57+ Vacation Rentals Near Grand Boulevard

NearbyHoliday - Vacation Rentals in Grand Boulevard

a bedroom with a black bed and a large mirror at Luxéry Stay Chicago - Themed Units! Close to Downtown, McCormick Place & Wintrust Arena in Chicago

From US $250

Luxéry Stay Chicago - Themed Units! Close to Downtown, McCormick Place & Wintrust Arena

8.9 (194 Reviews) Apartment

The entire place is yours • 60 m² size • Kitchen

Chicago Near South Side • In Grand Boulevard · 4.6km to center

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a living room with a couch and a tv at Forrestville Ave Large Suite in Chicago

From US $160

Forrestville Ave Large Suite

8.6 (103 Reviews) Apartment

The entire place is yours • 130 m² size • Free parking

Chicago Grand Boulevard • In Grand Boulevard · 414m to center

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a living room with a couch and a ceiling fan at The Penthouse, Lux stay near Downtown, UofC & Lake in Chicago

From US $266

The Penthouse, Lux stay near Downtown, UofC & Lake

9.2 (37 Reviews) Apartment

The entire place is yours • 135 m² size • Kitchen

Chicago Kenwood • In Grand Boulevard · 1.7km to center

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a living room with a green couch and a table at Chicago 2BR Suite Perfect for Convention and Business Trips Near McCormick Place, Arena, Soldier Field and Grant Park in Chicago

From US $167

Chicago 2BR Suite Perfect for Convention and Business Trips Near McCormick Place, Arena, Soldier Field and Grant Park

8.6 (31 Reviews) Apartment

The entire place is yours • 88 m² size • Kitchen

Chicago Near South Side • In Grand Boulevard · 4.7km to center

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a living room with a blue couch and a table at South Loop 2BR Getaway with Smart TVs & Optional Parking Near McCormick Place, Museum Campus & Downtown in Chicago

From US $153

South Loop 2BR Getaway with Smart TVs & Optional Parking Near McCormick Place, Museum Campus & Downtown

8.2 (17 Reviews) Apartment

The entire place is yours • 79 m² size • Kitchen

Chicago Near South Side • In Grand Boulevard · 4.7km to center

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a rooftop patio with a fire pit and a building at Modern 2BR in South Loop Near Soldier Field, Grant Park, Downtown, & Lakefront Trail in Chicago

From US $145

Modern 2BR in South Loop Near Soldier Field, Grant Park, Downtown, & Lakefront Trail

8.0 (35 Reviews) Apartment

The entire place is yours • 88 m² size • Private parking

Chicago Near South Side • In Grand Boulevard · 4.6km to center

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a couch and chair on a balcony with a view of the city at McCormick Place 3BR Luxury Penthouse Duplex with Personal Rooftop and Optional Parking for 8 guests in Chicago South Loop in Chicago

From US $245

McCormick Place 3BR Luxury Penthouse Duplex with Personal Rooftop and Optional Parking for 8 guests in Chicago South Loop

9.7 (7 Reviews) Apartment

The entire place is yours • 220 m² size • Private parking

Chicago Near South Side • In Grand Boulevard · 4.7km to center

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a living room with a green couch and two chairs at Spacious 2BR Vacation Rental with City View, Optional Parking and Gym Near McCormick Place & Downtown Chicago Attractions in Chicago

From US $145

Spacious 2BR Vacation Rental with City View, Optional Parking and Gym Near McCormick Place & Downtown Chicago Attractions

8.2 (16 Reviews) Apartment

The entire place is yours • 88 m² size • Private parking

Chicago Near South Side • In Grand Boulevard · 4.7km to center

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Luxury Places to Stay in Grand Boulevard

Over 29+ Luxury Places to Stay in or Near Grand Boulevard

a view of a city skyline with a tall building at Marriott Marquis Chicago in Chicago

From US $269

Marriott Marquis Chicago

8.5 (314 Reviews) Hotel

Breakfast • Private parking • 4 restaurants

Chicago Near South Side • In Grand Boulevard · 4.5km to center

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a large building with lights in front of it at The Study at the University of Chicago in Chicago

From US $259

The Study at the University of Chicago

9.1 (1047 Reviews) Hotel

Private parking • Restaurant • Pet friendly

Chicago Woodlawn • In Grand Boulevard · 3.6km to center

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a large building with many windows at night at Sophy Hyde Park in Chicago

