Estia Villas - Vacation Rentals in Sherwood
House
10.0
(
41 Reviews
)
5 Bedrooms
5 Bathrooms
10 Guests
4500 ft²
-
Private Pool -
Hot Tub -
Spa -
Fireplace/Heating
US $1,638
/Night
7 Nights - $11,469
10.0
(
1 Review
)
2 Bedrooms
2 Bathrooms
4 Guests
1119.45 ft²
-
Pet Friendly -
Kitchen -
Parking -
Internet
US $175
/Night
7 Nights - $1,225
9.4
(
142 Reviews
)
1 Bedroom
1 Bathroom
-
Fireplace/Heating
-
Pool -
Balcony/Terrace -
View
US $259
/Night
7 Nights - $1,810
House
10.0
(
39 Reviews
)
8 Bedrooms
9 Bathrooms
12 Guests
12000 ft²
-
Private Pool
-
Oceanfront -
Fireplace/Heating
-
Pool
US $2,109
/Night
7 Nights - $14,761
House
10.0
(
23 Reviews
)
4 Bedrooms
4 Bathrooms
8 Guests
-
Private Pool
-
Fireplace/Heating
-
Pool
-
Balcony/Terrace
US $740
/Night
7 Nights - $5,177
Cottage
10.0
(
20 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
650 ft²
-
Fireplace/Heating
-
Balcony/Terrace
-
Pet Friendly
-
Kitchen
US $320
/Night
7 Nights - $2,237
House
10.0
(
15 Reviews
)
4 Bedrooms
2 Bathrooms
8 Guests
1710 ft²
-
Fireplace/Heating
-
Balcony/Terrace
-
View
-
Pet Friendly
US $702
/Night
7 Nights - $4,915
House
10.0
(
12 Reviews
)
5 Bedrooms
4 Bathrooms
10 Guests
6000 ft²
-
Private Pool
-
Oceanfront
-
Fireplace/Heating
-
Pool
US $2,199
/Night
7 Nights - $15,392
See More Sherwood Vacation Rentals
Luxury Places to Stay in Sherwood
Over 60+
Luxury Places to Stay in or Near Sherwood
House
6 Bedrooms
7 Bathrooms
12 Guests
-
Oceanfront
-
Hot Tub
-
Fireplace/Heating
-
Ocean View
US $1,593
/Night
7 Nights - $11,148
House
9.6
(
9 Reviews
)
5 Bedrooms
4 Bathrooms
10 Guests
3408 ft²
-
Private Pool
-
Fireplace/Heating
-
Pool
-
Balcony/Terrace
US $1,432
/Night
7 Nights - $10,024
5 Bedrooms
5 Bathrooms
10 Guests
3412.16 ft²
-
Fireplace/Heating
-
Pool
-
Pet Friendly
-
Parking
US $1,372
/Night
7 Nights - $9,604
House
10.0
(
52 Reviews
)
4 Bedrooms
2 Bathrooms
8 Guests
-
Private Pool
-
Fireplace/Heating
-
Pool
-
Balcony/Terrace
US $1,094
/Night
7 Nights - $7,660
House
10.0
(
3 Reviews
)
3 Bedrooms
2 Bathrooms
6 Guests
-
Private Pool
-
Fireplace/Heating
-
Pool
-
Ocean View
US $990
/Night
7 Nights - $6,930
House
9.4
(
15 Reviews
)
3 Bedrooms
3 Bathrooms
6 Guests
2060 ft²
-
Private Pool
-
Hot Tub
-
Fireplace/Heating
-
Pool
US $928
/Night
7 Nights - $6,493
House
4 Bedrooms
3 Bathrooms
8 Guests
3083 ft²
-
Private Pool
-
Fireplace/Heating
-
Pool
-
Balcony/Terrace
US $845
/Night
7 Nights - $5,915
See More Sherwood Luxury Vacation Rentals
Find More Sherwood Villas, Resorts, & Rentals on BedroomVillas
Top-Rated Vacation Rentals with a Pool in Sherwood
Over 18+
Top-Rated Vacation Rentals with a Pool in or Near Sherwood
Cottage
10.0
(
27 Reviews
)
3 Bedrooms
2 Bathrooms
6 Guests
1350 ft²
-
Private Pool
-
Fireplace/Heating
-
Pool
-
Balcony/Terrace
US $391
/Night
7 Nights - $2,740
Cottage
10.0
(
6 Reviews
)
1 Bedroom
1 Bathroom
2 Guests
-
Fireplace/Heating
-
Pool
-
Balcony/Terrace
-
Kitchen
US $312
/Night
7 Nights - $2,181
House
9.8
(
45 Reviews
)
4 Bedrooms
2 Bathrooms
9 Guests
2121 ft²
-
Private Pool
-
Fireplace/Heating
-
Pool
-
Ocean View
US $711
/Night
7 Nights - $4,974
Cottage
9.6
(
4 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
-
Fireplace/Heating
-
Pool
-
Kitchen
-
Parking
US $358
/Night
7 Nights - $2,504
9.4
(
388 Reviews
)
1 Bathroom
-
Pool
-
Balcony/Terrace
-
Breakfast -
Kitchen
US $165
/Night
7 Nights - $1,155
Hotel
9.0
(
98 Reviews
)
1 Bathroom
-
Spa
-
Fireplace/Heating
-
Pool
-
Balcony/Terrace
US $427
/Night
7 Nights - $2,986
Cottage
9.0
(
4 Reviews
)
