Compare Cottages, Resorts, & Rentals in Oakland, Maryland, USA
About Oakland Vacation Rentals
There are over 929 amazing vacation rentals available in Oakland. Choose from a variety of options including villas, hotels, and other rental properties. Explore a vast selection of luxury amenities at unbeatable prices, providing you with the ideal spot for your next getaway. Life is Better at the Cottage with Vacation Cottage, where you can discover fantastic stays in Oakland.
Vacation Cottage offers numerous last-minute deals on villas, hotels, and rentals, both near you and across the globe. Whether you need accommodations for a group or event, such as a hotel or vacation rental (including cabins and private luxury villas), let us assist you. With Vacation Cottage in Oakland, you can easily compare options from multiple suppliers with just a click to find the perfect price point, amenities, and style of stay for you. Whether you're seeking group discounts, private pools, hot tubs, pet-friendly options, or spacious master suite bedrooms with open-air showers, you can find it all with Vacation Cottage vacation rentals, resorts, and Airbnb-style properties in Oakland. The average size of places to stay near Oakland is approximately 1841.59 ft², with prices averaging US $472 per night.
Vacation Cottage helps you discover the perfect holiday rental to create lasting travel memories in Oakland. Prices listed often feature discounts compared to rack rates. Simply search for your destination and secure your ideal place to stay today.
Find Vacation Cottage Rentals in these Cities and Neighborhoods Oakland, MD
Frequently Asked Questions About Oakland?
What are the top cottages, summer homes, and lake houses in Oakland?
- Quaint and So Cozy Deep Creek Lake Log Cabin in Sought After Yellowstone Village
- The Love Shack- The BEST Couples and Small Family Retreat at Deep Creek Lake!
- Sunny Escape 2 - A new era for a familiar lake front home
- Level lakefront, family-friendly, hot tub, low fees, private dock
- Timroc II, FIVE STAR REVIEWS! LAKE ACCESS, GREAT SWIMMING, PRIVATE 2 ACRES!
- Lakefront, 3 Amazing Decks, Tennis/Pickle Ball, Boat Slip, Hot Tub, Bed Swingn
- Stunning 7 Bedroom 6.5 Bath Lakefront Home with Dock Slip
- Fall Fun at our Centrally Located Lake View Condo that sleeps 6!
- Lakefront, dog friendly, dock slip, hot tub, and fire pit
- Unobstructed lake views from living areas. Restaurants & activities in minutes
How many rentals, hotels, or resorts are available in Oakland?
Vacation Cottage consistently updates its selection, offering a blend of new options alongside well-established accommodations in prime locations. Currently, there are over 929 properties listed by Vacation Cottage in the Oakland area for the year 2025, with this number increasing daily. By aggregating listings from various websites and travel providers, Vacation Cottage ensures a diverse array of choices for the best luxury stays in Oakland.
Nearby Neighborhood (6)
| Neighborhood | Property Count |
|---|---|
| Mountainside Rental Cottages and Private Getaways in Cumberland, Maryland | 75 |
| Blakeslee Rental Cottages and Private Getaways in Cumberland, Maryland | 53 |
| Paradise Point Rental Cottages and Private Getaways in Cumberland, Maryland | 31 |
| Silver Ridge Rental Cottages and Private Getaways in Cumberland, Maryland | 1453 |
| The View Rental Cottages and Private Getaways in Cumberland, Maryland | 1734 |
| Timbers on the Yough Rental Cottages and Private Getaways in Cumberland, Maryland | 104 |