From US $258

Sophy Hyde Park

9.0 (202 Reviews) Hotel

Private parking • Restaurant • Pet friendly

Chicago Hyde Park • In Grand Boulevard · 2.7km to center

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a view of the trump international hotel tower from a rooftop at Hyatt Regency McCormick Place Chicago in Chicago

From US $210

Hyatt Regency McCormick Place Chicago

8.2 (827 Reviews) Hotel

Breakfast • Private parking • 3 restaurants

Chicago Near South Side • In Grand Boulevard · 4.4km to center

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a living room with a couch and a kitchen at Chic Euro City Getaway- Close to Downtown in Chicago

From US $210

Chic Euro City Getaway- Close to Downtown

8.4 (29 Reviews) Apartment

The entire place is yours • 111 m² size • Free WiFi

Chicago Grand Boulevard • In Grand Boulevard · 903m to center

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a living room with a couch and a ceiling fan at The Penthouse, Lux stay near Downtown, UofC & Lake in Chicago

From US $266

The Penthouse, Lux stay near Downtown, UofC & Lake

9.2 (37 Reviews) Apartment

The entire place is yours • 135 m² size • Kitchen

Chicago Kenwood • In Grand Boulevard · 1.7km to center

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a bedroom with a black bed and a large mirror at Luxéry Stay Chicago - Themed Units! Close to Downtown, McCormick Place & Wintrust Arena in Chicago

From US $250

Luxéry Stay Chicago - Themed Units! Close to Downtown, McCormick Place & Wintrust Arena

8.9 (194 Reviews) Apartment

The entire place is yours • 60 m² size • Kitchen

Chicago Near South Side • In Grand Boulevard · 4.6km to center

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a living room with a couch and a tv at Hamaline Luxury Guest House in Chicago

From US $348

Hamaline Luxury Guest House

8.5 (7 Reviews) Villa

The entire place is yours • 1400 m² size • Free on-site parking

Chicago Douglas • In Grand Boulevard · 1.6km to center

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Pet-Friendly Vacation Rentals in Grand Boulevard

Over 21+ Pet-Friendly Vacation Rentals in or Near Grand Boulevard

a hotel room with a large bed and a couch at Hampton Inn Chicago McCormick Place in Chicago

From US $119

Hampton Inn Chicago McCormick Place Pets allowed

8.6 (750 Reviews) Hotel

Breakfast • Indoor swimming pool • 5 restaurants

Chicago Near South Side • In Grand Boulevard · 4.4km to center

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a hotel room with a couch and a bed at Home2 Suites By Hilton Chicago McCormick Place in Chicago

From US $116

Home2 Suites By Hilton Chicago McCormick Place Pets allowed

8.7 (283 Reviews) Hotel

Breakfast • Indoor swimming pool • 5 restaurants

Chicago Near South Side • In Grand Boulevard · 4.4km to center

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a hotel room with a bed and a chair and a window at Hilton Garden Inn Chicago McCormick Place in Chicago

From US $129

Hilton Garden Inn Chicago McCormick Place Pets allowed

7.6 (348 Reviews) Hotel

Breakfast • Indoor swimming pool • 5 restaurants

Chicago Near South Side • In Grand Boulevard · 4.4km to center

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a bedroom with a black bed and a large mirror at Luxéry Stay Chicago - Themed Units! Close to Downtown, McCormick Place & Wintrust Arena in Chicago

From US $250

Luxéry Stay Chicago - Themed Units! Close to Downtown, McCormick Place & Wintrust Arena Pets allowed

8.9 (194 Reviews) Apartment

The entire place is yours • 60 m² size • Kitchen

Chicago Near South Side • In Grand Boulevard · 4.6km to center

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a large building with lights in front of it at The Study at the University of Chicago in Chicago

From US $259

The Study at the University of Chicago Pets allowed

9.1 (1047 Reviews) Hotel

Private parking • Restaurant • Pet friendly

Chicago Woodlawn • In Grand Boulevard · 3.6km to center

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a living room with a couch and a yellow wall at The Black And White Suite in Chicago

From US $575

The Black And White Suite Pets allowed

7.1 (20 Reviews) Holiday_home

The entire place is yours • 223 m² size • Free parking

Chicago Grand Boulevard • In Grand Boulevard · 972m to center

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a car parked in a parking lot next to a building at Chicago Lakeshore Hotel in Chicago

