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Galesville Vacation Rentals

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Our top choices for Galesville vacation rentals

1. 3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access

3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access
Shady Side
9.0 out of 10, Wonderful, (2 reviews)
"The location was spectacular, the host was communicative, and we had a great time! A beautiful and clean home with everything needed to make a trip a success. One small issue with some needed essentials meant a quick run to the store (TP!) but otherwise a great location, great stay, and would stay again!"
United States
David S.
The price is CA $243
CA $540 total
includes taxes & fees
Oct 21 - Oct 22
3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access

2. Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
Shady Side
10.0 out of 10, Exceptional, (5 reviews)
"Our family enjoyed staying at the Sunset Cottage. It was clean, had everything we needed for a great trip and the communion was amazing."
United States
Michelle H.
The price is CA $348
CA $719 total
includes taxes & fees
Nov 10 - Nov 11
Sunset Cottage - West River Access and Views!

3. 3-bedroom house in Deale located on Bay many amenities and great views

3-bedroom house in Deale located on Bay many amenities and great views
Deale
The price is CA $256
CA $621 total
includes taxes & fees
Oct 18 - Oct 19
3-bedroom house in Deale located on Bay many amenities and great views

4. Family Home on Mayo Peninsula | Deck | Sleeps 10

Family Home on Mayo Peninsula | Deck | Sleeps 10
Edgewater
10.0 out of 10, Exceptional, (6 reviews)
"House was clean and comfortable. Great layout. "
United States
Kristin G.
The price is CA $375
CA $1,047 total
includes taxes & fees
Oct 21 - Oct 22
Family Home on Mayo Peninsula | Deck | Sleeps 10

5. Renovated Bungalow | Walk to Beach | Dog-Friendly

Renovated Bungalow | Walk to Beach | Dog-Friendly
Edgewater
9.8 out of 10, Exceptional, (13 reviews)
"This is a cute place. Well stocked nicely renovated kitchen. Having coffee and a bottle of wine was a definite plus. "
United States
Diane D.
The price is CA $297
CA $830 total
includes taxes & fees
Oct 19 - Oct 20
Renovated Bungalow | Walk to Beach | Dog-Friendly

6. The Cozy Crab- Your Charming Haven in Lovely North Beach!

The Cozy Crab- Your Charming Haven in Lovely North Beach!
North Beach
9.6 out of 10, Exceptional, (30 reviews)
"Wonderful place to visit "
United States
James L.
The price is CA $169
CA $411 total
includes taxes & fees
Oct 16 - Oct 17
The Cozy Crab- Your Charming Haven in Lovely North Beach!

7. Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Arundel on the Bay
9.6 out of 10, Exceptional, (19 reviews)
"The perfect off-season get-away! "
United States
Pamela B.
The price is CA $269
CA $668 total
includes taxes & fees
Oct 20 - Oct 21
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

8. Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Stevensville
9.8 out of 10, Exceptional, (55 reviews)
"Our host Adam was wonderful and very communicative. We love the house and the location was just great. It was close to everything and had water views. We will certainly come back again."
United States
Rebecca B.
The price is CA $143
CA $435 total
includes taxes & fees
Oct 19 - Oct 20
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

9. Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Annapolis
8.8 out of 10, Excellent, (3 reviews)
"The place is very nice and comfortable inside. Quiet. Great place to sleep - no noise."
United States
William
The price is CA $320
CA $788 total
includes taxes & fees
Oct 21 - Oct 22
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

10. Londontowne Rancher | 3BR | Near Waterfront

Londontowne Rancher | 3BR | Near Waterfront
Edgewater
7.0 out of 10, Good, (2 reviews)
"The house was much smaller then it originally appeared to be in the listing photos and what they had available was the bare minimum. The neighborhood was rowdy and there was screaming late into the night. The shower also sprayed water all over the floor and caused a massive puddle. The house was overall nice and clean but not worth the price that it was listed for. A hotel would have much better accommodated our needs. "
United States
rebekah h.
The price is CA $375
CA $1,047 total
includes taxes & fees
Oct 19 - Oct 20
Londontowne Rancher | 3BR | Near Waterfront

11. Beachside Oasis with Beach Passes & King Suite by A Haven Away

Beachside Oasis with Beach Passes & King Suite by A Haven Away
North Beach
10.0 out of 10, Exceptional, (24 reviews)
"Cute, family friendly home. Had everything we needed for a comfortable stay."
United States
Johanna S.
The price is CA $137
CA $479 total
includes taxes & fees
Oct 19 - Oct 20
Beachside Oasis with Beach Passes & King Suite by A Haven Away

12. Annapolis Retreat - 7 mins from downtown Annapolis!

Annapolis Retreat - 7 mins from downtown Annapolis!
Hillsmere
10.0 out of 10, Exceptional, (6 reviews)
"Great house in cute neighborhood. Thanks for a very comfortable stay!"
United States
Paul C.
The price is CA $316
CA $853 total
includes taxes & fees
Nov 3 - Nov 4
Annapolis Retreat - 7 mins from downtown Annapolis!

