The project dashboard is a free tool that is only available to verified hoteliers to make adopting new technology easier by streamlining their research and simplifying their communication workflow.
TLDR
We analyzed 528 verified hotelier reviews, compared feature sets, pricing, and real-world case studies to break down where each platform delivers. The right choice depends on your property type and priorities:
Oaky by Plusgrade shines in ease of use and customer support — especially for brand properties (5.0/5) , with exclusive features like Guest Segmentation & Targeting and Multi-Channel Delivery (Email, SMS, WhatsApp, Chat).
Simple Night shines .
Side-by-side ratings based on 528 verified hotelier reviews on HTR.
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| Starting Price | From $300/mo | Contact sales |
| Verified Reviews | 528 | 0 |
After analyzing 528 verified reviews, Oaky by Plusgrade users most value its upselling efficiency, user interface and system usability, customer support experience, while Simple Night users highlight . Click any theme to see what reviewers say.
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Upselling Efficiency
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User Interface and System Usability
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Customer Support Experience
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Personalization and Targeted Promotions
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Reporting System Challenges
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Integration with PMS
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How each product ranks among Upselling Software vendors for different property sizes, types, and regions — based on verified reviews from hoteliers in each segment.
By Hotel Size
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| Small (10-24 rooms) ▾ | #5 42 reviews | — |
| Mid-Size (25-74 rooms) ▾ | #2 263 reviews | — |
| Large (75-199 rooms) ▾ | #1 141 reviews | — |
| X-Large (200+ rooms) ▾ | #2 57 reviews | — |
By Property Type
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| Boutique ▾ | #2 216 reviews | #27 0 reviews |
| Luxury ▾ | #2 278 reviews | — |
| Branded / Chain ▾ | #2 208 reviews | — |
| Extended Stay ▾ | #3 33 reviews | — |
By Region
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| North America ▾ | #7 29 reviews | #24 0 reviews |
| Europe ▾ | #1 315 reviews | — |
| Asia Pacific ▾ | #2 81 reviews | — |
| Middle East ▾ | #2 52 reviews | — |
Choosing between Oaky by Plusgrade and Simple Night hinges on your hotel’s upselling goals and operational focus. Oaky is a dedicated upselling platform designed to enhance revenue through personalized offers, automation, and real-time integrations, while Simple Night functions as a broader experience platform that manages activities, dining, and entertainment bookings alongside distribution and payments. Both aim to boost ancillary revenue but approach it from different angles.
Oaky’s highly specialized upselling capabilities, extensive feature set, and strong regional presence make it the clear leader for hotels prioritizing targeted revenue growth. Simple Night, by contrast, is better suited if your hotel wants to incorporate experience bookings and activities into a unified distribution ecosystem. But which product best suits your needs?
Oaky’s core strength is its focus on upselling, with features tailored specifically to optimize guest upgrades, ancillary services, and pre-arrival offers. It boasts a robust feature library, including guest segmentation, offer experimentation, dynamic pricing, and multi-channel delivery, all aimed at increasing revenue per guest.
Simple Night’s offering centers on experience distribution—connecting hotels with activity suppliers in a white-label environment. It enables a hotel to sell tours, dining, and entertainment as part of a broader experience portfolio, but it lacks the focused upselling functionalities that Oaky provides.
Both platforms offer digital tools to enhance guest engagement, but Oaky’s in-depth personalization and automation give it a decisive edge for hotels seeking to maximize upsell revenue. Do you prioritize targeted upselling or experience distribution?
If your hotel needs a dedicated upselling tool that integrates seamlessly with PMS systems, leverages segmentation, and offers dynamic pricing, go with Oaky. It’s ideal for hotels aiming to increase ancillary revenue from room upgrades, packages, or personalized offers, especially if they operate across multiple regions or property types.
If your hotel’s goal is to expand its inventory of activities, tours, and experiences, and you want a platform that simplifies distribution and booking of these offerings, Simple Night is the better choice. It suits hotels that want to embed activity sales into their existing booking channels without a focus solely on upsell automation.
Oaky’s recent review count (443 reviews, with 7 in the last 6 months) and high ratings (4.84/5 overall) underscore its maturity and strong customer satisfaction. Simple Night’s review data is unavailable, which makes it harder to assess its current market standing or performance.