From US $129

Chicago Lakeshore Hotel Pets allowed

6.3 (92 Reviews) Hotel

Free on-site parking • Pet friendly • Free WiFi

Chicago Kenwood • In Grand Boulevard · 2.8km to center

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a living room with a couch and a rug with records on it at Greater Grand Crossing/Hyde Park in Chicago

From US $175

Greater Grand Crossing/Hyde Park Pets allowed

7.4 (23 Reviews) Apartment

The entire place is yours • 12 m² size • Pet friendly

Chicago Greater Grand Crossing • In Grand Boulevard · 4.6km to center

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Vacation Rentals in Grand Boulevard

Over 38+ Vacation Rentals in or Near Grand Boulevard

a bedroom with a black bed and a large mirror at Luxéry Stay Chicago - Themed Units! Close to Downtown, McCormick Place & Wintrust Arena in Chicago

From US $250

Luxéry Stay Chicago - Themed Units! Close to Downtown, McCormick Place & Wintrust Arena

8.9 (194 Reviews) Apartment

The entire place is yours • 60 m² size • Kitchen

Chicago Near South Side • In Grand Boulevard · 4.6km to center

Best Price Match

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a living room with a couch and a tv at Forrestville Ave Large Suite in Chicago

From US $160

Forrestville Ave Large Suite

8.6 (103 Reviews) Apartment

The entire place is yours • 130 m² size • Free parking

Chicago Grand Boulevard • In Grand Boulevard · 414m to center

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a living room with a couch and a ceiling fan at The Penthouse, Lux stay near Downtown, UofC & Lake in Chicago

From US $266

The Penthouse, Lux stay near Downtown, UofC & Lake

9.2 (37 Reviews) Apartment

The entire place is yours • 135 m² size • Kitchen

Chicago Kenwood • In Grand Boulevard · 1.7km to center

Best Price Match

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a living room with a green couch and a table at Chicago 2BR Suite Perfect for Convention and Business Trips Near McCormick Place, Arena, Soldier Field and Grant Park in Chicago

From US $167

Chicago 2BR Suite Perfect for Convention and Business Trips Near McCormick Place, Arena, Soldier Field and Grant Park

8.6 (31 Reviews) Apartment

The entire place is yours • 88 m² size • Kitchen

Chicago Near South Side • In Grand Boulevard · 4.7km to center

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a living room with a blue couch and a table at South Loop 2BR Getaway with Smart TVs & Optional Parking Near McCormick Place, Museum Campus & Downtown in Chicago

From US $153

South Loop 2BR Getaway with Smart TVs & Optional Parking Near McCormick Place, Museum Campus & Downtown

8.2 (17 Reviews) Apartment

The entire place is yours • 79 m² size • Kitchen

Chicago Near South Side • In Grand Boulevard · 4.7km to center

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a rooftop patio with a fire pit and a building at Modern 2BR in South Loop Near Soldier Field, Grant Park, Downtown, & Lakefront Trail in Chicago

From US $145

Modern 2BR in South Loop Near Soldier Field, Grant Park, Downtown, & Lakefront Trail

8.0 (35 Reviews) Apartment

The entire place is yours • 88 m² size • Private parking

Chicago Near South Side • In Grand Boulevard · 4.6km to center

Best Price Match

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a couch and chair on a balcony with a view of the city at McCormick Place 3BR Luxury Penthouse Duplex with Personal Rooftop and Optional Parking for 8 guests in Chicago South Loop in Chicago

From US $245

McCormick Place 3BR Luxury Penthouse Duplex with Personal Rooftop and Optional Parking for 8 guests in Chicago South Loop

9.7 (7 Reviews) Apartment

The entire place is yours • 220 m² size • Private parking

Chicago Near South Side • In Grand Boulevard · 4.7km to center

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a living room with a green couch and two chairs at Spacious 2BR Vacation Rental with City View, Optional Parking and Gym Near McCormick Place & Downtown Chicago Attractions in Chicago

From US $145

Spacious 2BR Vacation Rental with City View, Optional Parking and Gym Near McCormick Place & Downtown Chicago Attractions

