Sherwood Forest Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Sherwood Forest vacation rentals

A modern kitchen with white cabinets, a stainless steel refrigerator, and a central island with bar stools.

1. 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, (31 reviews)
"Great stay"
United States
Guillaume P.
$170 nightly
The price is $193
Nov 15 - Nov 16
Total with taxes and fees
Cute, Cozy 2-bedroom house near Annapolis with water access
A living room with a sofa, a coffee table, a dining table with chairs, a lamp, and a beach-themed artwork on the wall.

2. Lower Level Loft - Adorable Studio Apt. Near BWI

Lower Level Loft - Adorable Studio Apt. Near BWI
South Gate
9.0 out of 10, Wonderful, (20 reviews)
"This was an adorable little place, perfect for my husband and I. With a few minor tweaks and upgrades, this would easily be a five star stay. I would happily stay here again. Thank you!"
United States
Deanna
$81 nightly
The price is $92
Nov 9 - Nov 10
Total with taxes and fees
Lower Level Loft - Adorable Studio Apt. Near BWI
A kitchen with wooden cabinets, a stainless steel refrigerator, a coffee maker, and a water dispenser.

3. Large 2 bedroom house with private parking in a nice neighborhood

Large 2 bedroom house with private parking in a nice neighborhood
Arnold
9.4 out of 10, Exceptional, (44 reviews)
"This was a lovely place for my mom and I to stay - we were dealing with a challenging situation and Solmaz was very kind and was easy to communicate with. The community is nice and parking was easy. "
United States
Linda B.
$269 nightly
The price is $307
Nov 9 - Nov 10
Total with taxes and fees
Large 2 bedroom house with private parking in a nice neighborhood
A living room with a beige sofa, two framed floral pictures, a wooden cabinet, and a small table with a lamp.

4. 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.
$112 nightly
The price is $128
Nov 8 - Nov 9
Total with taxes and fees
Cozy 1-bedroom studio in pleasant Crofton with AC
Aft deck with spiral staircase to the rooftop, sliding glass doors, and an unobstructed sunset view across the Magothy River from Ferry Point Marina.

5. Houseboat Suite for Two near Annapolis

Houseboat Suite for Two near Annapolis
Arnold
9.8 out of 10, Exceptional, (14 reviews)
"Beautiful location! Amazing restaurant down the street. Best crab dip and cream of crab soup you’ll ever have."
United States
Anonymous traveler
$342 nightly
The price is $390
Nov 15 - Nov 16
Total with taxes and fees
Houseboat Suite for Two near Annapolis
A cozy cabin interior with a leather sofa, a wooden dining table, and a view of a lake through large windows.

6. The Hideaway Spot- Waterfront w/ Dock on Long Cove

The Hideaway Spot- Waterfront w/ Dock on Long Cove
Glen Burnie
9.4 out of 10, Exceptional, (18 reviews)
"Very clean and well stocked Beautiful location Will definitely book againBroken oar and paddle restaurant nearby excellent food and service"
United States
Chris H.
$306 nightly
The price is $349
Nov 9 - Nov 10
Total with taxes and fees
The Hideaway Spot- Waterfront w/ Dock on Long Cove
Stylish kitchen with open layout and island seating

7. Pool Loft Suite | Bay Access & Beach Passes

Pool Loft Suite | Bay Access & Beach Passes
Cape Saint Claire
10.0 out of 10, Exceptional, (9 reviews)
"This place has a fantastic location and an incredibly welcoming host! The area also features wonderful walking trails."
United States
Ana S.
$395 nightly
The price is $450
Nov 9 - Nov 10
Total with taxes and fees
Pool Loft Suite | Bay Access & Beach Passes
A modern lobby with a blue sofa, two framed abstract paintings, a potted plant, and a marble floor.

8. Upscale Condo in Annapolis w/Private Parking

Upscale Condo in Annapolis w/Private Parking
Historic District
10.0 out of 10, Exceptional, (4 reviews)
"Great condo! Very clean and convenient to everything in Annapolis. We will definitely be back."
United States
Scott P.
$409 nightly
The price is $467
Nov 17 - Nov 18
Total with taxes and fees
Upscale Condo in Annapolis w/Private Parking
A wooden dock extending into a calm body of water with boats docked at the end.

