Is this Grimstead cottage pet-friendly for guests?

Yes, pets are allowed at this property. Check the guest reviews to learn what guests had to share.

Does the Grimstead cottage have a swimming pool?

No, this Grimstead cottage does not have a swimming pool. Check the Facility Overview section for details about the pool and other available facilities.

How much does it cost per night to stay in Grimstead cottage?

Best-rates for the Grimstead cottage starts from $300 per night with includes Sports/Activities, Ocean View, Balcony/Terrace, Child Friendly, Pet Friendly, TV, Wellness Facilities, Fireplace/Heating, Entertainment, Air Conditioner, Parking, View, Security/Safety, Bedding/Linens, Barbecue/Outdoor Cooking, Internet, Kitchen, Laundry with all other facilities. matches every traveler with their perfect accommodation, whether you are traveling with a group, friends, family, or pets.

Is Grimstead cottage a family-friendly place to stay?

Based on the information we have received from the owner or our partner, this is considered to be a family-friendly property. Families have rated this cottage Good or guests have recommended them suitable for families. As reported by the owner or manager, the cottage has specified that children are welcome. Please see details about suitability for your family or inquire with the property to learn more.

Is the Grimstead cottage wheelchair accessible or offer services for disabled guests?

Based on the information received from our partner, the Grimstead cottage has not specified they are wheelchair accessible. Likewise, there is not an elevator specified as being available at the property. Specific accessibility details may be addressed in the property details section of this page.

What is the minimum night stay policy for the Grimstead cottage?

Based on the information reported by the owner or manager, the Grimstead cottage indicates 1 day stay policy at this cottage. Guests are cautioned that the minimum stay policy may differ based on seasonality or availability and may be at the discretion of the owner or manager.

What cancellation policy is in place for Grimstead cottage?

Guests are cautioned that the cancellation policy may differ based on seasonality, availability, or current travel restrictions. Guests should also be aware that this policy may be subject to change and should be confirmed prior to booking. More details may be available on this page in the property description. However, early check-in or late check-out can sometimes be negotiated between the guest and the owner or the manager of this property.

Gwynn's Island Cottage-Waterfront, Private Beach nBOOK YOUR SUMMER '26 WEEK NOW! | Cottage in Grimstead

10.0 (220 Reviews) | Pet Friendly 2 Bedrooms 1 Bathroom 4 Guests

Grimstead Cottage | Gwynn's Island Cottage-Waterfront, Private Beach nBOOK YOUR SUMMER '26 WEEK NOW!

2 Bedroom Cottage in Grimstead

Gwynn's Island Cottage is a waterfront cottage on the Chesapeake Bay with panoramic views and sunsets over the water. The small, private beach - entirely on the property and not shared - is mere steps away. We are pet friendly. During the summer months, we rent weekly, Sunday to Sunday.
The Cottage is located on quaint and historic Gwynn's Island with a public marina and restaurant 1/3 of a mile away on the island. The Cottage sleeps 4 guests in 2 bedrooms.
On your private beach, guests can swim, kayak, paddle board, fish and crab, bird watch, float on a raft, lounge or just enjoy a good book or an adult beverage. The Shed is full of everything you don't need to bring: beach chairs, zero gravity chairs, 3 kayaks, a stand up paddleboard, crab nets, crab pot, floats, rafts, noodles, children's beach toys, life vests, a croquet set, and hammock. Hills Bay is clean, shallow, and sandy-bottomed, with little current or tow, so perfect for children and explorers alike. Guests can fish right from the beach or from kayaks and can catch drum, trout, rockfish, croaker, spot and flounder. The crab pot or the fishing nets allow guests to catch crabs when they are in season.
After a quick rinse in the outdoor shower after your day on the beach and on the water, use the Weber kettle charcoal grill for cooking up the day’s catch or fresh seafood from a nearby market. Enjoy dinner al fresco on the deck overlooking the water as you watch that sunset... For cooler evenings, light a fire in the Bonfire Solo stove under the stars.
From the Cottage, guests experience bird life such as bald eagles nesting, blue herons, osprey, seagulls, white tundra swans, bufflehead ducks, loons, and dolphins, depending on the season. Boat watching is plentiful as there is a yacht club just across the water, with boats coming in and out of Hills Bay from the Chesapeake Bay.
Or bring your own boat. There's plenty of room on the long, circular driveway to trailer in and out. The island's public boat landing is 1/3 of a mile away, with parking for your trailer while you are on the water and a restaurant for provisions.
The Cottage is pet-friendly! Four legged guests enjoy the beach with its shallow, clean water. We provide doggie towels. We own the small woods next door where dogs can "get their sniffs on."
If you plan to bring your pet, please message the manager with the age, breed, gender, weight, and name of your animal/s. We charge a pet fee of $125 for all animals for your entire stay (less than kennels or pet sitters). They will enjoy being with you on vacay.
Between Memorial Day weekend and Labor Day weekend, we rent weekly, Sunday to Sunday, Just a two-night minimum the rest of the year.
We have a large capacity washer, dryer, and the laundry room has space to air dry. Our outdoor shower also has foot spigots. The Cottage has a 50" smart TV with cable and wifi. If you bring your electric or hybrid vehicle, we have an electrical outlet (120v) on the front of the Cottage for charging.
The Cottage has a retro Frigidaire Mini-fridge that chills 6 cans of your favorite beverage and doubles as a Bluetooth speaker. Take it outside to play your tunes on the beach or deck!
The Cottage is perfect for special occasions or gatherings (with approval of management) because photos with a water view are ah-mazing.
Please read the over 200 reviews from the Cottage's guests over our last 10 years of renting, with guests returning over and over again. Our positive reviews reflect the guest-centered experience that we try to provide, continually using our guests' suggestions to improve amenities.
We are sorry but smoking is not permitted in the house or anywhere on our property.
Gwynn's Island Cottage is dedicated to welcoming all people regardless of their race, color, religion, ethnicity, national origin or gender orientation.