8.2 (16 Reviews) Apartment

The entire place is yours • 88 m² size • Private parking

Chicago Near South Side • In Grand Boulevard · 4.7km to center

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Villa Places to Stay in Grand Boulevard

Over 1+ Villa Places to Stay in or Near Grand Boulevard

a living room with a couch and a tv at Hamaline Luxury Guest House in Chicago

From US $348

Hamaline Luxury Guest House

8.5 (7 Reviews) Villa

The entire place is yours • 1400 m² size • Free on-site parking

Chicago Douglas • In Grand Boulevard · 1.6km to center

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Hotels in Grand Boulevard

Over 19+ Hotels in or Near Grand Boulevard

a brick building with a cafe sign in front of it at The Polo Inn Bridgeport U.S.A. in Chicago

From US $285

The Polo Inn Bridgeport U.S.A.

9.6 (50 Reviews) Bed_and_breakfast

Breakfast • Free on-site parking • Restaurant

Chicago Bridgeport • In Grand Boulevard · 3.6km to center

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a hotel room with a large bed and a couch at Hampton Inn Chicago McCormick Place in Chicago

From US $119

Hampton Inn Chicago McCormick Place

8.6 (750 Reviews) Hotel

Breakfast • Indoor swimming pool • 5 restaurants

Chicago Near South Side • In Grand Boulevard · 4.4km to center

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a living room with a couch and two blue chairs at SpringHill Suites by Marriott Chicago Chinatown in Chicago

From US $116

SpringHill Suites by Marriott Chicago Chinatown

9.0 (624 Reviews) Hotel

Breakfast • On-site parking • Free WiFi

Chicago Armour Square • In Grand Boulevard · 4.2km to center

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a view of the trump international hotel tower from a rooftop at Hyatt Regency McCormick Place Chicago in Chicago

From US $210

Hyatt Regency McCormick Place Chicago

8.2 (827 Reviews) Hotel

Breakfast • Private parking • 3 restaurants

Chicago Near South Side • In Grand Boulevard · 4.4km to center

Best Price Match

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a large building with many windows at night at Sophy Hyde Park in Chicago

From US $258

Sophy Hyde Park

9.0 (202 Reviews) Hotel

Private parking • Restaurant • Pet friendly

Chicago Hyde Park • In Grand Boulevard · 2.7km to center

Best Price Match

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a hotel room with a couch and a bed at Home2 Suites By Hilton Chicago McCormick Place in Chicago

From US $116

Home2 Suites By Hilton Chicago McCormick Place

8.7 (283 Reviews) Hotel

Breakfast • Indoor swimming pool • 5 restaurants

Chicago Near South Side • In Grand Boulevard · 4.4km to center

Best Price Match

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a hotel room with a bed and a chair and a window at Hilton Garden Inn Chicago McCormick Place in Chicago

From US $129

Hilton Garden Inn Chicago McCormick Place

7.6 (348 Reviews) Hotel

Breakfast • Indoor swimming pool • 5 restaurants

Chicago Near South Side • In Grand Boulevard · 4.4km to center

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a building on a city street at night at Hyatt Place Chicago-South/University Medical Center in Chicago

From US $169

Hyatt Place Chicago-South/University Medical Center

8.3 (367 Reviews) Hotel

Breakfast • Shuttle service (free) • Pet friendly

Chicago Hyde Park • In Grand Boulevard · 2.8km to center

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Cheap Places to Stay in Grand Boulevard

Over 19+ Cheap Places to Stay in or Near Grand Boulevard

a waiting room with leather furniture and a sign on the wall at Chinatown Hotel Chicago in Chicago

From US $58

Chinatown Hotel Chicago

5.7 (1136 Reviews) Hotel

Free WiFi • View • Private bathroom

Chicago Armour Square • In Grand Boulevard · 4.5km to center

Best Price Match

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a hotel with a car parked in front of it at Chicago South Loop Hotel in Chicago

From US $75

Chicago South Loop Hotel

6.4 (3608 Reviews) Hotel

Free on-site parking • Free WiFi • View

Chicago Douglas • In Grand Boulevard · 3.7km to center

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a small bedroom with a bed and a window at Chateau de Woodlawn - Room III - The Dream Catcher in Chicago

