Holiday Rentals in Rose Haven

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Rose Haven

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Miscellaneous
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
10.0 out of 10, Exceptional, (202)
"Incredible location! The process was easy and the house completely suited our needs! We would definitely stay again!"
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Charming Annapolis WaterVIEW Home
Outdoor dining
Charming Annapolis WaterVIEW Home
9.6 out of 10, Exceptional, (48)
"This house was perfect for our group of friends especially with infants. Easy check in, comfortable beds and room for pack and plays. Water view is amazing. Definitely worth the rent and would be interested in coming back!"
Charming Annapolis WaterVIEW Home
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Exterior
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
10.0 out of 10, Exceptional, (202)
"This was a lovely home. I especially appreciated how clean and well-stocked it was. Liz and Tom were very responsive and accommodating! This truly added to a wonderful reunion weekend with friends and family. Thank you!"
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Property grounds
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
9.6 out of 10, Exceptional, (112)
"Our stay in St Michael's was wonderful. The location of this property could not be better. Close to marina, parks, restaurants, historic downtown and the maritime museum. We never needed to use our car! Tom is an excellent host. "
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Outdoor dining
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
9.8 out of 10, Exceptional, (34)
"Family stayed for my 50th birthday over a long weekend. Amazing property. Beautiful view and amazing amenities with hosts who are flexible. We had a small issue with the alarm system that we finally resolved. Will definitely book again."
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Relaxing Waterfront Cottage Near St Michaels, Maryland
Exterior
Relaxing Waterfront Cottage Near St Michaels, Maryland
9.8 out of 10, Exceptional, (216)
"Were pleased with the property and surroundings. Very beautiful, ancient trees. Neighborhood was quiet and the river and dock were favorite reading spots. Enjoyed!!!"
Relaxing Waterfront Cottage Near St Michaels, Maryland
Mid-Century Modern and Marvelous on the Bay
Property grounds
Mid-Century Modern and Marvelous on the Bay
10.0 out of 10, Exceptional, (70)
"The house was amazing! From the moment the front door opened it was a visual feast. The views are incredible, it's quiet, private and very relaxing. There were personal elements reflecting the current and original owners which we found very interesting and the attention to detail throughout was superb! Everything was incredibly well stocked with a multitude of extras. "
Mid-Century Modern and Marvelous on the Bay
Pool and Bay Views on wrap around deck in Kent Island
Outdoor pool
Pool and Bay Views on wrap around deck in Kent Island
9.6 out of 10, Exceptional, (24)
"We loved everything about the Kent Island House! Would book again in a hot minute"
Pool and Bay Views on wrap around deck in Kent Island
The Blue Crab Beach House - Free beach passes
Miscellaneous
The Blue Crab Beach House - Free beach passes
10.0 out of 10, Exceptional, (47)
"Everything close by!"
The Blue Crab Beach House - Free beach passes
3 Story Stunner in Murray Hill <1 mile from USNA!
Terrace/patio
3 Story Stunner in Murray Hill <1 mile from USNA!
10.0 out of 10, Exceptional, (16)
"Beautiful house in great location! It was the perfect house for our annual trip (group of 10 friends) to Annapolis! It was spacious, clean, and well equipped with everything you need in a rental house. Eric and team were super responsive and accommodating! Highly recommended! Will definitely come back next year!"
The price is €836
includes taxes & fees
18 Nov - 19 Nov
3 Story Stunner in Murray Hill <1 mile from USNA!
Chesapeake Houseboat Getaway on Kent Island, Maryland
Marina
Chesapeake Houseboat Getaway on Kent Island, Maryland
9.6 out of 10, Exceptional, (20)
"We had a wonderful stay on this luxurious houseboat! Clean, comfortable & fun and Julia is an excellent host. We highly recommend Julia's Arc!"
Chesapeake Houseboat Getaway on Kent Island, Maryland
Amazing views, short walks to great dining!
View from property
Amazing views, short walks to great dining!
10.0 out of 10, Exceptional, (72)
"The place is very comfortable and tucked away on the creek with nice water views. The host was accessible but I didn’t need a thing! The screened porch is a wonderful spot to enjoy my scone and tea fresh from the Great Harvest bakery just up the road. The golden sunset was a bonus each evening. "
Amazing views, short walks to great dining!
Cozy place close to the city dock
Beach
Cozy place close to the city dock
9.8 out of 10, Exceptional, (66)
"Liked everything. Perfect for what we wanted. "
Cozy place close to the city dock
Relax on Kent Island in 3 Bedroom Home w/Waterview
Marina
Relax on Kent Island in 3 Bedroom Home w/Waterview
9.8 out of 10, Exceptional, (29)
"Excellent experience."
The price is €247
includes taxes & fees
14 Nov - 15 Nov
Relax on Kent Island in 3 Bedroom Home w/Waterview
USNA Quintessential Charm ~ Downtown Annapolis.
Fridge, microwave, oven, stovetop
USNA Quintessential Charm ~ Downtown Annapolis.
9.8 out of 10, Exceptional, (6)
"Limited living room seating for family of 5"
The price is €432
includes taxes & fees
18 Nov - 19 Nov
USNA Quintessential Charm ~ Downtown Annapolis.
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
Terrace/patio
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
10.0 out of 10, Exceptional, (30)
"We needed a place that would take our 2 dogs for a week stay leading up to 40th USNA reunion. The Antonelli's had availability for their carriage house and WAY exceeded our hopes & expectations. Ideal location, 1 block from the stadium, close to USNA campus. The Homewood neighborhood is ideal for walking dogs and so friendly. It truly was a great experience. The hosts are awesome, attentive, and have a lovely family making it a really enjoyable stay. The apartment is so well appointed and...
The price is €459
includes taxes & fees
14 Nov - 15 Nov
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
Walk to Everything House
Fridge, microwave, oven, stovetop
Walk to Everything House
10.0 out of 10, Exceptional, (72)
"We thoroughly enjoyed the convenience of walking to shops, restaurants, and waterfront! Residence was charming and clean! Only minor issue was we couldn’t locate the iron- just the ironing board! We still had fun but we’re just a bit wrinkled!😁"
Walk to Everything House
Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND
Sun-loungers, beach towels
Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND
10.0 out of 10, Exceptional, (31)
"House was spacious, clean, and exactly as described in the listings. We had a great time!"
Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND
2-story, riverfront home with private dock, inviting deck & dog-friendly yard
Fridge, microwave, oven, stovetop
2-story, riverfront home with private dock, inviting deck & dog-friendly yard
9.6 out of 10, Exceptional, (12)
"We appreciate the hospitality and responsiveness of our gracious host. We would stay again and look forward to our next visit. Recommend staying to all looking for a tranquil getaway in the Annapolis area."
2-story, riverfront home with private dock, inviting deck & dog-friendly yard
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
View from property
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
9.8 out of 10, Exceptional, (87)
"This lovely home sets in a beautful location. The hosts are available and accommodating. They are definitely available if needed. The house itself is very comfy. All amenities you need are there. "
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
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.
Don't see what you're looking for?
See all available properties in Rose Haven
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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

