Bozman Holiday Rentals

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Holiday Rentals in Bozman

Directly Across from Gate One & Steps from the Waterfront
10.0 out of 10, Exceptional, 180 reviews
"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
Pool and Bay Views on wrap around deck in Kent Island
9.6 out of 10, Exceptional, 21 reviews
"Everyone really loved the house and the location. The pool was great"
Pool and Bay Views on wrap around deck in Kent Island
Recently Renovated Annapolis Home - Conveniently Located
10.0 out of 10, Exceptional, 44 reviews
"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
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Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
10.0 out of 10, Exceptional, 186 reviews
"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
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
10.0 out of 10, Exceptional, 25 reviews
"I chose to stay at this property for the duration of my wedding weekend. It was really great to be able to spend that extra time with family all together! Getting ready at the house, rather than a hotel was also really nice because we had much more room to space out. The make up artist and hair stylist also complimented the ample natural light and space to work. The pool and hot tub were beautiful! The only downside was a lack of curtains in the master bedroom. The sunrise is beautiful but...
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Charming Annapolis WaterVIEW Home
9.6 out of 10, Exceptional, 43 reviews
"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 NZ$1,247
includes taxes & fees
6 Jun - 7 Jun
Charming Annapolis WaterVIEW Home
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
9.6 out of 10, Exceptional, 105 reviews
"This is our third visit. You can’t have a better location! We love St. Michael’s and this historical cottage."
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Bay View Studio Apartment
10.0 out of 10, Exceptional, 25 reviews
"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
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
9.6 out of 10, Exceptional, 4 reviews
"We extremely enjoyed our stay. The house was beautiful, kitchen was well equipped and the view was spectacular, especially with the Eagles that have nested on the 32 acre property. However was disappointed in the fact that the fire places were not in working conditions and rooms should have been number. We enjoy kayaking up and down the bay and taking it all in. I would definitely stay again."
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
10.0 out of 10, Exceptional, 73 reviews
"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
The Blue Crab Beach House - Free beach passes
10.0 out of 10, Exceptional, 39 reviews
"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
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!
10.0 out of 10, Exceptional, 81 reviews
"421Irie is a great property, well managed and maintained by Liz. It was perfect for a weekend of sailing, golf, family and friends. We hosted a small cookout for eight one night, and the cottage was just right for the group. The kitchen is well stocked, the big grill outside was just fine, and the multiple seating locations were ideal for the various attendees. We would love to stay at the cottage again next time we are in Annapolis"
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!
Chesapeake Houseboat Getaway on Kent Island, Maryland
10.0 out of 10, Exceptional, 7 reviews
"My husband and I and our dog had a lovely getaway on "Julia's Arc". This was our first time on a Houseboat and it was a wonderful experience. So much light! And the movement of the boat was just enough to be comforting. The home was very clean and beautifully adorned with great attention to detail. Julia, the host, was very responsive and very generous in doing all she could to make our trip as comfortable and pleasurable as possible. The views over the water were gorgeous and we really...
Chesapeake Houseboat Getaway on Kent Island, Maryland
Waterfront, dog-friendly home with private dock, kayaks, firepit & amazing yard
9.6 out of 10, Exceptional, 12 reviews
"Our stay in Oyster Harbor was very nice. The weather didn't cooperate but the house itself was very nice and I would certainly stay there again. It's about a 10 minute drive to downtown Annapolis so that made it convenient as well!"
Waterfront, dog-friendly home with private dock, kayaks, firepit & amazing yard
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
9.6 out of 10, Exceptional, 108 reviews
"VRBO link hasn’t enabled me to communicate with property manger/owner as I’m unable to access account via the VRBO link. I’ve re-registered multiple times now."
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
The Lazy Crab Beach House - Free beach passes
10.0 out of 10, Exceptional, 24 reviews
"My husband and I moved from the area two years ago and so are in town frequently to visit friends and family. Weve stayed at the Lazy Crab and the owner's other property next door at the Blue Crab multiple times. The properties are located in a quiet neighborhood within easy walking distance of restaurants and shopping, and plenty of parking is provided. The houses are well appointed and provisioned, nicely decorated and comfortable, and always beautifully clean. Danielle is very easy to work...
The Lazy Crab Beach House - Free beach passes
Waterfront Cottage on the Eastern Shore
9.0 out of 10, Wonderful, 2 reviews
"the view and access to the beach just a short walk away is the best part of this house! with little kids we could go whenever we wanted for however short or long we wanted to stay and run to the house for snacks or toys! huge bedrooms for everyone to be comfortable. plenty of bathrooms. great food next door as well!"
The price is NZ$1,845
includes taxes & fees
17 Jun - 18 Jun
Waterfront Cottage on the Eastern Shore
Indulge or be still near Naval Academy/ Annapolis
9.2 out of 10, Wonderful, 9 reviews
"Great place, super neighborhood!"
Indulge or be still near Naval Academy/ Annapolis
Relaxing Waterfront Cottage Near St Michaels, Maryland
9.8 out of 10, Exceptional, 197 reviews
"We had our boat with us. Split out time between being on the water and going into St Michaels"
Relaxing Waterfront Cottage Near St Michaels, Maryland
USNA home Downtown Annapolis
10.0 out of 10, Exceptional, 4 reviews
"Nice relaxing getaway space. It served as a homebase for our vacay to MD/DC. It had all the amenities a family would need. The proximity to Annapolis harbor and access to the highway made staying local or heading to the city easy. The host was prompt and responsive on any question which arose. We were thoroughly satisfied with our experience."
The price is NZ$721
includes taxes & fees
3 Jun - 4 Jun
USNA home Downtown Annapolis
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See all available properties in Bozman
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 Bozman you may be interested in

Historic Inns of Annapolis
3.5 star property
9.0 out of 10, Wonderful, 1,619 reviews
"Absolutely love these properties and the so-rounding area! Great places to eat and shop all within walking distance. "
The price is NZ$291
includes taxes & fees
1 Jul - 2 Jul
Historic Inns of Annapolis
Hyatt Regency Chesapeake Bay
4.0 star property
8.8 out of 10, Excellent, 1,005 reviews
"It's the second time I've gone and I love it! What I like most is that they close the jacuzzi very late sometimes until 3 am!"
The price is NZ$449
includes taxes & fees
2 Jun - 3 Jun
Hyatt Regency Chesapeake Bay
Graduate Annapolis
4.0 star property
9.4 out of 10, Exceptional, 1,037 reviews
"The graduate hall/decor was interesting. Staffs were friendly. Place is clean and bed is comfortable. AC is strong but weirdly that it stops cooling (maybe trigger by motions?) during sleep. Plenty of parking onsite if needed(extra)."
The price is NZ$345
includes taxes & fees
1 Jul - 2 Jul
Graduate 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 holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Bozman holiday 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. 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 holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Bozman. 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 Bozman. Seeing all the best attractions is bound to make you fall in love with Bozman. Who knows, you may even be tempted to extend your 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 holiday 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 Bozman short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there holiday rentals in Bozman?

Yes, there are holiday rentals close to the most popular sights in Bozman, or you can select a more secluded option if you're looking for a relaxing stay. Bozman is known for its waterfront and restaurants. Make sure you have time to check out the shopping while you're in the area.

What are some of the best holiday rentals that Bozman has to offer?

Directly Across from Gate One & Steps from the Waterfront : This holiday home rental outside Bozman is located in the city centre, and has a fireplace, a patio and a BBQ 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 that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals will I find in Bozman?

Expedia has 9 holiday rentals for your stay in Bozman.

What’s there to see and do in Bozman?

Explore the area and family-friendly sights such as Chesapeake Bay Maritime Museum, or get out into nature at a spot like Chesapeake Bay Environmental Center. In the wider area, you’ll find St. Michaels Winery and Avalon Theatre.

What’s a holiday rental in Bozman like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Bozman. Holiday rentals feature amenities like kitchens and laundry facilities so you'll be comfy for your stay. If you're concerned about a sanitised environment, holiday rentals can offer a sense of security away from shared hotel lifts and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular option for a family getaway.

Recent reviews of Bozman properties
Expedia verified reviews