13. Charming Coastal/Country Home w/3 Acres & Sauna!

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (47 reviews)
"Great location, house was very clean, ample space and Adam was super communicative. Will definitely stay again!"
United States
Michelle P.
The price is CA $129
CA $416 total
includes taxes & fees
Oct 18 - Oct 19
Charming Coastal/Country Home w/3 Acres & Sauna!

14. Cute, Cozy 2-bedroom house near Annapolis with water access

Cute, Cozy 2-bedroom house near Annapolis with water access
Herald Harbor
9.8 out of 10, Exceptional, (27 reviews)
"The property was very clean nice open kitchen and comfortable rooms . Very nice experience definitely recommend."
United States
Antonio
The price is CA $93
CA $296 total
includes taxes & fees
Oct 19 - Oct 20
Cute, Cozy 2-bedroom house near Annapolis with water access

15. Londontowne Home | Beach | 3BR

Londontowne Home | Beach | 3BR
Edgewater
9.4 out of 10, Exceptional, (3 reviews)
"The property was beautiful with plenty of space to have a getaway with friends. The host was super communicative when we had issues with check in. Would highly recommend staying here!"
United States
Sam A.
The price is CA $410
CA $1,144 total
includes taxes & fees
Oct 18 - Oct 19
Londontowne Home | Beach | 3BR

16. The Harness Creek Retreat in Annapolis

The Harness Creek Retreat in Annapolis
Hillsmere
The price is CA $384
CA $603 total
includes taxes & fees
Oct 18 - Oct 19
The Harness Creek Retreat in Annapolis

17. Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
North Beach
10.0 out of 10, Exceptional, (40 reviews)
"We enjoyed our stay in North Beach at this lovely residence. It was spacious, clean, nicely furnished and only a few minutes walk to the bay. The beds were so comfortable too!!"
United States
Penny N.
The price is CA $213
CA $661 total
includes taxes & fees
Nov 3 - Nov 4
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

18. Cozy 1-bedroom studio in pleasant Crofton with AC

Cozy 1-bedroom studio in pleasant Crofton with AC
Crofton
9.0 out of 10, Wonderful, (2 reviews)
"Host was very friendly and accommodating. The location is wonderful. Lots of shops and festivities nearby could not have asked for better. Her cat was also very friendly "
United States
Michaela C.
The price is CA $154
CA $207 total
includes taxes & fees
Oct 18 - Oct 19
Cozy 1-bedroom studio in pleasant Crofton with AC

19. Rose Haven Coastal Cottage

Rose Haven Coastal Cottage
North Beach
10.0 out of 10, Exceptional, (2 reviews)
"We had a great stay at this home in North Beach, MD! The house was clean, comfortable, and conveniently located near The Inn at Herrington Harbour, making it a great choice for our visit. Everything worked well for our stay, and we appreciated having a nice place to relax. We would happily recommend this property to anyone looking for a comfortable and convenient place to stay in the area!"
United States
Jeremy P.
The price is CA $320
CA $616 total
includes taxes & fees
Oct 18 - Oct 19
Rose Haven Coastal Cottage

20. Your Annapolis Waterfront retreat for a weekend or any-day getaway!

Your Annapolis Waterfront retreat for a weekend or any-day getaway!
West Annapolis
10.0 out of 10, Exceptional, (94 reviews)
"Lovely location and Jim was very helpful all the way around!"
United States
Jill R.
The price is CA $407
CA $613 total
includes taxes & fees
Nov 5 - Nov 6
Your Annapolis Waterfront retreat for a weekend or any-day getaway!
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.
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Top Galesville Hotel Reviews

Find out more about Galesville

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 Galesville. 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

Are there vacation rentals in Galesville?

Yes, we give you a choice of vacation rentals close to top points of interest in Galesville, or you can choose a more secluded option if you're looking for a relaxing stay. Galesville is known for its shopping and restaurants. Make sure you have time to check out the museums while you're in the area.

What are some of the best vacation rentals in Galesville?

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach: This vacation home rental outside of Galesville is located near the beach and has a fireplace, a balcony, 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. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals will I find in Galesville?

Choose from 3 Expedia vacation rentals in Galesville for a memorable vacation.

What’s there to see and do in Galesville?

Enjoy the area's cultural attractions such as Galesville Heritage Museum, or get outdoors into nature at a spot like Maryland Quiet Waters Park. In the larger area, you’ll find Thanksgiving Farm Wines and London Town.

What’s a vacation rental in Galesville like?

Vacation rentals are private properties where you can stay for short or long periods in Galesville. Vacation rentals provide amenities such as laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about cleanliness, vacation rentals can offer a sense of security away from public hotel elevators and busy reception areas while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive choice for family trips.