Rose Haven Vacation Rentals

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Vacation Rentals in Rose Haven

Fridge, microwave, oven, stovetop
Directly Across from Gate One & Steps from the Waterfront
10.0 out of 10, Exceptional, (180)
"Charming spot in the heart of Annapolis, just a few moments walk from anything you might need."
Directly Across from Gate One & Steps from the Waterfront
Fridge, microwave, oven, stovetop
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
9.8 out of 10, Exceptional, (25)
"My family and I enjoyed our stay at the Carpenter Alley Cottage in Saint Michaels! The location was perfect -- walking distance from everything! Appreciated that there was a ground floor bedroom for my parents so they didn't have to climb the stairs and my daughter loved having her own bunk bed room! I did have a few questions about the cottage and the check-in process and my inquiries were all met with a prompt response. Would love to stay here again! (One note though is that it is a smaller,...
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Exterior
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
10.0 out of 10, Exceptional, (186)
"The cottage is fully stocked, clean, and cozy. We thoroughly enjoyed sitting on the deck and watching all the wildlife."
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
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Terrace/patio
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
10.0 out of 10, Exceptional, (19)
"Ingrid was a fabulous host. We already plan to return. Beautiful property inside and out. Thank you beyond words, Ingrid!"
The price is CA $541
CA $794 total
includes taxes & fees
May 25 - May 26
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
Exterior
Relax on Kent Island in 3 Bedroom Home w/Waterview
9.8 out of 10, Exceptional, (19)
"We have nothing but great things to say about Adam and his beautiful home! He was so accommodating and the home was comfortable and spacious for our family of 5! Couldn’t have had a better experience :)"
The price is CA $137
CA $390 total
includes taxes & fees
May 27 - May 28
Relax on Kent Island in 3 Bedroom Home w/Waterview
Property grounds
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
9.6 out of 10, Exceptional, (107)
"Wonderful return visit to St Michaels. This time at a fantastic historical home in perfect location. Home was everything you could ask for and more. Park your car and walk anywhere, within a very quiet neighborhood, yet minutes from all St Michaels offers. Highly recommend this Property and host."
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Outdoor spa tub
Bay View Studio Apartment
10.0 out of 10, Exceptional, (25)
"If you are looking for a very spacious well-appointed one bedroom apt. style accommodation in a residential setting with lovely waterfront bay views, I highly recommend this place!"
Bay View Studio Apartment
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
10.0 out of 10, Exceptional, (73)
"The cottage provides a wonderful way to experience Deale and the surrounding area. Well equipped and clean, I had everything I needed and didn't want to leave,"
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
Beach nearby, sun loungers, beach umbrellas, beach towels
The Blue Crab Beach House - Free beach passes
10.0 out of 10, Exceptional, (39)
"It was clean and had everything we needed. We had a very comfortable stay. There are one or two steps between many of the rooms so keep that in mind."
The Blue Crab Beach House - Free beach passes
Fridge, microwave, oven, stovetop
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!
10.0 out of 10, Exceptional, (80)
"Excellent stay."
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!
Fridge, microwave, oven, stovetop
Recently Renovated Annapolis Home - Conveniently Located
10.0 out of 10, Exceptional, (44)
"This house was perfect for a group of friends celebrating a 50th birthday! The house was so clean and well cared for! The front porch and outdoor backyard space provided even more room for us to gather together. We will be back!"
Recently Renovated Annapolis Home - Conveniently Located
Property grounds
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
10.0 out of 10, Exceptional, (24)
"This house and property is GORGEOUS. Well maintained, beautiful setting. Amazing amenities (pool, hot tub) which enhanced our stay. We had no problem finding multiple places to all hang out and chat- the living room with plenty of seating, the dining room table with seating for at least 14, and outside in the hot tub. It was a perfect setting for valuable time away with friends! Additionally, the owner was STELLAR in communication. I very much appreciated his quick and attentive responses...
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Property grounds
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
10.0 out of 10, Exceptional, (151)
"Quaint yet period correct. Plenty of room with decent kitchen. Especially love location and screaned back porch. Have stayed in house several times and does not disappoint!! Will go again for sure!"
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Property grounds
Charming Annapolis WaterVIEW Home
9.6 out of 10, Exceptional, (43)
"Beautiful house and views. Amenities and grounds were great. Loved the playground and beach. Peace and quiet at its finest in nature."
The price is CA $452
CA $925 total
includes taxes & fees
May 28 - May 29
Charming Annapolis WaterVIEW Home
Outdoor pool
Pool and Bay Views on wrap around deck in Kent Island
9.6 out of 10, Exceptional, (21)
"Everyone really loved the house and the location. The pool was great"
Pool and Bay Views on wrap around deck in Kent Island
Property grounds
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
9.6 out of 10, Exceptional, (104)
"Loved this historic house! Perfect location, peaceful neighborhood and walking distance to entire town."
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
3 bedrooms, desk, iron/ironing board, free WiFi
Breathtaking Views, 450 pier, kayaks, fossils, priv beach, 45 min to D.C.
10.0 out of 10, Exceptional, (101)
"The house was very well maintained, beach access and views were wonderful. This location was very quiet, and if you are a nature lover this location is perfect. Many miles to walk and explore, lots of birds to watch. Very enjoyable weekend. Hope to return."
Breathtaking Views, 450 pier, kayaks, fossils, priv beach, 45 min to D.C.
Fridge, microwave, oven, stovetop
2-story, riverfront home with private dock, inviting deck & dog-friendly yard
9.4 out of 10, Exceptional, (8)
"The home was lovely. We very much enjoyed our stay. The one thing that I would recommend is direction on the heat and air. We were unable to figure out what to do The downstairs was cold and when we tried to raise the temp the upstairs was unbearably hot. I also wanted to let you know there was a leak from the ceiling in the master bedroom. Lastly, My daughter lost a small hoop earring. If you find it could you please contact me to have it returned. Thank you,"
2-story, riverfront home with private dock, inviting deck & dog-friendly yard
Property grounds
Quaint cottage with serene water view!
10.0 out of 10, Exceptional, (24)
"Studio with plenty of space for one. Nicely decorated, ample supplies. Petite front porch to watch the river from. Pam was friendly and welcoming, and I will certainly happily stay here again!"
Quaint cottage with serene water view!
Fridge, microwave, oven, stovetop
Waterfront Cottage on the Eastern Shore
The price is CA $820
CA $1,552 total
includes taxes & fees
Jun 17 - Jun 18
Waterfront Cottage on the Eastern Shore
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See all available properties in Rose Haven
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other types of properties in Rose Haven you may be interested in

