Vacation rentals in Glasgow

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Top-rated vacation rentals in Glasgow

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favorite

Home in Middle River

4.95 out of 5 average rating, 39 reviews

Waterfront Home with Private Beach, Stunning Views

Escape to paradise at our Chesapeake Bay waterfront vacation home in Oliver Beach! Our home is the ideal place to unwind and appreciate the beauty of Chesapeake Bay. You'll love the stunning views, the private beach, the spacious upper deck and the beachside deck surrounded by trees. You'll have so much fun fishing, swimming, kayaking, paddle boarding, or just relaxing by the water! It's the perfect spot for a dreamy retreat, a romantic sojourn, or for shared fun with group of friends or family.

Guest favorite

Home in Bridgeton

4.98 out of 5 average rating, 165 reviews

Serene Lake House with private pool and views!

Welcome to your very own Lakeside paradise! Picturesque enough to feel like a real getaway, but cozy just like home. Featuring a private pristine, heated swimming pool (open May 15-Sep 14), a 6 person hot tub (open Sep 17-May tbd) and stunning views, you will not be disappointed! Tons of room to spread out: huge living room with fireplace, screened-in porch, two outdoor fire pits, and several sitting areas. There are plenty of ways to relax and unwind. Enjoy your next getaway at Sunset Lagoon!

Top guest favorite

Home in North East

4.96 out of 5 average rating, 46 reviews

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

Top guest favorite

Cottage in Charlestown

4.98 out of 5 average rating, 101 reviews

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

Top guest favorite

Home in Perryville

4.99 out of 5 average rating, 114 reviews

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!

Guest favorite

Guesthouse in Chesapeake City

5 out of 5 average rating, 163 reviews

High-End Cottage, Water View, Chesapeake City, MD

"Fairwinds Cottage" is a newly renovated coastal themed guest cottage with a water view on the quiet side of the canal in Chesapeake City, Maryland. Enjoy watching the ships pass through the canal, take a walk on the beautiful 17-mile Ben Cardin/Mike Castle Recreational Trail just steps from the house. Walk to Schaefer's Canal House for their amazing crab cakes and libations. Stay with us and learn why Chesapeake City was voted the #1 most charming town in Maryland in 2018.

Guest favorite

Home in Elkton

4.84 out of 5 average rating, 360 reviews

Cozy Cottage Elkton North East 3bed 2 bath Patio

Hacienda on the Hill! Perfect country & city location! Close to North East activities, fishing tournaments & shows. Newark & UofDE(20min). Sandy Cove & North Bay(20 min). Quiet, end of gravel road location. Offering 3 bedrooms 2 full baths & stocked kitchen. Backyard patio t w/seating, & fire pit. The best part, just 1 mile to quaint downtown North East with free parking!! 1 mile from seafood, mexican, steak house, coffee shops, grocer, convenience store etc.

Guest favorite

Home in Gap

4.9 out of 5 average rating, 135 reviews

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.

Top guest favorite

Guest suite in Darlington

4.97 out of 5 average rating, 278 reviews

Syd Acres

Unplugged retreat. Great for birders, piano players, gardening fans, antiquers. Twenty minutes from historic Havre de Grace. Nearby gardens include: Longwood Gardens; Chanticleer Garden; Winterthur Museum, Garden, and Library; and LaDew Topiary Gardens. Small kitchen with microwave, sink, fridge, and coffee maker. Private entrance. Smoke detectors, hair dryer. No WiFi. No stove.

Top guest favorite

Condo in Betterton

5 out of 5 average rating, 16 reviews

Beach Haven Hideout

We are a small enclave of condos, perched high on a bluff, overlooking the Chesapeake Bay. From the deck you have wonderful views of the beach and the best Bay sunsets! We are no more than 100 steps to the beach, where you have a picnic pavilion, beach volleyball, and BBQ area with communal grills and picnic tables. This is the perfect getaway for small families or couples.

Guest favorite

Home in Essex

4.81 out of 5 average rating, 78 reviews

Sunset Haven on Sue Creek

Unparalleled Sunsets on the Water! This unique simple renovated cottage, offers an amazing waterfront experience with a private sandy beach, amazing nightly sunsets and a 60 foot pier which can hold most vessels up to 45 feet. Owners are very friendly live next door and are happy to help make your relaxation complete.

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What guests are saying

A 5-Star Haven: 4BR, Fireplace, Family-friendly

5 out of 5 average rating, 79 reviews3 weeks ago

Although we have stayed in many rentals, this "home away from home" was the best by far. It was the perfect, peaceful get-away for a trip. Everything was explained. And while in many homes someone has to stay in the "not so nice" bedroom, each room was modern, equally beautiful and the beds were comfortable. Each bedroom even had its own sound machine to help you fall asleep if you're not used to the quiet of the countryside. It was magical to wake-up every morning to the horses and chickens on the property. One could even feed the chickens! It was delightful to enjoy a cup of coffee in the morning or play games at night in the sun room while enjoying the nature surrounding us. The kitchen was well-stocked with everything one could imagine. They even had a delightful coffee and tea bar! All of the bathrooms had everything we needed including soaps, shampoo, and conditioner. It was close to all of the tourists sites such as Sight and Sound, buggy tours, etc. We didn't want to leave!

Home in Paradise

What guests are saying

Vintage Waterfront Cottage with Stunning Sunsets

5 out of 5 average rating, 33 reviews4 months ago

This was our second stay at this cozy cottage, and it was just as wonderful as the first! Every detail is thoughtfully considered, from the clean, stylish interiors to the warm ambiance. The indoor fireplace and outdoor fire pit (perfect for s’mores under the stars) were highlights, and the bay views from the viewing platform never disappoint. Sue & Mark are incredibly friendly and communicative, always quick to help with anything we needed. We also appreciated the provided firewood and all the little extras that made the space feel so comfortable and welcoming. Thank you for another amazing stay – we can’t wait to return!

Cottage in North East

What guests are saying

Newly renovated modern home

4.67 out of 5 average rating, 123 reviews3 months ago

Overall we enjoyed our stay here and would recommend it to others. A few small spots could have been cleaned a bit more and the price was a bit steep compared to similar locations, but ultimately happy we chose to stay here and the size of the home was perfect for what we needed.

Home in Newtown Square

What guests are saying

Charming Home w/Great Porch

5 out of 5 average rating, 29 reviews3 months ago

We had a great stay at the cottage! The space is beautiful and well maintained. Beds are very comfortable and everyone (including our kids) slept surprisingly well for being in a new space! The kitchen has essentials and a very high quality stove and oven. Wendy and Barry were quick to help us troubleshoot a flipped breaker (completely beyond their control) right after we checked in and followed up with us the next morning to make sure all was well. They are great hosts and have a beautiful property. If you’re looking for a private, quiet getaway near the water this is a great option!

Cottage in Betterton