Vacation rentals in Galena

Cozy 3-bedroom home w/ Hot tub & firepit

This cozy, recently renovated home has the charm of days gone by. It is located with-in a 5 minute walk to the grounds of Washington College and a fifteen minute walk to Historic Downtown. There is an abundance of food and other conveniences close by. A perfect place to unwind and relax. A 20 minute drive to Rock Hall. Take in the beautiful Chester River and Chesapeake Bay area. Fishing, hiking and other outdoor activities to be enjoyed. Newly furnished rooms and fully stocked kitchen.

Location · Family · Grill

Beautiful Waterfront Chestertown Getaway

Lovely three room waterfront guest suite conveniently located less than 10 minutes from historic Chestertown and Washington College. Beautiful views of our tidal creek, full kitchen, wooded lot, quiet neighborhood, bird watching, kayaking, great biking & running. Friendly pets (indoor cats and dogs who can share the yard with us and our dog) are welcome. We donate a portion of proceeds to Kent Attainable Housing, the Animal Care Shelter of Kent County or ShoreRivers conservation—your choice.

Location · Value · Quiet

Connection Pointe•River views•Quiet•Peaceful

Connection Pointe is a great getaway for your family vacation or to reconnect with friends, you will be sure to enjoy this beautiful property that sits right along the Sassafras River, it is quiet and peaceful with amazing views from the house and the screened in deck. Come enjoy the sounds of nature as you take time to relax and refocus! There is no boat access to the river from the property. There is a fairly steep bank going down to the river, so please be mindful of this with children.

Family · Value · Bathroom

Harbor View Haven | Waterfront w/ Hot Tub + Dock!

BNB Breeze Presents Harbor View Haven This exquisite waterfront property offers a captivating retreat to relax and recharge with stunning views and an array of desirable features! With a serene waterfront location, this idyllic home provides a picturesque setting for unplugging and experiencing outdoor enjoyment. Your extensive amenity list includes: 💦 Hot Tub 🔥 Outdoor Gas Fireplace ☕️ Jura Espresso Machine 🚤 Private Dock + Kayaks 🚴 Bikes for Exploring 🏓 Ping-Pong Table 🌅 Bay Views

Value · Family · Sleep quality

Upper Chesapeake Getaway

Come relax with expansive views of the Upper Chesapeake with family or friends. Tucked away in Carpenter's point, you'll find peace watching boats pass by and local wildlife. The newly renovated home features newly 3BR, 1.5 Bath with a fully functional kitchen. You'll enjoy the beautiful sunrise views, water access, kayaks and deck. Local amenities include Great Wolf Water Park, Elk Neck State Park, local restaurants, and Perryville Casino. We welcome you to join the relaxing experience!

Family · Location · Decor

Stunning 2BR Cottage w/River views

Cozy Riverside Cottage in Scenic Hacks Point on the Bohemia 2BR | 1.5BA | Steps from the Water | Family-Friendly Escape the everyday and unwind in this charming riverside cottage with views of the Bohemia River. Whether you're looking for a weekend getaway, a week-long family retreat, or a beautiful place to stay while attending a nearby event or wedding, our 2-bedroom, 1.5-bathroom cottage offers the perfect blend of comfort and charm with direct access to the beautiful Bohemia River.

Family · Location · Nearby

Quiet Country Relaxing Farm

Forget your worries in this spacious and serene space. This 3 bedroom 2 bath home is set way out in the country surrounded by state hunting lands .With some farm animals on the property now and then .So much wild life. Lots of deer and turkeys to name a few . Would be a perfect place to stay during hunting season with a short walk out the front door you will be deep in the state hunting lands .Also just up the road is Double Tap Tavern cold drinks and amazing food. High speed internet

Location · Family · Condition

Anchors Away

Anchors Away beckons as your tranquil waterfront escape! Inside, the cozy gas fireplace awaits. Savor a coffee bar experience and utilize the well-appointed kitchen. Unwind in the screened-in porch with a book and river views. Outdoors, the dock invites relaxation by the water. Gather around the wood fire pit for memorable nights under the stars. Enjoy Kayaks, fishing poles and family games! Anchors Away promises an unforgettable riverside retreat. We look forward to hosting you!

Family · Location · Grill

Ruby's Sea Glass Cottage near Betterton Beach

This cute 1900 cottage is in the center of Betterton. There's a full kitchen & three beautiful outdoor porches to unwind. There's one bathroom (on the first floor) and an amazing outdoor shower available seasonally! There are three bedrooms (all on the second floor). Enjoy Betterton Beach which is down the street! Look for sea glass or watch the sunset! There is a cute park with a playground in town that the kids love! It also has pickleball, tennis and basketball courts.

Family · Location · Kitchen

Hunter's Lodge

Escape to our charming countryside cottage nestled on a picturesque farm on the Eastern Shore and just a stone’s throw from Delaware. Surrounded by rolling fields, this cozy retreat offers the perfect blend of rustic charm and modern comfort. Enjoy morning coffee on the porch, explore nearby towns and outdoor experiences. With easy access to local attractions, you can experience farm life while being close to charming towns and beautiful landscapes. Your serene getaway awaits!

Location · Family · Bathroom

River front cottage with private dock & water fun

Private cottage on the banks of the Chester River. Sleeps 8-14. Private dock with plenty of water activities. This property offers relaxation and serenity as soon as you pull in! Located right on the water with spectacular views of the Chester River, the house is renovated in a cozy, casual farmhouse style. While you will love the house you will spend your days outside enjoying life on the river thanks to your private access to the water and lots of water fun!

Family · Value · Check-in

High Tide & Hound

Welcome to your perfect getaway in the heart of historic Chestertown! This charming home is just two minutes from the iconic High Street Wharf, where you can enjoy scenic views, fishing, and waterfront strolls. We’re proudly family friendly , pet friendly, so bring your furry friends along for the adventure. Whether you’re here for the festivals, the river, or just to relax this is your ideal place. Comfortable , private, and conveniently located.

Location · Family · Decor