Oaky’s user interface is rated 4.84/5, praised for its intuitiveness and quick onboarding process. Many users describe it as easy to manage, with rapid setup and minimal training needed, supported by high-quality onboarding and support ratings of 4.87/5.
In contrast, Simple Night has no publicly available ratings or user reviews, making it impossible to gauge its ease of use. Given the prominence of Oaky’s recent positive feedback and high usability scores, edge: Oaky.
Oaky offers 12 unique features including guest segmentation, offer experimentation, room upgrade merchandising, multi-channel delivery, dynamic pricing, offer templates, and offer orchestration. It also provides advanced automation, data security (Type 2 SOC 2 certification), and multi-property dashboards.
Simple Night lacks documented features, with no unique or shared features listed. It functions primarily as a distribution and activity management platform, not offering the specialized upselling functionalities that Oaky provides.
Edge: Oaky.
Oaky has a support rating of 4.87/5, with reviews highlighting prompt, knowledgeable assistance and a strong partnership approach. Customers praise their onboarding process, responsiveness, and ongoing support, citing testimonials such as “We really have a fantastic partnership and continue to learn from each other every day.”
Simple Night offers no publicly available support ratings or reviews, making it impossible to compare support quality. Based on available data, edge: Oaky.
Oaky boasts 54 verified integration partners, including major PMS and channel managers like ManCloud, RoomRaccoon, and Hotelkit. These integrations facilitate real-time data exchange, automation, and better upselling execution.
Simple Night currently lists zero verified integrations, limiting its connectivity options. For hotels relying on seamless tech stack integration, edge: Oaky.
Oaky’s recent reviews (7 in the last 6 months) with an overall rating of 4.84/5 and a likelihood to recommend of 96% suggest strong, recent customer satisfaction. Hotels of various segments, from luxury to boutique, praise its ease of use, automation, and revenue impact, with independent hotels rating it 4.92/5.
Simple Night lacks public reviews and ratings, so no comparative data exists. Given the recent, high-quality reviews for Oaky, edge: Oaky.
Oaky charges a flat monthly fee of $300, with no implementation fees or freemium options. Pricing clarity makes budgeting straightforward, especially for hotels seeking predictable costs.
Simple Night does not specify pricing details publicly, making it difficult to compare costs directly. Based on available information, edge: Oaky.
Not ideal if you prefer a broad experience distribution platform without a focus on upselling. Smaller hotels with limited budgets might find Oaky’s costs a consideration.
Not ideal if your primary goal is targeted upselling or revenue optimization through personalized offers. Smaller properties with no experience offerings may find limited value.
Oaky is a dedicated upselling tool with a proven track record, extensive features, and high customer satisfaction. It is best suited for hotels focused on increasing revenue through personalized, automated offers integrated into their PMS.
Simple Night serves as a broader experience distribution platform, ideal if your hotel wants to embed activity and entertainment sales into your overall booking ecosystem. Its focus is more on expanding experience offerings rather than targeted upselling.
If your priority is boosting ancillary revenue through personalized, automated upselling, Oaky is the clear choice. For expanding experience bookings and activity distribution, Simple Night offers a streamlined solution, but with less emphasis on upselling specifics.
In conclusion, for revenue-driven hoteliers, Oaky’s specialization and recent reviews make it the stronger candidate. If your hotel’s strategy centers on guest experience and experience sales, Simple Night might fit, but its limited details and lack of recent reviews leave it behind in the upselling race.
Upselling Software pricing is rarely straightforward. Here is what we know from each vendor's public pricing data. Always request a custom quote for your property size.
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| Starting Price | From $300/mo | — |
According to HTR's product database, Oaky by Plusgrade and Simple Night share 0 features. Here are the key differences — features one has that the other lacks.
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| Dynamic Upgrade Pricing | ||
| Guest Segmentation & Targeting | ||
| Multi-Channel Delivery (Email, SMS, WhatsApp, Chat) | ||
| Offer Experimentation & A/B Testing | ||
| Offer Templates Library | ||
| Room Upgrade Merchandising |
We analyzed 8 verified case studies to compare what hotels actually achieve with each platform across four key business objectives.
"With Oaky, guests can clearly see what extra services or products we have to offer. By looking through all our services they can choose to add things they did not even know they wa..."
No published case study for this goal yet.
