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Sherwood Forest Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

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, (22 reviews)
"Great stay! Very clean home in a quiet neighborhood. Easy drive to downtown, and there’s a local restaurant right down the street. We really enjoyed our stay!"
United States
Taylor C.
The price is ￥10,900
￥33,045 total
includes taxes & fees
Oct 12 - Oct 13
Cute, Cozy 2-bedroom house near Annapolis with water access
A kitchen with wooden cabinets, a stainless steel refrigerator, a coffee maker, and a water dispenser.

2. 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, (41 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.
The price is ￥21,941
￥50,115 total
includes taxes & fees
Sep 30 - Oct 1
Large 2 bedroom house with private parking in a nice neighborhood
A bedroom with a bed, a chair, a bedside table with a lamp, a picture on the wall, and a window with curtains.

3. 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 ￥30,843
￥46,610 total
includes taxes & fees
Oct 5 - Oct 6
Your Annapolis Waterfront retreat for a weekend or any-day getaway!
A living room with a sofa, a coffee table, a dining table with chairs, a lamp, and a beach-themed artwork on the wall.

4. 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
The price is ￥11,167
￥18,109 total
includes taxes & fees
Sep 29 - Sep 30
Lower Level Loft - Adorable Studio Apt. Near BWI

5. Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views

Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views
Arnold
9.8 out of 10, Exceptional, (12 reviews)
"Great place!"
United States
Chris A.
The price is ￥24,772
￥58,721 total
includes taxes & fees
Oct 12 - Oct 13
Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views
A wooden dock extending into a calm body of water with boats docked at the end.

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

Cozy 2br home w/ parking in downtown Annapolis
Historic District
10.0 out of 10, Exceptional, (86 reviews)
"Location, amenities, cleanliness, parking all great!"
United States
Nancy N.
The price is ￥33,815
￥64,189 total
includes taxes & fees
Oct 5 - Oct 6
Cozy 2br home w/ parking in downtown Annapolis

7. Pool Loft Suite | Bay Access & Beach Passes

Pool Loft Suite | Bay Access & Beach Passes
Cape Saint Claire
10.0 out of 10, Exceptional, (6 reviews)
"This place has a fantastic location and an incredibly welcoming host! The area also features wonderful walking trails."
United States
Ana S.
The price is ￥35,703
￥78,354 total
includes taxes & fees
Oct 5 - Oct 6
Pool Loft Suite | Bay Access & Beach Passes
A white building with a balcony on stilts, a metal roof, and a small tower with a light on top.

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)
"We had a wonderful stay. The house was perfect and Adam stayed in contact constantly in case we needed anything. But our stay went smoothly and we had everything we needed."
United States
Dawn G.
The price is ￥12,331
￥41,528 total
includes taxes & fees
Sep 29 - Sep 30
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
A kitchen counter with a marble top, a striped basket, a tissue box, and a potted plant.

9. 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.
The price is ￥32,003
￥73,240 total
includes taxes & fees
Oct 1 - Oct 2
Dean Street's Lower Deck House!
A modern kitchen with a central island, built-in oven, and microwave.

10. Cute bungalow blocks to Stadium

Cute bungalow blocks to Stadium
Admiral Heights
9.4 out of 10, Exceptional, (12 reviews)
"We loved the layout, location, and porch- quality time with family with plenty to do and close USNA. We will stay here again!"
United States
Tammy L.
The price is ￥32,557
￥78,146 total
includes taxes & fees
Oct 6 - Oct 7
Cute bungalow blocks to Stadium
A living room with a beige sofa, two framed floral pictures, a wooden cabinet, and a small table with a lamp.

11. 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 ￥16,986
￥22,950 total
includes taxes & fees
Oct 12 - Oct 13
Cozy 1-bedroom studio in pleasant Crofton with AC
A modern kitchen with wooden cabinets, stainless steel appliances, and a large island.

12. Luxe Row Home Steps to USNA Gate 3!

Luxe Row Home Steps to USNA Gate 3!
Historic District
10.0 out of 10, Exceptional, (7 reviews)
"Fantastic stay! The VRBO was clean, comfortable and had everything I needed. The backyard/patio area was great for relaxing and communication with the host made everything simple. I plan to stay again and whole-heartedly recommend it to others."
United States
Christine A.
The price is ￥30,040
￥185,753 total
includes taxes & fees
Sep 29 - Sep 30
Luxe Row Home Steps to USNA Gate 3!
A lighthouse with a white exterior, a balcony, and a metal roof.

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 ￥11,450
￥40,552 total
includes taxes & fees
Sep 29 - Sep 30
Charming Coastal/Country Home w/3 Acres & Sauna!
A two-story brick house with a dark shingled roof, a front porch, and a well-maintained lawn.

