Holiday houses in Oakland

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Top-rated holiday rentals in Oakland

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

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Guest favourite

Home in Oakland

4.95 out of 5 average rating, 192 reviews

Private-Retreat|CARC|Firewood|Hot Tub|Essentials

Business Name: LAZY BEAR LODGE AT DEEP CREEK LAKE Need some QUALITY TIME away but want to avoid crowds & still be close to everything at the Lake? SECLUDED & PRIVATE, located on 3 acres in a SERENE FOREST OF HEMLOCK TREES & BOULDERS, this natural space is CALMING & Architecturally pleasing to the eye and soul! Let your cares slip away with the smell of a real wood fire, rustic décor, warm color paints, stone and wood. HOT TUB by FIREPLACE on deck. CARC membership, lots of firewood and supplies.

6–13 Dec

$1,019 NZD per night

Guest favourite

Tiny home in Oakland

4.98 out of 5 average rating, 168 reviews

The Original Hob

We have the Original Hob and Molly (separate listing) overlooking our creek at the point of 7 little waterfalls for your sleeping and hangout pleasure! A shared sweet kitchen and bath completes the 3 small structures. Full bath plus an outdoor shower makes for great accommodations. We're within 5 miles of State Parks and Deep Creek Lake. Come see the Garrett County stars, hear the creek and birds and be a million miles from where you are. Friendly dogs are welcomed -see "other things to note".

20–27 Aug

$242 NZD per night

Guest favourite

Home in Oakland

4.82 out of 5 average rating, 146 reviews

General Kelly Guesthouse

Welcome to our guesthouse! This place is perfectly situated for those who love the outdoors. Long walks down the lane, the rolling mountains and fields, and quiet nights can be yours to enjoy. The views are truly spectacular and can be enjoyed from the front porch in the summer or the enclosed sunroom on those chilly mornings. This house is perfect for couples or families wanting a quiet space to relax and recharge. Quaint and comfortable, each room is clean and personally decorated.

10–17 Dec

$269 NZD per night

Guest favourite

Guest suite in Swanton

4.8 out of 5 average rating, 198 reviews

The View now with Wi-Fi

Spacious, clean, modern basement efficiency apartment. Private entrance, private bath w/shower, private kitchenette with full size fridge & microwave (no stove), 1 queen size bed. Pool table, bar area and living room space with large TV equipped with satellite service. More space than a hotel room. View of Deep Creek Lake from front lawn in the distance, 11 Miles to Wisp, 6 miles to Deep Creek State Park and 1 mile to Thousand Acres Golf Course. NO Smoking, No Pets. We now have WIFI!!

7–14 Jun

$150 NZD per night

Guest favourite

Cabin in Oakland

4.98 out of 5 average rating, 158 reviews

SUGARBUSH - Sweet Serenity Tiny House

Welcome to SUGARBUSH! "Suga" is a 450 sq. ft. custom built tiny house. She will comfortably accommodate 2 adults or a family with 2 small children. AGE REQUIREMENT to book this space is 25+. At this time we DO NOT allow pets. Suga sits on a 3+ acre lot that use to be used for cross country skiing. She got her name from two trails, Sugarbush Run and Sugarbush Shortcut that ran through the lot! We welcome you to stay and enjoy our wonderful little getaway here in Pleasant Valley.

11–18 Sep

$244 NZD per night

Guest favourite

Cabin in Deep Creek

4.98 out of 5 average rating, 105 reviews

Boulder Ridge Cabin, close to Deep Creek, Maryland

Boulder Ridge Cabin is surrounded by woods, but within 15 minutes of Deep Creek Lake, swimming, boating, hiking, shopping, restaurants, Wisp Resort with skiing, snowboarding, mountain coaster, whitewater rafting at Adventure Sports Center International, rock climbing, hiking. Swallow Falls State Park and Herrington Manor State Park are about 15 minutes drive. Piney Mountain State Forest is within walking distance. Mountain biking and fishing are also close by.

30 Mar – 6 Apr

$258 NZD per night

Guest favourite

Tiny home in Accident

4.96 out of 5 average rating, 165 reviews

Romantic Getaway In The Pines

Looking for a romantic stay for you and your significant other??Then this unique romantic cabin is the perfect place for you! Nestled in the mountains near Deep Creek Lake, you can enjoy the fresh mountain air from the deck or hot tub with peaceful, scenic views. Propane and wood fireplaces outside along with and outdoor tv that you can watch from the hot tub! Soak in the beauty of Garrett County and all Deep Creek Lake has to offer. Hope to see you soon!

16–23 Sep

$306 NZD per night

Guest favourite

Cottage in Oakland

4.93 out of 5 average rating, 57 reviews

Cheerful cottage minutes from Wisp and Deep Creek

Just the right size and location for enjoying all Deep Creek Lake has to offer- including scenic hikes on many nearby trails, skiing at Wisp, or just enjoying time on the lake amongst bustling lake life. Then retreat back to our quaint cottage and enjoy time together. You will love our place because of its coziness, location, cleanliness, affordability and perfect size for a single family stay. *bathroom is in the bedroom *we have parking for a boat*

2–9 Mar

$252 NZD per night

Guest favourite

Cabin in Oakland

4.95 out of 5 average rating, 188 reviews

Lakehound Lodge - lake view, pet friendly

Cozy cabin in the middle of all that Deep Creek Lake area has to offer! Enjoy a dip in the hot tub by the fire with peekaboo lake views under twinkle lights. This three level cabin boasts a bedroom and bathroom on each level, two wood burning fireplaces, two living rooms, and an enclosed side porch with hot tub. Pets welcome for a fee. Close to the lake, Wisp, parks, golfing, fishing, and much more! Follow insta @lakehoundlodge

27 May – 3 Jun

$581 NZD per night

Guest favourite

Cabin in Davis

4.97 out of 5 average rating, 269 reviews

The Davis Loft - The Best Location in Davis!

