Vacation rentals in Love Point

4.96 out of 5 average rating, 408 reviews

Cottage in Annapolis

Relaxing Water Views - Mill Creek Cottage

Eclectic three level water view cottage in unique wooded location overlooking beautiful Mill Creek. Minutes from downtown Annapolis and the US Naval Academy; walk to Cantler’s Riverside Inn for crabs, convenient to US 50 and the Bay Bridge and Eastern Shore. Due to the stairs and loft, this accommodation may not be appropriate for toddlers and the mobility challenged Parties are not permitted. Please note that there is no water access on the property, but there is nearby public water access.

4.93 out of 5 average rating, 278 reviews

❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

Enjoy your vacation in this Stylish Coastal-Country 3+ Bedroom Home w/Sauna & 3 acres of outdoor living! Perfect for Families & Wedding Groups. We are conveniently located to many areas/cities: Annapolis- 15 miles Baltimore- 40 Wash. DC- 45 Easton- 30 Enjoy a Self-Check-in to this Beautiful Home that is perfectly situated near all the local Kent Island Restaurants, Shops, Attractions, including Chesapeake Beaches. This is a Non-Smoking House. Also No Pets Parties & 14 max guests. Book Today!

Guesthouse in Stevensville

5 out of 5 average rating, 35 reviews

Private | Near BayBridge | Wedding Venue Proximity

Welcome to your Kent Island getaway! This thoughtfully decorated, private guesthouse is minutes from the Bay Bridge, offering the perfect retreat for families, couples, or friends. Skip the hotel and relax in a fully stocked home with plenty of space, a large backyard for activities, and cozy touches throughout. Whether you're here for a wedding, visiting the Naval Academy or DC, or simply exploring the Eastern Shore, you'll love the comfort, convenience, and local charm this home has to offer.

4.99 out of 5 average rating, 178 reviews

Houseboat in Grasonville

Cass-Away A Luxury Houseboat

Kent Narrows Rentals welcomes you aboard Cass-Away! A 640sqft luxury getaway in the Kent Narrows. Fully equipped with a living room, kitchen, 2 bedrooms, 2 full baths, and a magnificent view from the rooftop deck! With 9 waterfront bars/restaurants within walking distance, you can get a taste of what the eastern shore has to offer. Minutes from the Bay Bridge and a short drive to Annapolis, D.C., St. Michael’s, and Ocean City. NO Fishing/Crabbing on property! Check our website for more info!

4.96 out of 5 average rating, 671 reviews

Guest suite in Arnold

Old Bay Bungalow

This in-law apartment located in the lower level of my occupied home is just moments outside of Annapolis, mere blocks from the Magothy River. I enjoy inviting guests into the space, and take pride in treating new friends like family. Come rest your weary bones in your private retreat with its own separate entrance, relaxing sunporch, and stocked kitchenette. Reach into the fridge and enjoy cold soda or a local beer on me! Sit around our fireplace and relax. Settle into the Old Bay Bungalow!

Superhost

Guesthouse in Stevensville

4.62 out of 5 average rating, 116 reviews

Kent Island Waterfront Cottage

Private 2 bedroom 1 bathroom waterfront cottage on the Chester River. Enjoy the solitude that this property offers, including spectacular sunrises and fishing off the pier (rockfish are very abundant). Perfect for families, couples, or friend groups who are looking to get away from it all. If you are traveling with small children, we have high chairs and a pack and play available upon request. Recent June 2022 updates include new memory foam mattresses, new outdoor lounge chairs, and Roku.

4.94 out of 5 average rating, 176 reviews

Guest suite in Arnold

Coastal Comfort Suite Near Annapolis, Hottub, EV

Hot tub is open for the season. Pool will be open May 12 through Labor Day weekend. Ideal for a couple's retreat, this king suite guest room has a massive bedroom with a seating area, mounted TV, and coffee bar with microwave/mini-fridge. An ensuite bathroom provides a luxurious shower with dual shower heads and a spacious closet. The pool and hot tub are seasonal. Please don’t hesitate to reach out with any questions, concerns, or expectations so that we can address them prior to your stay.

5 out of 5 average rating, 66 reviews

Love Point Idyll - 240' Private Beachfront

Spacious, comfortable vacation home located on Love Point, northern tip of Kent Island, in the heart of the upper Chesapeake. Beachfront property adjacent to former grounds of the historic Love Point Hotel grand resort, where well-to-do families once took steamboats from Baltimore piers to vacation in style (now Love Point State Park). On the coveted northeastern side of Kent Island, you have views of pleasure craft, fishing vessels, and an array of wildlife (including dolphins on occasion).

