Tiptoe Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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Your Tiptoe Vacation

The stress-free way to experience this interesting city is with a tailor-made Tiptoe vacation package. Stay in the neighborhood of Southbourne, which is good for dining, shopping and bars and pubs or go someplace else — our package deals are all about you. Any trip to Tiptoe needs a well-thought-out itinerary. Fill yours with attractions like Milford on Sea Beach, Hurst Beach and Lymington Sea Water Baths. Whatever your travel plans or the size of your budget, putting together a tailored Tiptoe vacation is a cinch with Expedia.

Top Tiptoe Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Winchester Wessex Hotel by Sunday

Winchester Wessex Hotel by Sunday

4 out of 5
Price was CA $1,712, price is now CA $1,472 per person
CA $1,472
per person
Sep 9 - Sep 15
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Southampton (SOU)
7.6/10 Good! (1,000 reviews)
Good location. Bed was very comfortable. Special room a view of cathedral was 90% blocked by trees. Sink drain was plugged w hair.

Reviewed on Jun 29, 2026

Forest Lodge

Forest Lodge

4 out of 5
Price was CA $2,147, price is now CA $1,994 per person
CA $1,994
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Southampton (SOU)
8.2/10 Very good! (231 reviews)
The stay was great, I’ve left one star as we accidentally left our expensive apple laptop charger in the room, we phoned the hotel to see if we could get it back and the staff were very unhelpful, it was definitely left there (which we should have been more observant of when packing and leaving) but when a mistake like that happens you fully expect the staff & cleaners to at least have the decency & trust to keep it aside for a period of time. I feel let down that this has happened. I’m just glad it wasn’t something sentimental like jewellery as I don’t trust it would have been reported or followed up. Shame because the stay outside of this was nice.

Reviewed on Jun 30, 2026

Best Western Chilworth Manor Hotel

Best Western Chilworth Manor Hotel

3 out of 5
Price was CA $1,976, price is now CA $1,862 per person
CA $1,862
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Southampton (SOU)
8/10 Very good! (1,002 reviews)
Good choice of breakfast items

Reviewed on Jun 29, 2026

The Mortimer Arms

The Mortimer Arms

4 out of 5
Price was CA $2,063, price is now CA $1,946 per person
CA $1,946
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Southampton (SOU)
8.6/10 Excellent! (322 reviews)
perfect location for paultons park

Reviewed on May 31, 2026

Leonardo Hotel Southampton

Leonardo Hotel Southampton

4 out of 5
The Polygon
Price was CA $2,016, price is now CA $1,913 per person
CA $1,913
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Southampton (SOU)
8.6/10 Excellent! (1,339 reviews)
Nice easy check in, helpful staff, great breakfast. We saw a manager personally greet two staff laying tables, who must have been new, they seemed a bit overawed after he went out of his way to stop and chat to them and shake their hands. A mark of excellent people management which didn't go unnoticed.

Reviewed on Jul 2, 2026

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Tiptoe Hotel Deals

Laguna Hotel

Laguna Hotel

3 out of 5
6 Suffolk Road South Bournemouth England
Fully refundableReserve now, pay when you stay
The price is CA $89 per night from Jul 7 to Jul 8
CA $89
CA $107 total
Jul 7 - Jul 8
includes taxes & fees
7.2/10 Good! (1,032 reviews)
"It was my second time staying at Laguna hotel, and once again it was a great experience. The location is excellent, just a 15-minute walk from the beach. The pleasant walk, swimming pool, and free parking are real advantages in this area. I'm pretty sure we'll be back again soon!"

Reviewed on Jun 30, 2026

Laguna Hotel
Leonardo Hotel Southampton

Leonardo Hotel Southampton

4 out of 5
1 Charlotte Place Southampton England
Fully refundableReserve now, pay when you stay
The price is CA $110 per night from Jul 5 to Jul 6
CA $110
CA $133 total
Jul 5 - Jul 6
includes taxes & fees
8.6/10 Excellent! (1,350 reviews)
"Nice easy check in, helpful staff, great breakfast. We saw a manager personally greet two staff laying tables, who must have been new, they seemed a bit overawed after he went out of his way to stop and chat to them and shake their hands. A mark of excellent people management which didn't go ..."

Reviewed on Jul 2, 2026

Leonardo Hotel Southampton
Moxy Southampton

Moxy Southampton

3 out of 5
Harbour Parade Southampton England
Fully refundableReserve now, pay when you stay
The price is CA $133 per night from Jul 5 to Jul 6
CA $133
CA $159 total
Jul 5 - Jul 6
includes taxes & fees
9/10 Wonderful! (1,019 reviews)
"Nice new hotel, had no hot water or A/C for a few days."

Reviewed on Jul 2, 2026

Moxy Southampton
See all 4,303 properties in Tiptoe
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

What to do in Tiptoe

Isle of Wight: Osborne Admission Ticket

Isle of Wight: Osborne Admission Ticket

CA $44
per adult
100% of travellers recommend
Isle of Wight: Osborne Admission Ticket
Southampton: Guided Ghost Walk

The Southampton Ghost Walk

CA $28
per adult
100% of travellers recommend
The Southampton Ghost Walk
Private Southampton Walking Tour

Private Southampton Walking Tour

CA $43
per adult
100% of travellers recommend
Private Southampton Walking Tour
See all activities in Tiptoe

Frequently asked questions

How much does a Tiptoe vacation package cost?
Offering excellent value package deals from CA $1,472 on Expedia, you'll be surprised at how little a vacation to Tiptoe costs! Expedia's packages make travel planning easier and your savings go further.
What are the cheapest months to go to Tiptoe?
If you're hoping to snag a cheap Tiptoe vacation package, consider visiting in January, February and November. You're likely to find lower rates on hotels and airfares during these months — perfect for travellers wishing to save money.
How many days is enough for Tiptoe?
For your Tiptoe vacation, a few days will be enough to explore the top spots. Be sure to visit Lymington Sea Water Baths — it's one of the main attractions in this destination. If you want more adventure, consider basing yourself here and going on some day tours from Tiptoe.
How to find the best Tiptoe package deals?
Begin your search for a Tiptoe package deal by entering your destination and travel dates under our "Packages" tab. Then apply a few filters, like "Popular locations" and "Amenities," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with big savings. If you don't find the ideal Tiptoe package deal right away, simply switch up your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Tiptoe adventure underway.
Is it cheaper to book a Tiptoe vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to booking hotels and flights separately. Better still, you can customize your Tiptoe escape to match your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a vacation package to Tiptoe?
If you're considering a spur-of-the-moment Tiptoe getaway, check out our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can land sensational deals on your hotels and flights by booking ahead.
How to plan a trip to Tiptoe?

  1. Pick your travel dates: What you plan to do in Tiptoe and your favourite season will help you decide when to travel.
  2. Figure out your budget: Make sure you have enough money to cover everything from dining out and transportation to experiences and flights. Your accommodations will likely be the largest expense during your trip to Tiptoe.
  3. Decide how long to go away for: Now that you know more about Tiptoe, you can work out the perfect length of your vacation. Put together a draft itinerary and give yourself enough time to get through everything on your must-do list.
  4. Combine your airfare and accommodations: After you've nailed down your trip dates and duration, lock in the right Tiptoe vacation package for you.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.