Graduate by Hilton Annapolis
View from property
Graduate by Hilton Annapolis
4.0 star property
9.4 out of 10, Exceptional, (1000)
"Very smooth checkin. The property is in a great location and is very clean. "
The price is €145
includes taxes & fees
24 Nov - 25 Nov
Graduate by Hilton Annapolis
Historic Inns of Annapolis
Exterior
Historic Inns of Annapolis
3.5 star property
9.0 out of 10, Wonderful, (1688)
"It was great , good price "
The price is €166
includes taxes & fees
24 Nov - 25 Nov
Historic Inns of Annapolis
Crowne Plaza Annapolis, an IHG Hotel
Pool
Crowne Plaza Annapolis, an IHG Hotel
3.5 star property
8.8 out of 10, Excellent, (1001)
"The hotel was priced right and overall nice. Room was modern with a comfortable bed and good shower water pressure"
The price is €118
includes taxes & fees
26 Nov - 27 Nov
Crowne Plaza Annapolis, an IHG Hotel
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.

Frequently asked questions

Can I find a holiday rental in Rose Haven?

Yes, there are holiday rentals close to the most popular sights in Rose Haven, or you can select a more secluded option if you're looking for a relaxing stay.

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

Directly Across from Gate One & Steps from the Waterfront : This holiday home rental outside of Rose Haven 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 Rose Haven?

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

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 wider area, you’ll find Rod n Reel Charter Fishing and Show Place Arena.

What’s a holiday rental in Rose Haven like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Rose Haven. Holiday rentals feature amenities like WiFi and washers and dryers so you'll be comfy for your stay. If you're concerned about a clean environment, holiday rentals can offer a sense of safety away from shared hotel lifts and busy concierge desks while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular choice for a family trip or a small group gathering.