From US $76

Chateau de Woodlawn - Room III - The Dream Catcher

7.5 (35 Reviews) Guest_house

Free on-site parking • Free WiFi • Family rooms

Chicago Woodlawn • In Grand Boulevard · 4.3km to center

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a living room with a blue couch and chairs at Chateau de Woodlawn - Room II - Le Parisienne in Chicago

From US $76

Chateau de Woodlawn - Room II - Le Parisienne

7.7 (22 Reviews) Guest_house

Free on-site parking • Free WiFi • Non-smoking rooms

Chicago Woodlawn • In Grand Boulevard · 4.3km to center

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a bedroom with a large bed with a blue blanket at Chateau de Woodlawn - Room I - La Tour Eiffel in Chicago

From US $81

Chateau de Woodlawn - Room I - La Tour Eiffel

9.5 (13 Reviews) Guest_house

Free on-site parking • Shuttle service (free) • Free WiFi

Chicago Woodlawn • In Grand Boulevard · 4.3km to center

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a bedroom with a large bed with two lights above it at Villa Dubois Guest House in Chicago

From US $90

Villa Dubois Guest House

6.7 (227 Reviews) Guest_house

Free parking • Free WiFi • View

Chicago Douglas • In Grand Boulevard · 1.5km to center

Best Price Match

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a dining room with a table and chairs at McCormick Place Guest House in Chicago

From US $97

McCormick Place Guest House

7.6 (173 Reviews) Guest_house

Free parking • Free WiFi • View

Chicago Douglas • In Grand Boulevard · 1.7km to center

Best Price Match

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a hotel room with a couch and a bed at Home2 Suites By Hilton Chicago McCormick Place in Chicago

From US $116

Home2 Suites By Hilton Chicago McCormick Place

8.7 (283 Reviews) Hotel

Breakfast • Indoor swimming pool • 5 restaurants

Chicago Near South Side • In Grand Boulevard · 4.4km to center

Best Price Match

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About Grand Boulevard Vacation Rentals

Looking for places to stay in Grand Boulevard? Compare top options in Chicago.

With more than 57 Grand Boulevard vacation rentals, we can help you find a place to stay. These rentals, including vacation homes, holiday homes, and other short-term private accommodations, offer top-notch amenities with strong value, giving you comfort and luxury at the same time. Get more value and more room when you stay in Grand Boulevard.

Looking for last-minute deals or the best offers on cottages, condos, private villas, and large vacation homes? NearbyHoliday makes it easy to compare different options with a single click. Looking for a rental by owner with swimming pools, hot tubs, pet-friendly stays, or large-suite comforts? You can compare vacation rentals by owner and other popular Airbnb-style properties in Grand Boulevard. Prices average US $205 a night.

NearbyHoliday makes it easy and safe to find and compare vacation rentals in Grand Boulevard, 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 Stay Categories in Grand Boulevard

Category	Count
Vacation Rentals	38
Luxury Rentals	29
Pet-Friendly	21
Cheap Rentals	19
Hotels	19
Hotels with Suites	8
Villa Rentals	1

Use These Quick Filters to Find a Vacation Rental in Grand Boulevard

Browse the most useful filters to narrow down vacation rentals, holiday homes, and other places to stay in Grand Boulevard.

Pro Tip: Use the quick filters above to compare vacation rentals, holiday homes, hotels, resorts, cabins, villas, and pet-friendly places to stay in Grand Boulevard. These links help you narrow your search faster, discover short-term rentals with the amenities and pricing that fit your trip, and browse popular stay types before checking availability, last-minute options, and the best deals for your preferred travel style.

Weather in Grand Boulevard

Average temperatures and rainfall by month range to help plan your stay in Grand Boulevard.

Mar - May

Avg High17°C / 62°F

Avg Low6°C / 42°F

Rainfall106 mm / 4.2 in

Jun - Aug

Avg High28°C / 83°F

Avg Low18°C / 65°F

Rainfall90 mm / 3.5 in

Sep - Nov

Avg High18°C / 65°F

Avg Low9°C / 48°F

Rainfall70 mm / 2.7 in

Dec - Feb

Avg High3°C / 38°F

Avg Low-5°C / 22°F

Rainfall62 mm / 2.4 in

Other Places to Stay Near Grand Boulevard

Grand Boulevard Vacation Rental Frequently Asked Questions

There are a lot of options in Grand Boulevard. If you plan on staying in the Grand Boulevard area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Grand Boulevard: