35 Grimstead Cabin Rentals By Owner

Grimstead Cabin Rentals

Private Sandy Beach & Chesapeake Bay Sunsets

New

House

Private Sandy Beach & Chesapeake Bay Sunsets

3 Bedrooms 2 Baths 8 Guests

AU $614/Night 7 Nights - AU $4,298

View Deal

Adventures on the Bay - Bayfront Escape, Private Dock, Large Deck, and Lake Views!

House

Adventures on the Bay - Bayfront Escape, Private Dock, Large Deck, and Lake Views!

3 Bedrooms 2 Baths 6 Guests 2002.09 ft²

AU $679/Night 7 Nights - AU $4,753

View Deal

Gwynn's Island Cottage - Private Beach on the Chesapeake Bay!

Highly Rated

Cottage

Gwynn's Island Cottage - Private Beach on the Chesapeake Bay!

10.0

Exceptional

(224 Reviews)

2 Bedrooms 1 Bath 4 Guests 1200 ft²

AU $425/Night 7 Nights - AU $2,973

View Deal

Gwynn's Island Gem | Private Beach & Bay Views

House

Gwynn's Island Gem | Private Beach & Bay Views

3 Bedrooms 2 Baths 8 Guests 1302.43 ft²

AU $530/Night 7 Nights - AU $3,711

View Deal

House

Cozy little home on Gwynn's Island with semi-private Chesapeake Bay beach access

10.0

Exceptional

(5 Reviews)

2 Bedrooms 2 Baths 5 Guests

AU $370/Night 7 Nights - AU $2,590

View Deal

House

Kimary Cove - Waterfront Relaxation and NO CLEANING FEE

9.6

Exceptional

(22 Reviews)

2 Bedrooms 1 Bath 4 Guests 1460 ft²

AU $201/Night 7 Nights - AU $1,408

View Deal

House

Oyster Haven/Waterfront Retreat on Lanes Creek/Mathews, VA

2 Bedrooms 1 Bath 4 Guests

AU $352/Night 7 Nights - AU $2,467

View Deal

Highly Rated

House

PRIVATE BEACH on the Chesapeake Bay

10.0

Exceptional

(141 Reviews)

5 Bedrooms 3 Baths 12 Guests 2760 ft²

AU $890/Night 7 Nights - AU $6,230

View Deal

Top 10% in Grimstead

House

Beach House on Chesapeake Bay!

10.0

Exceptional

(137 Reviews)

3 Bedrooms 2 Baths 8 Guests 1800 ft²

AU $766/Night 7 Nights - AU $5,363

View Deal

Sand and Sun Beachfront Home on Chesapeake Bay - Gwynn’s Island, Mathews County

Highly Rated

House

Sand and Sun Beachfront Home on Chesapeake Bay - Gwynn’s Island, Mathews County

10.0

Exceptional

(50 Reviews)

3 Bedrooms 3 Baths 8 Guests 1800 ft²

AU $569/Night 7 Nights - AU $3,984

View Deal

House

Private Beach - Peaceful Retreat - Kayaks Bicycles Firepit and Pet-Friendly!

10.0

Exceptional

(35 Reviews)

3 Bedrooms 1 Bath 6 Guests

AU $422/Night 7 Nights - AU $2,956

View Deal

House

Beach House Getaway, exclusive location on "Chesapeake Bay" with private beach

10.0

Exceptional

(16 Reviews)

3 Bedrooms 2 Baths 8 Guests 2100 ft²

AU $543/Night 7 Nights - AU $3,799

View Deal

More Top-Rated Cabin Rentals in Grimstead Area

Why Choose Rent By Owner for your Grimstead Cabin Rentals?

What makes our Cabin Rentals special?

Verified Listings

Book with confidence knowing every property meets our quality and safety standards.

Unbeatable Value

Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.

Diverse Options

From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Best Times to Visit Grimstead

When should you plan your Cabin Rentals stay?

To make the most of your stay, consider visiting during the shoulder seasons when the area's natural beauty is at its peak and accommodation options are more available, ensuring a relaxed and enjoyable vacation in this destination's scenic surroundings.

Peak Season Highlights

Late Spring to Early Summer (May - June)

Experience the region at its most vibrant during late spring to early summer, when the weather is warm and ideal for outdoor activities. This is a popular time to enjoy your stay in a cozy cabin setting while taking advantage of longer daylight hours.

Average Temperature Daytime: 75°F - Nighttime: 55°F

Early Fall (September - October)

Visit during early fall to enjoy the area's stunning fall foliage and mild temperatures. This season provides a serene backdrop for exploring the region's natural beauty from your comfortable cabin retreat.

Average Temperature Daytime: 70°F - Nighttime: 50°F

Off-Season Highlights

Winter (December - February)

During winter, the quietness of this destination offers a peaceful escape. If you prefer a more tranquil experience, this is an excellent time to book your stay in a cabin while enjoying crisp air and snow-covered scenery.

Average Temperature Daytime: 45°F - Nighttime: 30°F

Early Spring (March - April)

In early spring, the region begins to emerge from winter dormancy, offering fewer crowds and a picturesque setting for a relaxing getaway. It's an ideal period for those seeking solitude and fresh seasonal blooms from their cabin experience.

Average Temperature Daytime: 60°F - Nighttime: 40°F

Weekly Weather Forecast for Grimstead

How to Book Your Grimstead Cabin Rentals

What's our booking process?

Our platform allows you to browse a curated selection of cabin rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

Search Properties

Use our filters to find the right property that fits your needs.