1 Bedroom
1 Bathroom
2 Guests
-
Fireplace/Heating
-
Pool
-
Kitchen
-
Air Conditioner
US $251
/Night
7 Nights - $1,755
House
9.0
(
1 Review
)
4 Bedrooms
3 Bathrooms
8 Guests
-
Fireplace/Heating
-
Pool
-
Pet Friendly
-
Parking
US $683
/Night
7 Nights - $4,781
Pet-Friendly Vacation Rentals in Sherwood
Over 12+
Pet-Friendly Vacation Rentals in or Near Sherwood
House
10.0
(
1 Review
)
2 Bedrooms
2 Bathrooms
4 Guests
-
Fireplace/Heating
-
Balcony/Terrace
-
Pet Friendly
-
Kitchen
US $346
/Night
7 Nights - $2,419
1 Bedroom
2 Bathrooms
6 Guests
1474.66 ft²
-
Fireplace/Heating
-
View
-
Pet Friendly
-
Parking
US $587
/Night
7 Nights - $4,107
House
9.8
(
56 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
1100 ft²
-
Fireplace/Heating
-
Balcony/Terrace
-
Pet Friendly
-
Kitchen
US $491
/Night
7 Nights - $3,437
House
9.6
(
12 Reviews
)
3 Bedrooms
2 Bathrooms
6 Guests
-
Fireplace/Heating
-
Balcony/Terrace
-
Pet Friendly
-
Kitchen
US $357
/Night
7 Nights - $2,496
House
6.0
(
2 Reviews
)
3 Bedrooms
2 Bathrooms
6 Guests
1476 ft²
-
Fireplace/Heating
-
Balcony/Terrace
-
Pet Friendly
-
Kitchen
US $748
/Night
7 Nights - $5,235
House
10.0
(
10 Reviews
)
4 Bedrooms
3 Bathrooms
8 Guests
-
Private Pool
-
Fireplace/Heating
-
Pool
-
Balcony/Terrace
US $600
/Night
7 Nights - $4,203
House
10.0
(
1 Review
)
3 Bedrooms
2 Bathrooms
6 Guests
2558 ft²
-
Private Pool
-
Fireplace/Heating
-
Pool
-
Balcony/Terrace
US $983
/Night
7 Nights - $6,879
House
9.8
(
60 Reviews
)
2 Bedrooms
2 Bathrooms
4 Guests
1124 ft²
-
Oceanfront
-
Fireplace/Heating
-
Ocean View
-
Balcony/Terrace
US $296
/Night
7 Nights - $2,072
See More Pet-Friendly Vacation Rentals in Sherwood on PetFriendly.io
Large Vacation Homes & Villas in Sherwood
Over 7+
Large Vacation Homes & Villas in or Near Sherwood
House
10.0
(
96 Reviews
)
5 Bedrooms
4 Bathrooms
10 Guests
3400 ft²
-
Oceanfront
-
Fireplace/Heating
-
Ocean View
-
Balcony/Terrace
US $439
/Night
7 Nights - $3,070
House
10.0
(
24 Reviews
)
6 Bedrooms
4 Bathrooms
12 Guests
-
Private Pool
-
Hot Tub
-
Fireplace/Heating
-
Pool
US $1,751
/Night
7 Nights - $12,258
House
10.0
(
3 Reviews
)
11 Bedrooms
7 Bathrooms
12 Guests
-
Private Pool
-
Hot Tub
-
Fireplace/Heating
-
Pool
US $2,933
/Night
7 Nights - $20,533
House
9.6
(
7 Reviews
)
7 Bedrooms
6 Bathrooms
12 Guests
-
Private Pool
-
Fireplace/Heating
-
Pool
-
Balcony/Terrace
US $1,784
/Night
7 Nights - $12,491
House
10.0
(
36 Reviews
)
6 Bedrooms
3 Bathrooms
12 Guests
3475 ft²
-
Private Pool
-
Fireplace/Heating
-
Pool
-
Balcony/Terrace
US $954
/Night
7 Nights - $6,675
House
4.8
(
28 Reviews
)
4 Bedrooms
3 Bathrooms
10 Guests
-
Private Pool
-
Pool
-
Balcony/Terrace
-
Pet Friendly
US $500
/Night
7 Nights - $3,500
House
6 Bedrooms
7 Bathrooms
12 Guests
-
Private Pool
-
Fireplace/Heating
-
Pool
-
Balcony/Terrace
US $844
/Night
7 Nights - $5,911
See More Family Vacation Rentals in Sherwood on FVR
Sherwood Vacation Rentals and Airbnb Places to Stay Under $200
Over 1+
Sherwood Vacation Rentals and Airbnb Places to Stay Under $200
Cottage
9.8
(
35 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
-
Kitchen
-
Internet
-
TV -
Security/Safety
US $163
/Night
7 Nights - $1,139
See More Sherwood Vacation Rental Deals
Instantly Bookable Vacation Homes in Sherwood
Over 9+
Instantly Bookable Vacation Homes in or Near Sherwood
House
10.0
(
11 Reviews
)
3 Bedrooms
2 Bathrooms
6 Guests
-
Fireplace/Heating
-
Balcony/Terrace
-
Kitchen
-
Parking
US $366
/Night
7 Nights - $2,562
House
10.0
(
5 Reviews
)
2 Bedrooms
2 Bathrooms
4 Guests