14. 5 Mi to Main St! Cozy Couple's Escape in Laurel

5 Mi to Main St! Cozy Couple's Escape in Laurel
South Laurel
10.0 out of 10, Exceptional, (2 reviews)
"The host was super nice and accommodating and the place was clean and quiet. Thanks for hosting me."
United States
Sam N.
The price is ￥11,324
￥35,545 total
includes taxes & fees
Sep 29 - Sep 30
5 Mi to Main St! Cozy Couple's Escape in Laurel

15. Historic Row Home | Hot Tub - 1 Block from Gate 1!

Historic Row Home | Hot Tub - 1 Block from Gate 1!
Historic District
9.0 out of 10, Wonderful, (10 reviews)
"Perfect location. Very clean. Had everything we needed and front porch swing was a nice bonus. Would stay here every visit! "
United States
Tracie B.
The price is ￥30,198
￥83,195 total
includes taxes & fees
Sep 29 - Sep 30
Historic Row Home | Hot Tub - 1 Block from Gate 1!
A kitchen with wooden cabinets, a central island with stools, a refrigerator, and a brick accent wall.

16. Annapolis Gem- Tranquil 4 BR Murray Hill Victorian

Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
Historic District
10.0 out of 10, Exceptional, (1 review)
"The host was very responsive to questions and very easy to communicate with. The house was amazing and so close to downtown. Would definitely stay again!"
United States
Colleen W.
The price is ￥43,567
￥109,541 total
includes taxes & fees
Oct 5 - Oct 6
Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
A cozy cabin interior with a leather sofa, a wooden dining table, and a view of a lake through large windows.

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

The Hideaway Spot- Waterfront w/ Dock on Long Cove
Glen Burnie
9.2 out of 10, Wonderful, (15 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.
The price is ￥25,731
￥63,043 total
includes taxes & fees
Oct 1 - Oct 2
The Hideaway Spot- Waterfront w/ Dock on Long Cove
A sunset view from a balcony with a glass-top table and a fire feature, overlooking the sea.

18. FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views

FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views
Pasadena
10.0 out of 10, Exceptional, (2 reviews)
"FLOHOM 14 did not disappoint!!! This was my first stay on a houseboat. Now I know why babies fall asleep when rocked. The boat is beautifully appointed & well equipped. Bring a good book. I’m already missing it!!!"
United States
Maria D.
The price is ￥24,772
￥62,845 total
includes taxes & fees
Sep 29 - Sep 30
FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views
A two-story house with a stone pathway leading to the front door, surrounded by lush greenery and other houses.

19. Stadium-Side Annapolis | Chef Kitchen | Sleeps 10

Stadium-Side Annapolis | Chef Kitchen | Sleeps 10
Admiral Heights
9.8 out of 10, Exceptional, (12 reviews)
"The home was well stocked with all the items needed to cook and spotless. Very comfortable and easy walk to the Navy stadium. Enjoyed our stay and all that Annapolis has to share. "
United States
Veronica D.
The price is ￥46,004
￥130,440 total
includes taxes & fees
Sep 29 - Sep 30
Stadium-Side Annapolis | Chef Kitchen | Sleeps 10
A kitchen with a wooden countertop, a stove, and a refrigerator.

20. 18th Cent. Charm in Historic Downtown Annapolis

18th Cent. Charm in Historic Downtown Annapolis
Historic District
9.0 out of 10, Wonderful, (14 reviews)
"Jen was an amazing host. The property was meticulously maintained. She made sure we had everything we needed! Shen created an environment where we could socialize with other guests or keep to ourselves. She made plenty of recommendations for local eateries and entertainment. We would definitely stay again!"
United States
Maureens B.
The price is ￥36,662
￥62,594 total
includes taxes & fees
Sep 29 - Sep 30
18th Cent. Charm in Historic 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

Hyatt Place Baltimore Inner Harbor

Hyatt Place Baltimore Inner Harbor

10/10 Excellent
"Perfect for staying with your family. Very friendly staff. Very clean. Beds are comfortable. A lot of variety for the breakfast that is included. The location is great. Restaurants, supermarkets, pharmacies and convenience stores within walking distance or very short drive. Definitely recommended. Would come back and stay there again."
Jose 1-night trip
Posted less than an hour ago
Hyatt Place Baltimore Inner Harbor

Find out more about Sherwood Forest

Search for holiday rentals in Sherwood Forest on Expedia! You can easily find your home rentals, villas, holiday apartments in Sherwood Forest using one of the methods below:

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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.