9. Cozy 2br home w/ parking in downtown Annapolis

Cozy 2br home w/ parking in downtown Annapolis
Historic District
10.0 out of 10, Exceptional, (87 reviews)
"Location, amenities, cleanliness, parking all great!"
United States
Nancy N.
$362 nightly
The price is $413
Nov 30 - Dec 1
Total with taxes and fees
Cozy 2br home w/ parking in downtown Annapolis
A swimming pool with lounge chairs, a brick patio, and a house in the background.

10. Large Home w/ Pool, 7 Bedrms, Sleeps 21

Large Home w/ Pool, 7 Bedrms, Sleeps 21
Severn
9.4 out of 10, Exceptional, (38 reviews)
"This was a weekend celebrating our son's retirement from the Navy. The weather and accommodations were great. The family loved the big yard, front and back, and the pool. We would gladly rent it again if we could get our whole family together."
United States
Perry S.
$706 nightly
The price is $808
Nov 15 - Nov 16
Total with taxes and fees
Large Home w/ Pool, 7 Bedrms, Sleeps 21
A hot tub area with a covered patio, outdoor seating, and a view of the surrounding landscape.

11. Idyllic Pasadena Retreat with Garden + Hot Tub!

Idyllic Pasadena Retreat with Garden + Hot Tub!
Green Haven
10.0 out of 10, Exceptional, (38 reviews)
"Place was very accommodating for our needs!"
United States
Antonia P.
$400 nightly
The price is $456
Nov 15 - Nov 16
Total with taxes and fees
Idyllic Pasadena Retreat with Garden + Hot Tub!
Exterior detail

12. Elegant & Bright Historic Home 3BR/2,5BA, 2 kings, 1 queen, 5 min to USNA

Elegant & Bright Historic Home 3BR/2,5BA, 2 kings, 1 queen, 5 min to USNA
Historic District
10.0 out of 10, Exceptional, (6 reviews)
"Very nice, comfortable, convenient property. Host was very communicative. "
United States
Brian L.
$435 nightly
The price is $496
Nov 10 - Nov 11
Total with taxes and fees
Elegant & Bright Historic Home 3BR/2,5BA, 2 kings, 1 queen, 5 min to USNA
A sunset view from a balcony with a glass-top table and a fire feature, overlooking the sea.

13. Bay Sunsets for Two • Rooftop Fire Pit

Bay Sunsets for Two • Rooftop Fire Pit
Pasadena
10.0 out of 10, Exceptional, (4 reviews)
"We had a phenomenal time celebrating our engagement at Flohom! The space was spotlessly clean, super comfortable, and peaceful. The location was fantastic, and the hosting was top-notch from start to finish. We couldn't have asked for a better experience to"
United States
Charles W.
$372 nightly
The price is $424
Nov 8 - Nov 9
Total with taxes and fees
Bay Sunsets for Two • Rooftop Fire Pit
A modern kitchen with white cabinetry, a stainless steel refrigerator, a wooden countertop, and a window with a view of greenery.

14. Mins to Historic Downtown Annapolis - Parking

Mins to Historic Downtown Annapolis - Parking
Annapolis
10.0 out of 10, Exceptional, (6 reviews)
"Wonderful home with very attentive host. Great place for family getaway. Will definitely be back! Go Navy."
United States
Nader E.
$471 nightly
The price is $537
Nov 9 - Nov 10
Total with taxes and fees
Mins to Historic Downtown Annapolis - Parking
A kitchen counter with a marble top, a striped basket, a tissue box, and a potted plant.