Gwynn's Island Cottage-Waterfront, Private Beach nBOOK YOUR SUMMER '26 WEEK NOW! is located in Grimstead. Gwynn's Island Cottage-Waterfront, Private Beach nBOOK YOUR SUMMER '26 WEEK NOW! provides accommodation, featuring Pet Friendly, TV, Air Conditioner, among other amenities. This Cottage features Pet Friendly, TV, Air Conditioner, to make your stay a comfortable one.

Gwynn's Island Cottage-Waterfront, Private Beach nBOOK YOUR SUMMER '26 WEEK NOW! has 2 Bedrooms , 1 Bathroom, and max occupancy of 4 people. The minimum rental for this property is 1 nights, but this can change depending on the season you plan on staying. Previous guests have given good rated it, and VRBO labeled it a top-rated Cottage because of the excellent services rendered by the owner or manager of this Cottage, and has consistently provided great experiences for their guests. Most families or guests that use it recommend it to their friends and some of them are repeat guests. Cottage has a friendly neighborhood, and the Grimstead has interesting places to visit. If you want to learn more about the Cottage in Grimstead, such as places to visit and things to do nearby, you can check below to learn more.

This Property is OneKey Eligible

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Amenities

Air Conditioner

Parking

Pet Friendly

View

Ocean View

Balcony/Terrace

Security/Safety

Sports/Activities

Bedding/Linens

Wellness Facilities

Fireplace/Heating

Entertainment

Barbecue/Outdoor Cooking

Child Friendly

Internet

Kitchen

Laundry

Facility Overview

Air Conditioner

Heating

Air conditioning

Bathrooms

Shampoo

Bathtub or shower

Hair dryer

Towels provided

1 bathroom

Toilet paper

Soap

Bedroom

Bed sheets provided

2 bedrooms

Dining table

Living room

Kitchen

Ice maker

Oven

Microwave

Spices

Toaster

Refrigerator

Dishwasher

Stovetop

Kitchen island

Laundry

Washing machine and dryer

Near laundromat

Laundry facilities

Ocean view

Beach sun loungers

Beach towels

Private beach

Parking

Onsite parking

Car recommended

Onsite parking options include a garage

Pet Friendly

2 total (up to 50 lbs per pet)

Pet friendly

Welcoming cats and dogs only

Accessibility

Wheelchair-accessible path of travel

No elevator (single level property)

If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.

Tile flooring in public areas

Smoke-free property

Thin carpet in public areas

Activities

Birdwatching nearby

Fitness facilities nearby

Kayak on site

Power boating nearby

Marina nearby

Jet skiing nearby

Golf nearby

Bicycle on site

Golfing on site

Water skiing nearby

Water sports equipment

Winery tours nearby

Ecotours nearby

Fishing nearby

Entertainment

Books

Stereo

Video library

Games

Smart TV with cable/satellite service

DVD player

General

Unit size: 1200 sq ft (111 sq m)

English

Near a health or beauty spa

On the waterfront

Near the bay

On the river

In a rural location

In a village

Near a hospital

Guest Services

Children's books

Children's games

Children's dinnerware

Children's toys

Limited housekeeping

Iron/ironing board

Internet

Free WiFi

Outdoors

Garden

Yard

Patio

Charcoal grill

Outdoor furniture

Security/Safety

Deadbolt lock

First aid kit

Fire extinguisher

Smoke detector installed (host has indicated there is a smoke detector on the property)

Carbon monoxide detector installed (host has indicated there is a carbon monoxide detector on the property)

Policies

Check-in

Check-in time starts at 3:00 pm minimum check-in age: 22

Check-out

Check-out before 11:00 am contactless check-out available

Child Policy

Children are welcome. note from host: small beach and shallow water are great for kids

Event Policy

Events allowed: family gatherings, birthday parties, weddings;maximum event attendees: 30;special events and parties with okay of management

Pet Policy

2 total (up to 50 lbs per pet) note from host: with advance ok of management and pet fee of $125 pets allowed restrictions apply; for more information contact the property at the number on the booking confirmation service animals are welcome, and are exempt from fees welcoming dogs and cats only

Smoking Policy

Smoking is not permitted

Extra-person charges may apply and vary depending on property policy government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges host has indicated there is a carbon monoxide detector on the property host has indicated there is a smoke detector on the property note from host: special events and parties with okay of management parties and events (including family gatherings, birthday parties and weddings) are allowed on site; maximum attendees: 30 safety features at this property include a fire extinguisher, a first aid kit, and a deadbolt lock special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed this property is managed through our partner, vrbo. you will receive an email from vrbo with a link to a vrbo account, where you can change or cancel your reservation

Reviews

Haley C.

Sep 17, 2025 10:45:30 PM

Review Score: 10

Summary: We absolutely love staying here—it’s become a tradition for us to return year after year. From the moment we arrive, Cheri always makes us feel so welcome and goes above and beyond to ensure everything is perfect for our stay. The house itself is beautiful, spotless, and so well taken care of—it truly feels like a home away from home. Every detail is thoughtfully provided, and it makes our trips so relaxing and enjoyable. Cheri is one of the kindest and most attentive hosts we’ve ever met, and it’s clear how much she cares about her guests. We couldn’t imagine staying anywhere else and are already looking forward to coming back next year!

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