Anderson Island Living - Vacation Rentals in Sidney

Fishing Kayaks Firepit Paddleboat From US $259
         

|
10.0 (3 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
The Winona Lake Chalet 2 From US $292
         

10.0 (34 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Hampton Inn Warsaw From US $109
         

9.0 (655 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Fishing · Kayaks · Firepit · Paddleboat From US $222
         

10.0 (22 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • Pet Friendly
Winona Lake Access With Pier From US $216
         

10.0 (21 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Downtown loft apartment with rooftop balcony From US $190
         

10.0 (19 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Balcony/Terrace

Luxury Places to Stay in Sidney

Over 58+ Luxury Places to Stay in or Near Sidney
The Winona Lake Chalet 1 From US $312
         

10.0 (7 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
NEW Spacious Lakehouse Retreat +private pier From US $295
         

9.6 (30 Reviews)
House
  • Air Conditioner
  • Parking
  • TV

Top-Rated Vacation Rentals with a Pool in Sidney

Over 11+ Top-Rated Vacation Rentals with a Pool in or Near Sidney
Holiday Inn Express & Suites Warsaw - E Center by IHG From US $104
         

9.0 (471 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Holiday Inn Express & Suites - Warsaw - E Center by IHG From US $97
         

|
8.3 (168 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Best Western Plus Warsaw From US $88
         

7.8 (1005 Reviews)
Hotel
  • Parking
  • Pool
  • TV
Comfort Inn & Suites Warsaw near US-30 From US $98
         

7.8 (504 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Wyndham Garden Warsaw From US $76
         

|
7.6 (1002 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Best Western Plus Warsaw From US $78
         

|
7.0 (297 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Comfort Inn & Suites Warsaw near US-30 From US $86
         

|
6.9 (117 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly

Pet-Friendly Vacation Rentals in Sidney

Over 12+ Pet-Friendly Vacation Rentals in or Near Sidney
King Suite 2 Full Baths Stocked Kitchen From US $182
         

|
9.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Trail Side in the Heart of Winona Lake From US $259
         

9.8 (42 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Lake Palestine Paradise. Charming 2-bedroom, 1-bath cottage in Warsaw. From US $176
         

Winona Lake Cottage w/Deck From US $244
         

10.0 (39 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Cabin on 22 Acres near Eel River: Sleeps 4, Trails, Nature, Fishing! From US $231
         

2-bedroom house in Warsaw, Indiana close to Winona Lake From US $140
         

10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
See More Pet-Friendly Vacation Rentals in Sidney on PetFriendly.io

Large Vacation Homes & Villas in Sidney

Over 3+ Large Vacation Homes & Villas in or Near Sidney
Avalon on the Lake From US $400
         

4.6 (7 Reviews)
House
  • Air Conditioner
  • Child Friendly
  • Laundry
Fabulous 5-bedroom mobile home with AC in Pierceton From US $367
         

Wheelchair Accessible Vacation Homes in Sidney

Over 4+ Wheelchair Accessible Vacation Homes in or Near Sidney
Tru By Hilton Warsaw, In From US $95
         

|
9.0 (188 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Tru by Hilton Warsaw From US $91
         

9.0 (379 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
Hampton Inn Warsaw From US $115
         

|
8.3 (76 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Designated Smoking Area
DELUXE INN From US $69
         

|
3.8 (24 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly

Sidney Vacation Rentals and Airbnb Places to Stay Under $200

Over 10+ Sidney Vacation Rentals and Airbnb Places to Stay Under $200
Days Inn by Wyndham Warsaw From US $88
         

7.8 (28 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
Park model located at Yogi Jellystone Park. Not far from the beach. From US $113
         

9.4 (10 Reviews)
RV Rental
  • Air Conditioner
  • Balcony/Terrace
  • Security/Safety
Winona Trail's Edge From US $110
         

10.0 (16 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Cozy Winona Lake Retreat From US $122
         

10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • TV

Instantly Bookable Vacation Homes in Sidney

Over 9+ Instantly Bookable Vacation Homes in or Near Sidney
Pony Creek Cottage From US $287
         

10.0 (11 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
2 Mi to Dtwn: Family Home in Warsaw! From US $219
         

Lux Loft Downtown Warsaw From US $274
         

10.0 (2 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Security/Safety
Cozy 3 Bedroom Winona Lakefront Home From US $350
         

LAKEFRONT Newly Remodeled & Late Checkout! From US $295
         

New
House
  • Air Conditioner
  • TV
  • Balcony/Terrace

About Sidney Vacation Rentals

With more than 67 Sidney vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Andersonislandliving 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 Sidney.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Andersonislandliving Sidney, 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 Sidney. Places to stay near Sidney are 457.09 ft² on average, with prices averaging $234 a night.

Andersonislandliving makes it easy and safe to find and compare vacation rentals in Sidney 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 Sidney

Type Count
Vacation Homes 36
Hotels with Suites 14
Holiday Apartments 6
Cottages 4
Cabin Rentals 2
Others 1

Use these Quick Filters to Find a Vacation Rental in Sidney

Pro Tip: Andersonislandliving makes it easy to compare the best listings on Andersonislandliving homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Andersonislandliving 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 Sidney.

Weather in Sidney

View the weather forecast for Sidney before booking your Sidney 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 Sidney, IN

Andersonislandliving offers a large selection of top attractions around Sidney. Research things to do on your vacation before you visit Sidney.


Sidney Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Sidney?
How many vacation rentals are available in Sidney?

Currently, the total number of properties listed in 2026 is over 67 in the Sidney area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Sidney.