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Grimstead

More Top-Rated Cabin Rentals in Grimstead Area

Common Cabin Rentals Amenities

What amenities can you expect?

Our Cabin Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:

Indoor Features

Fully-equipped kitchens with modern appliances
Comfortable living areas with flat-screen TVs
Free Wi-Fi for staying connected
Air conditioning and heating for year-round comfort
In-unit washers and dryers for convenience
Luxurious bedrooms with premium bedding
Spa-like bathrooms with soaking tubs or walk-in showers

Outdoor Amenities

Enjoy spacious outdoor patios or decks perfect for relaxing and entertaining.
Take advantage of private gardens or lush yards to connect with nature during your stay.
Make use of outdoor grilling areas to prepare delicious meals amidst scenic surroundings.
Relax on hammocks or lounge chairs while soaking in the peaceful views of the area.
Explore nearby trails and paths directly from the property for outdoor adventures.
Utilize fire pits or outdoor fireplaces for cozy evenings under the stars.
Benefit from access to private docks, piers, or waterfront spaces if your rental is near the water, for boating or fishing activities.

Top Attractions Around Grimstead

What attractions are nearby?

During your stay, you can explore a range of outdoor activities nearby, from tranquil lakeside fishing and boating to scenic hiking trails that showcase the area's natural beauty and offer a perfect setting for relaxing retreats in traditional cabins.

Family Activities

Smith Point Marina Enjoy a family day out on the water by exploring the scenic Smith Point Marina, where you can engage in boating and fishing activities suitable for all ages.
Rappahannock River Cruises Take a relaxing river cruise along the Rappahannock River, offering picturesque views and educational opportunities for children and adults alike.
Grace Marie's Nature Center Discover local flora and fauna at this nature center that provides interactive exhibits and outdoor trails perfect for family outings in the region.
Grimstead Community Park Spend quality time together at this inviting park, featuring playgrounds, picnic areas, and open spaces for games and outdoor fun for the entire family.

Adult Activities

Boating and Fishing: Enjoy a relaxing day on the water by exploring local lakes and rivers, perfect for casting a line or cruising in a boat rental here.
Hiking and Nature Walks: Discover scenic trails and lush landscapes within nearby parks that offer peaceful opportunities to connect with nature.
Historical Tours: Delve into the area's rich history through guided tours or visits to local landmarks that highlight its unique heritage.
Wildlife Watching: Observe native birds and wildlife in the natural habitats surrounding this destination, ideal for outdoor enthusiasts seeking tranquility.

Grimstead Travel Tips

How Can You Make the Most of Your Stay?

Plan Your Visits in Advance: Booking your cabins in Grimstead early ensures you secure the best accommodations and take full advantage of the area's seasonal offerings.
Explore Local Nature: Make time to enjoy the scenic outdoor spaces surrounding this destination, perfect for relaxing hikes and picturesque moments right from your private cabins.
Discover Nearby Activities: Check out the region’s outdoor recreation options to enhance your stay and create memorable experiences close to your chosen cabins.
Maximize Comfort and Convenience: Select well-equipped cabins that offer modern amenities and easy access, making your visit both comfortable and enjoyable in this serene setting.

Transportation Options

Virginia Railway Express (VRE): Offers convenient commuter rail options for travelers looking to access nearby urban centers from the area.
Local Taxi Services: Provides on-demand transportation within and around this destination, ensuring easy access to accommodations and local points of interest.
Rental Car Agencies: Available at regional airports and in nearby towns, giving you flexibility to explore the region at your own pace.
Public Bus Transit: Connects various parts of the area, making it a practical choice for budget-conscious visitors seeking economical transportation options.

Local Customs Options

Southern Hospitality Visitors often experience warm welcomes and friendly interactions that reflect the region's tradition of southern hospitality.
Fishing Customs Engaging in local fishing practices is common here, with many residents sharing tips on the best spots along the nearby waterways.
Community Gatherings Neighborhood events and local festivals are cherished traditions that foster a sense of community and belonging.
Historical Respect Respect for the area's history is evident through the preservation of local landmarks and traditional storytelling sessions.

Frequently Asked Questions About Grimstead Rental Cabins

1. What are the top Cabins in Grimstead?

There are a lot of options in Grimstead. If you plan on staying in the Grimstead area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Cabins in Grimstead:

2. How many Cabins are available in Grimstead?

Currently, the total number of properties listed by RBO in 2026 is over 35 in the Grimstead area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Cabins in Grimstead. 

3. What is the cancellation policy for cabins in Grimstead, Virginia?

The cancellation policy varies depending on the specific listing you choose. You should review the individual cabin's policy details on the listing page or contact the owner directly for precise information.

4. Are there any additional fees I should be aware of when booking a cabin here?

Additional fees such as cleaning fees, service charges, or security deposits may apply to certain listings. Details are provided in the property description, and it’s recommended to review them carefully before completing your reservation.

5. How do I confirm my reservation and what is required upon check-in?

Confirmation typically occurs after booking through the listing platform. The owner will provide check-in instructions, which may include ID verification, payment confirmation, or other requirements noted in the property details.

6. Is there a minimum stay requirement for cabins in this area?

Minimum stay requirements can differ by property and season. Please check the specific listing for the exact number of nights required or contact the host directly for clarification.

7. What amenities are generally included in cabins in this region?

Amenities vary between listings, but common features include basic kitchen facilities, Wi-Fi, heating or air conditioning, and outdoor spaces. For detailed amenities, refer to the individual property descriptions or contact the owner for more information.