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Hotels with Outdoor Pool and Swimming Pool in Woolford

41 HOTELS IN AND AROUND WOOLFORDRanking can be influenced by the commissions we receive.
Saddle Beach Waterfront on the Chesapeake main photo
$
Info
Categories
Pool
Heated Pool
Outdoor Pool
Dog Friendly
Parking
Saddle Beach Chesapeake Waterfront Estate w/Pool, Private Beach main photo
$
Info
Categories
Pool
Heated Pool
Private Pool
Outdoor Pool
Dog Friendly
Parking
Chesapeake Waterfront - 7BR 5BA - Beach Pool Dock main photo
$
Info
Categories
Pool
Outdoor Pool
Dog Friendly
Free Wi-Fi
17 more hotels nearby!
Waterfront Cambridge Home Pool and Dock! main photo
Waterfront Cambridge Home Pool and Dock!
3.2 mi from Woolford
Vacation Home in Cambridge MDUS flag
0.0
$
Info
Categories
Pool
Outdoor Pool
Free Wi-Fi
Parking
The Point at Little Choptank main photo
The Point at Little Choptank
3.4 mi from Woolford
Vacation Home in Madison MDUS flag
0.0
$
Info
Categories
Pool
Outdoor Pool
Free Wi-Fi
Very Private and Spacious Waterfront Family House main photo
Very Private and Spacious Waterfront Family House
3.5 mi from Woolford
Vacation Home in Cambridge MDUS flag
0.0
$
Info
Categories
Pool
Outdoor Pool
Dog Friendly
Free Wi-Fi
My Chesapeake Retreat Cambridge, Maryland main photo
My Chesapeake Retreat Cambridge, Maryland
6.2 mi from Woolford
Vacation Home in Cambridge MDUS flag
0.0
$
Info
Categories
Pool
Outdoor Pool
Dog Friendly
Parking
Less Than 1 Mi to Dtwn Waterfront Townhome in Cambridge! main photo
Less Than 1 Mi to Dtwn Waterfront Townhome in Cambridge!
8.8 mi from Woolford
Vacation Home in Cambridge MDUS flag
0.0
$
Info
Categories
Pool
Outdoor Pool
Free Wi-Fi
Parking
Walkable Condo with Drawbridge Views in Cambridge main photo
Walkable Condo with Drawbridge Views in Cambridge
8.8 mi from Woolford
Apartment in Cambridge MDUS flag
0.0
$
Info
Categories
Pool
Outdoor Pool
Free Wi-Fi
Parking
Jewel of the Tred Avon main photo
Jewel of the Tred Avon
9.1 mi from Woolford
Vacation Home in Oxford MDUS flag
0.0
$
Info
Categories
Pool
Outdoor Pool
Free Wi-Fi
Parking
Hyatt Regency Chesapeake Bay Golf Resort, Spa & Marina main photo
Hyatt Regency Chesapeake Bay Golf Resort, Spa & Marina
10.0 mi from Woolford
Resort in Cambridge MDUS flag
8.6
Very Good
From $265
$
Info
Summary of reviews
The Hyatt Regency Chesapeake Bay Golf Resort, Spa & Marina is a highly recommended destination for those looking for a relaxing and enjoyable vacation. The hotel's stunning location with its beautiful views of the Choptank and proximity to historic sites, makes it an ideal base for exploring the area. Guests appreciate the wide selection of food options available at the breakfast buffet, though some noted occasional availability issues. The dinner options received mixed reviews with some praising the food and others finding it substandard. The rooms are comfortable, spacious and clean with modern decor and breathtaking views. The hotel is also praised for its cleanliness with many guests commenting on how well-maintained the resort is. The staff is exceptional with many guests noting their kindness, accommodation and helpfulness. The pool area is fantastic with multiple options for relaxation and fun and the hotel is an excellent destination for families with children. The beds are super comfortable, though some guests noted issues with blankets and sofa beds. Overall, the Hyatt Regency Chesapeake Bay Golf Resort, Spa & Marina is a great choice for a safe and enjoyable getaway with superb facilities.
Categories
Pool
Indoor Pool
Children's Pool
Pool Water Slide
Outdoor Pool
Beachfront
Family
Wylder Hotel - Tilghman Island main photo
Wylder Hotel - Tilghman Island
12.5 mi from Woolford
Hotel in Saint Michaels MDUS flag
8.8
Excellent
From $240
$
Info
Categories
Pool
Heated Pool
Outdoor Pool
Romantic
Parking
25 Bedrooms - Retreat Center Waterfront Renovated main photo
25 Bedrooms - Retreat Center Waterfront Renovated
12.7 mi from Woolford
Vacation Home in Neavitt MDUS flag
0.0
$
Info
Categories
Pool
Outdoor Pool
Waterfront Bliss- Ultimate Tilghman Retreat home main photo
Waterfront Bliss- Ultimate Tilghman Retreat home
12.9 mi from Woolford
Vacation Home in Tilghman Island MDUS flag
9.0
Excellent
$
Info
Categories
Pool
Private Pool
Outdoor Pool
Dog Friendly
Parking
Tilghman Island Inn main photo
Tilghman Island Inn
13.1 mi from Woolford
Hotel in Tilghman Island MDUS flag
9.1
Excellent
From $223
$
Info
Categories
Pool
Outdoor Pool
Parking
Luxury
The Oaks Waterfront Hotel main photo
The Oaks Waterfront Hotel
13.8 mi from Woolford
Inn in Saint Michaels MDUS flag
9.7
Excellent
From $439
$
Info
Categories
Pool
Outdoor Pool
Parking
Luxury
Spacious Trappe Getaway with Outdoor Pool and Gazebo! main photo
Spacious Trappe Getaway with Outdoor Pool and Gazebo!
14.0 mi from Woolford
Vacation Home in Easton MDUS flag
0.0
$
Info
Categories
Pool
Private Pool
Outdoor Pool
St. Michaels Inn main photo
St. Michaels Inn
15.3 mi from Woolford
Hotel in Saint Michaels MDUS flag
7.6
Good
From $94
$
Info
Summary of reviews
St. Michaels Inn offers a convenient, centrally located stay that allows guests easy access to the quaint shops, restaurants and attractions of St. Michaels and its surroundings. The inn is especially valued for its peaceful setting, ample and easy parking and serves as an excellent base for exploring the Eastern Shore. Guests frequently praise the clean, spacious rooms featuring thoughtful amenities like refrigerators and microwaves with many finding the decor cozy and inviting.

The complimentary breakfast is well-received overall with guests enjoying an array of options from scrambled eggs and sausage to muffins and fresh fruit. While some found the breakfast room well-organized and the continental setup convenient, others noted limited options and occasional restocking issues. The inn’s cleanliness is consistently highlighted with terms like "spotless" and "well-maintained" frequently used to describe both the rooms and common areas, including the swimming pool.

The staff at
St. Michaels Inn is often lauded for their friendliness, professionalism and readiness to assist with any needs, greatly enhancing the guest experience. Numerous reviews commend individual staff members and appreciate their polite, helpful nature.

However, the inn does show signs of aging with some rooms featuring outdated furnishings and occasional odors. Reviews suggest uneven experiences with bed comfort with some guests finding the mattresses too firm or the pillows inadequate. The WiFi service also garnered mixed feedback with some guests experiencing weak signals and connectivity issues.

The pool, when available, is a well-maintained and pleasant spot for relaxation, though its inconsistent availability and early closing times were noted as drawbacks. The inn's outdoor spaces, including a patio, gazebo and courtyard, are appreciated for their cleanliness and tranquility.

Overall,
St. Michaels Inn provides good value for those looking for affordable, basic accommodations in a prime location. Its combination of strategic positioning, friendliness of staff and generally clean and comfortable environment make it a solid choice for budget-conscious travelers seeking a functional and pleasant stay.
Categories
Outdoor Pool
Pool
Outdoor Pool
Accessible
Luxury Waterfront Private Pool Dock Near Cambridge main photo
Luxury Waterfront Private Pool Dock Near Cambridge
15.6 mi from Woolford
Vacation Home in East New Market MDUS flag
0.0
$
Info
Categories
Pool
Outdoor Pool
Dog Friendly
Free Wi-Fi
Brand-New Pool! Waterfront Bozman Village Home main photo
Brand-New Pool! Waterfront Bozman Village Home
15.8 mi from Woolford
Vacation Home in Saint Michaels MDUS flag
0.0
$
Info
Categories
Pool
Outdoor Pool
Free Wi-Fi
Parking
*Additional taxes or fees may apply. Please check the final price before completing your booking.Showing 1-20 out of 41 hotels in and around Woolford
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