15. Dean Street's Lower Deck House!

Dean Street's Lower Deck House!
Historic District
10.0 out of 10, Exceptional, (4 reviews)
"We had a great time—the location is fantastic and our dog loved the backyard! A great base to rest and recover between adventures in Annapolis. "
United States
Nathaniel R.
$398 nightly
The price is $453
Nov 8 - Nov 9
Total with taxes and fees
Dean Street's Lower Deck House!
A kitchen with a bar area, a ceiling fan, and a sliding glass door leading to a deck.

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

Renovated Bungalow | Walk to Beach | Dog-Friendly
Edgewater
9.6 out of 10, Exceptional, (14 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.
$448 nightly
The price is $510
Nov 8 - Nov 9
Total with taxes and fees
Renovated Bungalow | Walk to Beach | Dog-Friendly
A lighthouse with a white exterior, a balcony, and a metal roof.

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

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (50 reviews)
"Great stay"
United States
Michael V.
$257 nightly
The price is $277
Nov 9 - Nov 10
Total with taxes and fees
Charming Coastal/Country Home w/3 Acres & Sauna!
A kitchen with wooden cabinets, a central island with stools, a refrigerator, and a brick accent wall.

18. Annapolis Gem- Tranquil 4 BR Murray Hill Victorian

Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
Historic District
10.0 out of 10, Exceptional, (2 reviews)
"Good location."
United States
Rosie G.
$675 nightly
The price is $764
Nov 9 - Nov 10
Total with taxes and fees
Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
A two-story brick house with a dark shingled roof, a front porch, and a well-maintained lawn.

19. 5 Mi to Main St! Comfortable stay in Laurel

5 Mi to Main St! Comfortable stay in Laurel
South Laurel
8.8 out of 10, Excellent, (3 reviews)
"The host was super nice and accommodating and the place was clean and quiet. Thanks for hosting me."
United States
Sam N.
$190 nightly
The price is $215
Nov 8 - Nov 9
Total with taxes and fees
5 Mi to Main St! Comfortable stay in Laurel
A modern kitchen with wooden cabinets, a built-in island, and a dining area with a grey sofa and purple chairs.

20. 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.
$473 nightly
The price is $539
Nov 29 - Nov 30
Total with taxes and fees
Annapolis Retreat - 7 mins from downtown 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.
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Top Sherwood Forest Hotel Reviews

A multi-story Microtel by Wyndham hotel with a parking lot and a landscaped area in front.
Microtel Inn & Suites by Wyndham Gambrills/Odenton

Microtel Inn & Suites by Wyndham Gambrills/Odenton

Microtel Inn & Suites by Wyndham Gambrills/Odenton
Gambrills

10/10 Excellent

Great stay!! All of the staff was incredible! Especially Channing
United States
Anonymous traveler
Reviewed March 30, 2025
Microtel Inn & Suites by Wyndham Gambrills/Odenton

Find out more about Sherwood Forest

Everything you need to know about Sherwood Forest vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Sherwood Forest vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Sherwood Forest vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Sherwood Forest vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Sherwood Forest. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Sherwood Forest in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $92 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Sherwood Forest rentals

At Expedia, we put the best Sherwood Forest vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Sherwood Forest rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Sherwood Forest vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Sherwood Forest. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently Asked Questions

Are there vacation rentals in Sherwood Forest?

Yes, you can find vacation rentals close to popular attractions in Sherwood Forest, or you can go with a more remote option if you'd like a relaxing place to stay.

What are some of the best vacation rentals that Sherwood Forest has to offer?

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach: This vacation home rental near Sherwood Forest 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.

What can I see and do in Sherwood Forest?

While exploring the area, visit family-friendly sights like Maryland Renaissance Festival, or get outside and enjoy nature at Maryland Quiet Waters Park. Westfield Annapolis Mall and Annapolis Mall Shopping Center are a couple of places you'll find in the larger area.

What are vacation rentals like in Sherwood Forest?

Vacation rentals are private properties you can stay in for a short or long stay in Sherwood Forest. Vacation rentals provide amenities such as hot tubs, fire pits, and patios so you'll feel just like you're staying in your own home. If you're concerned about a sanitized environment, vacation rentals can provide a sense of safety away from public hotel elevators and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great choice for a family getaway.