Exterior
Historic Inns of Annapolis
3.5 star property
9.0 out of 10, Wonderful, (1613)
"Beautiful, central location, well appointed! Heating/cooling system is way loud."
The price is CA $214
CA $275 total
includes taxes & fees
Jun 9 - Jun 10
Historic Inns of Annapolis
View from property
Graduate Annapolis
4.0 star property
9.4 out of 10, Exceptional, (1045)
"Unique property, close to everything. Costly, but every hotel in the area is. "
The price is CA $267
CA $304 total
includes taxes & fees
Jun 9 - Jun 10
Graduate Annapolis
Lobby
DoubleTree by Hilton Hotel Annapolis
4.0 star property
8.6 out of 10, Excellent, (1001)
"I was sadly visiting for a funeral and was there for a 4 nite stay. The staff was so kind and very helpful. The room was clean and comfortable. Perfect location to everything I needed. I will 100% stay at this double tree when I come back into town. "
The price is CA $173
CA $198 total
includes taxes & fees
Jun 9 - Jun 10
DoubleTree by Hilton Hotel Annapolis
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Rose Haven. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a vacation rental in Rose Haven?

Yes, you can find vacation rentals near the most popular attractions in Rose Haven, or you can choose a more remote option if you'd like a relaxing place to stay.

What's the top vacation rental that Rose Haven has to offer?

Directly Across from Gate One & Steps from the Waterfront : Visitors like this Rose Haven vacation home rental. It is located in the city center and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

How many vacation rentals will I find in Rose Haven?

Choose from 4 Expedia vacation rentals in Rose Haven for a memorable vacation.

What’s there to see and do in Rose Haven?

While exploring the area, visit family-friendly sights like Chesapeake Beach Water Park, or get outside and enjoy nature at Breezy Point Beach. In the larger area, you’ll find Rod n Reel Charter Fishing and Chesapeake Beach Railway Museum.

What’s a vacation rental in Rose Haven like?

Vacation rentals are privately owned properties you can stay in for a couple of days or more in Rose Haven. Vacation rentals offer amenities like WiFi and washers and dryers so you'll feel right at home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of seclusion away from shared hotel elevators and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great choice for a family trip or a small group gathering.

Recent reviews of Rose Haven properties
Expedia verified reviews