4.99 out of 5 average rating, 116 reviews

Kent Island Waterfront Home with Amazing Sunsets

Relax with the whole family at this peaceful and beautiful home on Thompson Creek! Enjoy the gorgeous sunsets all year-long. Bring your boat, fishing gear or other watercraft and discover Kent Island! Thompson Creek is accessible to the Chesapeake Bay and a short ride to discover Annapolis, The Kent Narrows or St. Michaels. In the mornings, sip coffee on the screened-in porch and bring a book - you may be there for a while! Our home feels remote but is accessible to convenient shopping.

4.9 out of 5 average rating, 203 reviews

Home in Annapolis

Country House on the Bay

My home (owner occupied/shared) sports a spectacular view of the Chesapeake Bay with access to the beach. The home is spacious with a family, dining, breakfast and living room. Significant kitchen space is available with all of the cookware and place settings you would need for a meal. The master bath is handicapped accessible. My deck can be used for cookouts and relaxation. Hosting a gathering - lets talk- my home is perfect for celebrations. Close to Annapolis & Naval Academy.

5 out of 5 average rating, 236 reviews

Guest suite in Annapolis

Cape St Claire waterfront getaway "The Apartment"

This is a private over the garage apartment located in Cape St Claire, about 5 miles from downtown Annapolis, 2 miles to the Bay Bridge. Private entrance, on site parking, 1- 2 guests. We encourage our guests to enjoy the large back yard patio with magnificent views of the Magothy River and Chesapeake Bay ! Approximately 30 miles to Washington, and Baltimore. 30 minutes to BWI airport. TV and internet. A community beaches just a short walk away. ADULTS ONLY, NO SMOKING, NO PETS.

Guesthouse in Stevensville

4.99 out of 5 average rating, 279 reviews

Waterfront Getaway - View of bay from your bed

Enjoy this newly renovated, waterfront private studio apartment with a beautiful view of the Chesapeake Bay. It's a perfect getaway for anyone looking for rest and relaxation amidst a quiet, breath-taking location. Enjoy swimming in the pool, fishing off the point, sitting around an evening gas fire, visiting any of the local sandy beaches, or simply watching stunning sunsets from a private patio. Ample parking, WiFi, TV, boat-ramp access. One pet is welcome.

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Other great vacation rentals in Love Point

4.96 out of 5 average rating, 55 reviews

Home in Rock Hall

Eastern Neck Water Paradise w/Brick oven & Beach

JuanitaRating, 5 stars3 weeks ago

Our stay at this place was so amazing! It had something for everyone to do! I feel it was very kid-friendly with lots of sand toys, a kiddie pool and inside toy too. The kitchen was well- stocked! We used the brick oven one night and boiled crabs. Martha responded quickly to our questions. She made it very easy for us to get into the house. We most definitely would come back again!

5 out of 5 average rating, 32 reviews

Home in Annapolis

Cozy Getaway – Beach Access, Fire Pit, Fenced Yard

AriannaRating, 5 starstoday

This place was great!! We had a business trip at the Naval Academy and this was the perfect spot! Super close to the beach and to downtown Annapolis so it was the perfect balance of peace and fun! The hosts were super responsive and even let us check in early; the house was gorgeous and accommodated 7 girls! We loved it!

4.93 out of 5 average rating, 43 reviews

Home in Arnold

Cozy Arnold House Near Annapolis

SymoneRating, 5 stars2 weeks ago

We enjoyed our stay. It was spacious, charming and peaceful. Close to everything we needed. Joel was very responsive and kind. Would definitely recommend this place.

5 out of 5 average rating, 59 reviews

Home in Grasonville

Bay Breeze - 3BR Waterfront Chester River Retreat

BrianRating, 5 stars4 days ago

Stayed at Katie's place for a long weekend getaway with my family and a couple of friends. We all loved the house, its location, and the beautiful and relaxing waterfront views. The house was pristine and beautiful. We all would love to go back again. Thank you Katie for offering up your lovely home and looking forward to potential future trips there!

5 out of 5 average rating, 15 reviews

Home in Chester

Spacious waterfront home private pier dog-friendly

KarenRating, 5 stars2 weeks ago

The accommodations did not disappoint! Fabulous view, fun choices to take advantage of on the water, great neighborhood and local seafood restaurants! Our family gathering was memorable as a result of this venue! Will be sure to return!

5 out of 5 average rating, 5 reviews

Bay Bliss House

IanRating, 5 stars1 week ago

Beautiful property and well maintained. Unique views and plenty to do when the weather is not so good. Great proximity to Annapolis and the Eastern Shore and plenty of great dining spots on the water.

4.93 out of 5 average rating, 43 reviews

Guest suite in Annapolis

Bayside Beach Getaway

DeniseRating, 5 stars1 week ago

This was a perfect getaway for my boyfriend and I. The weather wasn’t conducive for the beach, but it looked like a nice place to rest. There was a nice selection of restaurants nearby and close to Annapolis for sightseeing. Allison was responsive to questions and this was a nice, quiet spot for r and r. Thanks!!