Book a Place to Stay in Sherwood for Your Summer Getaway
About Sherwood Summer Rental on Vacation Cottage
Elevate your summer travels with 65 top-notch stay to make the most of your summer adventures? Consider a summer resort or villa rental in or near Sherwood. Choosing the perfect holiday rental for your upcoming summer getaway on Vacation Cottage is a breeze. Whether you're traveling with family, friends, or a group to Sherwood or its surrounding areas, Vacation Cottage offers a plethora of luxury summer accommodations to select from. Many of these accommodations boast top-notch amenities such as private pools, indoor/outdoor pools, hot tubs, WiFi, beach access, nearby parks, luxurious bedrooms, bathtubs, and pet-friendly environments.
Searching for a tranquil retreat in Sherwood for an unforgettable summer holiday? Vacation Cottage's summer rental homes are ready to provide you with the utmost comfort you deserve. Whether you're in need of a premium summer condo, luxury flat, resort, villa, bungalow, cozy cabin, RV, or cottage in Sherwood, Vacation Cottage has you covered for your next summer escapade.
Frequently Asked Questions About Sherwood Luxury Rentals
What are the top rated Summer Rentals in Sherwood?
There are a lot of options in Sherwood. If you plan on staying in the Sherwood area, consider making a reservation for a few nights at one of these properties as these have been rated the top Summer Rentals in Sherwood:
- Overlook on Dun's Cove - Luxury waterfront hideaway minutes from St. Michaels
- Hurry, reserve your stay for nSummer & Fall of 2025nSTR #22-30
- Secluded Waterfront Property on 3 acres with swimming pool and dock.
- Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND
- Private Retreat with HUGE Water Views!
- Eastern Shore Waterside Cottage Near St. Michaels
- Waterfront Home on Chesapeake Bay with Dock, Bikes & Sunset Views
- 6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access
- House on the Chesapeake Bay
- Minutes from Downtown St. Michaels | Waterfront | Pet Friendly | Private Dock
How many summer rentals are available around Sherwood, MD?
In 2025, Vacation Cottage offers 65 summer rentals in or around Sherwood. Find unique home rentals for your summer holiday or a weekend getaway with family and friends.
How much does it cost to rent a summer rental in Sherwood?
The average price per night for a summer rental in Sherwood is $609. Check the full list of summer accommodations in Sherwood.
How many summer rentals are available to book in Sherwood?
There are 65 summer rentals, cabins, cottages and properties that are available to rent. Book for your next trip with Vacation Cottage.
Do any summer rentals in Sherwood have a private pool?
Yes, here are some popular summer holiday rentals in Sherwood that have a private or indoor pool:
- Overlook on Dun's Cove - Luxury waterfront hideaway minutes from St. Michaels
- St Michaels Area Cottage - Walk to Water and Marina
- The Tilghman Island Inn
- "Point of View" Waterfront cottage with panoramic views on Tilghman Island
Check all holiday rentals with a pool in Sherwood on Vacation Cottage.
Can I rent pet-friendly summer rentals in Sherwood?
Yes, We have 65 summer rental homes in Sherwood and types of place to stay in Sherwood include:
- Vacation Homes: 65 available for rent
- Villas: 65 Rentals available for rent
- Holiday Apartments: 65 Rentals available for rent
- Hotels with Suites: 65 Rentals available for book
Do you have a luxury summer rental with a pool in Sherwood?
Yes, of course! There are many luxury summer rental properties in Sherwood. Use our search filter to discover all of our luxury summer accommodations with an indoor/outdoor pool. Sorting by price is another way to find the most and least expensive luxury summer rentals in Sherwood.