"Oaky allows us to be creative and feature relevant and exciting offers to our guests. The solution is extremely flexible and easy to use, helping our teams to offer unique services..."
No published case study for this goal yet.
What hoteliers love
Reviewers consistently commend Oaky's ability to streamline and enhance the upselling process, making it easier to generate additional revenue. Users... Reviewers consistently commend Oaky's ability to streamline and enhance the upselling process, making it easier to generate additional revenue. Users appreciate the ease of promoting room upgrades and packages, contributing significantly to boosting hotel revenue.
The platform's user-friendly design is repeatedly praised, allowing both new and experienced users to engage effectively with the software. This acces... The platform's user-friendly design is repeatedly praised, allowing both new and experienced users to engage effectively with the software. This accessibility helps hotels employ upselling strategies without extensive training.
Oaky's customer support is largely praised for its efficiency and knowledge, with special mention of certain team members who consistently ensure a po... Oaky's customer support is largely praised for its efficiency and knowledge, with special mention of certain team members who consistently ensure a positive experience. Prompt assistance is highlighted as a particular strength.
Where hoteliers push back
Several reviews identify challenges with Oaky's reporting system, noting a need for improvements in clarity and integration with existing hotel system... Several reviews identify challenges with Oaky's reporting system, noting a need for improvements in clarity and integration with existing hotel systems. Users express difficulty in accessing comprehensive data on upselling activities.
Oaky offers seamless integration with many hotel property management systems, enhancing real-time data synchronization. Issues do exist, however, as s... Oaky offers seamless integration with many hotel property management systems, enhancing real-time data synchronization. Issues do exist, however, as some users encounter complications requiring manual input, specifically when tracking upselling offers.
Ranks higher for
Unique capabilities
Where the ratings diverge most
It depends on your requirements. Oaky by Plusgrade and Simple Night share many core Upselling Software features, but each has unique capabilities. Oaky by Plusgrade offers 54 verified integration partners, while Simple Night offers 0. Review the feature comparison above to see where they differ before switching.
Small hotels should prioritize ease of use and fast onboarding. Oaky by Plusgrade leads in ease of use at 4.8/5 vs 0.0/5. Look for transparent pricing and a trial or demo option. Filter reviews on each product page by property size to hear from hotels like yours.
Oaky by Plusgrade: No. Simple Night: No. Neither product currently offers a free tier. Most Upselling Software vendors offer demos or trials — request one from each to evaluate before committing.
The HT Score is a composite ranking that considers 4 criteria groups and over a dozen variables to help hoteliers objectively compare hotel technology products. Oaky by Plusgrade has an HT Score of 96 and Simple Night has 0. Here is how the score is calculated.
| Criteria Group | Weight | What It Measures |
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| Customer Ratings & Reviews |
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How highly do users recommend this product? Ratings Score, Review Volume, Share of Voice, Review Depth, Review Recency, Success Stories ▾ The most heavily weighted factor. Analyzes average satisfaction ratings (likelihood to recommend, ease of use, support, ROI), total review count relative to category peers, review recency (at least 20 reviews in the trailing 6 months), and share of voice across unique hotel clients to detect selection bias. |
| Partner Ecosystem |
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How highly do tech partners recommend this company? Partner Recommendations, Integration Quantity, Integration Quality ▾ Evaluates partner recommendations as expert votes of confidence, the number of verified integrations, and ecosystem quality — the average HT Scores of integration partners. Products with higher-quality integration ecosystems are more likely to deliver a connected tech stack. |
| Customer Centricity |
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How customer-centric is this organization? Certified Support, Review Consistency, Profile Completeness ▾ Assesses whether the company has earned HTR Customer Support Certification, maintains consistent review collection over time (an indicator of feedback-driven culture), and keeps product profiles complete with capabilities, screenshots, pricing, and features. |
| Reach, Staying Power & Resources |
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How extensive is this company's reach and resourcing? Geographic Reach, Staying Power, Company Resources, Trending Score ▾ Measures global presence (countries and regions served), years in business as a stability proxy, team headcount as a resource proxy, and a trending score based on trailing-twelve-month buyer inquiries, reviews, partner recommendations, and press activity. |
Customer ratings and reviews are by far the most important factor in the HT Score algorithm. HTR does not accept payment for higher rankings. All reviews are verified — only hotel industry practitioners with confirmed affiliations can submit ratings. View full HT Score methodology →
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