Ingleside Vacation Rentals & Ski-in/Ski-out Homes
Apartment
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
4 Guests
Parking
Balcony/Terrace
Kitchen
Air Conditioner
US $140/Night
7 Nights - US $979
Villa
- Maryland
- ·
- Centreville
- 1.82 mi to center
10.0Exceptional
(2 Reviews)
6 Bedrooms
6 Baths
12 Guests
5005.22 ft²
- Parking
Pool
View- Air Conditioner
US $1,067/Night
7 Nights - US $7,467
Apartment
- Maryland
- ·
- Millington
- 0.14 mi to center
9.8Exceptional
(29 Reviews)
1 Bedroom
1 Bath
2 Guests
- Parking
- Kitchen
- Air Conditioner
Internet
US $118/Night
7 Nights - US $825
House
10.0Exceptional
(1 Review)
4 Bedrooms
2 Baths
8 Guests
1797.57 ft²
Hot Tub- View
- Air Conditioner
- Internet
US $845/Night
7 Nights - US $5,915
Cabin
1 Bedroom
1 Bath
2 Guests
320 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $194/Night
7 Nights - US $1,359
House
- Maryland
- ·
- Chestertown
- 1.91 mi to center
7.4Very Good
(3 Reviews)
3 Bedrooms
1 Bath
6 Guests
1000 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $303/Night
7 Nights - US $2,118
Apartment
10.0Exceptional
(93 Reviews)
1 Bedroom
1 Bath
5 Guests
650 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $218/Night
7 Nights - US $1,529
Cabin
- Maryland
- ·
- Chestertown
- 8.68 mi to center
9.8Exceptional
(27 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $296/Night
7 Nights - US $2,074
Cottage
- Maryland
- ·
- Centreville
- 1.78 mi to center
8.4Excellent
(12 Reviews)
1 Bedroom
1 Bath
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $219/Night
7 Nights - US $1,532
Luxury Places to Stay in Ingleside
Over 50+ Luxury Places to Stay in or Near Ingleside
House
- Maryland
- ·
- Sudlersville
- 3.88 mi to center
10.0Exceptional
(3 Reviews)
7 Bedrooms
3 Baths
25 Guests
3887 ft²
Private Pool- Parking
- Pool
- Kitchen
US $1,707/Night
7 Nights - US $11,950
House
- Maryland
- ·
- Sudlersville
- 3.88 mi to center
1 Bedroom
2 Baths
25 Guests
3885.77 ft²
- Parking
- Pool
- Air Conditioner
- Internet
US $1,539/Night
7 Nights - US $10,771
House
- Maryland
- ·
- Centreville
- 1.60 mi to center
10.0Exceptional
(10 Reviews)
5 Bedrooms
3 Baths
12 Guests
5000 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $1,428/Night
7 Nights - US $9,995
House
- Maryland
- ·
- Centreville
- 2.29 mi to center
10.0Exceptional
(22 Reviews)
5 Bedrooms
6 Baths
16 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $1,331/Night
7 Nights - US $9,317
House
- Maryland
- ·
- Chestertown
- 2.32 mi to center
9.6Exceptional
(27 Reviews)
4 Bedrooms
4 Baths
14 Guests
3232 ft²
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $1,024/Night
7 Nights - US $7,165
Villa
- Maryland
- ·
- Centreville
- 1.82 mi to center
10.0Exceptional
(26 Reviews)
6 Bedrooms
6 Baths
12 Guests
5000 ft²
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $1,005/Night
7 Nights - US $7,037
House
- Maryland
- ·
- Chestertown
- 2.32 mi to center
4 Bedrooms
5 Baths
14 Guests
3229.17 ft²
- Parking
- Pool
- Balcony/Terrace
- Internet
US $941/Night
7 Nights - US $6,585
New
House
- Maryland
- ·
- Centreville
- 2.53 mi to center
6 Bedrooms
4 Baths
12 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $781/Night
7 Nights - US $5,469
House
9.8Exceptional
(12 Reviews)
7 Bedrooms
4 Baths
10 Guests
3200 ft²
- Hot Tub
- Parking
- Kitchen
- Air Conditioner
US $671/Night
7 Nights - US $4,698
Top-Rated Vacation Rentals with a Pool in Ingleside
Over 9+ Top-Rated Vacation Rentals with a Pool in or Near Ingleside
House
- Maryland
- ·
- Greensboro
- 3.01 mi to center
10.0Exceptional
(70 Reviews)
2 Bedrooms
2 Baths
6 Guests
1700 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $479/Night
7 Nights - US $3,354
House
- Maryland
- ·
- Centreville
- 2.38 mi to center
10.0Exceptional
(8 Reviews)
3 Bedrooms
1 Bath
6 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $471/Night
7 Nights - US $3,296
House
10.0Exceptional
(5 Reviews)
4 Bedrooms
2 Baths
8 Guests
1798 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $548/Night
7 Nights - US $3,837
New
House
- Maryland
- ·
- Chestertown
- 4.45 mi to center
8.0Excellent
(1 Review)
1 Bedroom
1 Bath
4 Guests
1200 ft²
- Parking
- Pool
Ocean View- Balcony/Terrace
US $311/Night
7 Nights - US $2,174
House
7.0Very Good
(2 Reviews)
1 Bedroom
1 Bath
2 Guests
1798 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $436/Night
7 Nights - US $3,051
House
- Maryland
- ·
- Chestertown
- 2.97 mi to center
10.0Exceptional
(8 Reviews)
11 Bedrooms
9 Baths
30 Guests
10000 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $2,873/Night
7 Nights - US $20,108
House
- Maryland
- ·
- Church Hill
- 4.45 mi to center
10.0Exceptional
(2 Reviews)
5 Bedrooms
3 Baths
14 Guests
2352 ft²
- Private Pool
- Hot Tub
- Pool
- Balcony/Terrace
US $805/Night
7 Nights - US $5,636
House
- Maryland
- ·
- Chestertown
- 2.32 mi to center
9.8Exceptional
(22 Reviews)
4 Bedrooms
3 Baths
10 Guests
- Private Pool
Oceanfront- Parking
- Pool
US $1,166/Night
7 Nights - US $8,162
House
- Maryland
- ·
- Church Hill
- 4.32 mi to center
8.4Excellent
(6 Reviews)
5 Bedrooms
3 Baths
16 Guests
- Hot Tub
- Parking
- Pool
- Kitchen
US $755/Night
7 Nights - US $5,284
Pet-Friendly Vacation Rentals in Ingleside
Over 9+ Pet-Friendly Vacation Rentals in or Near Ingleside
House
- Maryland
- ·
- Chestertown
- 3.00 mi to center
10.0Exceptional
(96 Reviews)
3 Bedrooms
2 Baths
10 Guests
- Oceanfront
- Parking
Spa- Ocean View
US $595/Night
7 Nights - US $4,166
House
- Maryland
- ·
- Centreville
- 1.78 mi to center
9.2Exceptional
(10 Reviews)
1 Bedroom
1 Bath
4 Guests
592.02 ft²
- Parking
- Balcony/Terrace
- View
- Kitchen
US $267/Night
7 Nights - US $1,867
House
- Maryland
- ·
- Centreville
- 2.81 mi to center
10.0Exceptional
(13 Reviews)
4 Bedrooms
3 Baths
8 Guests
3500 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $301/Night
7 Nights - US $2,110
House
- Maryland
- ·
- Centreville
- 0.67 mi to center
3 Bedrooms
2 Baths
4 Guests
- Air Conditioner
- Internet
Pet Friendly
Laundry
US $655/Night
7 Nights - US $4,588
House
10.0Exceptional
(1 Review)
4 Bedrooms
1 Bath
7 Guests
1700 ft²
- Parking
- Ocean View
- Balcony/Terrace
- View
US $347/Night
7 Nights - US $2,432
Apartment
- Maryland
- ·
- Greensboro
- 3.15 mi to center
9.8Exceptional
(50 Reviews)
2 Bedrooms
1 Bath
6 Guests
1200 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- View
US $245/Night
7 Nights - US $1,713
House
2 Bedrooms
2 Baths
8 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $255/Night
7 Nights - US $1,783
House
- Maryland
- ·
- Chestertown
- 2.89 mi to center
10.0Exceptional
(25 Reviews)
4 Bedrooms
2 Baths
10 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $729/Night
7 Nights - US $5,105
Cabin
4.0Average
(1 Review)
3 Bedrooms
2 Baths
8 Guests
- Kitchen
- Air Conditioner
- Pet Friendly
Child Friendly
US $138/Night
7 Nights - US $966
Large Vacation Homes & Villas in Ingleside
Over 7+ Large Vacation Homes & Villas in or Near Ingleside
House
- Maryland
- ·
- Chestertown
- 3.50 mi to center
10.0Exceptional
(32 Reviews)
3 Bedrooms
2 Baths
10 Guests
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
US $525/Night
7 Nights - US $3,678
House
7 Bedrooms
4 Baths
10 Guests
3196.88 ft²
- Hot Tub
- Parking
- Internet
Wellness Facilities
US $549/Night
7 Nights - US $3,841
New
House
10.0Exceptional
(7 Reviews)
7 Bedrooms
4 Baths
8 Guests
- Hot Tub
- Parking
- Kitchen
- Air Conditioner
US $503/Night
7 Nights - US $3,522
House
- Maryland
- ·
- Chestertown
- 3.92 mi to center
10.0Exceptional
(1 Review)
3 Bedrooms
2 Baths
10 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- View
US $527/Night
7 Nights - US $3,687
House
9.8Exceptional
(55 Reviews)
5 Bedrooms
2 Baths
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $378/Night
7 Nights - US $2,645
House
- Maryland
- ·
- Chestertown
- 3.61 mi to center
9.6Exceptional
(17 Reviews)
3 Bedrooms
3 Baths
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $622/Night
7 Nights - US $4,351
House
7 Bedrooms
3 Baths
12 Guests
4800 ft²
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $623/Night
7 Nights - US $4,361
Ingleside Resorts and Airbnb Homes Under $200
Over 5+ Ingleside Resorts and Airbnb Homes Under $200
House
- Maryland
- ·
- Sudlersville
- 5.94 mi to center
3 Bedrooms
1 Bath
5 Guests
- Kitchen
- Air Conditioner
- Internet
- Laundry
US $195/Night
7 Nights - US $1,365
House
1 Bedroom
1 Bath
2 Guests
322.92 ft²
- Parking
- Internet
Security/Safety
US $180/Night
7 Nights - US $1,260
US $200/Night
7 Nights - US $1,400
House
- Maryland
- ·
- Greensboro
- 1.33 mi to center
2 Bedrooms
1 Bath
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $194/Night
7 Nights - US $1,359
New
Apartment
1 Bedroom
1 Bath
- Child Friendly
US $153/Night
7 Nights - US $1,068
Instantly Bookable Vacation Homes in Ingleside
Over 8+ Instantly Bookable Vacation Homes in or Near Ingleside
House
- Maryland
- ·
- Chestertown
- 2.01 mi to center
10.0Exceptional
(31 Reviews)
3 Bedrooms
2 Baths
7 Guests
1440 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $291/Night
7 Nights - US $2,034
House
- Maryland
- ·
- Chestertown
- 8.61 mi to center
10.0Exceptional
(3 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $408/Night
7 Nights - US $2,857
House
- Maryland
- ·
- Greensboro
- 3.78 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
3 Baths
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $372/Night
7 Nights - US $2,604
Apartment
- Maryland
- ·
- Greensboro
- 1.34 mi to center
9.4Exceptional
(10 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $304/Night
7 Nights - US $2,126
Other
- Maryland
- ·
- Greensboro
- 1.60 mi to center
10.0Exceptional
(1 Review)
3 Bedrooms
2 Baths
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $424/Night
7 Nights - US $2,968
New
House
4 Bedrooms
3 Baths
8 Guests
3150 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $358/Night
7 Nights - US $2,504
House
- Maryland
- ·
- Chestertown
- 3.49 mi to center
10.0Exceptional
(60 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $459/Night
7 Nights - US $3,215
Apartment
- Maryland
- ·
- Greensboro
- 1.36 mi to center
4.0Average
(2 Reviews)
3 Bedrooms
2 Baths
8 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $311/Night
7 Nights - US $2,177
Book a Last Minute Place to Stay in Ingleside
About Ingleside Vacation Rentals
Explore over 59 vacation rentals in Ingleside with SunSki Resorts. These accommodations, comprising vacation homes, cottages, cabins, and condos, boast excellent amenities at great value, ensuring comfort and luxury. Enhance your stay with SunSki Resorts in Ingleside for more space and value.
In search of last-minute deals or the best bargains on vacation rentals? With SunSki Resorts, you can conveniently compare various options and deals in Ingleside. Discover rentals with desirable amenities like swimming pools, hot tubs, and pet-friendly options. Find the ideal vacation rental in Ingleside tailored to your preferences. On average, these rentals offer 1340.87 ft² of space, and are priced at an average of US $576 per night.
SunSki Resorts simplifies and secures the process of finding and comparing vacation rentals in Ingleside at prices typically 30-40% lower than hotels. Discover your perfect vacation rental and book now.
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Top Types of Ski Accommodations in Ingleside
| Type | Count |
|---|---|
| Vacation Homes | 45 |
| Holiday Apartments | 7 |
| Cabin Rentals | 3 |
| Villas | 2 |
| Cottages | 1 |
| Others | 1 |
Use these Quick Filters to Find a Vacation Rental in Ingleside
★ Pro Tip: Discover Your Ideal Vacation Rental in Ingleside with SunSki Resorts™. Compare a diverse array of properties, including RBO homes, vacation rentals, cottages, cabins, and more. Utilize our advanced filters to search by location, amenities, and price. Book with confidence and enjoy savings of up to 40-60% compared to a hotel stay. Create unforgettable memories with SunSki Resorts™.
Weather in Ingleside, MD
View the weather forecast for Ingleside before booking your Ingleside 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
Frequently Asked Questions About Ingleside?
What are the top vacation rentals in Ingleside?
When organizing your trip to Ingleside, don't miss the chance to explore the top-rated vacation rentals in the vicinity. With a plethora of options available, you're bound to discover the ideal accommodation for your stay in Ingleside. Peruse our collection of highly-rated properties and secure your reservation today.
- Private Waterfront Paradise w/Pier - Kayak to Historic Chestertown!
- Eastern Shore Get Away
- Stunning Waterfront Hideaway on Michener's Choptank River. Special Rates*
- Harbor View Haven | Waterfront w/Hot Tub + Dock!
- Lovely Home in Chestertown - Free EV Charging for guests
- Blake House Historic Estate with Private Inn
- Waterfront oasis, tranquil masterpiece for relaxing and recreating beautifully
- Family Retreat at Lansdowne Manor
- The Colonial Farmhouse with Private Boat Rental
- HGTV quality, private guest suite, country getaway with hot tub & fire pit
Which vacation homes or resorts in Ingleside are best for families?
Choose SunSki for a wide variety of vacation rentals, including family-friendly homes, ski cabins, cottages, and more in Ingleside. Enjoy great views, locations and save money with SunSki Resorts.™
How many SunSkiResorts vacation rentals or resorts are available in Ingleside?
Discover the ideal vacation rental in Ingleside with SunSki Resorts™. We provide an extensive selection of over 59 properties, encompassing vacation homes, private villas, cottages, and more. Explore our listings to find the perfect place to stay for your upcoming trip to Ingleside.
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