1500 ft²
-
Fireplace/Heating
-
Balcony/Terrace
-
Kitchen
-
Parking
US $254
/Night
7 Nights - $1,778
House
10.0
(
1 Review
)
3 Bedrooms
3 Bathrooms
6 Guests
-
Kitchen
-
Parking
-
Air Conditioner
-
Internet
US $610
/Night
7 Nights - $4,273
House
9.8
(
15 Reviews
)
3 Bedrooms
2 Bathrooms
6 Guests
-
Fireplace/Heating
-
Balcony/Terrace
-
Kitchen
-
Parking
US $609
/Night
7 Nights - $4,266
US $319
/Night
7 Nights - $2,232
House
10.0
(
14 Reviews
)
4 Bedrooms
3 Bathrooms
8 Guests
-
Fireplace/Heating
-
Balcony/Terrace
-
Kitchen
-
Parking
US $276
/Night
7 Nights - $1,935
House
9.6
(
50 Reviews
)
3 Bedrooms
3 Bathrooms
6 Guests
2080 ft²
-
Fireplace/Heating
-
Balcony/Terrace
-
View
-
Kitchen
US $641
/Night
7 Nights - $4,485
House
9.0
(
2 Reviews
)
2 Bedrooms
2 Bathrooms
4 Guests
925 ft²
-
Kitchen
-
Parking
-
Air Conditioner
-
Internet
US $405
/Night
7 Nights - $2,836
See More Sherwood Short-Term Vacation Rentals
About Sherwood Vacation Rentals
With more than 69 Sherwood vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Estiavillas and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Sherwood.
Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Estiavillas Sherwood, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Sherwood. Places to stay near Sherwood are 1250.63 ft² on average, with prices averaging US $676 a night.
Estiavillas makes it easy and safe to find and compare vacation rentals in Sherwood with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.
Top Rental Accommodation Types in Sherwood
| Type | Count |
|---|---|
| Vacation Homes | 56 |
| Cottages | 8 |
| Hotels | 4 |
| Holiday Apartments | 1 |
Use these Quick Filters to Find a Vacation Rental in Sherwood
★ Pro Tip: Estiavillas makes it easy to compare the best listings on Estiavillas homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Estiavillas homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Sherwood.
Weather in Sherwood
View the weather forecast for Sherwood before booking your Sherwood Vacation Rentals to confirm your best time to go.
December - February
High 60°F Low 26°F
March - May
High 77°F Low 40°F
June - August
High 91°F Low 64°F
September - November
High 84°F Low 38°F
Top Attractions Around Sherwood, MD
Estiavillas offers a large selection of top attractions around Sherwood. Research things to do on your vacation before you visit Sherwood.
U.S. Naval Academy
Westfield Annapolis Mall
Annapolis City Dock
Chesapeake Bay Bridge
Sandy Point State Park
Chesapeake Beach Water Park
Anne Arundel Medical Center
Maryland State House
Navy-Marine Corps Memorial Stadium
Rod n Reel Charter Fishing
Annapolis Harbour Center
Kunta Kinte–Alex Haley Memorial
St. Michaels Winery
Queenstown Premium Outlets
Annapolis Maritime Museum
Great Marsh Park
Chesapeake Bay Maritime Museum
Harriet Tubman Museum and Educational Center
Oxford Museum
Queenstown Harbor Golf Club
Sherwood Vacation Rental Frequently Asked Questions
How many vacation rentals have private pools in Sherwood?
There are 1 vacation rentals with private pools near Sherwood. Top-rated homes that have access to a swimming pool include:
Which vacation homes in Sherwood are best for families?
If you are looking for a family-friendly vacation home in Sherwood, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Sherwood:
How many vacation rentals are available in Sherwood?
Currently, the total number of properties listed in 2026 is over 69 in the Sherwood area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Sherwood.
