A Perfect Home For Family Summer Vacations!

This expansive and family-oriented home is situated on Sugarloaf, offering 5 bedrooms, 4.5 bathrooms, two spacious living areas, and a generously sized kitchen and dining space. Located on the Winter shuttle route and within close proximity to hiking/biking trails, the Carrabassett River and golf course! Enjoy the gas fireplace after a day on the slopes or a game of ping pong with the family! Nestled in the mountains, this exquisite home presents an ideal setting for your upcoming vacation.

4.77 out of 5 average rating, 47 reviews

Two comfortable chairs are positioned on a wooden deck, facing a serene view of Rangeley Lake. Lush greenery surrounds the area, and a single tree stands prominently near the water's edge. The scene reflects a calm and peaceful atmosphere.

Cabin in Rangeley

Waterfront Cabin on Rangeley Lake!

True Lyons Cabin 1. Two bedroom, plus sleeping loft, right on Rangeley Lake! Comfy beds and new furnishings! Wonderful little wood stove for those cold nights! 150’ beach with large dock right out front! Large fire pit. Gorgeous views all day long and amazing sunsets! Walking distance to the LOON LODGE & FARM HOUSE Downtown Rangeley 1.5miles away. One bedroom has a queen bed and other has two twins. Loft has full bed. Great WiFi! Brand new Air Conditioning system in entire cabin!

4.83 out of 5 average rating, 6 reviews

Home in Boothbay

Tailwinds - Upscale Oceanfront! Stunning Views!

Welcome to Tailwinds in East Boothbay, where you will enjoy stunning sunsets over Linekin Bay from the comfort of this beautifully updated home. Formerly a B&B, this is a perfect place to gather frinds and family with en-suite baths 2 living rooms and a large porch. You will also find all new beds and furniture, luxurious 100% cotton linens, and AC window units in the bedrooms. Located between downtown Boothbay Harbor and Ocean Point, this is a gorgeous spot for your next family vacation!

4.98 out of 5 average rating, 47 reviews

A serene lakeside view is captured at sunset, showcasing the soft glow of the sun reflecting on the water. A wooden dining table with chairs is positioned on the deck, accompanied by a large umbrella, enhancing the inviting outdoor space.

Home in Liberty

Peaceful Lakeside Getaway with Hot Tub!

Enjoy our fully renovated, lakeside, four season retreat. During the summer spend time fishing, kayaking, swimming, lounging in the hammock and then escape the heat inside the fully air conditioned house! In any season, unwind in the lakeside hot tub, take in every gorgeous sunset and dark starry night or gather around the campfire. The winter months bring snow shoeing, ice fishing, snuggling up in the living room playing games or watching a movie fireside. There is something for everyone!

4.89 out of 5 average rating, 303 reviews

The A-frame cabin features a wooden deck supported by a sturdy frame, providing access to outdoor seating and a hot tub. Large windows offer views of the surrounding trees, while a snow-covered ground adds to the tranquil winter setting.

Tiny home in Harrison

Million $ views, Hot Tub, Crooked River- Private

Secluded A-frame nestled along Crooked River, breathtaking views and world-class fly fishing beckon. Swim in the river or explore scenic hiking trails right from your doorstep. Inside, savor modern comforts including central AC. Just minutes from pristine lakes, primo golf courses, and thrilling ski slopes, this charming private oasis offers an ideal mix of tranquil relaxation and outdoor adventure. Book your unforgettable getaway today and immerse yourself in this one-of-a-kind retreat!

Cottage in South Thomaston

A serene ocean view showcases a sailboat gliding across calm waters, framed by lush greenery and a rocky coastline. The expansive sky is filled with soft clouds, creating a tranquil atmosphere that invites relaxation and reflection.

4.95 out of 5 average rating, 104 reviews

Cottage by the sea private oceanfront shoreline

Breathtaking oceanfront private cottage. Spiral staircase to second floor bedroom. Sliding glass doors open to wrap-around deck and lawn that slopes to Ocean. 300 + feet of deep water frontage. Separated from lawn by broad rock ledge. Perfect spot for sunbathing or having a campfire in the evening. Enjoy your morning coffee watching lobster and sailboats in the Mussel Ridge Channel. Unbelievable and peaceful views out to ocean and north to the Camden Hills. Unparalleled views everywhere.

4.98 out of 5 average rating, 51 reviews

A wooden staircase leads upward, illuminated by natural light. A framed art piece hangs on the wall, and a potted plant is positioned on the landing. The railing features a curved design, complementing the warm wooden tones of the stairs.

Guesthouse in Belfast

Adorable cottage 5 minute walk from downtown

Newly custom renovated 1 BR, 2 floor cottage 5 minute walk from downtown, 2 minutes from farmers market & bay. Each floor has a balcony for AM coffee/evening drinks. Loft style master BR connecting bathroom, first floor kitchen/living room combo - full (compact) kitchen - Custom woodwork, great design. Bathroom accessible from 2nd Fl BR. (The couch was recently replaced it’s not the one pictured (it’s actually much more comfortable) Crib available upon request No pets No smoking

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Popular amenities for Oakland vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Stay near Oakland's top sights

Colby College17 locals recommend

Colby Museum of Art45 locals recommend

Quarry Road Trails11 locals recommend

Buen Apetito9 locals recommend

Tree Spirits9 locals recommend

Belgrade Boat Shop6 locals recommend

Other great vacation rentals in Oakland

Home in Carrabassett Valley

A spacious interior showcases a modern design with exposed wooden beams and large windows allowing natural light to fill the area. Glass railings overlook an open space below, creating a sense of openness and connection to the surrounding greenery.

5 out of 5 average rating, 4 reviews

The Epic Sugarloaf Family Getaway!

5 out of 5 average rating, 103 reviews

An outdoor seating area is presented with a spacious sectional sofa made of dark wicker, positioned under a covered patio. The lawn extends towards the private sandy beach and dock by the lake, with a view of kayaks and trees in the background.

Cottage in Belgrade

Lakefront Home, Sandy Beach, Belgrade Lakes Maine

4.97 out of 5 average rating, 63 reviews

Home in Gray

cozy 3 bedroom ranch with deck and screen porch

Home in Dallas Plantation

4.93 out of 5 average rating, 29 reviews

Ski/snowmobile retreat-hot tub

5 out of 5 average rating, 3 reviews

The sun sets over Great Moose Lake, casting warm orange and golden hues across the water's surface. Reflections of the sunlight dance on the rippling waves, while silhouettes of trees mark the shore in the distance.

Home in Hartland

The Great Moose in Stunning Maine Swim, Fish & Ka

4.95 out of 5 average rating, 92 reviews

A cozy cabin interior features a blend of wooden walls and laminate flooring. Comfortable seating is arranged around a wooden table. Windows allow natural light, and a door provides access to the outside. A small kitchen area is also visible, showcasing basic amenities.

Cabin in Moscow

Cabins/Sporting camps-great location

5 out of 5 average rating, 101 reviews

Two black Adirondack chairs are positioned around a stone fire pit on a stone patio. In the background, a serene view of Winnegance Creek is visible, framed by trees and a cloudy sky.

Home in Bath

Waterfront Farmhouse with Modern Flair!