Vacation rentals in Odessa

The Pearl: a 70s vibe, hip/cozy

The Pearl is located in the heart of historic Chesapeake City; just steps from all the boutiques, restaurants & nightlife with a lovely view of the C&D Canal. It's cozy, but functional with 2 workspaces, 2 bedrooms & all the amenities you'd want in your home away! We provide a Nespresso machine & excellent coffee, snacks, sparkling water, full kitchen,etc. It's got a 70s vibe, an eclectic combo of euro/scan/boho hip! It's not your usual Victorian spot. Come stay with us, you won't regret it!

Boho River Cottage

A Chesapeake Bay getaway located on the North East River. The renovated cottage sleeps 4 people. Nap in our secluded backyard gardens. The cottage includes water access, kayaks, bikes, and a SUP board. Explore the town of NE to shop and dine in the region's top restaurants. Minutes from Elk Neck State Park which offers hiking, fishing, bird watching & mountain biking. Visit historic Havre de Grace, Hollywood Casino, or relax and catch a sunset and the cool breeze coming off the North East River

Blue on the Bay

2 bedroom cottage in historic Charlestown with screened porch, large yard & sitting area located in walking distance to the river and beach area. Walk to 3 local restaurants. Community playground, tennis courts, basketball court, pickle ball court, skate park & baseball field all in walking distance. Bring your boat, kayak & fishing poles. Boat launch available . Kayak, sup & pontoon rentals available. 15 minute drive to Great Wolfe Lodge. Monthly discount available, ask for details

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!

Charming Home w/Great Porch

We would love to share our well-loved cottage on the Bay with you. Most loved for its beautiful views and quiet town, it is a perfect place to relax with great beach access. We think you'll love it too. Plenty of space to spread out and comfy spaces to enjoy together: whether on the screened porch (our favorite), in the updated foodie-kitchen, or swinging on the swing, snoozing in hammock or walking to the beach - you will be glad you found this place-we definitely are!

Dream View

Welcome to our beautiful 3 bedroom,2 bath home with an attached 1 bedroom,1 bath apartment that’s perfect for families or groups who value privacy and convenience. Enjoy breathtaking views of the picturesque surroundings right from the comfort of your home or bask in the serene atmosphere of the big backyard where you will possibly see wildlife. The hot tub is an added bonus,perfect for a relaxing evening under the stars.

The Peaceful Getaway (with private pool & hot tub)

Kick back and relax at this charming peaceful getaway, the perfect place to enjoy with friends and family! This beautiful 2 story spacious house is back off a dead end road, but still only minutes from the main highway. It’s very private with a beautiful in ground pool and hot tub behind the house! And also lots of space for outdoor cooking. Please no pets

Heron Creek- Historic home on Main Street

Beautiful home located in the heart of downtown. This 3 full bath/3 bedroom was recently renovated. Original hardwood floors throughout. This is an older home with narrow steps. It offers off street parking & is walkable to shops, restaurants, water sports & bike rentals. Close to Turkey Point Lighthouse, the park, fishing, boating & hiking.

Charming Cape By The Bay!

Ideal location only one block from the bay! Bay views from second story. Three blocks from the beach and a short walk or bike ride into downtown. Walk to several restaurants. Amazing place to make lasting family memories.