The Davis Loft is the closest home rental to Blackwater Falls and is within walking distance to all that Davis has to offer. The loft has all the modern touches you would expect but still retains the right amount of rustic nostalgia that blends in so perfectly with the culture and landscape of the magnificent Canaan Valley. Have a front row seat to one of the most beautiful places in eastern North America.

16–23 Mar

$230 NZD per night

Guest favourite

Home in Swanton

4.97 out of 5 average rating, 186 reviews

Bev's House at Sunny Meadows

Looking for a place to stay that is quiet and relaxing, but also close to many outdoor activities? Bev's House at Sunny Meadows is just that! Located just minutes from several state parks that offer boating, fishing, kayaking, swimming, hiking and biking, there's always plenty to do. Bev's House offers a quiet place with spectacular mountain views to escape the rush and noise of everyday life.

29 May – 5 Jun

$344 NZD per night

Guest favourite

Apartment in Oakland

4.9 out of 5 average rating, 112 reviews

Private Unit on Farm with Kitchen & Balcony

The Herrington Suite is a private-entry apartment located on the first floor of our historic carriage house. Your stay will bring you to Haley Farm, a 65-acre inn and retreat center located just minutes from the lake. It includes a kitchen, sitting area, bedroom and ensuite bath with a LARGE jetted tub and walk-in shower. It also has a balcony overlooking the pond and farm.

29 Mar – 5 Apr

$349 NZD per night

Holiday rentals for every style

Get the amount of space that is right for you

Popular amenities for Oakland holiday rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Stay near Oakland's top sights

Walmart Supercenter75 locals recommend

Browning's Shop n Save48 locals recommend

El Canelo Restaurant13 locals recommend

Farmers Market44 locals recommend

China Wok5 locals recommend

Englander’s Antiques and Grill46 locals recommend

Other great holiday rentals in Oakland

Guest favourite

Cottage in Oakland

4.98 out of 5 average rating, 97 reviews

Pet friendly-Cottage in the Woods

20–27 Oct

$299 NZD per night

Superhost

Home in Oakland

4.87 out of 5 average rating, 62 reviews

The Wise Quack - A Taste of Deep Creek Lake!

18–25 Nov

$261 NZD per night

Guest favourite

Home in Oakland

4.98 out of 5 average rating, 45 reviews

Lovers Loft Lodge on the Lake, NO cleaning Fee!

13–20 Jan

$253 NZD per night

Guest favourite

Home in Oakland

4.86 out of 5 average rating, 42 reviews

Victorian Farmhouse with view of pleasant valley

5–12 Aug

$281 NZD per night

Guest favourite

Cabin in Oakland

5.0 out of 5 average rating, 29 reviews

Cabin in the Woods

10–17 Jul

$314 NZD per night

Guest favourite

Tiny home in Swanton

5.0 out of 5 average rating, 9 reviews

Tiny House-Dream Catcher Cabin #3

23–30 May

$185 NZD per night

Guest favourite

Farm stay in Swanton

5.0 out of 5 average rating, 20 reviews

The Country Nook at Waters Run Farmlands w/WI-FI

13–20 Mar

$149 NZD per night

Guest favourite

Farm stay in Accident

4.96 out of 5 average rating, 24 reviews

Honey Moon Farm Stay

20–27 May

$190 NZD per night

Show all

Quick stats about holiday rentals in Oakland

Total rentals	10 properties
Popular amenities	Self check-in, Gym and BBQ grill
Wi-Fi availability	10 properties include access to Wi-Fi
Rentals with dedicated workspaces	10 properties have a dedicated workspace
Total number of reviews	230 reviews
Nightly prices starting at	$68 NZD before taxes and fees

Holiday houses in Oakland

Top-rated holiday rentals in Oakland

Home in Oakland

Tiny home in Oakland

Home in Oakland

Guest suite in Swanton

Cabin in Oakland

Cabin in Deep Creek

Tiny home in Accident

Cottage in Oakland

Cabin in Oakland

Cabin in Davis

Home in Swanton

Apartment in Oakland

Holiday rentals for every style

Hotels

Unique stays

Homes

Popular amenities for Oakland holiday rentals

Stay near Oakland's top sights

Other great holiday rentals in Oakland

Cottage in Oakland

Home in Oakland

Home in Oakland

Home in Oakland

Cabin in Oakland

Tiny home in Swanton

Farm stay in Swanton

Farm stay in Accident

Quick stats about holiday rentals in Oakland

Total rentals

Popular amenities

Wi-Fi availability

Rentals with dedicated workspaces

Total number of reviews

Nightly prices starting at

Destinations to explore